Erythroxylaceae

Bibliography

1. M. A. R. Y. C. Acock, \relax J. O. H. N. Lydon, \relax E. M. A. N. U. E. L. Johnson, and \relax R. O. N. A. L. D. Collins, “Effects of Temperature and Light Levels on Leaf Yield and Cocaine Content in Two Erythroxylum Species,” Annals of Botany, vol. 78, no. 1, pp. 49–53, Jul. 1996. doi: 10.1006/anbo.1996.0094. Abstract
   Published information on the response ofErythroxylumcrops to temperature and photosynthetic photon flux density (PPFD) is more descriptive than quantitative. The objective of this study was to quantify the effects of temperature and PPFD on leaf growth and cocaine content in the major cocaine-producing species. Plants ofErythroxylum cocavar. coca (Coca) andErythroxylum novogranatensevar. novogranatense (Novo) were grown in artificially-lighted controlled environment chambers with a 12h photoperiod and at day/night temperatures of 20/16, 25/21, 30/26 or 35/31°C and at PPFDs of 155, 250 or 400μmolm−2s−1for 53d before leaves were harvested for dry weight and cocaine concentration determinations. Subsequently, chamber temperatures were altered to provide constant day/night temperatures of 19, 23 or 27°C. Plants were grown for 180d under these conditions and harvested a second time. Leaf yields in response to temperature were best expressed as quadratic functions. The optimum average daily temperature for leaf growth was near 27°C in both species. Novo was more vegetatively vigorous than Coca. Leaf mass at the first harvest was lowest in plants grown under 155μmol m−2s−1for both species. At the second harvest the only change was that there was no difference in leaf mass between 155 and 250μmol m−2s−1in Coca. Leaf cocaine concentration was not affected by PPFDs<400μmol m−2s−1but was affected by temperature. In Coca, leaf cocaine concentration was maximum at a mean daily temperature of 24°C at the first harvest and at 19°C at the second harvest. In Novo, leaf cocaine concentration was maximum at a mean daily temperature of 25°C at the first harvest but there was no effect of temperature at the second harvest. Coca leaves had higher cocaine concentration than Novo leaves at all temperatures at the first harvest but at the second harvest, there was no significant difference in leaf cocaine concentration between species except in the lowest temperature treatment when leaf cocaine concentration was higher for Coca. Cocaine production on a per plant basis was largely a function of leaf mass.
2. M. C. Acock, C. S. T. Daughtry, G. Beinhart, E. Hirschmann, and B. Acock, “Estimating Leaf Mass from Light Interception Measurements on Isolated Plants of Erythroxylum Species,” Agronomy Journal, vol. 86, no. 3, pp. 570–574, 1994. doi: 10.2134/agronj1994.00021962008600030021x. Abstract
   To determine the extent of coca (Erythroxylum spp.) production in the world, some method for estimating yield (leaf mass) in a variety of habitats is required. A computer model that simulates the growth of coca plants has the versatility for making these estimates, but there must be some reliable method to validate the model. The objective of this research was to validate the use of measurements of light interception and specific leaf area (SLA, m2 kg−1) for estimating yield. Leaf area was calculated from light interception measurements made on plants grown as hedgerow or as isolated plants, then converted to leaf mass using measurements of SLA. Light interception was measured with the Decagon Sunfleck Ceptometer (SC) and the LI-COR Plant Canopy Analyzer (PCA). Leaf disks of known area from Erythroxylum coca var. coca and Erythroxylum novogranatense var. novogranatense were cut, dried, and weighed to determine SLA values. Leaf fresh weights were measured and corrected to dry weight using the fresh to dry weight ratio obtained from a sample at harvest. Estimated leaf mass regressed on observed leaf mass demonstrated that PCA was superior to SC in estimating leaf mass on isolated plants of various sizes using the techniques described in this paper. Leaf area was consistently underestimated by the SC. The estimates of leaf mass from the PCA gave the lower mean, absolute mean, and root mean square error terms compared with SC, and the slope of the regression line of observed leaf mass vs. predicted leaf mass was closest to a value of 1.0.
3. M. C. Acock and E. L. Johnson, “Modeling the Effects of Nitrogen on Components of Coca Yield,” Journal of Plant Nutrition, vol. 21, no. 7, pp. 1501–1509, Jul. 1998. doi: 10.1080/01904169809365498. Abstract
   Estimating yields (leaf dry weights) of Erythroxylum coca var. coca Lam. (coca) in regions where there is no access requires a method that can be used remotely. A simulation model that characterizes coca growth under varying weather conditions offers such a method. To develop this model, crop response to its environment must be quantified. The current experiment examined how a range in nitrogen (N) availability affected N status of various parts of the coca plant and components of yield. Minimal and maximal values for N concentration in leaves, stems, and roots were determined and N status calculated. Young leaves (a small yield component) had the highest N concentration, the greatest demand for N, and snowed the greatest N stress. Old leaves had the next highest N concentration and a high demand for N, but showed the lowest N stress. Nitrogen status in old leaves was most affected by N availability. Dry weights of each leaf type increased with increased N availability, but leaf cocaine concentration was not affected. Stems and taproots had the lowest N concentrations and these were not affected by N availability. Lateral roots, closer to the source of N, had N concentrations that reflected N availability, however lateral root dry weights were not affected by N supply. Increased N availability increased (a) the number of growing points on the plant, (b) the number of leaves per growing point, and (c) the size of old leaves. Increases in these components translate into increased yields. Leaf yields correlated with the N status of leaves (r=0.58, p≤0.001), but variability in leaf yields for a given N status was too high to have strong predictive power.
4. M. C. Acock, “Two Methods for the Rapid Assessment of Leaf Yield of Erythroxylum Coca Var. Coca,” Agronomy Journal, vol. 90, no. 5, pp. 705–709, 1998. doi: 10.2134/agronj1998.00021962009000050021x. Abstract
   Methods for estimating yields of Erythroxylum coca var. coca were devised and compared. For the PCA method, yields were estimated from canopy light interception, specific leaf area (SLA), and a calibration factor. For the canopy subsample method (CSS), yield was estimated from leaf number, size, and SLA subsamples multiplied by the ratio of canopy to subsample volume. Corrected PCA overestimated yields by 9% and CSS underestimated yields by 7% for a test dataset. The CSS method requires more field time, but uses simple equipment that can be applied at any time. The PCA method requires expensive equipment and uniform light, and it cannot be used when it is raining.
5. V. L. A. Aguilar Ramos, “Detección de alcaloides de erythroxylum coca en muestras de orina y determinación de las características del consumo en personas investigadas y/o detenidas por la dirección territorial de la policía (dirtepol) región la libertad de enero – abril del 2014,” Universidad Nacional de Trujillo, 2015. http://dspace.unitru.edu.pe/handle/UNITRU/1218. Abstract
   Se realizó un estudio transversal y retrospectivo en el que se detecta los alcaloides de Erythroxylum coca “coca” en muestras de orina y se determina las características de consumo en personas investigadas y/o detenidas por las Dirección Territorial de Policía en La Libertad (DIRTEPOL-LL) durante el periodo de enero-abril del 2014. Se realizó el estudio con una población de 500 personas de ambos sexos y de diferentes edades, donde se encontró la presencia de alcaloides de Erythroxylum coca “coca” en mayor porcentaje, en la población masculina se encuentra dentro de las edades de 25-29 años lo cual está representado por el 30% y en las mujeres que a una edad de 30-34 años lo cual está representado por el 22,78%. El contacto con esta sustancia les lleva a cometer muchos delitos predominando Delito Contra la Salud Pública -T.I.D y el distrito donde más se llevó a cabo fue en La Esperanza
6. P. S. F. Alberts, M. Daneel, A. A. S. Marais, D. A. Baranenko, and J. J. M. Meyer, “Seasonal Analysis of the Tropane Alkaloid Ecgonine Methyl Ester and the Occurrence of Other Highly-Valued Tropanes in the South African Erythroxylum Trees,” Acta Physiologiae Plantarum, vol. 40, no. 2, p. 24, Jan. 2018. doi: 10.1007/s11738-017-2599-y. Abstract
   The coca family (Erythroxylaceae) consists of trees and shrubs sub-divided into four genera: Aneulophus, Nectaropetalum, Pinacopodium, and Erythroxylum, which include species with highly valuable medicinal compounds. E. delagoense, E. emarginatum, and E. pictum are endemic to southern Africa and have great pharmaceutical potential based on their traditional uses. Previous studies have shown certain inconsistencies in terms of the presence or absence of tropane alkaloids in these species, resulting in a need for further research and clarification. Therefore, the aim of this study was to determine the seasonal variation of the immediate biosynthetic precursor of cocaine, the tropane alkaloid, ecgonine methyl ester in the three South African Erythroxylum species by means of gas chromatography–mass spectrometry, as well as to conduct a phytochemical screening for observing the presence of other potential compounds and tropane alkaloids. We found significant differences in tropane concentrations from the seasonal variation study, explaining the discrepancies in previous reports on its presence/absence in these species. Furthermore, we report for the first time on the occurrence of selected highly valuable tropane alkaloids in E. emarginatum currently used in ‘blockbuster medicine’.
7. A. A. Alonso, S. R. Machado, A. A. Alonso, and S. R. Machado, “Morphological and Developmental Investigations of the Underground System of Erythroxylum Species from Brazilian Cerrado,” Australian Journal of Botany, vol. 55, no. 7, pp. 749–758, Nov. 2007. doi: 10.1071/BT07060. Abstract
   Brazilian cerrado, a neotropical savanna, is characterised by a strongly seasonal climate with distinctive wet and dry seasons, and deep and well drained soils that are acidic and with high aluminium content. Recurrent fires in the dry season place additional stress on the survival of plants, which exhibit an array of strategies of survival. The purpose of this work was to study the underground system of Erythroxylum nanum A.St-Hil. and E. campestre A.St-Hil., two sub-shrubby species, and E. tortuosum Mart., a shrubby species, verifying the possible relationship between the morphology of the underground organs and the resprouting ability of these plants. Anatomical analyses followed the usual techniques of plant anatomy. The cotyledons of the three species were green, foliaceous and photosynthesising. The two sub-shrubby species (Erythroxylum nanum and E. campestre) showed slow development of the aerial shoot system and extensive growth of the primary root in the initial stage of development. E. tortuosum presented the most pronounced development of the aerial system and a poorly developed primary root compared with the sub-shrubby species. The sub-shrubby species occurred in clumps and had underground systems interlinked, consisting of a deep axial primary root system besides soboles in E. nanum and xylopodium in E. campestre. Plants of the E. tortuosum were isolated, highly branched and their underground system consisted of a superficial primary root system. Abundance of reserves and the bud-forming potential of the soboles, xylopodium and roots resulted in production of vigorous branches that are highly valuable in the regeneration of the aerial biomass following fire or seasonal dry in cerrado.
8. anonymousgrower089, “Hydroponic E. Novo @ 2.5mo since Germination. Leaves the Soil-Grown E. Novos in the Dust. More Details in Comments.,” r/Cocagrowing. Mar-2022. www.reddit.com/r/Cocagrowing/comments/teetf6/hydroponic_e_novo_25mo_since_germination_leaves/.
9. G. H. Aynilian, J. A. Duke, W. A. Gentner, and N. R. Farnsworth, “Cocaine Content of Erythroxylum Species,” Journal of Pharmaceutical Sciences, vol. 63, no. 12, pp. 1938–1939, Dec. 1974. doi: 10.1002/jps.2600631223. Abstract
   Concentrations of cocaine ranging from 0.00008 to 0.00882% were found in herbarium specimens of seven of eight species of the genus Erythroxylum that were examined by GLC. A sample of E. coca which was at least 44 years old contained 0.03% cocaine.
10. B. R. Y. A. N. A. BAILEY, K. P. R. A. K. A. S. H. HEBBAR, M. STREM, L. E. E. C. DARLINGTON, and R. O. B. E. R. T. D. LUMSDEN, “An Alginate Prill Formulation of Fusarium Oxysporum Schlechtend: Fr. f. Sp. Erythroxyli for Biocontrol of Erythroxylum Coca Var. Coca,” Biocontrol Science and Technology, vol. 7, no. 3, pp. 423–436, Nov. 1997. doi: 10.1080/09583159730839. Abstract
    A rice alginate prill formulation of isolate EN - 4 of Fusarium oxysporum f . sp . erythroxyli, pathogenic to Erythroxylum coca var . coca (coca) , was evaluated in greenhouse and field studies for its ability to enhance pathogen populations in the soil and cause disease in coca . The formulation was applied to four different soil types in the greenhouse at 33 . 6 kg ha 1 . It enhanced the population of EN - 4 in each soil and most ( > 90%) of the fungal population remained in the upper 5 cm of soil during the 49 - day experiment . When applied in field experiments , the formulation enhanced the population of EN - 4 in the soil . Isolate EN - 4 was present in the upper 7 . 6 cm of soil 28 days after application at populations similar to those in the greenhouse studies (1 103 to 1 104 colony - forming units (CFUs) / g of soil) . Elevated populations of the pathogen (1 102 CFUs / g of soil) were still present in treated soils 229 days after application of the formulation . The areas used for field studies were already infested with the pathogen and typically developed high levels of fusarium wilt within 2 years of planting with coca . The formulated F. oxysporum began having a significant effect on plant death 100 - 200 days after application based on repeated measures analysis . These data suggest that a formulation of F. oxysporum f . sp . erythroxyli which enhances the incidence of fusarium wilt in coca fields can be produced using established techniques .
11. B. A. Bailey et al., “Formulations of Fusarium Oxysporum f.Sp. Erythroxyli for Biocontrol of Erythroxylum Coca Var. Coca,” Weed Science, vol. 46, no. 6, pp. 682–689, Dec. 1998. doi: 10.1017/S0043174500089712. Abstract
    Formulations of Fusarium oxysporum Schlechtend:Fr. f.sp. erythroxyli isolate EN-4, pathogenic to Erythroxylum coca var. coca (coca) were evaluated in greenhouse and field studies to determine their relative ability to enhance pathogen populations in the soil or cause disease in coca. The formulations rice-alginate prill, Pesta, and C6 were most thoroughly tested and are products of three formulation processes. The formulations were applied in the greenhouse and field at 33.6 kg ha−1. All the formulations tested enhanced the population of EN-4 in the soil during greenhouse (> 6 wk) and field (> 7 mo) experiments. EN-4 was present in the upper 1 cm of formulation-treated soil at > 200-fold higher populations than established below a depth of 7 to 10 cm in both greenhouse and field experiments. This population distribution was maintained throughout the 7-mo sampling period for field experiments. The enhanced soil populations of EN-4 were associated with an increase in root colonization by the pathogen EN-4 in the field 5 to 7 mo after treatment. The formulated F. oxysporum began to have a significant effect on plant death 100 to 200 d after application in two of three field experiments, based on repeated measures analysis. The various formulations tested tended to establish similar pathogen populations in soil and subsequently caused similar levels of disease. The primary factors influencing formulation performance may be environmental, since inoculum production is dependent on sporulation of the formulation, which, although rapid, may continue over several weeks subsequent to application.
12. B. A. Bailey, J. C. Jennings, and J. D. Anderson, “Sensitivity of Coca (Erythroxylum Coca Var. Coca) to Ethylene and Fungal Proteins,” Weed Science, vol. 45, no. 5, pp. 716–721, Oct. 1997. doi: 10.1017/S0043174500093395. Abstract
    Leaves of coca are the primary source of cocaine. There is interest in using Fusarium oxysporum as a mycoherbicide in addition to other measures to control coca production, but information on coca physiology, including the stress responses of coca leaves, is limited. Deleafing coca plants stimulates rapid production of new leaves, and young expanding leaves readily abscise if treated with ethylene. Commercial preparations of cell wall degrading enzymes, as well as a 24-kDa elicitor from Fusarium oxysporum, induced significant levels of ethylene production by coca leaves. Ethylene pretreatment of coca leaves enhanced the production of ethylene by coca leaves in response to the cell wall degrading enzyme preparation, Driselase, and the 24-kDa elicitor. However, ethylene pretreatment did not enhance the rate of necrosis induced in response to either Driselase or purified 24-kDa elicitor. Driselase failed to elicit levels of necrosis comparable to the 24-kDa elicitor even at 30-fold higher protein concentrations. The response of coca leaves to the 24-kDa elicitor saturated at 6.7 μg ml−1. Age of coca leaves influenced both the level of resulting necrosis and the amount of ethylene produced in response to protein. Very young leaves produced the highest levels of ethylene and necrosis in response to Driselase and the 24-kDa elicitor. The data suggest that responsiveness of coca leaves to control measures may be synchronized over the first few weeks following defoliation.
13. M. J. Balick, L. Rivier, and T. Plowman, “The Effects of Field Preservation on Alkaloid Content of Fresh Coca Leaves (Erythroxylum Spp.),” Journal of Ethnopharmacology, vol. 6, no. 3, pp. 287–291, Nov. 1982. doi: 10.1016/0378-8741(82)90051-4. Abstract
    In order to test the effects of commonly used preservation agents on the alkaloid content of herbarium specimens, fresh leaves of Erythroxylum coca, E. novogranantense, and E. novogranatense var. truxillense were airor heat-dried or treated with six different liquid preservatives. The leaves were then extracted and analyzed quantitatively for cocaine content. Leaves which were soaked in preservatives showed appreciable pre-extraction of cocaine and probably of other alkaloids. The results compare well with a similar experiment conducted on flavonoid content of the leaves of a palm Jessenia bataua. If portions of herbarium specimens are to be useful for phytochemical screening using microtechniques, at least part of the collection must be air- or heat-dried to retain the chemical constituents.
14. I. M. de C. Barros et al., “Chemical Composition and Antioxidant Activity of Extracts from Erythroxylum Suberosum A.St. Hil.Leaves,” Journal of Applied Pharmaceutical Science, vol. 7, no. 3, pp. 088–094, Mar. 2017. doi: 10.7324/JAPS.2017.70314.
15. I. Bauer, “Travel Medicine, Coca and Cocaine: Demystifying and Rehabilitating Erythroxylum – a Comprehensive Review,” Tropical Diseases, Travel Medicine and Vaccines, vol. 5, no. 20, Nov. 2019. doi: 10.1186/s40794-019-0095-7. Abstract
    Few travel health measures are as controversial as the use of coca leaves at high altitude; yet, there appears widespread ignorance among health professionals and the general public about coca, its origins as well as its interesting and often flamboyant history. Equally, the cultural and traditional significance to Andean people is not recognised. The coca leaves contain many alkaloids, one of which, cocaine, has gained notoriety as a narcotic, leading to the mistaken idea that coca equals cocaine. This article contrasts coca with cocaine in an attempt to explain the differences but also the reasons for this widespread misconception. By its very nature, there may never be scientific ‘proof’ that coca leaves do or do not work for travellers at altitude, but at least a solid knowledge of coca, and how it differs from cocaine, provides a platform for informed opinions and appropriate critical views on the current confusing and contradictory legal situation.
16. J. A. Bedford, C. E. Turner, and H. N. Elsohly, “Comparative Lethality of Coca and Cocaine,” Pharmacology Biochemistry and Behavior, vol. 17, no. 5, pp. 1087–1088, Nov. 1982. doi: 10.1016/0091-3057(82)90499-3. Abstract
    The 24 hour lethal effects of cocaine were compared to those of a crude ethanol extract of the coca leaf (Erthroxylon coca) in male, Swiss mice. Various doses of cocaine HCl and coca leaf extracts suspended in a Tween 60, Arlacel 83, and distilled water vehicle were injected IP into groups of 10 mice. The LD50 for cocaine was 95.1 mg/kg. The LD50 for the coca extract was 3450 mg/kg. The LD50 of the extract based on its cocaine content was 31.4 mg/kg. The results clearly indicate that the coca leaf contains constituents other than cocaine that can contribute to a toxic effect of the plant.
17. P. E. Berry, H. Tobe, and J. A. Gómez, “Agamospermy and the Loss of Distyly in Erythroxylum Undulatum (Erythroxylaceae) from Northern Venezuela,” American Journal of Botany, vol. 78, no. 5, pp. 595–600, 1991. doi: 10.1002/j.1537-2197.1991.tb12583.x. Abstract
    Erythroxylum undulatum is a gametophytic apomict that produces about 15% seed set independently of pollination. Embryo sac formation is aposporous, and the plants are largely pollen-sterile, which may be a result of polyploidy and hybrid origin. It appears to be derived from a distylous ancestor, as all other known species of Erythroxylum are distylous or secondarily dioecious, and all examined individuals of E. undulatum correspond to the normal long–styled morph. This is the first clearly documented case of agamospermy derived from distyly.
18. M. I. Bezerra Loiola and L. S. Cordeiro, “Erythroxylum Niziae (Erythroxylaceae): A New Species from the West-Central Cerrado of Brazil,” Systematic Botany, vol. 44, no. 3, pp. 659–663, Aug. 2019. doi: 10.1600/036364419X15620113920699. Abstract
    Abstract— A new species of Erythroxylum ( Erythroxylum niziae ) from west-central Brazil is presented here. Descriptions, illustrations, a map of geographic distribution, and morphological comparisons with morphologically similar species are provided. The novelty differs from its congeners by its subshrub habit 12 to 16 cm in height, firmly chartaceous to coriaceous leaves (8.8‐12.7 × 4.3‐7.9 cm), and single flowers produced per node along the distal portion of the main branch. A key is provided to differentiate the new species from others occurring in Parque Nacional de Brasília.
19. E. Bidault, S. Traclet, and M. Pignal, “Novelties in Erythroxylum P.Browne (Erythroxylaceae) from the Comoros Archipelago: Two New, Range-Restricted and Threatened Species, and Notes on the Mount Choungi Biogeographical Singularity,” Adansonia, vol. 44, no. 21, pp. 215–228, Sep. 2022. doi: 10.5252/adansonia2022v44a21. Abstract
    Nouveautés dans le genre Erythroxylum P.Browne (Erythroxylaceae) de l’archipel des Comores: deux espèces nouvelles menacées à aire de répartition restreinte, et notes sur la singularité biogéographique du Mont Choungi. Une étude du genre Erythroxylum P.Browne dans l’archipel des Comores révèle deux nouvelles espèces, Erythroxylum choungiense E.Bidault, Traclet & M.Pignal, sp. nov. de Mayotte et E. labatii E.Bidault & M.Pignal, sp. nov. de Mohéli et Grande Comore, qui sont décrites et illustrées. En conséquence, la distribution de Erythroxylum elegans Baill. est mise à jour, cette espèce étant désormais uniquement connue avec certitude de Mayotte et d’Anjouan, et possiblement de Grande Comore. Les caractères morphologiques permettant de distinguer les deux nouvelles espèces sont discutés, et des statuts de conservation selon les catégories et critères de la Liste Rouge de l’UICN sont proposés. Une clé de détermination des espèces du genre Erythroxylum à Mayotte et aux Comores est proposée, en français et en anglais. Erythroxylum choungiense sp. nov. est endémique du Mont Choungi, et est évaluée comme En Danger Critique. Le Mont Choungi présente un fourré hygrophile submontagnard, un type de végétation unique à Mayotte, dont au moins cinq espèces sont désormais connues pour y être endémiques: Cassipourea ovata Tul., Eugenia choungiensis Byng & N.Snow, Psiadia pascalii Labat & Beentje, Syzygium labatii Byng & N.Snow, et Erythroxylum choungiense, sp. nov. Erythroxylum labatii sp. nov. est uniquement connue des forêts submontagnardes de crêtes et de pentes fortes, entre 600 et 1300 m d’altitude, et est évaluée comme En Danger.
20. S. Bieri, A. Brachet, J.-L. Veuthey, and P. Christen, “Cocaine Distribution in Wild Erythroxylum Species,” Journal of Ethnopharmacology, vol. 103, no. 3, pp. 439–447, Feb. 2006. doi: 10.1016/j.jep.2005.08.021. Abstract
    Cocaine distribution was studied in leaves of wild Erythroxylum species originating from Bolivia, Brazil, Ecuador, Paraguay, Peru, Mexico, USA, Venezuela and Mauritius. Among 51 species, 28 had never been phytochemically investigated before. Cocaine was efficiently and rapidly extracted with methanol, using focused microwaves at atmospheric pressure, and analysed without any further purification by capillary gas chromatography coupled to mass spectrometry. Cocaine was reported for the first time in 14 species. Erythroxylum laetevirens was the wild species with the highest cocaine content. Its qualitative chromatographic profile also revealed other characteristic tropane alkaloids. Finally, its cocaine content was compared to those of two cultivated coca plants as well as with a coca tea bag sample.
21. S. Bieri, Y. Ilias, C. Bicchi, J.-L. Veuthey, and P. Christen, “Focused Microwave-Assisted Extraction Combined with Solid-Phase Microextraction and Gas Chromatography–Mass Spectrometry for the Selective Analysis of Cocaine from Coca Leaves,” Journal of Chromatography A, vol. 1112, no. 1, pp. 127–132, Apr. 2006. doi: 10.1016/j.chroma.2005.12.028. Abstract
    An effective combination of focused microwave-assisted extraction (FMAE) with solid-phase microextraction (SPME) prior to gas chromatography (GC) is described for the selective extraction and quantitative analysis of cocaine from coca leaves (Erythroxylum coca). This approach required switching from an organic extraction solvent to an aqueous medium more compatible with SPME liquid sampling. SPME was performed in the direct immersion mode with a universal 100μm polydimethylsiloxane (PDMS) coated fibre. Parameters influencing this extraction step, such as solution pH, sampling time and temperature are discussed. Furthermore, the overall extraction process takes into account the stability of cocaine in alkaline aqueous solutions at different temperatures. Cocaine degradation rate was determined by capillary electrophoresis using the short end injection procedure. In the selected extraction conditions, less than 5% of cocaine was degraded after 60min. From a qualitative point of view, a significant gain in selectivity was obtained with the incorporation of SPME in the extraction procedure. As a consequence of SPME clean-up, shorter columns could be used and analysis time was reduced to 6min compared to 35min with conventional GC. Quantitative results led to a cocaine content of 0.70±0.04% in dry leaves (RSD<5%) which agreed with previous investigations.
22. A. S. Biondich and J. D. Joslin, “Coca: The History and Medical Significance of an Ancient Andean Tradition,” Emergency Medicine International, vol. 2016, p. e4048764, Apr. 2016. doi: 10.1155/2016/4048764. Abstract
    Coca leaf products are an integral part of the lives of the Andean peoples from both a cultural and traditional medicine perspective. Coca is also the whole plant from which cocaine is derived. Coca products are thought to be a panacea for health troubles in regions of South America. This review will examine the toxicology of whole coca and will also look at medicinal applications of this plant, past, present, and future.
23. J. A. Bjorklund and E. Leete, “Biosynthesis of the Benzoyl Moiety of Cocaine from Cinnamic Acid via (R)-(+)-3-Hydroxy-3-Phenylpropanoic Acid,” Phytochemistry, vol. 31, no. 11, pp. 3883–3887, Jan. 1992. doi: 10.1016/S0031-9422(00)97546-0. Abstract
    trans-[3-13C,14C]Cinnamic acid and the N-acetylcysteamine thioester of [3-13C,14C]-trans-cinnamic acid served as precursors of the benzoyl moiety of cocaine when fed to intact Erythroxylum coca plants. The specific incorporation of the thioester into the benzoyl carbonyl group of cocaine was established by means of 13C NMR spectroscopy. (R)-(+)-[3-14C]-3-hydroxy-3-phenylpropanoic acid was 11 times more effective than its (S)-(-)-isomer as a precursor of the benzoyl moiety of cocaine. A chemical degradation of the cocaine indicated that all the 14C was located on its benzoyl moiety. Thus, the stereochemistry of the hydroxy group in 3-hydroxy-3-phenylpropanoic acid, is the same as that in the coenzyme A esters of 3-hydroxy fatty acids which are intermediates in the β-oxidation of fatty acids.
24. M. S. Blum, L. Rivier, and T. Plowman, “Fate of Cocaine in the Lymantriid Eloria Noyesi, a Predator of Erythroxylum Coca,” Phytochemistry, vol. 20, no. 11, pp. 2499–2500, Jan. 1981. doi: 10.1016/0031-9422(81)83080-4. Abstract
    Larvae of the lymantriid moth Eloria noyesi, which are obligate feeders on Erythroxylum coca, excrete most of the ingested cocaine as unchanged base. Cocaine, analysed by mass fragmentography, is readily, detectable in the blood of larvae and is presumably sequestered during larval feeding, since it is present in the bodies of adult moths that do not feed on E. coca. Cocaine is an effective feeding deterrent for the ant Monomorium pharaonis when present at a concentration below that found in the leaves of E. coca.
25. K. Boege and C. A. Domínguez, “Pre-Dispersal Seed Predation Reduces the Reproductive Compensatory Advantage of Thrum Individuals in Erythroxylum Havanense (Erythroxylaceae),” Evolutionary Ecology, vol. 22, no. 5, pp. 675–687, Sep. 2008. doi: 10.1007/s10682-007-9190-8. Abstract
    Male-sterility mutations in hermaphroditic species represent the first step in the evolution of gender specialization. Male-sterile individuals commonly compensate the loss of the male function by increasing the number or quality of seeds. Because the magnitude of compensation determines the maintenance of females within populations and the evolution of sexual specialization, plant-animal interactions may affect these evolutionary processes if animals are sensitive to such reproductive asymmetries. Here we explore the effect of seed predation on the reproductive compensation of Erythroxylum havanense, a distylous shrub with morph-biased partial male sterility, during two consecutive years. Seed predation reduced the compensatory advantage of thrums in 1987, but not in 1988. Annual differences in the intensity of seed predation seem to be accounted for differences in the onset and synchrony of flowering. Thus, although seed predators may reduce the compensatory advantage of thrums, their impact is modulated by the environmental cues triggering flowering and insect emergence.
26. F. D. Boesewinkel and J. Geenen, “Development of Ovule and Seed-Coat of Erythroxylum Coca Lamk.,” Acta botanica neerlandica, vol. 29, no. 4, pp. 231–241, Jan. 1980. doi: 10.1111/j.1438-8677.1980.tb01200.x. Abstract
    The inner and outer integuments of Erythroxylum coca are both of dermal derivation. The outer integument is initially 3 cells and later 3-5 cells thick. The inner integument is at first 3 cells thick to become multiplicative and ultimately about 20 cells thick and thus forming the greater part of the mass of the seed. The inner layer is developed as an endothelium. The nucellus is oblong by mitotic activity in the part beneath the embryo sac. The testa and legmen are crushed with the exception of the fibrous exotegmen. The flattened cells of the inner layer contain tannin. The relationship between Erythroxylaceae and Linaceae is discussed.
27. B. A. Bohm, F. R. Ganders, and T. Plowman, “Biosystematics and Evolution of Cultivated Coca (Erythroxylaceae),” Systematic Botany, vol. 7, no. 2, pp. 121–133, 1982. doi: 10.2307/2418321. Abstract
    Erythroxylum coca vars. coca and ipadu and E. novogranatense vars. novogranatense and truxillense are closely related taxa cultivated in South America for their cocaine-bearing leaves. Taxonomically they have been variously treated, ranging from one to three separate species. Erythroxylum novogranatense var. truxillense is morphologically somewhat intermediate between E. c. var. coca and E. n. var. novogranatense and has been suggested to be a hybrid between the two. Evidence from artificial hybridizations, leaf flavonoid chemistry, and breeding system studies was used to clarify the taxonomic and evolutionary relationships of these plants. This evidence suggests that E. n. var. truxillense is intermediate between E. coca and E. n. novogranatense but it is not a hybrid between them. These three taxa represent a linear evolutionary series, with E. c. var. coca the ancestral taxon, E. n. var. truxillense derived from it, and E. n. var. novogranatense derived from E. n. var. truxillense. Erythroxylum c. var. ipadu was independently derived from E. c. var. coca. All of the taxa are partially isolated genetically except E. c. var. coca and E. c. var. ipadu. The taxonomic treatment that best reflects their relationships is to regard E. novogranatense var. novogranatense and E. n. var. truxillense as varieties of a species distinct from E. coca. Only limited material of E. c. var. ipadu was available for study, but it might better be regarded as a cultivar of E. coca.
28. B. A. Bohm, D. W. Phillips, and F. R. Ganders, “Flavonoids of Erythroxylum Rufum and Erythroxylum Ulei,” ACS Publications. American Chemical Society, Jul-2004. doi: 10.1021/np50018a009.
29. A. Brachet, P. Christen, J.-Y. Gauvrit, R. Longeray, P. Lantéri, and J.-L. Veuthey, “Experimental Design in Supercritical Fluid Extraction of Cocaine from Coca Leaves,” Journal of Biochemical and Biophysical Methods, vol. 43, no. 1, pp. 353–366, Jul. 2000. doi: 10.1016/S0165-022X(00)00062-2. Abstract
    An optimisation procedure for the supercritical fluid extraction (SFE) of cocaine from the leaves of Erythroxylum coca var. coca was investigated by means of experimental design. After preliminary experiments where the SFE rate-controlling mechanism was determined, a central composite design was applied to evaluate interactions between selected SFE factors such as pressure, temperature, nature and percentage of the polar modifier, as well as to optimise these factors. Predicted and experimental contents of cocaine were compared and robustness of the extraction method estimated by drawing response surfaces. The analysis of cocaine in crude extracts was carried out by capillary GC equipped with a flame ionisation detector (GC–FID), as well as by capillary GC coupled with a mass spectrometer (GC–MS) for peak identification.
30. A. Brachet, P. Christen, and J.-L. Veuthey, “Focused Microwave-Assisted Extraction of Cocaine and Benzoylecgonine from Coca Leaves,” Phytochemical Analysis, vol. 13, no. 3, pp. 162–169, 2002. doi: 10.1002/pca.637. Abstract
    Extraction of cocaine and benzoylecgonine from coca leaves was performed by focused microwave-assisted extraction (FMAE). Cocaine extraction was optimised with respect to the nature of the extracting solvent, the particle size distribution, the moisture of the sample, the applied microwave power and the radiation time. A central composite design was used to optimise the two latter parameters and to assess the robustness of the extraction method around the best conditions. FMAE generated extracts similar to those obtained by conventional solid–liquid extraction but in a more efficient manner, i.e. 30 s were sufficient to extract cocaine quantitatively from leaves. Analyses of cocaine and benzoylecgonine in coca leaves was carried out by capillary GC-FID and GC-MS for peak identification, as well as by capillary electrophoresis with UV detection. Copyright © 2002 John Wiley & Sons, Ltd.
31. L. S. de O. Brito et al., “Tropane Alkaloids from the Stem Bark of Erythroxylum Bezerrae,” Phytochemistry, vol. 178, p. 112458, Oct. 2020. doi: 10.1016/j.phytochem.2020.112458. Abstract
    Six previously undescribed tropane alkaloids, designated as erythrobezerrines A-F, were isolated from the EtOH extract from the stem bark of Erythroxylum bezerrae Plowman. Their structures were elucidated based on the interpretation of the NMR and MS data and in some instances, confirmed by X-ray diffraction analysis. The cytotoxicity of the isolated compounds was evaluated against the cancer cell lines L929, PC-3, HCT-116, SNB-19 and NCI-H460, but only erythrobezerrine C showed moderate activity with IC50 values of 3.38 and 5.43 μM for HCT-116 and NCI-H460, respectively.
32. A. Brock, S. Bieri, P. Christen, and B. Dräger, “Calystegines in Wild and Cultivated Erythroxylum Species,” Phytochemistry, vol. 66, no. 11, pp. 1231–1240, Jun. 2005. doi: 10.1016/j.phytochem.2005.04.017. Abstract
    Calystegines were identified in the genus Erythroxylum for the first time. Erythroxylum novogranatense var. novogranatense, a species cultivated for cocaine production, contained 0.2% total calystegines in dry leaves. Forty six Erythroxylum herbarium species consisting mostly of leaf tissue were analysed for calystegines, and 38 were found positive. Calystegines were compared qualitatively and quantitatively between individual Erythroxylum species. Calystegines A3 and B2 were the major calystegines in most species. Total calystegine content reached up to 0.32% dry mass. The simultaneous occurrence of calystegines, cocaine, other alkaloids of a 3α-hydroxy- or 3β-hydroxytropane structure together with nicotine supports the concept of common biosynthetic steps of these alkaloids in Erythroxylum. The present results are the basis for further investigations of the phylogenetic origin of tropane alkaloid biosynthesis in the taxonomically remote families Solanaceae and Erythroxylaceae.
33. P. Browne and G. D. Ehret, The Civil and Natural History of Jamaica. London : Printed for the author, and sold by T. Osborne and J. Shipton in Gray’s-Inn, 1756. http://archive.org/details/mobot31753000808003.
34. F. J. Burczynski, “Some Bioìogical Effects Associated with Erythroxylum Coca, Cocaine and Ecgonine Methylester in the Rat,” Master's thesis, University of Manitoba, Winnipeg, Manitoba, Canada, 1982. http://hdl.handle.net/1993/15019.
35. F. J. Burczynski, R. L. Boni, J. Erickson, and T. G. Vitti, “Effect of Erythroxylum Coca, Cocaine and Ecgonine Methyl Ester as Dietary Supplements on Energy Metabolism in the Rat,” Journal of Ethnopharmacology, vol. 16, no. 2, pp. 153–166, Jun. 1986. doi: 10.1016/0378-8741(86)90086-3. Abstract
    The effects of dietary supplements of cocaine, ecgonine methyl ester, a coca leaf extract and powdered coca leaves on body weight and overall body metabolism were studied in the rat. Respiratory quotient was measured to assess the relative utilization of fats, carbohydrates and protein. The effect of cocaine and ecgonine methyl ester on protein metabolism was also assessed in terms of changes in the relative state of nitrogen balance. Rats maintained on a low protein/high carbohydrate diet containing cocaine (1 mg/g) exhibited normal body weight gain on normal food intake. Rats on the same diet with 2 mg/g cocaine as the hydrochloride or as coca dextrin lost weight, which was apparently related to diminished food intake. In contrast, rats received the same high level of cocaine as coca leaf powder in the same diet had minimal weight gain in spite of a high food intake. In contrast, rats receiving the same high level of cocaine as ly, rats receiving the same high level of cocaine (2 mg/g) in a high protein diet had normal food intake and body weight gain. An adequate protein diet appears to compensate for whatever inhibiting effect is imposed on the body by the high levels of cocaine. Ecgonine methyl ester appears to have no significant effect on food intake or body weight. Rats fed the low protein/high carbohydrate diet containing either the low (1 mg/g) or the high (2 mg/g) cocaine level exhibited significantly depressed respiratory quotients (near 0.75) suggesting increased fat utilization. The magnitude of the reduction appeared to be dose-related. Yet, the respiratory quotient of the rats receiving the high level of cocaine in a high protein diet remained at normal control values. Also, in a separate nitrogen balance-type of experiment, rats receiving the low level of cocaine (1mgg low protein/high carbohydrate diet) exhibited a normal ability to accumulate body nitrogen, presumably protein. These results support the idea that under conditions of protein deprivation cocaine helps spare amino acids through the preferential utilization of fat. Coca leaf in the low protein/ high carbohydrate diet equivalent to 2 mgg cocaine had a small but significant positive effect on respiratory quotient possibly due to the availability of utilizable nitrogenous components in the coca leaf. The respiratory quotient effects were less obvious with an extract of coca leaf incorporated in the diet as coca-dextrin, but showed the same trend. Ecgonine methyl ester at a level of 2 mgg diet was without effect on respiratory quotient.
36. M. Calixto Iglesias, “Aporte Del Inga Edulis a La Fertilidad Del Suelo Degradado Por El Cultivo De Coca (erythroxylum Coca) En El Caserio De Buenos Aires, Distrito Rupa Rupa, Provincia Leoncio Prado, Departamento Huánuco - 2018,” Universidad de Huánuco, 2018. http://localhost:8080/xmlui/handle/123456789/1460. Abstract
    Este estudio tuvo como objetivo determinar el aporte del Inga edulis a la fertilidad del suelo degradado por el cultivo de coca (Erythroxylum coca) en el Caserío Buenos Aires, Distrito Rupa Rupa, Provincia Leoncio Prado, Departamento Huánuco. El experimento se desarrolló durante 2 años, el área de revegetación fue de 0.5 hectáreas aproximadamente, donde se plantaron 556 plantones de Inga edulis. La metodología optada para el desarrollo del estudio fue con intervención del investigador, que sirvió para plantear los supuestos teóricos importantes de la tesis, a partir del planteamiento del problema, hasta la constatación de la hipótesis. El muestreo del suelo se realizó en dos profundidades (0-30 cm y 30-50cm) al inicio y al finalizar el estudio, los cuales fueron divididos en 3 zonas (A, B y C) de acuerdo con la topografía del terreno, se obtuvieron muestras simples y compuestas, para poder evaluar la fertilidad química (Materia Orgánica, pH, fosforo, potasio, bases totales (Ca+Mg+K), CICe, Saturación de aluminio) del suelo. Además de ello se registró el crecimiento (altura y diámetro) y la sobrevivencia del Inga edulis. De los análisis se determinó al finalizar el estudio, el Inga edulis aporta a la fertilidad del suelo, evidenciándose el incremento de la materia Orgánica, Potasio, Bases Totales, CICe y la reducción de la saturación de Aluminio, el pH permaneció constante. En cuanto a la altura y el diámetro, en promedio se incrementó a un rango de 1.880 m a 1.975 m y 13.075 cm a 14.532 cm respectivamente, la sobrevivencia de los plantones fue del 90.1%. Los resultados obtenidos han permitido determinar que el Inga edulis aporta a la fertilidad del suelo degradado por el cultivo de coca, por lo tanto el objetivo planteado en la investigación se cumplió.
37. P. H. S. A. Camargo, M. M. Martins, R. M. Feitosa, and A. V. Christianini, “Bird and Ant Synergy Increases the Seed Dispersal Effectiveness of an Ornithochoric Shrub,” Oecologia, vol. 181, no. 2, pp. 507–518, Jun. 2016. doi: 10.1007/s00442-016-3571-z. Abstract
    Seed dispersal may involve different vectors of dispersal in two or more sequential phases (i.e., diplochory). However, contributions of each phase to the overall seed dispersal effectiveness (SDE) are poorly understood and hard to evaluate due to post-dispersal processes that affect seed and seedling survival. We investigated the simultaneous bird (phase 1, in plant canopy) and ant (phase 2, on the floor) contributions to SDE with the ornithochoric shrub Erythroxylum ambiguum in a Brazilian Atlantic forest. Twelve species of birds fed on fruit and dispersed approximately 26 % of the seed crop. The remaining seed crop, 90 % of which contained viable seeds, fell to the ground beneath the parental plant. Ants either cleaned seeds in fruits or carried fallen fruit and seeds from bird feces to their nests. Although E. ambiguum has no adaptation for ant dispersal, ants were as quantitatively important as birds. Birds and ants equally increased germination rates compared to controls. However, birds deposited seeds farther from the parent, where seedling survival was higher (78 %) than it was beneath the parent (44 %), whereas ants carried seeds to their nests, where seedling survival was higher (83 %) than in controls away from their nests (63 %). Diplochory allowed a 42 % increase in SDE compared to dispersal in phase 1 alone. High lipid content in the fruit pulp of E. ambiguum may facilitate the inclusion of ants in a second step of dispersal after diaspores reach the floor. Ants can also buffer the dispersal of diplochorous plants against decreases in phase 1 dispersers.
38. J. Casale and J. Lydon, “Apparent Effects of Glyphosate on Alkaloid Production in Coca Plants Grown in Colombia,” Journal of Forensic Sciences, vol. 52, no. 3, pp. 573–578, 2007. doi: 10.1111/j.1556-4029.2007.00418.x. Abstract
    ABSTRACT: During the routine analysis of coca leaf material from South America, alkaloids in Erythroxylum coca var. ipadu (ECVI) leaf samples from fields suspected of being treated with glyphosate were compared with those from non-treated E. coca var. ipadu and Erythroxylum novogranatense var. novogranatense (ENVN) plants. Cocaine levels in leaf tissue from non-treated ECVI and ENVN were 0.53±0.08% and 0.64±0.08% (w/w), respectively, whereas leaves from treated plants were nearly devoid of cocaine. Further analysis demonstrated the presence of several previously undescribed N-nortropane alkaloids, several of which were tentatively identified. The results suggest that applications of glyphosate to coca plants can have dramatic effects on the quantity and quality of alkaloids produced by surviving or subsequent leaves. The analytical data presented will be of value to forensic chemists who encounter illicit cocaine preparations containing alkaloids produced from coca plants treated with glyphosate.
39. J. F. Casale, J. R. Mallette, and L. M. Jones, “Chemosystematic Identification of Fifteen New Cocaine-Bearing Erythroxylum Cultigens Grown in Colombia for Illicit Cocaine Production,” Forensic Science International, vol. 237, Apr. 2014. doi: 10.1016/j.forsciint.2014.01.012. Abstract
    Colombian coca farmers have historically cultivated three varieties of coca for cocaine production (Erythroxylum novogranatense var. novogranatense, Erythroxylum novogranatense var. truxillense, and Erythroxylum coca var. ipadu). Within the past 13 years, 15 new cultigens of cocaine-bearing Erythroxylum have been propagated by Colombian coca farmers; each with differing physical characteristics, yet producing cocaine alkaloids at similar levels found in the historical and native varieties. Fifteen new cultigens were collected from throughout Colombia and propagated along with the three historical varieties within an experimental field in Colombia. Five plants/cultigen were randomly selected and examined for alkaloid content to determine their varietal characteristics when compared to the three known varieties. Ten cultigens gave classic Erythroxylum coca var. ipadu alkaloid profiles, four cultigens produced alkaloid profiles consistent with a hybridization of Erythroxylum novogranatense and Erythroxylum coca var. ipadu, while one cultigen gave heterogeneous alkaloid profiles that could not be characterized.
40. J. F. Casale and J. R. Mallette, “Illicit Coca Grown in Mexico: An Alkaloid and Isotope Profile Unlike Coca Grown in South America,” Forensic Chemistry, vol. 1, pp. 1–5, Aug. 2016. doi: 10.1016/j.forc.2016.05.001. Abstract
    Illicit coca has historically been cultivated in the Andean ridge of South America. A field of illicit coca was seized in late 2014 within the state of Chiapas, Mexico. The leaf was identified chemosystematically and the cocaine extracted from it was subjected to alkaloid and isotope analyses to determine its geospatial profile. The leaf was determined to be Erythroxylum novogranatense var. truxillense containing 0.36% cocaine. The leaf contained extraordinary levels of 1-hydroxytropacocaine (21.3%) and cinnamoylcocaines (242%), relative to cocaine. The 2H incorporated within the cocaine was enriched (−178.3‰), while 15N was quite depleted (−12.9‰). Incorporation of 18O and 13C into the cocaine were mid-range (17.4‰ and −34.3‰, respectively). The alkaloid and isotope profiles of the extracted cocaine were unlike any of the known 19 regional profiles within South America. The unique profile of Mexican coca will be a useful indicator for determining if any cocaine samples seized within the United States actually originated from coca grown in Mexico.
41. J. F. Casale and J. M. Moore, “Lesser Alkaloids of Cocaine-Bearing Plants II. 3-Oxo-Substituted Tropane Esters: Detection and Mass Spectral Characterization of Minor Alkaloids Found in South American Erythroxylum Coca Var. Coca,” Journal of Chromatography A, vol. 749, no. 1, pp. 173–180, Oct. 1996. doi: 10.1016/0021-9673(96)00466-9. Abstract
    Alkaloid extracts from the leaves of Erythroxylum coca var. coca, grown in South America, were subjected to ion-pair chromatography and then to gas chromatographic-mass spectrometric analyses. Eight previously unreported trace level alkaloids were detected and characterized via comparison to synthesized standards, including 3α-benzoyloxytropane, 3α-phenylacetoxytropane, 3β-cis- and 3β-trans-cinnamoyloxytropane, 3β-2′-hydroxybenzoyloxytropane, 3α-3′,4′ 5′-tri-methoxybenzoyloxythropane, 3α- and 3β-3′,4′,5′-trimethoxy-trans-cinnamoyloxytropane. Two additional alkaloids 3α- and 3β-3′,4′,5′-trimethoxy-cis-cinnamoyloxytropane, were also tentatively identified.
42. J. F. Casale and J. M. Moore, “Lesser Alkaloids of Cocaine-Bearing Plants III. 2-Carbomethoxy-3-Oxo Substituted Tropane Esters: Detection and Gas Chromatographic-Mass Spectrometric Characterization of New Minor Alkaloids Found in South American Erythroxylum Coca Var. Coca,” Journal of Chromatography A, vol. 756, no. 1, pp. 185–192, Dec. 1996. doi: 10.1016/S0021-9673(96)00672-3. Abstract
    Crude alkaloid extracts from the leaves of South American Erythooxylum coca var. coca were subjected to alumina chromatography and recrystallization to isolate fractions containing eleven previously unreported 2-carbomethoxy-3-oxo substituted tropane alkaloids. Specifically, the butyroyl-, 2-methylbutyroyl-, isovaleroyl-, senecioyl-, tigloyl-, trans-4-hexenoyl-, hexanoyl-, trans-3-hexenoyl-, trans-2-hexenoyl-, trans-3-heptenoyl-, and trans-2,4,-hexadienoyl-ecgonine methyl esters were characterized via electron and chemical ionization gas chromatographic-mass spectrometric analyses and comparison to synthesized standards. Three additional alkaloids similar to the aforementioned esters were also presumptively identified as heptadienoylecgonine methyl ester (geometry not determined) and cis-, trans- and trans-, cis-2,4-hexadienoylecgonine methyl ester.
43. M. T. Castro, M. G. Raviña, M. T. Nájera, S. M. Carpano, L. A. Iácona, and E. D. Spegazzini, “Análisis Micrográfico de Erythroxylum Coca, Phaseolus Vulgaris y Canavalia Ensiformis de Muestras de Una Colección Textil Arqueológica Del Museo de La Plata,” Acta Farmacéutica Bonaerense, vol. vol. 23, no. 3, 2004. http://sedici.unlp.edu.ar/handle/10915/6657. Abstract
    Se determinó el "status taxonómico" de restos vegetales arqueológicos, hallados formando parte de piezas textiles arqueológicas de la cultura Nazca, pertenecientes a la Colección del Museo de Las Plata (Argentina). Las muestras fueron identificadas como hojas de Erythroxylum coca Lam., Canavalia ensiformis (L.) DC y Phaseolus vulgaris L. El posible valor ceremonial de estas piezas es discutido. Se corroboró el valor diagnóstico de la micrografía aplicada a la determinación de mezclas vegetales fragmentadas, pulverizadas o semicarbonizadas que constituyen parte del rescate de materiales etnoarqueológicos.
44. J. L. Castro Alvarado, “Detección de alcaloides de Erythroxylum coca ‘coca’ en muestras de orina y su relación con las características de consumo en personas investigadas Y/O detenidas por la III Dirección Territorial de Policía (DIRTEPOL) Región La Libertad, Mayo – Agosto del 2014,” Universidad Nacional de Trujillo, 2015. http://dspace.unitru.edu.pe/handle/UNITRU/15848. Abstract
    En el presente estudio se detectó alcaloides de Erythroxylum coca y su relación con las características de consumo en personas investigadas y/o detenidas por la Dirección Territorial de Policía (DIRTEPOL) Región La Libertad, mayo – agosto del 2014. Se realizó un estudio transversal y retrospectivo con una población de 450 personas de ambos sexos y de diferentes edades ,donde se encontró la presencia de alcaloides de Erythroxylum coca “coca” en mayor porcentaje en la población masculina se encuentra dentro de las edades de 25-29 años lo cual está representado por el 28.03%y en las mujeres de 20-24 años lo cual está representado por el 25%.El contacto con esta sustancia les conlleva a cometer delitos predominado el delito contra la salud pública y asimismo Alto Trujillo fue el Distrito de mayor porcentaje de delitos
45. A. Castro et al., “Evaluación química y antibacteriana in vitro del aceite esencial de Erythroxylum coca Lam.Var. ‘Coca Huánuco’: diseño de una formulación farmacéutica,” Theorēma (Lima, Segunda época, En línea), no. 1, pp. 65–72, 2014. https://revistasinvestigacion.unmsm.edu.pe/index.php/Theo/article/view/11939. Abstract
    Objective: To elucidate the composition chemistry of essential oil of Erythroxylum coca Lam.var. “Coca Huánuco” and determine their in vitro antioxidant and antibacterial activity against Streptoccocus mutans ATCC 35668 and the design of a pharmaceutical formulation. Design: Experimental, analytical, longitudinal and prospective study. Place: Three institutes and a research centre of San Marcos University. Biological material: coca leaves and cariogenic bacteria. Methods: preliminary analysis and structural elucidation by chromatography of Gases/spectrometry (GC/MS). In vitro antioxidant activity was carried out by DPPH, CDP and uptake of the superoxide anion radical. Antibacterial activity in vitro was made by the method of microdilusion colorimetric and diffusion in agar. Developed toothpastes containing essential oils of coca, mint and oregano to 1%. Results: The GC/MS analysis, identified the following chemicals: β-pinene, β-myrcene, stearic acid, neroridol, Phytol, acid methyl ester 7, 10, 13 hexadecatrienoico and nonacosano. The fitocompuestos of oil showed antioxidant capacity. Conclusions: The essential oil expressed antioxidant capacity that would participate in biological redox systems and a minimum inhibitory concentration (MIC) of 0,625µL/mL against Streptoccocus mutans ATCC 35668 and expressing inhibition zone of 37mm and 38mm intoothpastes.
46. M. T. Castro, M. G. Raviña, M. T. Nájera, S. M. Carpano, L. A. Iácona, and E. D. Spegazzini, “Micrographic Analysis of Erythroxylum Coca, Phaseolus Vulgaris, and Canavalia Ensiformis Samples from the Archaeological Textile Collection of the Museo de La Plata, Argentina,” acta farmacéutica bonaerense, vol. 23, p. 8, 2004. Abstract
    The taxonomic status was determined in plant remains found within archeological textile pieces from the Nasca culture, belonging to the Collection of the Museo de La Plata (Argentina). Plant samples were identified as leaves from Erythroxylum coca Lam., Canavalia ensiformis (L.)DC, and Phaseolus vulgaris L. The possible ceremonial value of these pieces is discussed. The diagnostic significance of micrography for the assessment of fragmented, pulverized, or semi-carbonized plant mixture findings is corroborated.
47. D. S. Chacon et al., “Proteome of Erythroxylum Pungens (Erythroxylaceae): An Endemic Species of the Semiarid Caatinga,” Plant Biosystems - An International Journal Dealing with all Aspects of Plant Biology, vol. 155, no. 6, pp. 1165–1167, Nov. 2021. doi: 10.1080/11263504.2021.1918784. Abstract
    Herein the descriptive label-free mass spectrometry (LC-MS/MS) proteome of Erythroxylum pungens (roots, barks, leaves) harvested from its natural habitat is described. Processes related to defense were most important in roots. Main protective proteins differed among organs, suggesting part-specific strategies of environmental adaptation.
48. D. Chan-Chin and J. Govinden-Soulange, “Germination Profile of Selected Plants from Mauritius – towards a Conservation Strategy,” Seed Science and Technology, vol. 43, no. 3, pp. 536–540, Dec. 2015. doi: 10.15258/sst.2015.43.3.07. Abstract
    Selected endemic Mauritian plants, Cossinia pinnata, Dracaena concinna, Erythroxylum sideroxyloides, Fernelia buxifolia and Lomatophyllum purpureum were assessed for germination based on the classification of embryo type, imbibition experiments, optimum temperature for germination (15 to 35°C), light conditions and the use of germination promoters (butenolide and gibberellic acid, GA3). Germination was between 62 and 79%. Most species responded positively to germination promoting treatments, under both light and dark conditions. These results demonstrate that the five species are typical of tropical seeds. They do not express physical dormancy and have the ability to germinate over a very wide range of normal physical environmental factors. The present study can be used to optimise storage methods and enable effective seed banking of these threatened species.
49. B. G. Chavez et al., “Elucidation of Tropane Alkaloid Biosynthesis in Erythroxylum Coca Using a Microbial Pathway Discovery Platform,” Proceedings of the National Academy of Sciences, vol. 119, no. 49, p. e2215372119, Dec. 2022. doi: 10.1073/pnas.2215372119. Abstract
    Tropane alkaloids (TAs) are heterocyclic nitrogenous metabolites found across seven orders of angiosperms, including Malpighiales (Erythroxylaceae) and Solanales (Solanaceae). Despite the well-established euphorigenic properties of Erythroxylaceae TAs like cocaine, their biosynthetic pathway remains incomplete. Using yeast as a screening platform, we identified and characterized the missing steps of TA biosynthesis in Erythroxylum coca. We first characterize putative E. coca polyamine synthase- and amine oxidase-like enzymes in vitro, in yeast, and in planta to show that the first tropane ring closure in Erythroxylaceae occurs via bifunctional spermidine synthase/N-methyltransferases and both flavin- and copper-dependent amine oxidases. We next identify a SABATH family methyltransferase responsible for the 2-carbomethoxy moiety characteristic of Erythroxylaceae TAs and demonstrate that its coexpression with methylecgonone reductase in yeast engineered to express the Solanaceae TA pathway enables the production of a hybrid TA with structural features of both lineages. Finally, we use clustering analysis of Erythroxylum transcriptome datasets to discover a cytochrome P450 of the CYP81A family responsible for the second tropane ring closure in Erythroxylaceae, and demonstrate the function of the core coca TA pathway in vivo via reconstruction and de novo biosynthesis of methylecgonine in yeast. Collectively, our results provide strong evidence that TA biosynthesis in Erythroxylaceae and Solanaceae is polyphyletic and that independent recruitment of unique biosynthetic mechanisms and enzyme classes occurred at nearly every step in the evolution of this pathway.
50. A. Chevalier, De la pomme de terre à la coca : statut de l'archéobotanique au Pérou et revue critique des données. British Archaeological Reports, 1999. https://archive-ouverte.unige.ch/unige:93865. Abstract
    In this article we review some of the main problems encountered by archeobotanical research in Peru as illustrated by studies conducted on two plants (i.e., Solanum tuberorsum L. and Erythroxylum coca Lam.) and briefly describe different archeobotanical analyses in order to understand their contributions, but also their limitations. Moreover, we discuss the development of this discipline in Peru, and retrace some of the main problems encountered. In addition, we present a table containing the first indices of different taxons in Peru. In this table we have purposely presented only data that is accurate in terms of identification and chronological context. Finally, we present a synthesis and a critical evaluation of some of this data.
51. R. T. Collins and C. S. Helling, “Surfactant-Enhanced Control of Two Erythroxylum Species by Glyphosate,” Weed Technology, vol. 16, no. 4, pp. 851–859, Dec. 2002. doi: 10.1614/0890-037X(2002)016[0851:SECOTE]2.0.CO;2. Abstract
    Glyphosate is the only herbicide used for controlling illicit coca (Erythroxylum coca and E. novogranatense), a source of cocaine. Because commercially available formulations of glyphosate were inconsistent in controlling coca, research was conducted in a large-scale aerial eradication program, greenhouse (in Maryland) and field (Hawaii), to develop more effective control systems. Sixteen surfactants (cationic, nonionic, or mixed) were tested with two commercial glyphosate herbicide formulations, in aqueous or oil-based carrier systems, for coca control. Ultimately, two glyphosate–surfactant systems (COC/OSI-U [a mixture of crop-oil concentrate, Agri-Dex® and organosilicone, Silwet L-77®] and CAT/ANA [cationic surfactant/anionic surfactant, Optima®]) were found that increased glyphosate phytotoxicity fourfold: 1.1 kg ae/ha of glyphosate + surfactant was equivalent to 4.4 kg ae/ha glyphosate without added surfactant, for both species. In consequence, the glyphosate mixture used in Colombia for coca eradication was modified with substantially improved results.
52. R. Conway, I. Evans, and D. Weeraman, “Assessing Travelers’ Knowledge and Use of Coca for Altitude Sickness,” Wilderness & Environmental Medicine, vol. 23, no. 4, pp. 373–374, Dec. 2012. doi: 10.1016/j.wem.2012.06.005.
53. T. A. Cordero Vilca, “Evaluación nutricional de la proteína de la hoja de coca ( Erythroxylum coca Lamarck var. Coca),” Universidad Nacional Mayor de San Marcos, 2002. https://cybertesis.unmsm.edu.pe/handle/20.500.12672/1088. Abstract
    Se ha estudiado el valor nutricional del contenido proteico de la hoja de coca (Erythroxylum coca Lamarck var. Coca). Para lograr éste objetivo se aislaron por precipitación a pH 5.1 y 4.0 dos fracciones proteicas de un extracto alcalino de ésta hoja preparado con una solución de “tocra” (sustancia alcalina utilizada con la coca en el hábito de su masticación).Después de una purificación parcial con solventes de extracción (éter dietílico ,acetona ,alcohol 96°) de la mezcla de ambas fracciones proteicas, se prepararon dos dietas Experimentales con diferentes niveles de proteína (FP COCA 4.5% y FP COCA 9.0%). De igual modo se prepararon dos dietas Controles a base de caseína (CAS 4.5% y CAS 9.0%). Estas dietas fueron administradas ad libitum por 10 días, a grupos de ratas (n=6-9) en desarrollo. Al término de éste periodo los animales fueron sacrificados ,determinándose los valores de los índices PER, las actividades de arginasa hepática y los pesos de los órganos y de sus contenidos proteicos. Los resultados mostraron que los índices PER fueron menores y las actividades de la arginasa hepática mayores en los animales de los grupos FP COCA ,que en los animales alimentados con caseína. En grupos mejor alimentados , FP COCA 9.0% y CAS 9.0% estos valores fueron PER:1.4 ; arginasa 63.6±14.6 μmoles de ornitina/mg de proteína hepática y PER: 3.8 ; arginasa 51.4±9.6 μmoles de ornitina /mg de proteína hepática respectivamente. Los pesos de los órganos fueron igualmente menores en los grupos FP COCA pero sus contenidos proteicos fueron semejantes al de los grupos controles. Estos hallazgos sugieren que la proteína de la coca, cuando es dada en un valor del 9.0% tiene un valor importante el cual puede ser mejorado si se lograse suplementar con otras proteínas. Así mismo los resultados sugieren que se debe obtener fracciones proteicas de mayor pureza para determinar con mayor exactitud su calidad.
54. A. R. Córdoba Belalcázar, “Modelamiento de la relación entre la población humana y el recurso natural Erythroxylum Coca,” PhD thesis, Universidad Nacional de Colombia, Manizales, Colombia, 2015. https://repositorio.unal.edu.co/handle/unal/57707. Abstract
    The following research focuses on the approach of a mathematical model It represents the dynamic between the human population and natural resource erythroxylum coca through a system of nonlinear ordinary differential equations, using to build the system dynamics model, after model calibration is done, numerical simulations are presented varying sensitive parameters and finally the stability analysis of equilibrium points and the problem optimal control to counter the problem of illicit crops.
55. A. R. Cortella, M. L. Pochettino, A. Manzo, and G. Raviña, “Erythroxylum Coca: Microscopical Identification in Powdered and Carbonized Archaeological Material,” Journal of Archaeological Science, vol. 28, no. 8, pp. 787–794, Aug. 2001. doi: 10.1006/jasc.2000.0575. Abstract
    Carbonized material adhering to the cavity wall was obtained from a wooden Peruvian illa (animal figure), held in the archaeological collections of the Museo de La Plata. This sample was analysed with a light microscope, petrographic microscope and scanning electron microscope and identified as Erythroxylum coca (presumably var.coca ). This finding appears to verify the hypothesis, generated by ethnohistorical and ethnoarchaeological records, thatillas were used to burn coca leaves during ceremonies in Andean region.
56. R. A. S. Cruz, G. da S. Botas, C. P. Fernandes, M. G. Santos, and L. Rocha, “Chemical Constituents of Essential Oils from Leaves of Two Erythroxylum Species,” Chemistry of Natural Compounds, vol. 54, no. 1, pp. 185–187, Jan. 2018. doi: 10.1007/s10600-018-2292-4. Abstract
    Erythroxylum P. Browne is the most representative genus from the Erythroxylaceae family, being constituted by approximately 97% of its species [1]. They are mainly spread through tropical and subtropical regions such as South America, Africa, and Madagascar [2–4]. Brazil has some species spread through “restinga,” a typical sandy coastal plain originated from quaternary marine deposits [5, 6]. This genus is recognized as a tropane alkaloid producer [7] and also by the presence of terpenoids and flavonoids [8, 9]. However, few studies were performed concerning the volatile constituents of this genus [10].
57. E. Cuevas, F. Molina-Freaner, L. E. Eguiarte, and C. A. Domínguez, “Patterns of Male Sterility within and among Populations of the Distylous Shrub Erythroxylum Havanense (Erythroxylaceae),” Plant Ecology, vol. 176, no. 2, pp. 165–172, Mar. 2005. doi: 10.1007/s11258-004-0057-6. Abstract
    Distyly, a reproductive system characterized by the presence of long-styled (thrum). and short-styled (pin) individuals within a population, has been repeatedly used as a model for the study of the evolution of the reproductive systems in plants. Erythroxylum havanense is a distylous species in which most thrum plants fail to develop a fertile androecium, thus behaving as male-sterile or partially male-sterile plants. Short-styled (thrum) individuals have an increased performance as female parents, thereby compensating for their loss of male fitness. Previous studies of populations within close proximity to each other suggest that E. havanense may be involved in a process of gender specialization in which, unlike other heterostylous species, thrum plants are specializing as females and pins (long-styled) as males. In this paper we describe more general patterns of male sterility, one of the first steps in the evolution of gender specialization, among populations of the distylous shrub Erythroxylum havanense. Pollen germination differed among populations (range 0.52 ± 0.03 to 0.06 ± 0.04), and between morphs. Pollen from pin plants was almost two times (1.89) as fertile as that from thrums (0.36 ± 0.03 and 0.19 ± 0.03, pin and thrums respectively). Thrums were significantly more male sterile in four out of five populations. The population where differences between the floral morphs were not apparent showed the lowest levels of pollen fertility. Accordingly, our results indicate that populations of E. havanense show marked differences in pollen fertility and higher male sterility associated with the thrum morph. We hypothesize that differences between morphs could be explained if restorers of male sterility are linked to the distyly haplotype, while differences in genes associated with male sterility could explain the variation among populations. Overall, the prevalence of thrum-biased male sterility across populations suggests that E. havanense is subject to a process of gender specialization.
58. J. L. da Costa-Lima, M. I. B. Loiola, and M. Alves, “A New Species of Erythroxylum (Erythroxylaceae) from Northeastern Brazil,” Brittonia, vol. 66, no. 1, pp. 60–64, Mar. 2014. doi: 10.1007/s12228-013-9309-x. Abstract
    Abstract. Erythroxylum nordestinum, a new species of Erythroxylum sect. Rhabdophyllum, is described and illustrated. It occurs in the semiarid region of Bahia, Pernambuco, and Sergipe states of northeastern Brazil. It is recognized by striate stipules that are longer than the petiole, subsessile flowers with the calyx lobes narrowly triangular and longer than the staminal cup, and a terete endocarp. Affinities of E. nordestinum with other species of E. sect. Rhabdophyllum are discussed, and a key is presented to the similar species of Erythroxylum with subsessile flowers from the semiarid region of Brazil.
59. C. A. G. Dantas et al., “Dereplication of Phenolic Derivatives of Three Erythroxylum Species Using Liquid Chromatography Coupled with ESI-MSn and HRESIMS,” Phytochemical Analysis, vol. 32, no. 6, pp. 1011–1026, 2021. doi: 10.1002/pca.3043. Abstract
    Introduction Given the diversity of secondary metabolites produced by species of the genus Erythroxylum, in addition to the many methods that have already been described in the literature, modern screening and identification methodologies, such as dereplication, represent an efficient and quick strategy compared to the classic techniques linked to natural product research. Objective The objective of the present study was to determine the phenolic profiles obtained from three species of Erythroxylum (Erythroxylum pauferrense Plowman, Erythroxylum pulchrum A.St.-Hil. and Erythroxylum simonis Plowman) by dereplication using liquid chromatography coupled with ESI-MSn and HRESIMS. Material and Methods Ethyl acetate and n-butanolic fractions from crude ethanolic extract of Erythroxylum species were analyzed by HPLC-ESI-MSn and HPLC-HRESIMS, in order to identify its corresponding compounds. Experiments were performed in negative ionization mode, and the metabolites were provisionally identified based on deprotonated molecules, molecular formulas, fragmentation patterns and literature data. The corresponding isolated compounds were characterized by 1H and 13C NMR spectroscopy. Results According to the dereplication method, it was possible to establish and compare the phenolic profile of the corresponding species by the assignment of 55 compounds, most of which were first described in these species and among which some were also new to the Erytroxylum genus. Additionally, nine compounds were isolated, including biphenyl-3,3′,4,4′-tetraol, where the mass spectral data were not sufficient for their identification, and reported for the first time in the Erythroxylaceae family. Conclusion This research contributes to the phytochemical knowledge of the Erythroxylum genus and demonstrates the importance of the dereplication method regarding the investigation of natural products, enabling accurate identification of the metabolites while avoiding the efforts and material expenses involved in the isolation of known compounds.
60. A. W. K. de Jong, “The Change in the Composition of the Cocaines in Java Coca Leaves during Their Growth. The Acids of the Esters of l-nor-Ecgonine from Coca Leaves,” Recueil des Travaux Chimiques des Pays-Bas, vol. 67, no. 6, pp. 484–488, 1948. doi: 10.1002/recl.19480670609. Abstract
    The contradiction noted previously, that the quantity of the cocaines in the leaves on a branch remains almost constant for 8 successive leaves with the exception of that of the youngest leaf, while the composition of the cocaines in the leaves alters during their growth, - young leaves contain more cinnamylcocaines than cocaine and old leaves more cocaine than cinnamylcocaines, - is explained as being caused by the continuous formation of fresh cocaines in the leaves, and the continuous decomposition of an almost equal quantity of cocaines containing less cocaine and more cinnamylcocaines than the percentages in the fresh formed cocaines. Reasons for the quicker decomposition of the cinnamylcocaines in the leaves are indicated. In agreement with this explanation it is noted, that the acids of the esters of l-nor-ecgonine consist for the main part of formic acid, benzoic acid being not present. The way in which l-nor-formylecgonine can be formed in the leaves from the cinnamylcocaines is indicated.
61. A. W. K. de Jong, “The Determination of Ecgonine Alkaloids in Coca Leaves,” Recueil des Travaux Chimiques des Pays-Bas, vol. 59, no. 7, pp. 687–693, 1940. doi: 10.1002/recl.19400590713. Abstract
    A method is communicated by which it is possible to obtain from coarsely pulverised coca leaves, as they are sold at Amsterdam, the same quantity of cocaines and methyl ester of l-ecgonine as is obtained from finely pulverised leaves. By converting the unknown ester of l-ecgonine from the coca leaves into l-cocaine it is proved that it is the methyl ester, which is present. This ester is present also in Cusko leaves.
62. V. De Luca, “Understanding How Plants Produce Cocaine,” Proceedings of the National Academy of Sciences, vol. 120, no. 1, p. e2218838120, Jan. 2023. doi: 10.1073/pnas.2218838120.
63. R. A. Diaz, “Unsupervised Cluster Analysis Reveals Molecular and Morphological Groups across Cultivated Coca (Erythroxylum Spp.; Erythroxylaceae),” Master's thesis, Queen Mary University of London, London, 2020. doi: 10.34885/193. Abstract
    The coca tree (Erythroxylum spp .) has been valued in Andean societies for millennia. Its traditional uses range from medicinal remedy to ritual sacrament, but as the natural source of cocaine, coca cultivation is restricted by international drug prohibition. For all its recognition, coca’s botanical origins have remained elusive. Given the value of vegetative characters in disentangling coca taxonomy in the past, we revisited leaf morphology to add clarity to the evolutionary relationships between cultivated coca varieties and their closest Neotropical relatives. Our methods supersede traditional qualitative descriptions of morphology, and offer an empirical basis for testing botanical descriptions against patterns of historic gene flow. Morphometrical analyses support the current classification of coca species, but the discrepancies we uncovered between molecular and morphological groups implicate nongenetic sources of phenotypic variation in cultivated varieties, and underscore the importance of integrating phenotypic and genetic datasets in systematic biology.
64. R. J. Dinis-Oliveira, “Metabolomics of Cocaine: Implications in Toxicity,” Toxicology Mechanisms and Methods, vol. 25, no. 6, pp. 494–500, Jul. 2015. doi: 10.3109/15376516.2015.1072612. Abstract
    Cocaine is the most commonly used illicit drug among those seeking care in Emergency Departments or drug detoxification centers. Cocaine, chemically known as benzoylmethylecgonine, is a naturally occurring substance found in the leaves of the Erythroxylum coca plant. The pharmacokinetics of cocaine is dependent on multiple factors, such as physical/chemical form, route of administration, genetics and concurrent consumption of alcohol. This review aims to discuss metabolomics of cocaine, namely by presenting all known metabolites of cocaine and their roles in the cocaine-mediated toxic effects.
65. T. Docimo et al., “The First Step in the Biosynthesis of Cocaine in Erythroxylum Coca: The Characterization of Arginine and Ornithine Decarboxylases,” Plant Molecular Biology, vol. 78, no. 6, pp. 599–615, Apr. 2012. doi: 10.1007/s11103-012-9886-1. Abstract
    Despite the long history of cocaine use among humans and its social and economic significance today, little information is available about the biochemical and molecular aspects of cocaine biosynthesis in coca (Erythroxylum coca) in comparison to what is known about the formation of other pharmacologically-important tropane alkaloids in species of the Solanaceae. In this work, we investigated the site of cocaine biosynthesis in E. coca and the nature of the first step. The two principal tropane alkaloids of E. coca, cocaine and cinnamoyl cocaine, were present in highest concentrations in buds and rolled leaves. These are also the organs in which the rate of alkaloid biosynthesis was the highest based on the incorporation of 13CO2. In contrast, tropane alkaloids in the Solanaceae are biosynthesized in the roots and translocated to the leaves. A collection of EST sequences from a cDNA library made from young E. coca leaves was employed to search for genes encoding the first step in tropane alkaloid biosynthesis. Full-length cDNA clones were identified encoding two candidate enzymes, ornithine decarboxylase (ODC) and arginine decarboxylase (ADC), and the enzymatic activities of the corresponding proteins confirmed by heterologous expression in E. coli and complementation of a yeast mutant. The transcript levels of both ODC and ADC genes were highest in buds and rolled leaves and lower in other organs. The levels of both ornithine and arginine themselves showed a similar pattern, so it was not possible to assign a preferential role in cocaine biosynthesis to one of these proteins.
66. T. Docimo et al., “Influence of Medium and Elicitors on the Production of Cocaine, Amino Acids and Phytohormones by Erythroxylum Coca Calli,” Plant Cell, Tissue and Organ Culture (PCTOC), vol. 120, no. 3, pp. 1061–1075, Mar. 2015. doi: 10.1007/s11240-014-0660-8. Abstract
    Erythroxylum coca (Erythroxylaceae) is the source of the tropane alkaloid cocaine. Several lines of evidence suggest that tropane alkaloid biosynthesis in E. coca differs from that in solanaceous species, but there are many gaps in our understanding of the pathways in both groups. The development of an E. coca cell culture that produces cocaine could provide a reproducible model system for discovering novel biosynthetic genes and study pathway regulation. Calli cultures were successfully established from young leaf explants on three different media: Anderson’s Rhododendron, Gamborg B5, and modified Murashige-Tucker, all supplemented with growth regulators: 2,4-D (0.6 mg L−1), indole butyric acid (0.06 mg L−1), and benzylaminopurine (0.5 mg L−1). All accumulated cocaine and cinnamoylcocaine at levels of 0.05–0.5 nmol per gram dry weight, as determined by LC–MS, several orders of magnitude below the concentration found in the intact plant. Anderson’s Rhododendron medium supported the highest level of tropane alkaloid production, as well as the highest level of the amino acids arginine, glutamate, proline and phenylalanine, all thought to be precursors of cocaine, but contained generally lower levels of hydroxycinnamate-quinate esters, such as chlorogenic acid. These differences may be ascribed to its relatively low content of nitrate or salts, or its high content of adenine. Addition of 100 μM salicylic acid or coronalon, an analog of the bioactive jasmonic acid-isoleucine conjugate, did not result in any increase in tropane alkaloid production. These E. coca calli could provide valuable material for studies on tropane alkaloid biosynthesis and regulation.
67. T. Docimo, G. W. Schmidt, K. Luck, S. K. Delaney, and J. C. D’Auria, “Selection and Validation of Reference Genes for Quantitative Gene Expression Studies in Erythroxylum Coca,” F1000Research, vol. 2, p. 37, Feb. 2013. doi: 10.12688/f1000research.2-37.v1. Abstract
    Real-time quantitative PCR is a powerful technique for the investigation of comparative gene expression, but its accuracy and reliability depend on the reference genes used as internal standards. Only genes that show a high level of expression stability are suitable for use as reference genes, and these must be identified on a case-by-case basis., Erythroxylum coca produces and accumulates high amounts of the pharmacologically active tropane alkaloid cocaine (especially in the leaves), and is an emerging model for the investigation of tropane alkaloid biosynthesis. The identification of stable internal reference genes for this species is important for its development as a model species, and would enable comparative analysis of candidate biosynthetic genes in the different tissues of the coca plant. In this study, we evaluated the expression stability of nine candidate reference genes in E. coca ( Ec6409, Ec10131, Ec11142, Actin, APT2, EF1α, TPB1, Pex4, Pp2aa3). The expression of these genes was measured in seven tissues (flowers, stems, roots and four developmental leaf stages) and the stability of expression was assessed using three algorithms (geNorm, NormFinder and BestKeeper). From our results we conclude that Ec10131 and TPB1 are the most appropriate internal reference genes in leaves (where the majority of cocaine is produced), while Ec10131 and Ec6409 are the most suitable internal reference genes across all of the tissues tested.
68. C. A. Dominguez and R. Dirzo, “Effects of Defoliation on Erythroxylum Havanese, a Tropical Proleptic Species,” Ecology, vol. 75, no. 7, pp. 1896–1902, 1994. doi: 10.2307/1941594. Abstract
    Proleptic flowering is common among plant species from tropical seasonal forests. In these species flower initiation and anthesis are separated by a prolonged rest period (the unfavorable season), and the two processes are controlled separately. Proleptic species are appropriate for assessing the within— and between—season) effects of herbivory on flowering and reproductive success. We investigated the reproductive consequences of artificial defoliation of the proleptic shrub Erythroxylum havanense, in a seasonal dry forest in western Mexico. Twenty individuals in each of three sites were randomly assigned to one of four treatments: control (no manipulation), and three levels of leaf area removed: 0, 25, and 100%. Plants in the latter three treatments were sprayed with insecticide to prevent additional foliage consumption by natural herbivores. Within a season undamaged plants (control and 0% defoliation) produced from two to four times more seeds than damaged ones (12 and 100% defoliation). In addition, completely defoliated plants exhibited a significant increase in both fruit maturation time (8 d) and average seed mass (9.5%), when compared to the plants in the other treatments. There was no evidence of a trade—off between seed number and seed mass, or between ripening time and seed mass. One year after defoliation, vegetative growth (basal area increment) was reduced only by 100% defoliation. Likewise, flower and fruit production were significantly reduced only in this treatment. Although defoliation reduced seed production in both years, only the first year’s reduction was a direct consequence of defoliation. Seed production decline in year 2 was an indirect effect of the reduction in flower number, suggesting that fruit and seed maturation do not depend on resources stored, but on annual production of photosynthates. Plant survival was not affected up to 5 yr after defoliation. Since most of the effects were evident only in the 100% defoliated plants, our results reflect those instances when insect outbreaks occur and E. havanese plants are completely defoliated.
69. N. A. dos Santos et al., “Analysis of Erythroxylum Coca Leaves by Imaging Mass Spectrometry (MALDI–FT–ICR IMS),” Journal of the American Society for Mass Spectrometry, vol. 32, no. 4, pp. 946–955, Apr. 2021. doi: 10.1021/jasms.0c00449. Abstract
    Matrix-assisted laser desorption/ionization imaging mass spectrometry (MALDI IMS) can determine the chemical identity and spatial distribution of several molecules in a single analysis, conserving its natural histology. However, there are no specific studies on the spatial distribution of alkaloids in Erythroxylum coca leaves by MALDI IMS, preserving the histology of the monitored compounds. Therefore, in this work, positive-ion mode MALDI Fourier-transform ion cyclotron resonance imaging mass spectrometry (MALDI(+)FT–ICR IMS) was applied to identify and analyze the distribution of alkaloids on the surface of coca leaves, evaluating the ionization efficiency of three matrices (α-cyano-4-hydroxycinnamic acid (CHCA), 2-mercaptobenzothiazole (MBT), and 2,5-dihydroxybenzoic acid (DHB)). The last was chosen as the best matrix in this study, and it was studied in five concentrations (0.5, 1.0, 2.0, 4.0, and 8.0 mg·mL–1), where 2 mg·mL–1 was the most efficient. The washing of coca leaves with the organic solvents (acetonitrile, methanol, toluene, and dichloromethane) tested did not improve the performance of the ionization process. Finally, a tissue section, 50 μm thick, was used to study the inner part of the leaf tissue, where alkaloids and flavonoid molecules were detected.
70. S. O. Duke and K. C. Vaughn, “Histochemical and Immunocytochemical Localization of Tropane Alkaloids in Erythroxylum Coca Var. Coca and E. Novogranatense Var. Novogranatense,” International Journal of Plant Sciences, vol. 159, no. 3, pp. 492–503, May 1998. doi: 10.1086/297566. Abstract
    The tropane alkaloids of Erythroxylum coca var. coca and Erythroxylum novogranatense var. novogranatense were localized using histochemical, cytochemical, and immunocytochemical probes. At the tissue level, these alkaloids were localized in leaves, stems, and fruits with Dragendorff’s reagent. Alkaloids were found in the mesophyll, including palisade, spongy, and vascular parenchyma cell layers, and in some cells of the collenchyma. No alkaloids were detected in the epidermis of either Erythroxylum species. Alkaloids were also detected in the endosperm and embryos of orange and mature red fruits but not in tissues of immature green fruits. Quantitative HPLC reveals that embryos had 2.5-5 times more cocaine (w/w%) than endosperms, but 40 times less than leaves. In contrast to leaves, cocaine was a minor alkaloid present in fruits. Dragendorff’s reagent was used to develop thin-layer chromatography plates and specifically stained the alkaloids extracted from leaves of both species. Complexing of alkaloids with tannins resulted in aggregates in the vacuole of E. coca leaf cells as visualized by transmission electron microscopy. Immunocytochemical localization, using anticocaine polyclonal antibodies on leaf tissues, proved that these compounds are localized in vacuoles of both photosynthetic and vascular parenchyma, as demonstrated by the use of Dragendorff’s reagent. The alkaloids were associated with intravacuolar globules and appear to be aggregates with a core formed by phenolic compounds and a periphery enriched in alkaloids. The vacuolar localization of the cocaine alkaloids indicate that they may be complexed with phenols in vivo, thereby rendering them relatively immobile. The implications of the cellular and tissue localization of tropane alkaloids in Erythroxylum are discussed.
71. J. A. Duke, D. Aulik, and T. Plowman, “Nutritional Value of Coca,” Botanical Museum Leaflets, Harvard University, vol. 24, no. 6, pp. 113–119, 1975. doi: 10.5962/p.295207.
72. Y. M. A. El-Imam, W. C. Evans, and T. Plowman, “Alkaloids of Some South American Erythroxylum Species,” Phytochemistry, vol. 24, no. 10, pp. 2285–2289, Jan. 1985. doi: 10.1016/S0031-9422(00)83028-9. Abstract
    Fourteen South American species of Erythroxylum representing four sections of the genus were examined for tropane and related alkaloids. The alkaloid content of the dried material ranged from 0.002 to 0.20 %. Commonly, the alkaloids involved were esters of various tropanols with benzoic and phenylacetic acids. A new alkaloid, nortropacocaine, was isolated from E. mamacoca. Mass spectrometry indicated the existence of other new bases, cuscohygrine and, in some species dihydrocuscohygrine. Chemotaxonomic implications are discussed.
73. S. D. Emche, D. Zhang, M. B. Islam, B. A. Bailey, and L. W. Meinhardt, “AFLP Phylogeny of 36 Erythroxylum Species,” Tropical Plant Biology, vol. 4, no. 2, pp. 126–133, Jun. 2011. doi: 10.1007/s12042-011-9070-9. Abstract
    Four taxa of the plant genus Erythroxylum; Erythroxylum coca var. coca (Ecc), Erythroxylum coca var. ipadu (Eci), Erythroxylum novogranatense var. novogranatense (Enn) and Erythroxylum novogranatense var. truxillense (Ent) are cultivated primarily for the illicit extraction and processing of cocaine. Despite their economic and medical importance, the evolutionary history of these species remains unknown in a modern phylogenetic framework. The aims of this study were to: (a) investigate the relationship among the cultivated and a select number of non-cultivated taxa, and (b) test Plowman’s (Journal of Psychodelic Drugs 11:103–117, 1979b) linear progression hypothesis of the cultivated Erythroxylum taxa versus Johnson’s et al. (Annals of Botany 95:601–608, 2005) hypothesis that Ec and En are sister species. AFLP phylogeny was used to compare the relationships among 36 Erythroxylum species (133 accessions) spanning the geographic distribution of the genus. A Maximum Parsimony tree revealed both geographic and taxonomic partitioning into clades representing species from Africa, Asia-Pacific and the New World (Tropical Americas). Ec and En formed distinct clades, indicating they are sister species and a cluster of non-cultivated species were the most closely related to the cultivated species. Multivariate ordination analysis was used to evaluate the relationship between cultivated and non-cultivated Erythroxylum taxa from the Tropical Americas. Our results support the hypothesis that the cultivated species are more closely related to each other than to any other species of Erythroxylum, but refute the hypothesis that Ent (and Enn) descended from Ecc. Instead our data suggest an independent, non-linear evolutionary relationship between Ec and En. Finally, the AFLP analyses identified significantly different genetic groups within Erythroxylum suggesting that the current intrageneric classification of this genus be revised.
74. E. Encarnación Puri, “Efecto del manejo convencional de Erythroxylum coca en indicadores fisicoquímicos de calidad del suelo, en Padre Abad - Ucayali,” PhD thesis, Universidad Nacional Agraria de la Selva, 2022. http://repositorio.unas.edu.pe/handle/UNAS/2196. Abstract
    The cultivation of E. coca dates to prehistoric times, with great cultural, medicinal, and spiritual value, contrary to these practices, in Peru 90% of production is destined for drug trafficking generating social violence, extreme poverty and negative impacts on soil quality. Therefore, the work evaluated the effect of conventional management of E. coca on physicochemical indicators of soil quality in Padre Abad, Ucayali region. Comparative descriptive research, with statistical of completely randomized design (DCA), the treatments are conventional management of E. coca of 2 (CO2) and 15 years (CO15), ex-coca with natural regeneration of 9 years (EC9), and secondary forest (BS). Physicochemical indicators were evaluated to determine quality through soil quality indices (ICS). The results show differences for sand, clay, silt, and resistance to penetrability (Rp), the latter with a sustained increase. The chemical indicators present differences, except for potassium, in addition, initially (CO2) shows positive effects on pH, MO, N, K+, Ca2+ and Mg2+, with a decrease in Al3+, %AC and %SAl, however, over time it presents negative effects on macronutrients and increases in Al3+, %AC and %SAl. In conclusion, there are negative changes in the physicochemical indicators and the quality that went from low to very low levels in 15 years of conventional management of E. coca, and slight recovery in the excoca area with 09 years of natural regeneration.
75. A. Engler, Botanische Jahrbücher Fur Systematik, Pflanzengeschichte Und Pflanzengeographie, vol. 20. Stuttgart [etc.]: Schweizerbart [etc.], 1895, pp. 1–918. https://www.biodiversitylibrary.org/item/678.
76. O. P. Estrada, “Biochemical Studies in the Elucidation of Genes Involved in Tropane Alkaloid Production in Erythroxylum Coca and Erythroxylum Novogranatense,” Master's thesis, Texas Tech University, Texas, 2017. https://ttu-ir.tdl.org/handle/2346/72666. Abstract
    Natural products are vastly used in the modern pharmacopoeia. Among the most abundant natural products in medicine, there are tropane and granatane alkaloids. Efforts in the investigation of tropane and granatane biosynthesis are now contributing to the metabolic engineering sciences. Here, we present a portion of the most fundamental research in tropane alkaloid-producing transcriptomics with the use of qPCR techniques along with enzyme characterization experiments. In addition, a brief study on the enzyme responsible for the formation of methyl salicylate in Erythroxylum species is presented.
77. W. C. Evans, “The Comparative Phytochemistry of the Genus Erythroxylon,” Journal of Ethnopharmacology, vol. 3, no. 2, pp. 265–277, Mar. 1981. doi: 10.1016/0378-8741(81)90057-X. Abstract
    Recent research suggests that, in addition to the well-documented occurrence of significant quantities of cocaine and related alkaloids in a limited number of species, the genus Erythroxylon will prove to be a rich source of tropane alkaloids. These bases are esters of a range of acids with tropine, 3α, 6βt-dihydroxy tropane and 3α,6β,7β-trihydroxytropane; the numbers are further increased by nor-derivatives, and stereoisomerism involving the C-3 hydroxyl of the tropane skeleton. The diterpenes of the genus also appear worthy of further study.
78. J. F. S. Ferreira and K. N. Reddy, “Absorption and Translocation of Glyphosate in Erythroxylum Coca and E. Novogranatense,” Weed Science, vol. 48, no. 2, pp. 193–199, Apr. 2000. doi: 10.1614/0043-1745(2000)048[0193:AATOGI]2.0.CO;2. Abstract
    Absorption and translocation of 14C-glyphosate was studied in greenhouse-grown Erythroxylum coca and E. novogranatense. Autoradiography indicated that translocation patterns were similar for both species and that E. novogranatense absorbed and translocated more glyphosate than E. coca. In both young and mature plants, absorption of leaf-applied 14C-glyphosate increased with increased exposure time, and 288 h after application, absorption was higher in E. novogranatense (79 and 52% of applied, respectively) compared with E. coca (60 and 14% of applied, respectively). Similarly, translocation of 14C-glyphosate increased with time in both species. In mature plants, after 288 h more 14C-glyphosate translocated in E. novogranatense (6.9% of applied) than E. coca (2.5%), but the opposite occurred in young plants. Most of the radioactivity translocated from the treated leaf accumulated in the main stems and roots of both species with little accumulation in tissues above the treated leaf. However, most of the applied radioactivity remained in the treated leaf regardless of growth stage and species. The absorption of 14C-glyphosate in young and mature plants of E. coca was 1.3 and 3.6 times lower, respectively, than in E. novogranatense 288 h after treatment. Differences in absorption and translocation of glyphosate in E. coca and E. novogranatense may partially explain the reported differential response to glyphosate.
79. J. F. S. Ferreira, R. J. Smeda, and S. O. Duke, “Control of Coca Plants (Erythroxylum Coca and E. Novogranatense) with Glyphosate,” Weed Science, vol. 45, no. 4, pp. 551–556, Aug. 1997. doi: 10.1017/S0043174500088809. Abstract
    Glyphosate applied at rates of 0, 0.3, 0.6, 1.1, 2.2, 3.4, 4.5, 6.7, 9.0, and 13.4 kg ai ha−1 was evaluated for the control of greenhouse-grown Erythroxylum novogranatense var. novogranatense and E. coca var. coca plants. Glyphosate reduced live weight of both species, 6 wk after treatment, at rates as low as 0.6 kg ha−1, but was more effective in reducing live weight and regrowth on E. novogranatense than E. coca. Glyphosate at 1.1 kg ha−1 killed 100% of E. novogranatense plants 5 mo after treatment. Glyphosate rates of 2.2 kg ha−1 and higher reduced regrowth of E. coca plants 65 to 100%, independent of leaf age at time of spraying. Control of regrowth persisted for over 17 mo after treatment, with 37% of E. coca plants dying at rates of 13.4 kg ha−1 between 6 mo and 1 yr after treatment. Glyphosate, applied up to 6.7 kg ha−1, had no significant effect on regrowth of E. coca when plants were defoliated 24 h before treatment. Glyphosate at 2.2 kg ha−1 effectively killed E. novogranatense plants and reduced leaf production of E. coca plants.
80. R. F. Fialho and A. L. S. Furtado, “Germination of Erythroxylum Ovalifolium (Erythroxylaceae) Seeds within the Terrestrial Bromeliad Neoregelia Cruenta,” Biotropica, vol. 25, no. 3, pp. 359–362, 1993. doi: 10.2307/2388797.
81. J. C. Follin and F. Rivano, “Thoughts on the development of an alternative to coca cultivation in Andean America,” Oléagineux Corps Gras Lipides (France), 2001. Abstract
    The cultivation of coca (Erythroxylum coca Lam.), a perennial shrub of the order Geraniales, goes back to ancient times in Bolivia and Peru, but its extension over wide areas is quite recent, beginning around 1960, with a period of strong expansion between 1975 and 1985 (coca boom). In 1992, it then started to decline in Bolivia and Peru, but continued to progress in Colombia, with an intensification of the crops. The integrated (alternative) development policies implemented over the last decade have had positive consequences for infrastructures (roads, public health facilities, education), but have had little success in replacing illicit crops with legal cash crops, primarily for market and price reasons. As a result, the forced eradication operations carried out to make up for the deficit have created serious social conflicts. The socio-economic situations in regions affected by illicit crops, and those in regions with production potential, may be very different depending on the country and the continent. Nevertheless, controlling illicit crops needs to be conceived in terms other than repression, and agricultural development needs to be proposed in terms other than prices and competitiveness. That means introducing fairer policies and markets, so that farmers are not marginalized and do not turn to illegal production
82. B. G and R. K. Suripeddi, “Development and Validation of HPTLC Method for Identification and Quantification of Sterols from Leaves of Erythroxylum Monogynum Roxb. and in Vitro Evaluation of Anti-Oxidant and Anti-Glycation Activities,” South African Journal of Botany, vol. 137, pp. 24–34, Mar. 2021. doi: 10.1016/j.sajb.2020.10.005. Abstract
    The petroleum ether extract from leaves of Erythroxylum monogynum when subjected to phytochemical analysis and chromatographic purification, resulted in the isolation of two new sterols namely 4-methyl ergosta-7, 23‑dien‑3β-ol and 4-methyl ergosta-7, 24 (28)‑dien‑3β-ol. Their structure was elucidated by NMR and Mass Spectrometry. The two sterols were separated on a silica gel 60F254 HPTLC plates impregnated with AgNO3 using dichloromethane: methanol (9:1 v/v) as a mobile phase. Upon densitometric scanning at 254 nm in a reflectance mode, the two sterols separated as sharp and compact bands with Rf of 0.47±0.02 and 0.52±0.01 respectively for 4-methyl ergosta-7, 23‑dien‑3β-ol and 4-methyl ergosta-7, 24 (28)‑dien‑3β-ol. Linear regression and calibration plots constructed (n = 6) showed excellent linearity at 100–500 ng per spot with a correlation coefficient, r = 0.9979±0.0004 and 0.9974±0.0007 for 4-methyl ergosta-7,23‑dien‑3β-ol and 4-methyl ergosta-7,24 (28)‑dien‑3β-ol, respectively.  The Limits of detection and quantification were found to be 21.07 ng and 57.23 ng/band for 4-methyl ergosta-7,23‑dien‑3β-ol and 25.18 ng and 63.86 ng/band for 4-methyl ergosta-7,24 (28)‑dien‑3β-ol, respectively. Both the sterols demonstrated good anti-oxidant and anti-glycation activities where, the IC50 values obtained were comparable with the positive control compounds, ascorbic acid and aminoguanidine. The 4-methyl ergosta-7,23‑dien‑3β-ol displayed 100% anti-oxidant activity at 100 µg/ml for both DPPH and H2O2 scavenging assays. In addition, both the sterols presented more than 90% inhibition of Advanced Glycation End products at 100 µg/ml concentration. The results obtained are remarkable indicating that these plant extracts could serve as a natural alternative to the conventional oral hypoglycemic molecules.
83. P. P. A. N. G, A. Rabinarayan, P. P, H. C. R, and S. V. J, “Pharmacognostic and Analytical Profile of Leaves of Erythroxylum Moonii Hochr. – An Ethno-Medicinal Plant,” International Journal of Ayurvedic Medicine, vol. 12, no. 2, pp. 353–359, Jun. 2021. doi: 10.47552/ijam.v12i3.1880. Abstract
    Erythroxylum moonii Hochr. is a shrub or small tree in family Erythroxylaceae and folklore claims report the use of its leaves in the treatment of helminthiasis. Aim: Hence, present study aims to evaluate the pharmacognostic and analytical characters including HPTLC of its leaves. Methods: E. moonii fresh and powdered leaves were explored for the macroscopic and microscopic features along with their physico-chemical, phytochemical properties and HPTLC following standard procedures. Results: The leaf of E. moonii is simple, alternate, petiolate, stipulate, elliptic and lanceolate with obtusely caudate-acuminate apex, acute base and entire margins. Fresh leaf is light green, slight astringent with characteristic odour and smooth texture. Powdered dry leaves were light green, slight astringent with aromatic odour and coarse, fibrous texture. Microscopic evaluation revealed the presence of simple, bilobed and stellate trichomes (with and without lignification), rosette, rhomboidal, prismatic and cluster crystals, paracytic stomata and starch grains as key characteristics both in fresh leaves and powdered leaves. Obtained values for loss on drying, total ash, acid insoluble ash, pH, water and methanol soluble extractive were 10.44±0.31%, 2.2±0.67%, 0.93±0.06%, 5, 7.63±0.57% and 6.44±0.38% respectively. Qualitative phytochemical analysis suggested the presence of carbohydrates, steroids, glycosides, saponins, alkaloids, tannins and flavonoids in the test sample. HPTLC study revealed 17 and 11 peaks at short (254nm) and long (366nm) ultraviolet consecutively. Conclusion: Obtained results can be used to establish pharmacognostic and analytical standards of leaves of E. moonii which can serve as an important source to determine the quality, purity and strength of the powdered drug.
84. A. Galindo Bonilla and J. L. Fernández Alonso, “Plantas de coca en Colombia. Discusión crítica sobre la taxonomía de las especies cultivadas del género Erythroxylum P. Browne (Erythroxylaceae),” 2010. https://digital.csic.es/handle/10261/38534. Abstract
    [EN]Forensic botany is in high demand in Colombia in connection with plant material, mainly “coca” from illicit crops. The taxonomic study of the two species and four varieties of Erythroxylum P. Browne (Erythroxylaceae) cultivated in Colombia was carried out. Hybridization between E. coca and E. novogranatense and between the two varieties of E. coca is suggested, and important changes in the geographic distribution of all taxa are described. Both, hybridization and changes in distribution patterns are due to anthropic intervention.
85. A. Galindo and J. L. Fernández-Alonso, “Especies cultivadas del género Erythroxylum P. Browne. Revisión del tema desde la perspectiva forense.,” Colombia Forense, vol. 1, pp. 7–15, Jan. 2009. Abstract
    Taxonomic analysis of vegetable material has gained a great importance for the Justice Administration at a worldwide level and it also has a promising application in Colombia. Until 2008, the main demand at a forensic level in the country was related to the study of plants coming from illicit crops with Erythroxylum P. Browne species, commonly named coca plants, being the main subject of study from 2006. A bibliographic review of the state of art about those species covering world wide and local perspective were done.
86. V. Gamarra et al., “Metabolitos en las hojas de Erythroxylum coca Lam y Erithroxylum novogranatense (Morris) Hieron y evaluacón de sus propiedades biológicas mediante bioensayos,” Rev. peru. med. integr, pp. 828–834, 2017. http://rpmi.pe/ojs/index.php/RPMI/article/view/70/77.
87. R. L. Glass, “Analysis of Hygrine in Coca Leaves Using a Novel High-Performance Liquid Chromatographic Method,” Journal of Liquid Chromatography, vol. 18, no. 14, pp. 2877–2883, Aug. 1995. doi: 10.1080/10826079508009331. Abstract
    A novel high-performance liquid chromatographic (HPLC) method is described for the determination of hygrine in leaves of Erythroxylum coca and Erythroxylum novo. The analysis was performed on a strong cation exchange HPLC column with a mobile phase consisting of MeOH: 0.1 M KH2HPO4, pH 7 (75%:25%, v/v) and a UV detector set at 220 nm. Recoveries of hygrine averaged about 64% from extracts fortified with 2.5 to 10.0 mg of hygrine per 10 ml of extract. Hygrine contents in leaves of E. coca and E. novo were determined as 0.09 and 0.10% of the dry weight, respectively.
88. R. L. Glass and M. B. Johnson, “Analysis of Cuscohygrine in Coca Leaves by High Performance Liquid Chromatography,” Journal of Liquid Chromatography & Related Technologies, vol. 19, no. 11, pp. 1777–1784, Jun. 1996. doi: 10.1080/10826079608014004. Abstract
    A novel high-performance liquid chromatographic (HPLC) method is described for the determination of the alkaloid cuscohygrine [1,3-bis(1-methyl-2-pyrrolidinyl)-2-propanone] in air-dried leaves of Erythroxylum coca var. coca. The analysis was performed on a weak cation exchange HPLC column using a mobile phase consisting of MeOH: 0.05 M KH2PO4, pH 7 (75:25, v/v) and with UV detection at 220 nm. Cuscohygrine content was determined as 0.21–0.23% in E. coca leaves.
89. R. L. Glass, “Analysis of Hygrine and Cuscohygrine in Coca Leaves Using Gas Chromatography and High-Performance Liquid Chromatography,” Journal of Agricultural and Food Chemistry, vol. 45, no. 8, pp. 3114–3117, Aug. 1997. doi: 10.1021/jf960967f. Abstract
    The alkaloids hygrine and cuscohygrine in Erythroxylum coca var. Coca leaves were analyzed by a gas chromatographic (GC) method using a dimethylsilicone capillary column and a high-performance liquid chromatographic (HPLC) method using a weak cation exchange column. Hygrine content in E. coca leaves was determined as 0.12% by GC and 0.07% by HPLC, whereas cuscohygrine content was 0.25% by GC and 0.21% by HPLC. Keywords: Hygrine; cuscohygrine; alkaloids; Erythroxylum; coca extracts
90. R. L. Glass and E. L. Johnson, “Comparison of High Performance Liquid Chromatographic and GAS Chromatographic Analyses of Cocaine in Coca Leaves,” Journal of Liquid Chromatography, vol. 16, no. 16, pp. 3543–3555, Oct. 1993. doi: 10.1080/10826079308019707. Abstract
    A high-performance liquid chromatographic (HPLC) method and a capillary gas chromatographic (GC) method are compared for the quantitative analysis of cocaine in Erythroxylum coca leaves. Cocaine was extracted by refluxing air-dried coca leaves (0.05–4.0 g) with 95% ethanol (30–100 mL) for 15 min. Aliquots of the crude ethanolic leaf extracts were removed for analysis while the remaining portions of the extracts were taken through a cleanup procedure. The mean cocaine contents determined by HPLC and GC methods in six replicated crude leaf (1.0 g) extracts were 0.56% and 0.54%, respectively. However, the cocaine contents in the cleanup extracts were 0.43% (HPLC) and 0.42% (GC). GC analysis gave better resolution of cocaine and related alkaloids, but HPLC analysis of cocaine was simpler and faster.
91. K. González-García, J. A. González-Lavaut, J. González-Guevara, and S. Prieto-González, “Género Erythroxylum: Análisis de la Información Científica,” acta farmacéutica bonaerense, vol. 24, 2005. Abstract
    Erythroxylum genus: Analysis of scientific information”. Only 63 species has been studied from the 369 species reported in scientific literature related to the genus Erythroxylum, which evidences that this genus has been little studied. This work is a bibliographic analysis of the Erythroxylum genus, which takes as references the databases related to natural products, such as the Dictionary of Natural Products, the Natural Products Alerts (NAPRALERT) and US National Libray of medicine (MedLine) databases, as well as the Chemical Abstracts Referative Journal (CDs) , among others. The leaves and the trunks are the plant organs more used for ethnomedical treatments or scientific studies. The ethnomedical properties more quoted for Erythroxylum species are stimulant, euphoriant and relief of fatigue. Citotoxic and antibacterial activities of extracts for some of the species are also mentioned. The chemical compounds more frequently mentioned in scientific literature are terpenoids, alkaloids and flavonoids. There are only 16 patents referred to the use of Erythroxylum species like herbicide, antimicrobiane, against the oxidative stress and anorexy.
92. L. Grinspoon and J. B. Bakalar, “Coca and Cocaine as Medicines: An Historical Review,” Journal of Ethnopharmacology, vol. 3, no. 2, pp. 149–159, Mar. 1981. doi: 10.1016/0378-8741(81)90051-9. Abstract
    Coca has been used in folk medicine in South America for thousands of years both as a general stimulant and for more specific medical purposes. It remains one of the most commonly used medicines in some areas of Bolivia and Peru. The medical use of coca and cocaine in the industrial world has a more dramatic and varied history. Coca extract and cocaine were introduced as panaceas for a wide variety of complaints in the late 19th century. Cocaine was the first effective local anesthetic; prescription drugs, patent medicines, and soda drinks containing it were also popular. When its dangers became apparent and substitutes became available, its medical use went into decline, especially when, in the 1930s, amphetamine began to replace it for some purposes. Today its only generally accepted medical use is as a topical anesthetic in certain kinds of minor surgery and other clinical procedures. There are, however, some recent and so far uncertain signs of reviving interest in cocaine and even coca itself for other medical purposes, in research as well as in diagnosis and treatment.
93. E. O. Gryj and C. A. Domíguez, “Fruit Removal and Postdispersal Survivorship in the Tropical Dry Forest Shrub Erythroxylum Havanense: Ecological and Evolutionary Implications,” Oecologia, vol. 108, no. 2, pp. 368–374, Oct. 1996. doi: 10.1007/BF00334663. Abstract
    We studied the relationship between the removal rate and the spatiotemporal availability of ripe fruits of the tropical deciduous shrub Erythroxylum havanense in western Mexico. We also evaluated the effects of dispersal on seed survival during the first stages of establishment. Fast and early dispersal should be favored in E. havanense, since propagules have more time to grow and accumulate resources before the beginning of the severe dry season. In general, high rates of fruit removal imply faster and earlier dispersal. Thus, plants producing large crops should benefit from high removal rates, which will increase the probability of successful establishment by their progeny. To characterize both individual and population fruiting patterns, we made daily counts of fruits on 51 plants arranged in six clumps of different sizes. The daily number of fruits removed per plant was higher for plants with larger initial crop sizes and larger numbers of ripe fruits on a given day, but decreased as clump size increased. Additionally, we monitored postdispersal survival and germination in an experiment manipulating seed density, distance from adult plants, and seed predation. Early establishment was independent of density or distance, and vertebrate seed predation was the main agent of seed mortality. Our results indicate that the critical variable with respect to fruit removal is the number of fruits a plant produces, large plants having higher dispersal rates. Large plants are also more likely to have more seeds escaping postdispersal seed predation.
94. C. Gutierrez-Noriega and V. W. Von Hagen, “The Strange Case of the Coca Leaf,” The Scientific Monthly, vol. 70, no. 2, pp. 81–89, 1950. https://www.jstor.org/stable/19900.
95. L. F. Haas, “Coca Shrub (Erythroxylum Coca).,” Journal of Neurology, Neurosurgery, and Psychiatry, vol. 59, no. 1, p. 25, Jul. 1995. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1073596/. Abstract
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96. C. A. Hastorf, “Archaeological Evidence of Coca (Erythroxylum Coca, Erythroxylaceae) in the Upper Mantaro Valley, Peru,” Economic Botany, vol. 41, no. 2, pp. 292–301, Apr. 1987. doi: 10.1007/BF02858976. Abstract
    Prehistoric remains of coca (Erythroxylum spp.) are rarely uncovered by archaeologists or positively identified by botanists because of their fragile nature and the lack of rigorous archaeological collection techniques. This absence of plant evidence has made evolutionary studies of diffusion and use of coca difficult. From special depositional conditions in the Mantaro area of central Peru, one coca leaf and two endocarps have been uncovered and identified as Erythroxylum coca var. coca. These three specimens came from elite-status contexts dating to the Late Intermediate and the Late Horizon-Early Colonial Periods. These remains provide the first highland evidence for access to coca-producing, ceja de montaña farms, which lie more than 50 km away on the eastern slope of the Andes.
97. J. Hellin and S. Higman, “Substituting Alternative Crops for Coca: A Viable Alternative for Farmers?,” vol. 27, pp. 10–13, Jan. 2000. Abstract
    Attempts to persuade smallholder farmers to replace highly profitable coca cultivation with alternative crops is proving much more difficult than first envisaged. A wide range of crops tried have not been suited to farmers’ situations or prevailing markets. Many species were promoted on the basis of results from on-station trials at a research station in Chapare and were not representative of on-farm conditions. Initial results were disappointing in terms of a long period without income between planting and first harvest (eg. Macadamia nuts and natural rubber), low yields (eg. Coffee), and disappointingly small markets (e.g. Macadamia nuts) and the absence of markets (e.g. Coffee). Following the forced coca eradication process, this further engendered a feeling of mistrust towards outsiders on the part of many farmers.
98. N. Hilgert, S. Reyes, and G. Schmeda-Hirschmann, “Alkaline Substances Used with Coca (Erythroxylum Coca, Erythroxylaceae) Leaf Insalivation in Northwestern Argentina,” Economic Botany, vol. 55, no. 2, pp. 325–329, 2001. https://www.jstor.org/stable/4256430.
99. N. I. Hilgert, “Especies Vegetales Empleadas En La Insalivación De Hojas De ‘Coca’ (Erythroxylum Coca Var. Coca, Erythroxylaceae),” Darwiniana, vol. 38, no. 3/4, pp. 241–252, 2000. https://www.jstor.org/stable/23223890. Abstract
    A study has been carried out in farming communities of the cloud forests in the Upper Bermejo Basin, Province of Salta, Argentina to document the use of plants involved in the manufacture of "yista". "Yista" is the name given to alkaline substances used during insalivation of "coca" (Erythroxylum coca Lam. var. coca) leaves. To obtain "yista", selected plants have to be burned. Twenty-seven native species and five exotic plant species were recorded as present or past sources of "yista". The scientific and common names, plant part employed as well as the communities where their use has been recorded are presented. The method employed to prepare "yista" is described and illustrated. El estudio se desarrolló en comunidades campesinas de la selva nublada, en la alta cuenca del río Bermejo, Provincia de Salta, Argentina con el objeto de documentar el uso de plantas involucradas en la elaboración de "yista". "Yista" es el nombre asignado a las sustancias alcalinas utilizadas durante la insalivación de hojas de coca (Erythroxylum coca Lam. var. coca). Para la obtención de la "yista" las plantas seleccionadas deben ser incineradas. Se registraron veintisiete especies nativas y cinco exóticas empleadas, en el presente o en el pasado, para preparar "yista". Se mencionan los nombres científicos y vulgares y las porciones de la planta utilizadas, y la comunidad donde se registró el uso. Se describe e ilustra el modo de preparar "yista".
100. B. Holmstedt, J.-E. Lindgren, L. Rivier, and T. Plowman, “Cocaine in Blood of Coca Chewers,” Journal of Ethnopharmacology, vol. 1, no. 1, pp. 69–78, Jan. 1979. doi: 10.1016/0378-8741(79)90017-5. Abstract
     Coca leaves (Erythroxylum coca Lamarck) and powder (5–10 g) were taken orally by human subjects in the same way as South American natives do. The cocaine, as measured by mass fragmentography, was immediately detected in the blood, reached peak concentrations from 10–150 ngml plasma at 0.38–1.95 hours, and persisted in the plasma for more than 7 hours. Half-lives of the elimination of cocaine were calculated and ranged from 1.0 to 1.9 hours. The absorption half-lives ranged from 0.2 to 0.6 hours. The shape of the curves fits with the subjective effects reported. There is no reason to believe that the stimulating effect achieved by the use of either coca leaves or powder is not due to cocaine.
101. B. Holmstedt, E. Jäätmaa, K. Leander, and T. Plowman, “Determination of Cocaine in Some South American Species of Erythroxylum Using Mass Fragmentography,” Phytochemistry, vol. 16, no. 11, pp. 1753–1755, Jan. 1977. doi: 10.1016/0031-9422(71)85082-3. Abstract
     Thirteen South American species of Erythroxylum have been analyzed for their cocaine content. Cocaine was found only in E. coca Lam., E. novogranatense (Morris) Hieron. and E. novogranatense var. truxillense (Rusby) Machado. The amount of cocaine was determined by mass fragmentography using deuterium labelled cocaine as internal standard
102. T. R. Hoye, J. A. Bjorklund, D. O. Koltun, and M. K. Renner, “N-Methylputrescine Oxidation during Cocaine Biosynthesis:\,Study of Prochiral Methylene Hydrogen Discrimination Using the Remote Isotope Method,” Organic Letters, vol. 2, no. 1, pp. 3–5, Jan. 2000. doi: 10.1021/ol990940s. Abstract
     The stereoselectivity of N-methylputrescine (3) oxidation to pyrrolinium ion 4 in Erythroxylum coca during cocaine (1) biosynthesis was studied. The remote isotope method was used to advantage. Each enantiomer of 4-monodeuterated N-methylputrescine served as a precursor for plant feeding. To facilitate mass-spectrometric analysis of products, a 2H313C-methyl group was also incorporated into the 4-deuterio-N-methylputrescines. Oxidative deamination of N-methylputrescine was found to be stereoselective; the pro-S hydrogen atom is removed with 6−10:1 selectivity.
103. M. N. Huang, T. W. Abraham, S. H. Kim, and E. Leete, “1-Methylpyrrolidine-2-Acetic Acid Is Not a Precursor of Tropane Alkaloids,” Phytochemistry, vol. 41, no. 3, pp. 767–773, Feb. 1996. doi: 10.1016/0031-9422(95)00667-2. Abstract
     1-Methylpyrrolidine-2-acetic acid and related compounds were studied as precursors in the biosynthesis of the tropane alkaloids in Erythroxylum coca and Datura innoxia. (R,S)-[1′,2-13C2,2-14C,15N]-1-Methylpyrolidien-2-accetic acid, (R,S)-[1′,2′-13C2,1′-14C]-1-methylpyrrolidine-2-acetic acid, (R,S) ethyl [1′,2′-13C2,1′-14C]-1- methylpyrrolidine-2-acetate, and (R,S)-[2′-14C]-1-methylpyrrolidine-2-acetic acid N-acetylcysteamine thioester were synthesized and fed to intact plants by leaf-painting or hydroponic-feeding. Specific incorporation of these compounds into (−)-hyoscyamine, (−)-scopolamine, (−)-cocaine and the biosynthetically related cuscohygrine were very low. These results indicate that 1-methylpyrrolidine-2-acetic acid is not an efficient precursor of tropane alkaloids.
104. T. James, “The Quantification of Cocaine from the Erythroxylum Coca Plant and the Comparison on High Performance Liquid Chromatography and Gas Chromatography Mass Spectroscopy as an Analytical Method.,” Master's thesis, City University of New York, 2017. https://academicworks.cuny.edu/jj_etds/29. Abstract
     Cocaine is derived from the Erythroxylum coca plant, is a highly addictive stimulant abused all over the world. There are two types of Erythroxylum coca plants that produce cocaine; the E. Coca and E. Novogranatense. Cocaine exists as the salt, and the freebase which is typically referred to as “crack” due to the crackling sound it makes when heated. It is popular because it is inexpensive and easily available on the streets, mainly in poor urban areas. The purpose of this project was to determine the amount of cocaine that can be extracted from E.coca and to assess which analytical technique, High Performance Liquid Chromatography or Gas Chromatography Mass Spectroscopy, is better to quantify the amount extracted. The amount of cocaine extracted from 3.0g of E.Coca leaves using GCMS and HPLC is, respectively, 3.90 x10-6g and 1.53 x10-5g. The limit of detection for both GCMS and HPLC was 0.002µg/mL and 0.004µg/mL respectively, and the limit of quantification was 0.008µg/mL for GCMS and 0.116µg/mL for the HPLC.
105. O. A. Jara-Muñoz and F. A. Ávila, “A New Species of Erythroxylum (Erythroxylaceae) from Colombia and Panama,” Phytotaxa, vol. 489, no. 3, pp. 293–298, Mar. 2021. doi: 10.11646/phytotaxa.489.3.6. Abstract
     A new species of Erythroxylum from Colombia and Panamá is described and illustrated. The new species is morphologically similar to Erythroxylum acuminatum from Ecuador, Peru, Brazil, and Bolivia but differs from this species by its longer and caducous stipules, with two longer lateral setae, and by the underdeveloped anterior ligule of the petals.
106. O. A. Jara-Muñoz, “Two News Species of Erythroxylum (Erythroxylaceae) from Ecuador and Peru,” Brittonia, vol. 63, no. 2, pp. 227–232, Jun. 2011. doi: 10.1007/s12228-010-9155-z. Abstract
     Two new species of Erythroxylum from the Amotape-Huancabamba region are described and illustrated. Erythroxylum dillonii occurs in the arid zones of northern Peru, and Erythroxylum gentryi is known only from the Ecuadorian side of Cordillera del Condor. Their habitats and taxonomic relationships are discussed.
107. J. Jirschitzka, G. W. Schmidt, M. Reichelt, B. Schneider, J. Gershenzon, and J. C. D’Auria, “Plant Tropane Alkaloid Biosynthesis Evolved Independently in the Solanaceae and Erythroxylaceae,” Proceedings of the National Academy of Sciences, vol. 109, no. 26, pp. 10304–10309, Jun. 2012. doi: 10.1073/pnas.1200473109. Abstract
     The pharmacologically important tropane alkaloids have a scattered distribution among angiosperm families, like many other groups of secondary metabolites. To determine whether tropane alkaloids have evolved repeatedly in different lineages or arise from an ancestral pathway that has been lost in most lines, we investigated the tropinone-reduction step of their biosynthesis. In species of the Solanaceae, which produce compounds such as atropine and scopolamine, this reaction is known to be catalyzed by enzymes of the short-chain dehydrogenase/reductase family. However, in Erythroxylum coca (Erythroxylaceae), which accumulates cocaine and other tropane alkaloids, no proteins of the shortchain dehydrogenase/reductase family were found that could catalyze this reaction. Instead, purification of E. coca tropinonereduction activity and cloning of the corresponding gene revealed that a protein of the aldo-keto reductase family carries out this reaction in E. coca. This protein, designated methylecgonone reductase, converts methylecgonone to methylecgonine, the penultimate step in cocaine biosynthesis. The protein has highest sequence similarity to other aldo-keto reductases, such as chalcone reductase, an enzyme of flavonoid biosynthesis, and codeinone reductase, an enzyme of morphine alkaloid biosynthesis. Methylecgonone reductase reduces methylecgonone (2-carbomethoxy-3tropinone) stereospecifically to 2-carbomethoxy-3β-tropine (methylecgonine), and has its highest activity, protein level, and gene transcript level in young, expanding leaves of E. coca. This enzyme is not found at all in root tissues, which are the site of tropane alkaloid biosynthesis in the Solanaceae. This evidence supports the theory that the ability to produce tropane alkaloids has arisen more than once during the evolution of the angiosperms.
108. E. L. Johnson, “Alkaloid Content in Erythroxylum Coca Tissue during Reproductive Development,” Phytochemistry, vol. 42, no. 1, pp. 35–38, May 1996. doi: 10.1016/0031-9422(96)00864-3. Abstract
     The content (% dry wt) of eight alkaloids in branch segments with and without flower buds, terminal leaves, and divided flower parts of Erythroxylum coca var. coca, varied greatly in the different tissues. Cocaine, the principal alkaloid in E. coca, was the most abundant alkaloid in all plant parts analysed. Cuscohygrine was least among the alkaloids, and observed only in leaf tissue. Cocaine content in unopened flower buds, pedicels, perianths and stamens was three times that in immature flower buds; and in pistils of opened flowers, two times that in the immature flower buds. Of all the tissue tested during reproductive development, young leaves at the terminal end of branches contained the most alkaloids.
109. E. L. Johnson, “Alkaloid Content in Two Erythroxylum Taxa During Juvenile Growth and Development,” Journal of Herbs, Spices & Medicinal Plants, vol. 10, no. 2, pp. 47–61, 2002. doi: 10.1300/J044v10n02_06. Abstract
     Erythroxylum coca var. coca Lam. And Erythroxylum novogranatense var. novogranatense (Morris) Hieron (E.n. var. novogranatense) were grown in a controlled environment for 52 weeks to monitor the content of hygrine, tropinone, tropacocaine, methyl ecgonine, cocaine and cis- and trans-cinnamoylcocaine in seeds, plant parts, and organs during juvenile growth. Embryos and endosperms of var. coca contained cocaine while only embryos of var. novogranatense contained cocaine. Tropacocaine was present in hypocotyls, stems and roots of var. novogranatense, but not in var. coca. Trans-cinnamoylcocaine was the most abundant alkaloid in cotyledons (12 weeks after seeding) and leaves (24 weeks after seeding) in both var. coca and var. novogranatense. After 52 weeks of seeding growth, cocaine was the preeminent alkaloid in leaves of both taxons with a cocaine content of 0.66 percent in var. coca and 1.04 percent in var. novogranatense.
110. E. L. Johnson and C. D. Foy, “Biomass Accumulation and Alkaloid Content in Leaves of Erythroxylum Coca and Erythroxylum Novogranatense Var. Novogranatense Grown in Soil with Varying pH,” Journal of Plant Physiology, vol. 149, no. 3, pp. 444–450, Jan. 1996. doi: 10.1016/S0176-1617(96)80147-7. Abstract
     Erythroxylum coca var. coca Lam. (E. coca) and Erythroxylum novogranatense var. novogranatense (Morris) Hieron (E. novo, novogranatense) were grown in greenhouse pots of Monmouth sandy loam, over a pH range of 3.5 through 7.0, to determine patterns for biomass accumulation and the content of hygrine, tropinone, methyl ecgonine, cuscohygrine, tropacocaine, cocaine, cis- and trans-cinnamoylcocaine in their leaves. Optimal growth for E. coca occurred at pH 3.5, and for E. novo. novogranatense at pH 4.7 through 6.0. The pH extreme (sub-optimal biomass accumulation, above and below optimal pH) for E. coca was ≥6.5 and for E. novo, novogranatense ≤ 3.5 and ≥ 6.5. Hence, E. coca is tentatively termed a calcifuge (Al-tolerant, Fe-inefficient) while E. novo. novogranatense more nearly resembles a calcicole (Fe-efficient, Alsensitive). Increases in leaf alkaloid content observed at the pH extremes for E. coca and E. novo, novogranatense appeared to be caused by plant stress. E. novo. novogranatense was more tolerant to the high pH extreme than E. coca. Twenty-two months after transplanting, 55% of E. coca plants grown at soil pH 7.0 died, and those that remained were chlorotic. In addition, among E. coca plants grown at soil pH 6.5, only 55 % were alive at the third harvest. Cocaine concentration in E. coca was independent of leaf biomass. Leaves of E. coca grown in soil at pH 3.5 through 6.0 had higher concentrations of cocaine than those of E. novo. novogranatense. Conversely, leaves of E. novo. novogranatense contained a higher concentration of trans- and cis-cinnamoylcocaine and methyl ecgonine than those of E. coca. The least abundant alkaloid observed in E. coca and E. novo. novogranatense was tropinone which was low or commonly not detected. Of the eight alkaloids monitored in leaves of E. novo. novogranatense grown in soils at various pH levels, methyl ecgonine was the most abundant.
111. E. M. A. N. U. E. L. L. JOHNSON and M. A. H. M. O. U. D. A. ELSOHLY, “Content and De Novo Synthesis of Cocaine in Embryos and Endosperms from Fruit of Erythroxylum Coca Lam,” Annals of Botany, vol. 68, no. 5, pp. 451–453, Nov. 1991. doi: 10.1093/oxfordjournals.aob.a088277. Abstract
     There is controversy as to whether the mature fruit of Erythroxylum coca var. coca Lam. contains the cocaine alkaloid (benzoylmethylecgonine). In the present study, cocaine was monitored to determine if it was present in embryos and endosperms of mature fruit of E. coca var. coca Lam., and if present, the time required for de novo synthesis in imbibing seed. Seeds from mature fruit of E. coca were dissected to separate the embryos from the endosperms. The separated embryos and endosperms were analysed for cocaine. Subsequently, endosperms and embryos from seed imbibed. under a light and dark treatment were separated on days 3, 6, 9, 12 and 15 and analysed for cocaine. Cocaine was present in embryos (0.005% of d. wt) and endosperms (0–001% of d. wt) of mature fruit of E. coca. De novo synthesis of cocaine occurred only in embryos of seed imbibed under light after day 9 of imbibition.
112. E. L. Johnson, “Diurnal Fluctuations of Cocaine and Potential Precursors in Leaves of Erythroxylum Coca,” Zeitschrift für Naturforschung C, vol. 48, no. 11-12, pp. 863–866, Dec. 1993. doi: 10.1515/znc-1993-11-1208. Abstract
     Cocaine is abundant in leaves of Erythroxylum coca var. coca Lam. Consequently, cocaine and two of its early biosynthetic precursors were monitored for 24 h to determine whether they fluctuated diurnally. E. coca was grown under controlled environmental conditions in a growth chamber in soil at pH 3.5. After 17.5 months of growth, leaves not less than 35 days old were harvested every 2 and 4 h for 24 h for arginine, phenylalanine and cocaine content, respectively. The content of cocaine was determined by GC/MS and amino acid content by HPLC. Diurnal fluctuation of cocaine occurred during the 24 h cycle. Cocaine was highest in leaves of E. coca at 8 and 16 h where its content was 7.67 and 9.45 mg·g -1 dry weight, respectively. Arginine and phenylalanine in leaves of E. coca also displayed diurnal rhythmic patterns of fluctuation. The content of arginine declined from hours 6 to 12 and increased to the highest content at 13 h (21.8 mg·g -1 dry weight). Overall, phenylalanine content was lower than arginine, but had two peak periods of accumulation during the 24 h cycle, occurring at 8 and 14 h. The content of phenylalanine in leaves of E. coca during the peak hours was 6.98 and 6.54 mg·g -1 dry weight, respectively.
113. E. L. Johnson, T. A. Campbell, and C. D. Foy, “Effect of Soil pH on Mineral Element Concentrations of Two Erythroxylum Species,” Journal of Plant Nutrition, vol. 20, no. 11, pp. 1503–1515, Nov. 1997. doi: 10.1080/01904169709365352. Abstract
     Erythroxylum coca var. coca Lam. (E. coca) and Erythroxylum novogranatense var. novogranatense (Morris) Hieron (E. n. novogranatense) are two of four Erythroxylum species grown in the tropics of South America for cultural medicines and the alkaloid benzoylmethylecgonine. In a published study of biomass production over a soil pH range of 3.5 to 7.0, E. coca grew best at a pH equal to and below 5.5, and E. n. novogranatense grew best within the pH range of 4.7 to 6.0. Erythroxylum coca was tentatively classified as more tolerant to metal toxicities [aluminum (Al) and manganese (Mn)] than E. n. novogranatense, however, concentration patterns of mineral elements for E. coca and E. n. novogranatense tissue have not been reported, nor have the mechanisms of differential acid‐soil‐tolerance been elucidated. In the current study, the effects of soil pH on concentrations of Al, calcium (Ca), copper (Cu), iron (Fe), potassium (K), magnesium (Mg), Mn, and zinc (Zn) in leaves, stems, and roots were investigated. At pH 3.5, roots of both species accumulated high concentrations of Al that decreased as soil pH increased, however, there was no pH × species interaction. The highest concentration of Ca was found in the leaves of both species, however, E. coca accumulated more Ca as soil pH increased than did E. n. novogranatense. Manganese and Zn levels were highest in roots of both species (E. coca and E. n. novogranatense); levels in all tissues decreased with increasing pH. Manganese concentration was highest in roots of E. coca and Zn concentration was highest in tissues of E. n. novogranatense. Copper, Fe, K, and Mg levels were erratic with increasing pH, indicating that sufficient amounts of these nutrients are acquired at low pH levels. Root concentrations of Fe and K in E. coca increased markedly between pH 3.5 and 4.7. At pH 3.5, E. coca demonstrated no symptoms of mineral deficiency and/or toxicity, however, chlorosis, leaf distortion and root atrophy were prevalent at pH 6.5 and 7.0. By contrast, E. n. novogranatense demonstrated diminished growth and root atrophy at soil pH 3.5, whereas at pH 6.5 and 7.0, although biomass production was reduced, no symptoms of mineral deficiency and/or toxicity were present. The species obviously behave differentially at pH extremes and E. coca appears to be most tolerant of extremely acid soils; the two species may also differ in mineral sensitivities between the species at higher pH levels. Erythroxylum coca may compete more effectively with Al for Ca binding sites within the root, and may have greater internal tolerance of Mn, compared with E. n. novogranatense.
114. E. L. Johnson and W. F. Schmidt, “Flavonoids as Chemotaxonomic Markers for Erythroxylum Ulei,” Zeitschrift für Naturforschung C, vol. 54, no. 11, pp. 881–888, Nov. 1999. doi: 10.1515/znc-1999-1105. Abstract
     Leaf extracts of Erythroxylum ulei O. E. Schulz, produced six O-conjugated flavonoids. Three of the flavonoid aglycones were isoflavones, two were isoflavanones and the remainder a flavonol (quercetin). The major glycosides of these flavonols included mono-and dirham-nosides, mono-glucosides and galactosides with either 3̕ 4̕, or 7 linkage or a combination thereof. The two isoflavanones, in addition to being glycosylated, possessed a methyl group at position 2 of the C-ring. These flavonoids may be used as chemotaxonomic markers for the taxon.
115. E. L. Johnson, W. F. Schmidt, and D. Cooper, “Flavonoids as Chemotaxonomic Markers for Cultivated Amazonian Coca,” Plant Physiology and Biochemistry, vol. 40, no. 1, pp. 89–95, Jan. 2002. doi: 10.1016/S0981-9428(01)01348-1. Abstract
     Purported ‘Amazonian coca,’ Erythroxylum coca var. ipadu Plowman (E. coca var. ipadu) was harvested from cultivated fields in Colombia, South America to determine: (a) its identity; (b) if its leaf flavonoids were complimentary to those present in leaf tissue of E. c. var. ipadu in our collection derived from Colombia; and (c) if complimentary, indicative of kinship to E. coca var. ipadu obtained from Colombia, or a related Erythroxylum taxon. Leaf extracts from Amazonian field-grown coca afforded eight O-conjugated flavonoids: two O-conjugates of taxifolin, one O-conjugate of quercetin, two O-conjugates of eriodictyol and three O-conjugates of kaempferol. Present also in leaf tissue of Amazonian field-grown coca, but lacking in leaf tissue from our collection of E. c. var. ipadu was an O-ethyl ester typically found in E. coca var. coca, kaempferols and a 7-O-rutinoside commonly encountered in the E. novogranatense taxons. Flavonoids found in our collection of E. coca var. ipadu were five O-conjugated derivatives of taxifolin and an O-conjugated quercetin. Leaf flavonoids of currently cultivated Amazonian coca are a mixture of those present in E. coca var. coca, E. coca var. ipadu and E. novogranatense var. truxillense, whereas those present in our authenticated living collection are derivatives of E. coca var. coca. Our data suggest that the Amazonian coca under cultivation in Colombia is a genetic hybrid cross between E. coca var. coca and E. novogranatense var. truxillense, occurring after 1972.
116. E. L. Johnson and W. F. Schmidt, “Flavonoids as Chemotaxonomic Markers for Erythroxylum Australe,” Zeitschrift für Naturforschung C, vol. 59, no. 11-12, pp. 769–776, Dec. 2004. doi: 10.1515/znc-2004-11-1201. Abstract
     Methanolic leaf extracts of Erythroxylum australe F. Muell. produced eight O-conjugated flavonoids. Six of the flavonoid aglycones were dihydroisoflavones (all dihydro-orobol derivatives), one a flavanone, eriodictyol, and one a flavonol, quercetin. The major glycosides of the flavonoids included mono-glucosyl-rhamnosyls and dirhamnosyl-glucosides with either 3,5,7 or 3′,4′ linkage or a combination thereof. The array of flavonoids present in E. australe suggests kinship to E. ulei and linkage to the four cultivated alkaloid-bearing Erythroxylum, especially the ancestral E. coca var. coca. Because of the uniqueness of the flavonoids present in leaf tissue of E. australe they are unambiguously useful as chemotaxonomic markers for the taxon.
117. E. L. Johnson, J. A. Saunders, S. Mischke, C. S. Helling, and S. D. Emche, “Identification of Erythroxylum Taxa by AFLP DNA Analysis,” Phytochemistry, vol. 64, no. 1, pp. 187–197, Sep. 2003. doi: 10.1016/S0031-9422(03)00206-1. Abstract
     Erythroxylum coca, indigenous to the Andean region of South America, is grown historically as a source of homeopathic medicine. However, in the last century, cultivation of E. coca and several closely-related species for the production of illicit cocaine has become a major global problem. Two subspecies, E. coca var. coca and E. coca var. ipadu, are almost indistinguishable phenotypically; a related cocaine-bearing species also has two subspecies (E. novogranatense var. novogranatense and E. novogranatense var. truxillense) that are phenotypically similar, but morphologically distinguishable. The purpose of this research was to discover unique AFLP DNA patterns (“genetic fingerprinting”) that characterize the four taxa and then, if successful, to evaluate this approach for positive identification of the various species of coca. Of seven different AFLP primer pairs tested, a combination of five proved optimal in differentiating the four taxa as well as a non-cocaine-bearing species, E. aerolatum. This method of DNA fragment separation was selective, and faster, for coca identification, compared with analyses based on flavonoid chemotaxonomy. Using the 5-primer AFLP approach, 132 known and unknown coca leaf accessions were evaluated. Of these, 38 were collected in 1997–2001 from illicit coca fields in Colombia, and all were genetically differentiated from coca originating in Peru and Bolivia. Based on the DNA profiling, we believe that the Colombian coca now represents a hybridization of E. coca var. ipadu. Geographical profiling within Colombia also seems feasible as new coca production areas are developed or new types of coca are introduced within traditional growing areas.
118. E. L. Johnson, “Inter- and Intra-Specific Variation among Five Erythroxylum Taxa Assessed by AFLP,” Annals of Botany, vol. 95, no. 4, pp. 601–608, Jan. 2005. doi: 10.1093/aob/mci062.
119. E. L. Johnson, W. F. Schmidt, S. D. Emche, M. M. Mossoba, and S. M. Musser, “Kaempferol (Rhamnosyl) Glucoside, a New Flavonol from Erythroxylum Coca. Var.Ipadu,” Biochemical Systematics and Ecology, vol. 31, no. 1, pp. 59–67, Jan. 2003. doi: 10.1016/S0305-1978(02)00071-6. Abstract
     A new flavonol, kaempferol rhamnosyl diglycoside, was isolated from leaf tissue of Amazonian field-grown coca Erythroxylum coca var. ipadu Plowman. The structure of the flavonol has been determined as kaempferol 4′-O-(rhamnosyl)glucoside by spectral analyses. The array of flavonoids present in E. c. var. ipadu currently under cultivation in Colombian fields is indicative of a recent cross, consistent with ancestralship to E. c. var. coca and the flavonol is useful as a chemotaxonomic marker for the taxon.
120. E. L. Johnson, W. F. Schmidt, and H. A. Norman, “Leaf Flavonoids as Chemotaxonomic Markers for Two Erythroxylum Taxa,” Zeitschrift für Naturforschung C, vol. 52, no. 9-10, pp. 577–585, Oct. 1997. doi: 10.1515/znc-1997-9-1004. Abstract
     Leaf extracts of Erythroxylum coca var. coca Lam. (E. c. var. coca) yielded six O-eonjugates of Eriodictyol flavonoids, while the equivalent extracts from Erythroxylum novogranatense var. novogranatense (Morris) Hieron (E. n. var. novogranatense) contained five flavonoids, two of which were O-conjugates of Luteolin and three were O-conjugates of Kaempferol. All six of E. c. var. coca methanolic extracted peaks (resolved by HPLC) were found to have a 2, 3 single bond, which in E. n. var. novogranatense is replaced by a 2- hydroxy allene. The other primary difference in the predominant flavonoids between these taxa is the chemical composition of the sugar and/or acyl O-conjugation and site(s) at which this conjugation occurred. The results suggest that the most abundant O-conjugated flavonoids of E. c. var. coca and E. n. var. novogranatense may be used as chemotaxonomic markers for the two taxa. Therefore, the O-conjugated peaks of Eriodictyol , are distinct chemotaxonomic markers for E. c. var. coca and the O-conjugated peaks Luteolin and Kaempferol for E. n. var. novogranatense. These taxa are two of the four cultivated Erythroxylum taxa that contain commercial quantities of the cocaine alkaloid in their leaves, this entity also sets apart the taxa from other members of Erythroxylum. We suggest that the biochemistry of flavonoids of other Erythroxylum taxa may also be species selective
121. E. L. Johnson, “Seed Viability of Two Erythroxylum Species Stored at 4 °C,” Planta Medica, vol. 55, no. 7, pp. 691–691, Dec. 1989. doi: 10.1055/s-2006-962311. Abstract
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122. E. L. Johnson, S.-H. Kim, and S. D. Emche, “Storage Effects on Genomic DNA in Rolled and Mature Coca Leaves,” BioTechniques, vol. 35, no. 2, pp. 310–316, Aug. 2003. doi: 10.2144/03352st03. Abstract
     Rolled and mature leaf tissue was harvested from Erythroxylum coca var. coca Lam. (coca) to determine a method for storage that would maintain DNA with high quality and content up to 50 days. Harvesting coca leaf tissue under Andean field conditions often requires storage from 3 to 10 days before extraction where tissue integrity is lost. All samples of rolled and mature coca leaf tissue were harvested and separately stored fresh in RNAlaterTM for 50 days at 4°, −20°, and 23°C, while similar samples were air-dried for 72 h at 23°C or ovendried for 72 h at 40°C after storage, before extraction. Triplicate samples of each tissue type were extracted for DNA at 10-day intervals and showed that DNA integrity and content were preserved in leaf tissue stored at 4° and −20°C for 50 days. Rolled and mature leaf tissue stored at 4°, −20°, and 23°C showed insignificant degradation of DNA after 10 days, and by day 50, only leaf tissue stored at 4° and −20°C had not significantly degraded. All air- and oven-dried leaf tissue extracts showed degradation upon drying (day 0) and continuous degradation up to day 50, despite storage conditions. Amplified fragment length polymorphism analysis of DNA from rolled and mature leaf tissue of coca stored at 4° and −20°C for 0, 10, and 50 days showed that DNA integrity and content were preserved. We recommend that freshly harvested rolled or mature coca leaf tissue be stored at 4°, −20°, and 23°C for 10 days after harvest, and if a longer storage is required, then store at 4° or −20°C.
123. E. L. Johnson and S. D. Emche, “Variation of Alkaloid Content in Erythroxylum Coca Leaves from Leaf Bud to Leaf Drop,” Annals of Botany, vol. 73, no. 6, pp. 645–650, Jun. 1994. doi: 10.1006/anbo.1994.1081. Abstract
     A sequential study describing the content (%) of alkaloids in leaves of Erythroxylum coca var. coca Lam. from leaf bud development to leaf drop has not previously been conducted. The length of time the leaf resides on the plant and its concurrent metabolic activity also has not been defined. In the present study, cocaine, methyl ecgonine, hygrine, tropinone, trans -cinnamoylcocaine, cis-cinnamoylcocaine, tropacocaine and cuscohygrine were monitored to determine: (1) their content and patterns of accumulation from leaf bud to leaf drop; (2) the time leaves resided on the plant; and (3) whether leaves were metabolically active until leaf drop. E. coca plants were grown in a controlled environment for 37 months. Leaves similar in chronological age were extracted and analysed for alkaloid content by gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS). Cocaine was highest in 7 d old rolled leaves (0·75%) and declined to 0·39% at leaf drop. Cocaine, methyl ecgonine, hygrine, tropinone, trans -cinnamoylcocaine, cis-cinnamoylcocaine, cuscohygrine and tropacocaine content in 35 d old (mature) leaves was 0·61, 0·59, 0·68, 0·08, 0·31, 0·55, 0·52, and 0·05%. respectively. Cocaine, methyl ecgonine, hygrine, cis -cinnamoylcocaine, and cuscohygrine displayed a gradual decline from week 2 to week 36 of leaf duration. Tropinone and tropacocaine were the least abundant of the alkaloids monitored. Cis-cinnamoylcocaine content exceeded cocaine at week 12, 16, and weeks 19 to 23 of leaf duration. Trans -cinnamoylcocaine was highest in rolled leaves (week 1) and in expanded leaves after week 30. The monitored alkaloids appeared to be part of the metabolically active pool of the leaf. Leaves remained on the E. coca plants for 36 weeks.
124. S. Katib and K. Rungsihirunrat, “Macroscopic-Microscopic Characteristics and AFLP Fingerprint for Identification of Erythroxylum Novogranatense, E. Cambodianum and E. Cuneatum Endemic to Thailand,” undefined, 2020. https://www.semanticscholar.org/paper/Macroscopic-microscopic-characteristics-and-AFLP-of-Katib-Rungsihirunrat/999d08359dd2aea358194839c70c0506d1de01a8. Abstract
     The combination of morphological characteristics, microscopic investigation and AFLP ingerprinting can be used to identify plant species and determine the genetic relationship among three Erythroxylum species. Erythroxylum novogranatense (Morris) Hieron, E. cambodianum Pierre and E. cuneatum (Miq.) Kurz in family Erythroxylaceae was traditionally used as an antipyretic, general stimulant and gastrointestinal diseases. Due to their morphological similarity, the correct identi ication was necessary for the quality control in herbal medicine. E. novogranatense (Morris) Hieron, E. cambodianum Pierre and E. cuneatum (Miq.) Macroscopic andmicroscopic characteristics evaluated Kurz endemic to Thailand according to WHO standard guideline and ampli ied fragment length polymorphism (AFLP) ingerprint. Morphological characters of E. novogranatense, E. cambodianum and E. cuneatum were similar in their lower, fruit and seed but different in stem and leaf. Microscopic characteristics from these three species, including constant leaf numbers, showed individual values. The stomata were classi ied as paracytic type. The midrib transverse section showed distinct characters of the epidermis, palisade cell, stomata, spongy cell, parenchyma, xylem vessel, phloem tissue and collenchyma. AFLP ingerprint showed highly polymorphisms 97.42% with the number of bands (349 bands) ranging between 50-750 bands. Primer E+ACG/M+CTT had the highest number of AFLP band (91 bands). The dendrogram generated from UPGMA could separate these three species. In summary, the combination of morphological characteristics, microscopic investigation and AFLP ingerprinting can be used to identify plant species and determine the genetic relationship among three Erythroxylum species.
125. N. Kim, “Tropane Alkaloid Biosynthesis in Erythroxylum Coca Involves an Atypical Type III Polyketide Synthase,” Doctor of Philosophy, Texas Tech University, 2020. https://ttu-ir.tdl.org/handle/2346/85851. Abstract
     Alkaloids represent 20% of all specialized metabolites. These important compounds are produced by plants to protect themselves from biotic or abiotic forces they may encounter. Tropane alkaloids and granatane alkaloids possess a wide array of pharmaceutical properties. Understanding the enzymes involved in the biosynthesis of these compounds will give a better insight on their evolutionary origins. This will aid synthetic biology endeavors to produce high yields of these important specialized metabolites. Although the biosynthesis of tropane alkaloids is well studied in the Solanaceae family, it is still not fully elucidated in the Erythroxylaceae family. Previous studies on these two families hypothesize a polyphyletic origin of enzymes. As more enzymes within the pathway are characterized, endeavors to metabolically engineer these pharmacologically active metabolites will increase. Here, I report a new atypical type III polyketide synthase enzyme from the Erythroxylaceae family involved in tropane alkaloid production. This unique enzyme also differs from that reported in the Solanaceae family. Furthermore, a similar enzyme involved in granatane alkaloid biosynthesis will be investigated.
126. J.-B. Lamarck and J.-L.-M. Poiret, Encyclopédie Méthodique. Botanique, vol. 2. Paris,Liège: Panckoucke;Plomteux, 1786, pp. 1–776. https://www.biodiversitylibrary.org/item/15260.
127. E. Leete, “2,3-Dehydrococaine: Not a Direct Precursor of Cocaine in Erythroxylum Coca,” Journal of Natural Products, vol. 50, no. 1, pp. 30–35, Jan. 1987. doi: 10.1021/np50049a005.
128. E. Leete, “Biosynthesis of Cocaine and Cuscohygrine in Erythroxylon Coca,” Journal of the Chemical Society, Chemical Communications, no. 23, pp. 1170–1171, Jan. 1980. doi: 10.1039/C39800001170. Abstract
     DL-[5-14C]Ornithine is a specific precursor of cocaine and cuscohygrine, and a degradation of the latter alkaloid suggests that this amino-acid is incorporated via a symmetrical intermediate.
129. E. Leete, “Biosynthesis of Cocaine and Cuscohygrine from [1-14C]Acetate and [4-3H]Phenylalanine in Erythroxylon Coca,” Phytochemistry, vol. 22, no. 3, pp. 699–704, Jan. 1983. doi: 10.1016/S0031-9422(00)86965-4. Abstract
     A mixture of sodium [1-14C]acetate and DL-[4-3H]phenylalanine (3H/14C  1.0) was administered to Erythroxylon coca plants by painting an aqueous solution of these compounds on the leaves. The leaves were removed after two weeks and yielded labeled cocaine (3H/14C  11.4)and cuscohygrine. A systematic degradation of the cocaine indicated that 96% of the 3H was located in the para-position of its benzoyl moiety, and the 14C was located in the ecgonine residue at positions in accord with the accepted biosynthesis of this alkaloid. The cuscohygrine, containing a negligible amount of 3H, was found to have 67% of its 14C located on the carbonyl carbon. Cocaine, isolated from a second crop of leaves, harvested 10 weeks after the initial feeding, was still labeled at specific positions.
130. E. Leete, J. A. Bjorklund, and H. K. Sung, “The Biosynthesis of the Benzoyl Moiety of Cocaine,” Phytochemistry, vol. 27, no. 8, pp. 2553–2556, Jan. 1988. doi: 10.1016/0031-9422(88)87026-2. Abstract
     [carboxyl-13C,14C]Benzoic acid,[carbonyl-13C,14C]-and [4-3H]-benzoic acid, S-(2-acetamidoethyl)ester served as precursors of the benzoyl moiety of cocaine when fed, by leaf painting, to Erythroxylum coca plants. The high (10.5%) specific incorporation, of the 13C-labelled thioester was established by 13C NMR. Aqueous Tween 80 was found to have a significant effect on the degree of incorporation of the benzoic acid, presumably facilitating the transport of the labelled compound through the leaf wax. A major component of the leaf wax is hentriacontane.
131. E. Leete, “Biosynthesis of the Pyrrolidine Rings of Cocaine and Cuscohygrine from [5-14C]-Ornithine via a Symmetrical Intermediate,” ACS Publications. American Chemical Society, May-2002. doi: 10.1021/ja00369a042.
132. E. Leete, S. H. Kim, and J. Rana, “The Incorporation of [2-13C,14C,15N]-1-Methyl-Δ1-Pyrrolinium Chloride into Cuscohygrine in Erythroxylum Coca,” Phytochemistry, vol. 27, no. 2, pp. 401–406, Jan. 1988. doi: 10.1016/0031-9422(88)83107-8. Abstract
     [2-13C,14C,15N]-1-Methyl-Δ1-pyrrolinium chloride was synthesized from potassium [13C,14C]cyanide and [15N]methylamine. The λmax at 267 nm previously reported for this iminium salt, was shown to be due to an impurity. Feth, F. et al. Phytochemistry24, 1653). The structure of this impurity was established as 1-methyl-3-(E)-(4′-methylaminobutylidene)-Δ1-pyrrolinium chloride formed by the acid cleavage of the dimer of the iminium salt. Administration of the labelled pyrrolinium salt to Erythroxylum coca plants resulted in the formation of radioactive cuscohygrine (specific inc. of14C: 0.25 %). The13CNMR spectrum of this alkaloid exhibited satellites at the signals due to C-2 and C-2′ arising from coupling of these carbons with the adjacent15N. The multiplicity of signals in the13C NMR spectrum of both natural and synthetic cuscohygrine indicated that the alkaloid is a mixture of its meso, (2 S,2′R), and optically active (2S,2′S), (2R,2′R), diastereomers.
133. E. Leete, “Recent Developments in the Biosynthesis of the Tropane Alkaloids1,” Planta Medica, vol. 56, no. 4, pp. 339–352, Aug. 1990. doi: 10.1055/s-2006-960979. Abstract
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134. J. Lemli, “[Iconography of the coca plant,” Verhandelingen - Koninklijke Academie voor Geneeskunde van Belgie, vol. 53, no. 5, pp. 437–462, Jan. 1991. Abstract
     We can distinguish four periods in the iconography of the cocaplant, namely the prehispanic period in South-America, the early period in Europe, from 1749 until 1860, the period of confusion (1860-1906) and finally the period of modern iconography. The iconography of the cocaplant before the arrival of the Spanish invaders was limited to the drawing of cocaleaves. In Europe, the first people who showed any interest for the cocaplant were the botanists. In the second half of the XVIIIth century, the botanists made especially good drawings of Erythroxylum coca. From the second half of the XIXth century, the industry became interested in coca and, consequently, a very intensive research arose, coming from several directions. This led to the discovery of new species, at that time often described by non botanists. This resulted in discussions and in serious confusion as to the nomenclature. Excellent pictures were however produced in this period. During the XXth century fundamental botanical research resulted in the final classification of the different coca species. The quality of the pictures was however not better.
135. Á. M. López et al., “Implementación de una extracción dinámica con disolvente asistida por sonicación (DSASE) en matrices de hoja de Erythroxylum coca para el posterior análisis de cocaína por cromatografía de gases con detector de ionización de llama (CG FID),” Scientia Chromatographica, vol. 8, no. 2, pp. 115–120, 2016. doi: 10.4322/sc.2016.022. Abstract
     The sample preparation technique called dynamic-assisted solvent extraction by sonication (DSASE) that uses sound waves to increase the efficiency of extraction of cocaine Erythroxylum coca leaves was implemented, evaluating different solvents and extraction time; for subsequent analysis by gas chromatography with flame ionization detector (GC-FID). The results show that the conditions for obtaining alkaloid are methanol: dichloromethane (20:80 v/v) with 25 min extraction at 50 ° C and 50 Hz; DSASE was coupled to the solid phase extraction (SPE) with conditions 1 mL of ethanol, 2 mL of sample, 1 mL of hexane and 1 mL of methanol: acetonitrile (20:80 v/v) for conditioning, loading, washing and elution respectively.
136. J. Lucas da Costa-Lima and E. Celestino de Oliveira Chagas, “Two New Species of Erythroxylum (Erythroxylaceae) from the EspinhaçoRange, Eastern Brazil,” Systematic Botany, vol. 45, no. 1, pp. 96–101, Feb. 2020. doi: 10.1600/036364420X15801369352351. Abstract
     Abstract— Two new species of Erythroxylum endemic to the Espinhaço Range, in eastern Brazil, are described. Erythroxylum itan occurs in seasonal forest on hilltops in the Itacambiruçu River valley, in the Grão Mogol region of northern Minas Gerais, and E. kanga occurs in campo rupestre and cerrado vegetation along the Espinhaço Range, in the states of Bahia and Minas Gerais. The new species are compared with morphologically similar species and illustrations and comments about distribution and habitat are provided. In addition, we present an updated list of Erythroxylum species from the Espinhaço Range.
137. K. Luck, J. Jirschitzka, S. Irmisch, M. Huber, J. Gershenzon, and T. G. Köllner, “CYP79D Enzymes Contribute to Jasmonic Acid-Induced Formation of Aldoximes and Other Nitrogenous Volatiles in Two Erythroxylum Species,” BMC Plant Biology, vol. 16, no. 1, p. 215, Oct. 2016. doi: 10.1186/s12870-016-0910-5. Abstract
     Amino acid-derived aldoximes and nitriles play important roles in plant defence. They are well-known as precursors for constitutive defence compounds such as cyanogenic glucosides and glucosinolates, but are also released as volatiles after insect feeding. Cytochrome P450 monooxygenases (CYP) of the CYP79 family catalyze the formation of aldoximes from the corresponding amino acids. However, the majority of CYP79s characterized so far are involved in cyanogenic glucoside or glucosinolate biosynthesis and only a few have been reported to be responsible for nitrogenous volatile production.
138. Y. Lv, T. Tian, Y.-J. Wang, J.-P. Huang, and S.-X. Huang, “Advances in Chemistry and Bioactivity of the Genus Erythroxylum,” Natural Products and Bioprospecting, vol. 12, no. 1, p. 15, Apr. 2022. doi: 10.1007/s13659-022-00338-z. Abstract
     Erythroxylum P. Browne is the largest and most representative genus of Erythroxylaceae family. It contains approximately 230 species that are mainly distributed in tropical and subtropical regions. Some species in this genus, such as E. monogynum and E. coca, have been used as folk medicines in India or South America for a long history. It is well known that Erythroxylum plants are rich in tropane alkaloids, and the representative member cocaine shows remarkable activity in human central nervous system. However, many other types of active compounds have also been found in Erythroxylum along with the broadening and deepening of phytochemical research. To date, a total of 383 compounds from Erythroxylum have been reported, among which only 186 tropane alkaloids have been reviewed in 2010. In this review, we summarized all remained 197 compounds characterized from 53 Erythroxylum species from 1960 to 2021, which include diterpenes, triterpenes, alkaloids, flavonoids, and other derivates, providing a comprehensive overview of phytoconstituents profile of Erythroxylum plants. In addition, the biological activities of representative phytochemicals and crude extracts were also highlighted.
139. J. Lydon, J. F. Casale, H. Kong, J. H. Sullivan, C. S. T. Daughtry, and B. Bailey, “The Effects of Ambient Solar UV Radiation on Alkaloid Production by Erythroxylum Novogranatense Var. Novogranatense†,” Photochemistry and Photobiology, vol. 85, no. 5, pp. 1156–1161, 2009. doi: 10.1111/j.1751-1097.2009.00562.x. Abstract
     Truxillines are alkaloids produced by Erythroxylum species and are thought to be derived from the UV-driven dimerization of cinnamoylcocaines. This study was conducted to determine the effects of ambient UV radiation on the production of truxillines in Erythroxylum novogranatense var. novogranatense. Field plants were grown under shelters covered with plastic filters that were transparent to UV radiation, filtered UV-B, or both filtered UV-B and UV-A radiation. The treatments had no significant effect on plant biomass or specific leaf weight. Absorption values in the UV-C and UV-A region of acidified-methanol leaf extracts were higher for plants exposed to UV radiation compared to the no UV radiation treatment. There was a trend in decreasing levels of trans-cinnamoylcocaine and a statistically significant decrease in levels of cis-cinnamoylcocaine in the leaves of plants exposed to UV radiation compared to the no UV radiation treatment. Truxilline levels increased in leaves from plants exposed to UV radiation compared to the no UV radiation treatment. Most significantly, the ratio of truxillines to total cinnamoylcocaines in the leaves was affected by UV, increasing with increased UV exposure. The results support the hypothesis that UV radiation is involved in the formation of truxillines from cinnamoylcocaines.
140. J. Lydon and L. Darlington, “Herbicide Residues in Leaves of Erythroxylvm Coca Var Coca Plants Treated with Soil‐applied Tebuthiuron and Hexazinone,” Journal of Environmental Science and Health, Part B, vol. 33, no. 5, pp. 581–594, Sep. 1998. doi: 10.1080/03601239809373164. Abstract
     The herbicide residue levels in leaves of Erythroxylum coca var. coca Lam. plants treated with soil applications of tebuthiuron and hexazinone at 3.36 and 6.72 kg a.i. ha‐1 were determined in order to estimate the potential for human exposure to these residues from consuming the leaves or cocaine produced from them. Field‐grown plants were treated with a commercial formulation of tebuthiuron or hexazinone and leaves were harvested at the first indication of herbicide injury (i.e. chlorosis and/or necrosis) and at the onset of leaf abscission. Herbicide residues were detected by HPLC in leaf samples from both harvests of all plants treated with tebuthiuron or hexazinone. At 3.36 kg ha‐1, herbicide residues in the leaves were less than 2 μg g‐1 dry wt. for both harvests of both experiments. The highest residue levels detected were 5.90 μg g‐1 dry wt. for tebuthiuron and 7.17 μg g‐1 dry wt. for hexazinone in leaves from plants treated with the herbicide at the rate of 6.72 kg ha‐1 and harvested at the onset of leaf drop. Based on published toxicity data and estimates of leaf consumption, the herbicide residues in leaves of E. coca var. coca plants treated with tebuthiuron or hexazinone at twice the recommended control rates or less would have a negligible contribution to the health risks of individuals who chew coca leaves. Furthermore, based on the most conservative estimates of cocaine yield and herbicide carry over, death by cocaine overdose would occur long before the NOEL for either herbicide was reached.
141. J. Lydon, R. H. Zimmerman, I. M. Fordham, and W. R. Lusby, “Tissue Culture and Alkaloid Production of Erthroxylum Coca Var. Coca,” Journal of Herbs, Spices & Medicinal Plants, vol. 2, no. 1, pp. 3–14, Dec. 1993. doi: 10.1300/J044v02n01_02. Abstract
     A tissue culture method was developed to study the biosynthesis of alkaloids in Erythroxylum coca var. coca. Shoot cultures were established from excised embryos of seed from Erythyroxylum coca var. coca and grown on a semi-solid medium. Alkaloids extracted from leaves of shoot cultures and the parent plant were identified by gas chromatography-mass spectrometric (GC/MS) analysis and quanitifed by gas chromatography. Shoot cultures that were developed from one Erythroxylum coca var. coca plant produced the major and minor alkaloids common to the species. The cocaine levels of the shoot cultures were 50 percent of that produced by the parent plant but within the range reported for the species. Maximal levels of cocaine were produced in the leaves of shoot cultures within eight days after transfer to fresh media. The production of alkaloids in the shoot cultures demonstrates that roots are not necessary for tropane alkaloid production in Erythroxylum coca var. coca.
142. J. D. Lynch and S. B. Arroyo, “Risks to Colombian Amphibian Fauna from Cultivation of Coca (Erythroxylum Coca): A Geographical Analysis,” Journal of Toxicology and Environmental Health, Part A, vol. 72, no. 15-16, pp. 974–985, Aug. 2009. doi: 10.1080/15287390902929733. Abstract
     The Colombian amphibian fauna is among the richest known in the world, with about 20 species of salamanders (order Caudata), 35 of the limbless caecilians (order Gymnophiona), and more than 700 species of frogs and toads (order Anura) recorded from localities within the country. The potential effects of exposure to glyphosate on amphibians arising from production of illegal crops (coca) were examined. The analysis was based on (1) behavior and ecology of species and (2) proximities of actual museum records to localities in which illegal crops are being grown and the subset of those that have been sprayed with glyphosate. Based on data on the location of amphibians collected in Colombia, records were obtained for 193 species (28% of the national diversity) of frogs and toads found in localities within 10 km of areas where coca is grown. Further analyses with ARC MAP software allowed for measurement of the direct distance separating collection locations for frogs, known coca fields, and areas where aerial spraying was being conducted. Records in or near coca fields included data for 11 of 13 families of frogs and toads known to be present in Colombia. Only Ceratophryidae and Pipidae were not reported from these locations and appear not to be at risk. For eight species (Dendrobates truncatus, Craugastor raniformis, Pristimantis gaigeae, Smilisca phaeota, Elachistocleis ovale, Hypsiboas crepitans, Trachycephalus venulosus, and Pseudis paradoxa) selected to represent several habitat preferences and life-cycle strategies, large areas of their distributions lie outside coca production regions and their populations as a whole are at low risk. For a limited number of species that barely enter Colombian territory, the consequences of coca production may be more serious and may have placed several species of frogs at risk. These include Ameerega bilingua, Dendropsophus bifurcus, Pristimantis colomai, P. degener, P. diadematus, P. quaquaversus, P. variabilis, and Trachycephalus jordani. Other species may also be at risk but exact numbers are unknown since few investigations were undertaken in these areas during the past 30 yr. The main ranges for these species were assumed to be in Ecuador.
143. D. G. Mantuano, C. F. Barros, and F. R. Scarano, “Leaf Anatomy Variation within and between Three ‘Restinga’ Populations of Erythroxylum Ovalifolium Peyr: (Erythroxylaceae) in Southeast Brazil,” Brazilian Journal of Botany, vol. 29, pp. 209–215, Jun. 2006. doi: 10.1590/S0100-84042006000200002. Abstract
     Erythroxylum ovalifolium is a woody shrub widespread in the "restinga", i.e. the open scrub vegetation of the Brazilian coastal sandy plains. We examined leaf anatomy variation of this species both within populations and between populations of three "restingas" in the state of Rio de Janeiro. Sites were ca.100 km far from each other and differed in regard to rainfall and vegetation structure: a dry, open site; a wet, dense site and an intermediate one. Microhabitats within sites were: (i) exposed to full irradiance, outside vegetation islands; (ii) partially exposed to full irradiance, at the border of vegetation islands; (iii) shaded, inside vegetation islands. Leaf anatomy parameters were measured for five leaves collected in each of five plants per microhabitat, in each population; they were thickness of the leaf blade, of the palisade and spongy parenchyma, and of the adaxial and abaxial epidermis. Leaves from the dry, open site had narrower abaxial epidermis and a smaller contribution of spongy parenchyma to total leaf blade thickeness than the other two sites, which we attributed to water stress. Adaxial epidermis and leaf are thicker in more exposed microhabitats (i and ii, above), irrespective of site. We proposed that between-site anatomical variation in traits related to water stress, and within-site anatomical variation in traits related to light-use are indicative of ecological plasticity and might help explain the high abundance of E. ovalifolium in the studied populations and along the State of Rio de Janeiro coast.
144. E. J. P. Marshall, K. R. Solomon, and G. Carrasquilla, “Coca (Erythroxylum Coca) Control Is Affected by Glyphosate Formulations and Adjuvants,” Journal of Toxicology and Environmental Health, Part A, vol. 72, no. 15-16, pp. 930–936, Aug. 2009. doi: 10.1080/15287390902929675. Abstract
     The aerial spray program for the eradication of coca in Colombia uses Glyphos, a local formulation of glyphosate tank-mixed with an adjuvant product, Cosmo-Flux. There are some potential risks to amphibians from direct overspraying of shallow waters. In order to evaluate potential alternative mixtures, a field experiment was conducted at the Center of National Training of Police Operations in Tolima province, Colombia. Plants of coca were established with irrigation and grown to 75 cm tall. A randomized split-plot design experiment was laid out and sprayed with a range of glyphosate formulations and different adjuvants using an experimental ground sprayer. Assessments were made of plant vigor, height, and above-ground standing crop (fresh weight) 3 wk after application. Resprouting of plants was assessed at 9 wk after treatment. Unformulated glyphosate applied as the product Rodeo gave poorer control of coca than two formulated products, Roundup Biactive (from Europe) and Colombian Glyphos. In general, these products performed well without added adjuvants, giving control similar to that of the eradication mixture with Cosmo-Flux. There was some evidence that addition of the adjuvant Silwet L-77 and to a lesser extent Mixture B (from the United Kingdom) gave more rapid herbicide symptoms. There were also indications that glyphosate rates of less than 3.69 kg acid equivalents (a.e.)/ha could give control in the range of 95%. Depending on the environmental risk requirements, the experiment indicates that, should other spray mixtures be required, there are potential alternatives. These would require extensive field testing to cover different environmental conditions, different coca varieties, and particularly aerial application, prior to a recommendation. Should the glyphosate product require changing, Roundup Biactive may be considered. Should the adjuvant require changing, then on the basis of this research, Silwet L-77 and Mixture B would be good candidates for further evaluation.
145. R. T. Martin, “The Role of Coca in the History, Religion, and Medicine of South American Indians,” Economic Botany, vol. 24, no. 4, pp. 422–438, 1970. doi: 10.1007/BF02860746.
146. R. Matias, R. Pérez-Barrales, and H. Consolaro, “Patterns of Variation in Distylous Traits and Reproductive Consequences in Erythroxylum Species and Populations,” American Journal of Botany, vol. 107, no. 6, pp. 910–922, 2020. doi: 10.1002/ajb2.1478. Abstract
     Premise Distylous species possess two floral morphs with reciprocal positioning of stigmas and anthers that is hypothesized to promote disassortative pollination. Theoretical models predict equal morph frequencies, but many populations depart from the expected 1:1 ratio, a pattern that often correlates with asymmetric mating between morphs and/or presence of a weak incompatibility system. Variation in reciprocity can also affect the likelihood of disassortative pollination and, hence, reproductive fitness. Methods We described variation in incompatibility systems and morph ratio in four Erythroxylum species to test if greater deviations from 1:1 ratios occur in populations of self-compatible species. Using adaptive inaccuracy, we described upper and lower organ reciprocity in species and populations and assessed the relationship of reciprocity to population means and coefficients of variation for fruit set to test if reciprocity could predict female reproductive success. Results Morphs occurred in 1:1 ratios in most populations of three Erythroxylum species with distylous self-incompatibility. In self-compatible E. campestre populations showed an excess of the long-styled morph, the short-styled morph, or were monomorphic for the short-styled morph. We detected deviations from reciprocity, with total inaccuracy ranging between 9.39% and 42.94%, and inaccuracy values were lowest in low organs. Across populations, we found a positive relationship between inaccuracy and the coefficient of variation of fruit set. Conclusions Erythroxylum species showed variation in the distylous syndrome, with changes in the incompatibility system that corresponded with deviations from 1:1 morph ratio, and variation in reciprocity that correlated with variation in female reproductive fitness.
147. R. Matias, M. T. Furtado, H. Consolaro, and R. Pérez-Barrales, “Variation in Pollen Sterility and Gender Specialization: An Investigation with Distylous Species of Erythroxylum (Erythroxylaceae),” Plant Biology, vol. 23, no. 6, pp. 947–955, 2021. doi: 10.1111/plb.13310. Abstract
     Differences in pollen sterility between morphs in distylous populations may represent the first step in the evolution of gender specialization. Theoretically, for partially or completely male sterile individuals to persist they must have some fitness advantage that compensates for the loss of male function. Gender specialization is considered a widespread process in Erythroxylum, but male sterility and the resource reallocation to female function have been investigated in few species and populations. In 18 populations of four distylous species of Erythroxylum, we quantified the levels of male sterility, estimated through pollen sterility, in short- and long-styled flowers to test if sterility is morph-biased. In one population per species, we also described the frequency of floral visitors, the production of flowers and fruits, and the quality of fruits and seeds of short- and long-styled plants to evaluate the expression of trade-offs in allocation to male and female function. In some populations of E. campestre and E. deciduum, short-styled flowers possessed higher levels of pollen sterility than long-styled flowers. Although most flowers of E. suberosum and E. tortuosum also expressed pollen sterility, the frequency of sterility was similar between morphs in all populations. Differences in reproductive output between morphs occurred only in populations of species with morph-biased sterility, but none of the variations reflect resource allocation to female fitness of short-styled plants. Differences in the level of sterility between morphs indicates the potential for gender specialization in populations of E. campestre and E. deciduum, despite the apparent lack of a trade-off in allocation.
148. D. Matuskey, “Erythroxylum Coca and Its Discontents: A Neurohistorical Case Study of Cocaine, Pleasure, and Empires,” RCC Perspectives, no. 6, pp. 55–60, 2012. https://www.jstor.org/stable/26240406.
149. R. C. Mayrinck, T. A. A. Vaz, and A. C. Davide, “Classificação Fisiológica De Sementes Florestais Quanto À Tolerância À Dessecação E Ao Comportamento No Armazenamento,” CERNE, vol. 22, no. 1, pp. 85–92, Mar. 2016. doi: 10.1590/01047760201622012064. Abstract
     This work aims to classify forest seeds native to the Alto Rio Grande region regarding the desiccation tolerance and storage behaviour. Germination and water content tests were performed in seeds of different species. The tests were conducted immediately after seed processing, at 12% and 5% of water content, and at 5% after 3 months of storage in -18°C. Based on the results obtained, seeds were classified into recalcitrant, intermediate and orthodox class. Seeds of Brosimum gaudichaudii, Erythroxylum deciduum, Eugenia pleurantha, Myrcia venulosa, Nectandra megapotamica were classified as recalcitrant (22.7% of all species). Seeds of Aegiphila sellowiana, Aspidosperma parvifolium, Blepharocalyx salicifolius, Casearia lasiophylla, Cassia occidentalis, Dalbergia miscolobium, Diospyros brasiliensis, Diospyros hispida, Ilex brevicuspis, Ilex cerasifolia, Myrocarpus fastigiatus, Senna aversiflora, Senna splendida e Blepharocalyx salicifolius were classified as intermediate (59.1% of all species). Seeds of Miconia albicans, Platycyamus regnellii, Styrax camporum and Piptadenia gonoacantha were classified as orthodox (18.2% of all species).
150. R. C. Mayrinck, T. A. A. Vaz, and A. C. Davide, “PHYSIOLOGICAL CLASSIFICATION OF FOREST SEEDS REGARDING THE DESICCATION TOLERANCE AND STORAGE BEHAVIOUR,” CERNE, vol. 22, no. 1, pp. 85–92, Apr. 2016. doi: 10.1590/01047760201622012064. Abstract
     This work aims to classify forest seeds native to the Alto Rio Grande region regarding the desiccation tolerance and storage behaviour. Germination and water content tests were performed in seeds of different species. The tests were conducted immediately after seed processing, at 12% and 5% of water content, and at 5% after 3 months of storage in -18°C. Based on the results obtained, seeds were classified into recalcitrant, intermediate and orthodox class. Seeds of Brosimum gaudichaudii, Erythroxylum deciduum, Eugenia pleurantha, Myrcia venulosa, Nectandra megapotamica were classified as recalcitrant (22.7% of all species). Seeds of Aegiphila sellowiana, Aspidosperma parvifolium, Blepharocalyx salicifolius, Casearia lasiophylla, Cassia occidentalis, Dalbergia miscolobium, Diospyros brasiliensis, Diospyros hispida, Ilex brevicuspis, Ilex cerasifolia, Myrocarpus fastigiatus, Senna aversiflora, Senna splendida e Blepharocalyx salicifolius were classified as intermediate (59.1% of all species). Seeds of Miconia albicans, Platycyamus regnellii, Styrax camporum and Piptadenia gonoacantha were classified as orthodox (18.2% of all species).
151. C. G. McWhorter and C. Ouzts, “Leaf Surface Morphology of Erythroxylum Sp. and Droplet Spread,” Weed Science, vol. 42, no. 1, pp. 18–26, Mar. 1994. doi: 10.1017/S0043174500084101. Abstract
     Studies were conducted to examine the micromorphology of leaf surfaces of coca and nova plants and to determine which spray diluents provided optimum coverage of leaf surfaces. Adaxial leaf surfaces of both species were covered with a smooth layer of polygonal-shaped epidermal cells which were covered with wax crystals. Abaxial leaf surfaces were composed only of papillae cells and the guard and subsidiary cells surrounding stomata. Abaxial leaf surfaces of both species were also covered with wax crystals. Average wax weights were 28 to 53 μg cm−2. Water droplets containing an organosilicone surfactant at 0.1% by vol spread better on leaf surfaces that did other adjuvants. Droplets of several different petroleum-based oils spread much better on leaf surfaces than either water droplets with adjuvants or droplets of soybean or cottonseed oil.
152. Y. Molina, T. Torres, E. Belmonte, and C. Santoro, “Uso Y Posible Cultivo De Coca (Erythroxylum Spp.) En Épocas Prehispánicas En Los Valles De Arica,” Chungara: Revista de Antropología Chilena, no. 23, pp. 37–49, 1989. https://www.jstor.org/stable/27801968. Abstract
     Este estudio ha permitido confirmar la presencia del género Erythroxylum y su posible cultivo en los valles de Arica desde épocas Tiwanaku. Por su naturaleza estos estudios constituyen una herramienta válida para la reconstrucción de paleoambientes y de las formas de vida de los pueblos prehispánicos. This study confirms the presence of the genus Erythroxylum and the possibility of its cultivation in the valleys of Arica from Tiwanaku times. These studies may constitute a valid tool for reconstruction of paleoenvironments and the way of life of prehispanic people.
153. J. M. Moore, P. A. Hays, D. A. Cooper, J. F. Casale, and J. Lydon, “1-Hydroxytropacocaine: An Abundant Alkaloid of Erythroxylum Novogranatense Var. Novogranatense and Var. Truxillense,” Phytochemistry, vol. 36, no. 2, pp. 357–360, May 1994. doi: 10.1016/S0031-9422(00)97075-4. Abstract
     A new alkaloid, 1-hydroxytropacocaine, was isolated from leaves of greenhouse-cultivated Erythroxylum novogranatense var. novogranatense and identified. Quantitative levels of this alkaloid in dry leaf were similar to those for cocaine, i.e. 0.3–0.5% w/w. 1-Hydroxytropacocaine was also detected at 0.04–0.07% w/w (relative to dry coca leaf) in greenhouse-cultivated Erythroxylum novogranatense var. truxillense and at similar levels in Erythroxylum novogranatense var. novogranatense, grown at a tropical site other than in South America. The presence of 1-hydroxytropacocaine was <0.01% w/w (relative to dry coca leaf) in suspected Erythroxylum novogranatense var. novogranatense and Erythroxylum coca var. coca, field-cultivated in Colombia and Bolivia, respectively.
154. J. M. Moore, J. F. Casale, R. F. X. Klein, D. A. Cooper, and J. Lydon, “Determination and In-Depth Chromatographic Analyses of Alkaloids in South American and Greenhouse-Cultivated Coca Leaves,” Journal of Chromatography A, vol. 659, no. 1, pp. 163–175, Jan. 1994. doi: 10.1016/0021-9673(94)85018-6. Abstract
     Methodology is described for the detection and/or determination of cocaine and minor alkaloids in South American coca as well as in greenhouse- and tropical-cultivated field coca of known taxonomy. Coca leaf from Bolivia, Peru, Ecuador and Colombia were subjected to the determination of cocaine, cis- and trans-cinnamoylcocaine, tropacocaine, hygrine, cuscohygrine and the isomeric truxillines. The greenhouse samples were cocaine-bearing leaves of the genus Erythroxylum and included E. coca var. coca, E. novogranatense var. novogranatense and E. novogranatense var. truxillense, and the alkaloids determined were cocaine, ecgonine methyl ester, cuscohygrine, tropacocaine and the cinnamoylcocaines. The tropical-cultivated coca were E. novogranatense var. novogranatense and E. coca var. coca. Cocaine and minor alkaloids were isolated from basified powdered leaf samples using a toluene extractant, followed by acid-Celite column chromatography. The isolated alkaloids were determined by capillary gas chromatography with flame ionization or electron-capture detection. Methodology is also presented for the isolation and mass spectral analysis of numerous trace-level coca alkaloids of unknown structure.
155. L. G. L. Moreira et al., “Erythroxylum Pungens Tropane Alkaloids: GC-MS Analysis and the Bioactive Potential of 3-(2-Methylbutyryloxy)Tropan-6,7-Diol in Zebrafish (Danio Rerio),” Planta Medica, vol. 87, no. 01/02, pp. 177–186, Feb. 2021. doi: 10.1055/a-1264-4302. Abstract

     Tropane alkaloids are specialized plant metabolites mostly found in the Erythroxylaceae and Solanaceae families. Although tropane alkaloids have a high degree of structural similarity because of the tropane ring, their pharmacological actions are quite distinct. Brazil is one of the main hotspots of Erythroxylum spp. diversity with 123 species (almost 66% of the species catalogued in tropical America). Erythroxylum pungens occurs in the Caatinga, a promising biome that provides bioactive compounds, including tropane alkaloids. As part of our efforts to investigate this species, 15 alkaloids in specimens harvested under different environmental conditions are presented herein. The occurrence of 3-(2-methylbutyryloxy)tropan-6,7-diol in the stem bark of plants growing in their natural habitat, greenhouse controlled conditions, and after a period of water restriction, suggests that it is a potential chemical marker for the species. This alkaloid was evaluated for several parameters in zebrafish (Danio rerio) as a model organism. Regarding toxicity, teratogenic effects were observed at 19.5 µM and the lethal dose for embryos was 18.4 µM. No mortality was observed in adults, but a behavioral screen showed psychostimulatory action at 116.7 µM. Overall, the alkaloid was able to cause zebrafish behavioral changes, prompting further investigation of its potential as a new molecule in the treatment of depression-like symptoms. In silico, targets involved in antidepressant pathways were identified by docking.

156. M. J. Moreno, “Revista Medicina Naturista - Enero 2020,” vol. 14, p. 10. Abstract
     The objective of the present study was to compare the effect between Aloe vera gel, Erythroxylum coca gel and mixed Aloe vera gel with Erythroxylum coca in healing after dental extractions in Rattus rattus. The sample consisted of 60 rats, divided into four groups to which dental extractions were performed. Aloe vera gel with Erythroxylum coca had a greater healing effect between days 5 and 7 days. It is concluded that the mixed gel of Aloe vera with Erythroxylum coca has a greater healing effect at all times.
157. L. L. Narayana, “Studies in Erythroxylaceæ—I,” Proceedings / Indian Academy of Sciences, vol. 51, no. 6, pp. 270–275, Jun. 1960. doi: 10.1007/BF03050043. Abstract
     The floral anatomy ofErythroxylum coca, E. mooni andE. monogynum and the embryology of the two latter species have been studied.
158. A. J. Nelson, K. S. Elias, E. Arévalo G., L. C. Darlington, and B. A. Bailey, “Genetic Characterization by RAPD Analysis of Isolates of Fusarium Oxysporum f. Sp. Erythroxyli Associated with an Emerging Epidemic in Peru,” Phytopathology®, vol. 87, no. 12, pp. 1220–1225, Dec. 1997. doi: 10.1094/PHYTO.1997.87.12.1220. Abstract
     An epidemic of vascular wilt caused by Fusarium oxysporum f. sp. erythroxyli is currently occurring on Erythroxylum coca var. coca in the coca-growing regions of the Huallaga Valley in Peru. Random amplified polymorphic DNA (RAPD) analysis of isolates of the pathogen was undertaken to elucidate its genetic complexity, as well as to identify a specific DNA fingerprint for the pathogen. Two hundred isolates of Fusarium were collected from 10 coca-growing regions in Peru. Of these, 187 were confirmed to be F. oxysporum, and 143 of the F. oxysporum were shown to be pathogens of coca by a root-dip pathogenicity test. The pathogens could be grouped into two subpopulations based on RAPD analysis, and no polymorphism in RAPD pattern was observed among isolates of either subpopulation. Both subpopulations were present in the central Huallaga Valley, where earliest reports of the epidemic occurred. RAPD analysis could easily distinguish the isolates of F. oxysporum f. sp. erythroxyli from the nonpathogenic isolates of F. oxysporum from E. coca var. coca, indicating its utility in DNA fingerprinting.
159. M. L. Newquist, T. W. Abraham, and E. Leete, “Biosynthetic Incorporation of Ethyl (RS) [2,3-13C2,3-14C]-4-(1-Methyl-2-Pyrrolidinyl)-3-Oxobutanoate into Cuscohygrine in Erythroxylum Coca,” Phytochemistry, vol. 33, no. 6, pp. 1437–1440, Aug. 1993. doi: 10.1016/0031-9422(93)85105-Z. Abstract
     Ethyl (RS)-2,3-13C2,3-14C]-4-(1-methyl-2-pyrrolidinyl)-3-oxobutanoate was administered to intact leaves of Erythroxylum coca which led to good incorporation (0.75% and 0.99%) into cuscohygrine. Specific incorporation was determined by radioactivity and by mass spectrometry. The positions of the isotopically enriched 13C atoms were determined by the presence of satellite peaks in the 13C NMR. Since hygrine was previously established as a precursor of cuscohygrine, [2-14C]-hygrine was fed to E. coca leaves as well. The results (0.13% specific incorporation) show that the β-keto ester is over five times more effective as a precursor than hygrine. From these results a modified biosynthetic pathway for cuscohygrine is proposed.
160. Y. Nishiyama et al., “Tropane Alkaloids from Erythroxylum Emarginatum,” Journal of Natural Medicines, vol. 61, no. 1, pp. 56–58, Jan. 2007. doi: 10.1007/s11418-006-0018-6. Abstract
     A tropane alkaloid, anhydroecgonine methyl ester N-oxide (2), was isolated for the first time as a naturally occurring compound, with anhydroecgonine methyl ester (1) from the bark of Erythroxylum emarginatum. Compound 1 was also isolated from the twigs. Their structures were elucidated mainly by spectroscopic methods.
161. “Alkaloid Content of the Seeds from Var.” . https://www.astm.org/jfs2005121.html. Abstract
     Alkaloid extracts from the seeds of Erythroxylum Coca var. Coca grown in the Chapare Valley of Bolivia were subjected to gas and liquid chromatographic-mass spectrometric analyses. Several alkaloids from these seeds were detected and characterized, includ
162. “Coca Cultivation and Cocaine Processing: An Overview | Office of Justice Programs.” . https://www.ojp.gov/ncjrs/virtual-library/abstracts/coca-cultivation-and-cocaine-processing-overview.
163. “Growers Experiences - Dbotany.” . https://www.dbotany.com/content/13-growers-experiences.
164. “Ha Ocurrido Un Error.” . https://alicia.concytec.gob.pe/vufind/Record/1609-9419_904add692738ca7544fb682ee2b10d53/Details.
165. “Publication : USDA ARS.” . https://www.ars.usda.gov/research/publications/publication/?seqNo115=102785.
166. “Refoliation of Erythroxylum Coca Var. Coca.: I. Measurement Techniques | 九大コレクション | 九州大学附属図書館.” http://hdl.handle.net/2324/8255. Abstract
     Online Public Access Catalog
167. “Refoliation of Erythroxylum Coca Var. Coca.: II. Effect of Temperature | 九大コレクション | 九州大学附属図書館.” http://hdl.handle.net/2324/8256. Abstract
     Online Public Access Catalog
168. “Tracing the Evolutionary History of Coca (Erythroxylum ) - ProQuest.” . https://www.proquest.com/openview/0b8abdcca3e7fff627b86bfb09d7bbf5/1?pq-origsite=gscholar&cbl=18750. Abstract
     Explore millions of resources from scholarly journals, books, newspapers, videos and more, on the ProQuest Platform.
169. M. Novák, C. A. Salemink, and I. Khan, “Biological Activity of the Alkaloids of Erythroxylum Coca and Erythroxylum Novogranatense,” Journal of Ethnopharmacology, vol. 10, no. 3, pp. 261–274, May 1984. doi: 10.1016/0378-8741(84)90015-1. Abstract
     The cultivated Erythroxylum varieties E. coca var. coca, E. coca var. ipadu, E. novogranatense var. novogranatense and E. novogranatense var. truxillense contain 18 alkaloids, identified so far, belonging to the tropanes, pyrrolidines and pyridines, with cocaine as the main alkaloid. The biological activity of the following alkaloids has been reported in the literature: cocaine, cinnamoylcocaine, benzoylecgonine, methylecgonine, pseudotropine, benzoyltropine, tropacocaine, α- and β-truxilline, hygrine, cuscohygrine and nicotine. The biological activity of cocaine and nicotine is not reviewed here, because it is discussed elsewhere in the literature. Hardly anything is known about the biological activity of the other alkaloids present in the four varieties mentioned. The biosynthesis of the coca alkaloids has been outlined.
170. M. Novák and C. A. Salemink, “The Essential Oil of Erythroxylum Coca,” Planta Medica, vol. 53, no. 1, pp. 113–113, Feb. 1987. doi: 10.1055/s-2006-962643. Abstract
     Thieme E-Books & E-Journals
171. S. L. Oliveira et al., “Tropane Alkaloids from Erythroxylum Genus: Distribution and Compilation of 13C-NMR Spectral Data,” Chemistry & Biodiversity, vol. 7, no. 2, pp. 302–326, 2010. doi: 10.1002/cbdv.200800290. Abstract
     Erythroxylum, the most representative genus of the Erythroxylaceae family, presents tropane alkaloids as main constituents. This class of compounds greatly contributes to the chemotaxonomic characterization of plants of this genus, and it has important medical uses and shows toxic effects. This review describes 186 tropane alkaloids in the 35 species of Erythroxylum distributed worldwide. In addition, a compilation of their 13C-NMR spectral data is presented.
172. A. Ortiz, “Coca leaf (Erythroxylum coca) cultivation and measurement of regional production concentration in Peru, 2000-2015,” Anales Científicos, vol. 79, no. 1, pp. 7–12, 2018. doi: 10.21704/ac.v79i1.1124. Abstract
     Coca leaf cultivation in Peru during the 2000-2015 periods has not changed much with respect to coca producing areas. Herfindhal-Hirschman, Horvath and Rosenbluth indices and the entropy coefficient show that there is a concentrated regional supply of coca leaf. Coca leaf buyers (for illicit purposes) possess a strong market power or oligopsony. A few cartels are the main buyers of coca leaf.
173. G. E. Ovalle, I. G. Parra, and E. C. G, “Separacion Y Determinacion De Los Alcaloides De Erythroxylum Coca Variedad Novogranatensis Por Metodos Cromatograficos,” Revista Colombiana de Ciencias Químico-Farmacéuticas, vol. 1, no. 4, pp. 95–118, Jan. 1971. https://revistas.unal.edu.co/index.php/rccquifa/article/view/56741. Abstract
     La presente investigación tiene por objeto el estudio de alcaloides aún no descritos en la planta Erythroxylum coca, variedad novogranatensis. Una vez extraídos los alcaloides del polvo de la hoja, se identificaron cromatográficamente y posteriormente fueron valorados. El trabajo se complementó con un estudio químico de cada alcaloide, determinando sus propiedades organolépticas, constantes físicas, solubilidad y espectro al I R. En esta forma se identificaron y valoraron cuatro alcaloides.
174. D. Pacini and C. Franquemont, “Effects on People and Policy in Latin America,” p. 33.
175. T. Pailler, L. Humeau, and J. D. Thompson, “Distyly and Heteromorphic Incompatibility in Oceanic Island Species ofErythroxylum (Erythroxylaceae),” Plant Systematics and Evolution, vol. 213, no. 3, pp. 187–198, Sep. 1998. doi: 10.1007/BF00985199. Abstract
     Surveys of oceanic island floras have shown that heterostyly is usually absent in such regions, probably because this floral polymorphism is often associated with a self-incompatibility system. In this context we describe the floral biology of three species ofErythroxylum on La Réunion island and examine the compatibility relationships of one of these species,E. laurifolium. All three species are distylous but differ in relative stigma-anther separation in the different morphs. In general, short-styled flowers have greater stigma-anther separation than long-styled flowers, which are often homostylous in appearance. This lack of stigma-anther separation in long-styled flowers is due to style twisting which improves reciprocity at the high organ level. The reduced stigma-anther separation does not appear to be associated with the evolution of selfing asErythroxylum laurifolium shows heteromorphic self-incompatibility. The presence of heteromorphic incompatibility in a group of species that have colonized an oceanic island is discussed.
176. J. C. Pardo Torre et al., “The Biosynthesis of Hydroxycinnamoyl Quinate Esters and Their Role in the Storage of Cocaine in Erythroxylum Coca,” Phytochemistry, vol. 91, pp. 177–186, Jul. 2013. doi: 10.1016/j.phytochem.2012.09.009. Abstract
     Complexation of alkaloids is an important strategy plants utilize to facilitate storage in vacuoles and avoid autotoxicity. Previous studies have implicated hydroxycinnamoyl quinate esters in the complexation of purine alkaloids in Coffea arabica. The goal of this study was to determine if Erythroxylum coca uses similar complexation agents to store abundant tropane alkaloids, such as cocaine and cinnamoyl cocaine. Metabolite analysis of various E. coca organs established a close correlation between levels of coca alkaloids and those of two hydroxycinnamoyl esters of quinic acid, chlorogenic acid and 4-coumaroyl quinate. The BAHD acyltransferase catalyzing the final step in hydroxycinnamoyl quinate biosynthesis was isolated and characterized, and its gene expression found to correlate with tropane alkaloid accumulation. A physical interaction between chlorogenic acid and cocaine was observed and quantified in vitro using UV and NMR spectroscopic methods yielding similar values to those reported for a caffeine chlorogenate complex in C. arabica. These results suggest that storage of cocaine and other coca alkaloids in large quantities in E. coca involves hydroxycinnamoyl quinate esters as complexation partners.
177. M. E. Penny et al., “Can Coca Leaves Contribute to Improving the Nutritional Status of the Andean Population?,” Food and Nutrition Bulletin, vol. 30, no. 3, pp. 205–216, Sep. 2009. doi: 10.1177/156482650903000301. Abstract
     BackgroundCoca leaves (Erythroxylum coca) have been promoted as a food that could address the dietary deficiencies of the Andean population, but this is based on nutrient analyses of a small sample of leaves.ObjectiveWe assessed the nutritional potential of eight samples of coca leaves grown in different regions of Peru.MethodsWe used AOAC techniques to measure nutrients, nutrient inhibitors (phytate, polyphenols, oxalic acid, and fiber), and alkaloid concentrations, all expressed per 100 g dry weight (DW) of the ground leaves. Minerals were measured by inductively coupled plasma-mass spectrometry in two independent laboratories.ResultsThe leaves contained protein, 20.28 g/100 gDW, with lysine as the limiting amino acid; ?-carotene, 3.51 mg/100 gDW; vitamin E, 16.72 mg/100 gDW; trace amounts of vitamin D; calcium, 990.18 and 1033.17 mg/100 gDW at two different laboratories; iron, 29.16 and 29.16 mg/100 gDW; zinc, 2.71 and 2.63 mg/100 gDW; and magnesium, 225.19 and 196.69 mg/100 gDW. Cocaine was the principal alkaloid, with a concentration of 0.56 g/100 gDW; other alkaloids were also identified. The results were compared with those for other edible leaves. The nutrient contributions of coca powder (5 g) and bread made with coca were compared with those of normal portions of alternative foods.ConclusionsTwo spoonfuls of coca leaf flour would satisfy less than 10% of dietary intakes for schoolchildren and adults for critical commonly deficient nutrients in the diet. Coca leaves do not provide nutritional benefits when eaten in the recommended quantities, and the presence of absorbable cocaine and other alkaloids may be potentially harmful; hence coca leaves cannot be recommended as a food.
178. C. M. Pereira et al., “Vallissiana Universitaria (Lepidoptera: Gracillariidae): A New Genus and Species of Leaf-Mining Moth Associated with Erythroxylum (Erythroxylaceae) in the Atlantic Forest of Brazil,” Zootaxa, vol. 4604, no. 1, pp. 141–160, May 2019. doi: 10.11646/zootaxa.4604.1.5. Abstract
     Vallissiana universitaria Pereira & Arévalo, a new genus and species of leaf-miner moth (Gracillariidae: Gracillariinae) is described and illustrated with the aid of optical and scanning electron microscopy, including adults, larva, pupa and the mine. Its monophyletic status is confirmed within the subfamily based on a DNA barcode CoI tree. The immature stages are associated with Erythroxylum argentinum O. E. Schulz (Erythroxylaceae) and four larval instars are found, all forming a round blotch mine from the beginning of ontogeny. The first two instars are sap-feeders, using only the epidermal cells, whereas the last two are tissue-feeders, mining the parenchyma cells. Pupation occurs inside the leaf mine within a flimsy, silk-made cocoon. This is the third endemic genus of gracillariid moths described from the Atlantic Forest of Brazil and the first associated with Erythroxylum P. Browne. Characteristics found on the forewing and in the last abdominal segments of the adult were determinant for the proposition of the new genus. The CoI tree indicated that it is closely related to Aspilapteryx, while this genus was recovered as polyphyletic in the analyses. Morphological evidence supports this polyphyly. Consequently, Sabulopteryx Triberti, 1985, stat. nov. is considered a valid genus.
179. P. a. N. G. Perera and A. Rabinarayan, “Review on Ethnomedicinal Claims of Erythroxylum Moonii Hochr,” European Journal of Medicinal Plants, pp. 41–49, Dec. 2020. doi: 10.9734/ejmp/2020/v31i1730334.
180. T. Plowman, “Amazonian Coca,” Journal of Ethnopharmacology, vol. 3, no. 2, pp. 195–225, Mar. 1981. doi: 10.1016/0378-8741(81)90054-4. Abstract
     A general overview of various aspects of Amazonian coca (Erythroxylum. coca var. ipadu) is presented. This plant is considered a distinct variety of coca which has been developed as a cultivated plant in the upper Amazon basin. It differs from typical Andean coca in morphological, physiological and chemical features as well as in the method of preparation and use by Amazonian tribes. The main topics here discussed are the history, distribution, botany, chemistry, origin, methods of preparation and use, and the effects of Amazonian coca.
181. T. Plowman, “Botanical Perspectives on Coca,” Journal of Psychedelic Drugs, vol. 11, no. 1-2, pp. 103–117, Jan. 1979. doi: 10.1080/02791072.1979.10472095.
182. T. Plowman and A. T. Weil, “Coca Pests and Pesticides,” Journal of Ethnopharmacology, vol. 1, no. 3, pp. 263–278, Oct. 1979. doi: 10.1016/S0378-8741(79)80015-X. Abstract
     The major pests of coca are listed and discussed along with methods used to control them in the past and present. Results of analyses for pesticide residues in samples of commercial Peruvian coca leaves are presented. Levels of pesticides found in these samples are too low to be considered a medical risk to coca chewers.
183. T. Plowman and L. Rivier, “Cocaine and Cinnamoylcocaine Content of Erythroxylum Species,” Annals of Botany, vol. 51, no. 5, pp. 641–659, May 1983. doi: 10.1093/oxfordjournals.aob.a086511.
184. T. Plowman, “The Ethnobotany of Coca (Erythroxylum Spp., Erythroxylaceae),” Advances in Economic Botany, vol. 1, pp. 62–111, 1984. https://www.jstor.org/stable/43931370.
185. T. Plowman, “Four New Species of Erythroxylum (Erythroxylaceae) from Northeastern Brazil,” Brittonia, vol. 38, no. 3, pp. 189–200, Jul. 1986. doi: 10.2307/2807336. Abstract
     Erythroxylum simonis, E. pauferrense, E. bezerrae, andE. tianguanum from northeastern Brazil are described and illustrated, and their taxonomic and phytogeographic relationships are discussed.
186. T. Plowman, “The Identity of Amazonian and Trujillo Coca,” Botanical Museum Leaflets, Harvard University, vol. 27, no. 1/2, pp. 45–68, 1979. doi: 10.5962/p.295220.
187. T. Plowman and N. Hensold, “Names, Types, and Distribution of Neotropical Species of Erythroxylum (Erythroxylaceae),” Brittonia, vol. 56, no. 1, pp. 1–53, Jan. 2004. doi: 10.1663/0007-196X(2004)056[0001:NTADON]2.0.CO;2. Abstract
     A list is provided of all 358 taxa ofErythroxylum described from the Neotropics through the year 2000, including type specimen citations, probable synonymy, geographic distribution, and designation of 41 new lectotypes and one new neotype. The list includes 187 accepted species, eight accepted varieties, 27 infraspecific names of uncertain status, and 136 synonyms. A searchable specimen database and type image archive may be accessed at www.fieldmuseum.org/research_collections/database.htm.
188. T. Plowman, “New Taxa of Erythroxylum (Erythroxylaceae) from the Venezuelan Guayana,” Brittonia, vol. 40, no. 3, pp. 256–268, Jul. 1988. doi: 10.2307/2807469. Abstract
     Erythroxylum foetidum Plowman,E. guanchezii Plowman, andE. macrophyllum Cav. var.savannarum Plowman are described and illustrated, and their taxonomic and phytogeographic relationships are discussed.
189. T. Plowman, “Three New Species of Erythroxylum (Erythroxylaceae) from Venezuela,” Brittonia, vol. 34, no. 4, pp. 442–457, Oct. 1982. doi: 10.2307/2806501. Abstract
     Erythroxylum steyermarkii Plowman,E. undulatum Plowman andE. williamsii Standley ex Plowman, all known only from Venezuela, are described and illustrated, and their taxonomic and phytogeographic relationships are discussed.
190. A. Poblete, C. López-Alarcón, E. Lissi, and A. M. Campos, “Oxygen Radical Antioxidant Capacity (Orac) Values of Herbal Teas Obtained Employing Different Methodologies Can Provide Complementary Data,” Journal of the Chilean Chemical Society, vol. 54, no. 2, pp. 154–157, Jun. 2009. doi: 10.4067/S0717-97072009000200013.
191. D. Posso, “Coca, Deforestation and Food Security in the Colombian Amazon Region,” vol. 51, pp. 32–35, Jan. 2000. Abstract
     From a purely economic point of view, illicit crops could be regarded as the most profitable rural economic activity in Colombia; they can generate far higher earnings for peasant growers than legitimate crops, therefore seeming to provide a possible answer to the poverty and marginalization of so many peasant farmers. However, as this article shows, coca has had a deleterious impact, not only on the Amazon forest, but also on the food security of the inhabitants of the Amazon region where most of Colombia’s coca crop is grown. Growers typically derive the least profit from the crop, and poverty and malnutrition have risen with the coca boom as a result of the inflationary effect of these activities on weak local economies.
192. L. M. S. Ramírez, “Phytochemical and ethnobotanical recognition of Erythroxylum coca in the Nasa population of the Department of Cauca – Colombia,” Revista Criterio Libre Jurídico, vol. 14, no. 1, pp. 10–19, 2017. doi: 10.18041/1794-7200/criteriojuridico.2017.v14n1.1601. Abstract
     In the following article, research result, the relationship between the secondary metabolites in the Erythroxylum coca var coca plant and its medicinal use in the Nasa population of the department of Cauca- Colombia is established, based on the review of scientific literature. Initially, the general aspects of the plant Erythroxylum coca var. coca, which has different secondary metabolites such as alkaloids: Benzomethylecgonine (cocaine), cis and transinamilcocaine, B-truxilin, tropacocaine, benzoylecgonine, B-higrin, dihydrocuscohigrin; flavonoids such as O-conjugates of Eriodictyol and terpenes such as β-pinene (monoterpene), β-myrcene (monoterpene), nerolidol (sesquiterpene); in the essential oil is also found Stearic acid, phytol, methyl ester 7, 10, 13 hexadecatrienoic acid and nonacosane. Then the biogenesis of each major metabolite and the most important extraction forms of each of them is mentioned, according to laboratory techniques and ancestral techniques in the Nasa community and, finally, a relationship is made between ethnobotany and phytochemistry to understand the medicinal use.
193. D. P. Ramos and S. M. C. Novaes, “Círculos de coca e fumaça: encontros noturnos e caminhos vividos pelos Hupd’äh (Maku),” 2014. doi: 10.11606/T.8.2014.tde-21102014-160908.
194. D. A. Restrepo et al., “Erythroxylum in Focus: An Interdisciplinary Review of an Overlooked Genus,” Molecules, vol. 24, no. 20, p. 3788, Jan. 2019. doi: 10.3390/molecules24203788. Abstract
     The genus Erythroxylum contains species used by indigenous people of South America long before the domestication of plants. Two species, E. coca and E. novogranatense, have been utilized for thousands of years specifically for their tropane alkaloid content. While abuse of the narcotic cocaine has impacted society on many levels, these species and their wild relatives contain untapped resources for the benefit of mankind in the form of foods, pharmaceuticals, phytotherapeutic products, and other high-value plant-derived metabolites. In this review, we describe the current state of knowledge of members within the genus and the recent advances in the realm of molecular biology and biochemistry.
195. J. E. da S. Ribeiro, E. dos S. Coêlho, A. P. Leite, R. de L. A. Bruno, E. U. Alves, and M. B. de Albuquerque, “Emergence and Initial Development of Erythroxylum Pauferrense Seedlings under Different Substrates,” Brazilian Archives of Biology and Technology, vol. 65, pp. 1–7, Apr. 2022. doi: 10.1590/1678-4324-2022210678. Abstract
     Erythroxylum pauferrense Plowman is an understory species native to Brazil, with great importance in the conservation of genetic resources and is used as a food source for animals in the regions where the species occurs. The species is currently listed in category EN (endangered). The objective of this work was to evaluate the effect of different substrates on the emergence and initial growth of E. pauferrense. The experiment was carried out in a protected environment, belonging to the Plant Ecology Laboratory of the Federal University of Paraíba, Areia-PB, Brazil. The substrates used were: sand; sand + vermiculite in the proportion of 1:1, 3:1 and 1:3; vegetal land; vegetal land + sand in the proportion of 1:1, 3:1 and 1:3; vegetal land + vermiculite in the proportion of 1:1, 3:1 and 1:3; vermiculite; Bioplant®; and Bioplant® + sand in a ratio of 1:1, 3:1 and 1:3. The experimental design was completely randomized, with 16 treatments (substrates) and four replications of 25 seeds. The percentage of emergence, first count, speed index, mean time, mean speed and relative emergency frequency were evaluated. The vermiculite substrate provided the best results for carrying out the emergence and vigor tests of E. pauferrense seedlings, being the most suitable substrate to initial growth seedlings of the species.
196. J. E. da S. Ribeiro, F. R. A. Figueiredo, E. dos S. Coêlho, M. B. de Albuquerque, and W. E. Pereira, “Environmental Factors Variation in Physiological Aspects of Erythroxylum Pauferrense,” BOSQUE, vol. 41, no. 2, pp. 157–164, Jul. 2020. doi: 10.4067/S0717-92002020000200157. Abstract
     Ecophysiological studies are highly important to seek understanding of the plant-environment relationship. The objective of this work was to evaluate the influence of environmental factors on physiological aspects in young plants of Erythroxylum pauferrense throughout the day. A completely randomized design with 10 treatments and 4 replicates was used. Treatments were at different evaluation times throughout the day (8:00 h-17:00 h) with a 60-minute interval between them. The physiological variables evaluated were: photosynthesis rate, internal CO2 concentration, transpiration, stomatal conductance, vapor pressure deficit, instantaneous water use efficiency, intrinsic water use efficiency, instantaneous carboxylation efficiency and leaf temperature. Internal and external temperature, relative humidity of the internal and external air of the greenhouse and photosynthetically active radiation were measured as climatic variables. The climatic variables presented correlations with the physiological parameters, with a strong association between photosynthetically active radiation and internal and external temperature of the greenhouse with the rate of photosynthesis, vapor pressure deficit, leaf temperature, transpiration, intrinsic efficiency of the use of water, stomatal conductance and instant water use efficiency. The influence of climatic factors on the physiological aspects in plants of E. pauferrense can be observed. The most suitable period of the day for conducting the physiological evaluations in species is between 11:00 h and 13:00 h.
197. J. E. da S. Ribeiro, E. dos S. Coêlho, F. R. A. Figueiredo, W. E. Pereira, M. B. de Albuquerque, and M. F. Melo, “Morphophysiological Aspects of Erythroxylum Pauferrense Plowman Seedlings Submitted to Shading,” Ciência Florestal, vol. 32, no. 1, pp. 395–416, Mar. 2022. doi: 10.5902/1980509862951. Abstract
     ABSTRACT Sunlight directly influences on the development of forest species by affecting the attributes of plant growth and physiology. Among these species, Erythroxylum pauferrense Plowman is considered a rare species, as its distribution is restricted only to the state of Paraíba. Therefore, studies are needed that seek to evaluate the adaptation, development and propagation of the species under different environmental conditions. This study aimed to evaluate morphophysiological aspects of Erythroxylum pauferrense seedlings submitted to different levels of shading. The experiment was carried out under greenhouse condition in a completely randomized design with five treatments (0, 30, 50, 70, and 90% shading) and eight replicates. Growth characteristics, morphofunctional attributes, gas exchange, chlorophyll (Chl) a fluorescence, and Chl content were evaluated. Data were submitted to analysis of variance followed by polynomial regression analysis. Results showed that plants grown under 30 to 50% shading showed higher plant height, stem diameter, absolute growth rate for plant height, leaf dry mass, stem dry mass, total dry mass, Dickson’s quality index, leaf area, and leaf area index, as well as net assimilation rate of CO2, stomatal conductance, transpiration, instantaneous water use efficiency, and Chl a, b, and a+b contents. Therefore, levels from 30 to 50% shading are the most recommended for the production of Erythroxylum pauferrense seedlings. We recommend using Erythroxylum pauferrense to reforest the understory in disturbed areas in Brejos de Altitude and large-scale production of seedlings under intermediate levels of shading.
198. J. E. da S. Ribeiro, A. P. Leite, J. S. Nóbrega, E. U. Alves, R. de L. A. Bruno, and M. B. de Albuquerque, “Temperatures and Substrates for Germination and Vigor of Erythroxylum Pauferrense Plowman Seeds,” Acta Scientiarum. Biological Sciences, vol. 41, pp. e46030–e46030, Nov. 2019. doi: 10.4025/actascibiolsci.v41i1.46030. Abstract
     Resumo Erythroxylum pauferrense is an endemic understory plant species of the Northeast Region of Brazil. The species is of great importance to the region and so ecophysiological studies are needed for its preservation. The objective of the present study was to determine the best substrates and temperatures for testing germination and seed vigor of E. pauferrense. An experiment was performed comprising a completely randomized design in a 5 x 4 factorial scheme, with five temperature regimes (20, 25, 30, 35°C constant and 20-30°C alternating) and four types of substrates (paper, vermiculite, sand and commercial substrate). The following characteristics were evaluated: germination percentage, first germination count, germination speed index, mean germination time, seedling length and dry mass (root and shoot). Paper and vermiculite substrates combined with constant temperatures of 20, 25, 30 and alternated between 20-30°C, provide greater seed germination and vigor while 35°C reduces seed physiological quality.
199. M. A. Rivera, A. C. Aufderheide, L. W. Cartmell, C. M. Torres, and O. Langsjoen, “Antiquity of Coca-Leaf Chewing in the South Central Andes: A 3,000 Year Archaeological Record of Coca-Leaf Chewing from Northern Chile,” Journal of Psychoactive Drugs, vol. 37, no. 4, pp. 455–458, Dec. 2005. doi: 10.1080/02791072.2005.10399820. Abstract
     Carbon- 14 (14C) dating from mummies o f the Alto Ramirez culture confirms that coca leaf chewing was an incipient practice among members of a population that peopled the valleys and coastal areas of Northern Chile by 3,000 years before the present (yr.B.P.). Out of eleven bodies from the burial site of Pisagua-7 (PSG-7, S 19° 35′, W 70° 13′) that were analyzed, two samples tested positive. Mummy 725-A C2 (dated 3,090 to 2,850 rwo sigma calibrated 14C years before the present) was shown to have a cocaine value of 13.3 nanograms/10 milligrams of sample (ng/10mg), and mummy 741 (2,890 to 2,760 two sigma cal yr B.P), a 5.6 ng/10mg value.
200. L. Rivier, “Analysis of Alkaloids in Leaves of Cultivated Erythroxylum and Characterization of Alkaline Substances Used during Coca Chewing,” Journal of Ethnopharmacology, vol. 3, no. 2, pp. 313–335, Mar. 1981. doi: 10.1016/0378-8741(81)90061-1. Abstract
     Several solvents were tested for the extraction of the alkaloids in Erythroxylum coca. The resulting crude extracts were analyzed by gas chromatography-mass spectrometry. Ethanol extraction was found to be the only quantitative method presenting no artifacts. It was established that cocaine and cis- and trans-cinnamoylcocaine were the endogenous alkaloids in E. coca leaves. From the several breakdown compounds arising during long-term extraction with H2SO4 or CHCl3, ecgonine methyl ester was the only alkaloid fully identified; ecgonidine methyl ester was tentatively identified on the basis of its mass spectrum fragmentation pattern. Quantification by mass fragmentography of the three endogenous compounds was performed using a stable-isotope dilution technique on individual leaves of single branches of E. coca, E. novogranatense and E. novogranatense var. truxillense. The relative amounts of these alkaloids changed with leaf age as well as between species and varieties. The variation in alkaloid levels between individual leaves was too great to allow the use of the ratio between cocaine and the cinnamoylcocaine levels as a taxonomic marker. The initial pH value of 17 different alkaline substances traditionally used during coca leaf chewing was measured after dissolution in H2O; values ranged between 10.1 and 12.8. Buffer capacity was determined by titration with HCl. Three types of curve shapes were obtained which could correspond to NaOH, Na2CO3 and NaHCO3 titration curves. One sample of alkaline material had no buffer capacity at all. The recovery and breakdown of the cocaine contained in E. coca leaf powder was monitored for one hour at various pHs at 37°C. The levels of cocaine and benzoylecgonine did not change by more than 17% at any of the pHs tested (6.0, 9.0 and 11.5). It was concluded that the alkaline substances are mainly responsible for the transformation of the alkaloids to free bases and not for a major hydrolysis of cocaine.
201. E. Rosas, J. Pierez-Alquicira, and E. A. Dominguez, “Distylous Shrub Erythroxylum Havanense (Erythroxylaceae),” undefined, 2005. https://www.semanticscholar.org/paper/DISTYLOUS-SHRUB-ERYTHROXYLUM-HAVANENSE-Rosas-Pierez-Alquicira/0b37793995601ef050ea50fbc6174b1ce873f6f6. Abstract
     Assessment of the effects of both male sterility and reproductive synchrony on the magnitude of female compensation of Erythroxylum havanense found that thrums were more male sterile than pins and the compensatory advantage of thrums changed by a factor of five depending on flowering synchrony. assessed the effects of both male sterility and reproductive synchrony (an environmentally affected trait) on the magnitude of female compensation of Erythroxylum havanense, a distylous shrub with morph-biased male sterility. In vitro measurements of pollen germination showed that thrums were more male sterile than pins. The compensatory advantage of thrums changed by a factor of five depending on flowering synchrony. Flowering in synchrony with the population increased fruit production in both morphs. However, because pins that flowered out of synchrony produced almost no fruits, the reproductive compensation of thrums was higher in these circumstances. Because the magnitude of compensation is frequently considered as a key factor in the evolution of sex specialization, the environmentally induced variation in the magnitude of the reproductive compensation of thrum plants may have profound effects on the evolutionary dynamics of the reproductive system of E. havanense.
202. L. F. Rosas, J. Pérez-Alquicira, and C. A. Domínguez, “Environmentally Induced Variation in Fecundity Compensation in the Morph-Biased Male-Sterile Distylous Shrub Erythroxylum Havanense (Erythroxylaceae),” American Journal of Botany, vol. 92, no. 1, pp. 116–122, 2005. doi: 10.3732/ajb.92.1.116. Abstract
     The evolution of male-sterile individuals in hermaphroditic species represents the first step in the evolution of sex specialization. For male-sterile individuals to persist they must have some fitness advantage that compensates for their loss of the male function. Female fecundity also depends on environmental factors as those determining the likelihood of pollination and fertilization. Here we assessed the effects of both male sterility and reproductive synchrony (an environmentally affected trait) on the magnitude of female compensation of Erythroxylum havanense, a distylous shrub with morph-biased male sterility. In vitro measurements of pollen germination showed that thrums were more male sterile than pins. The compensatory advantage of thrums changed by a factor of five depending on flowering synchrony. Flowering in synchrony with the population increased fruit production in both morphs. However, because pins that flowered out of synchrony produced almost no fruits, the reproductive compensation of thrums was higher in these circumstances. Because the magnitude of compensation is frequently considered as a key factor in the evolution of sex specialization, the environmentally induced variation in the magnitude of the reproductive compensation of thrum plants may have profound effects on the evolutionary dynamics of the reproductive system of E. havanense.
203. F. Rosas and C. A. Domínguez, “Male Sterility, Fitness Gain Curves and the Evolution of Gender Specialization from Distyly in Erythroxylum Havanense,” Journal of Evolutionary Biology, vol. 22, no. 1, pp. 50–59, 2009. doi: 10.1111/j.1420-9101.2008.01618.x. Abstract
     The evolution of dioecy from a monomorphic hermaphroditic condition requires two mutations, one producing females and one producing males. Conversely, a single mutation sterilizing one sexual function in one morph of distylous species would result in functional dioecy because such a mutation also affects the complementary function in the other morph. In this study, we tested these ideas with Erythroxylum havanense, a distylous species with morph-biased male sterility. Based on sex allocation theory we evaluated whether the invasion of thrum females is favoured over the maintenance of this morph cosexuals. Completely male sterile thrum plants obtained higher fitness returns than hermaphrodites or partial male sterile individuals of the same morph, thus favouring the invasion of female thrum plants. We concluded that because fruit production of pin individuals depends on the pollen produced by thrum plants, the invasion of thrum females would result on the evolution of functional dioecy.
204. A. Rottman, “Erythroxylum: The Coca Plant,” p. 5.
205. C. Rubio, S. Strano-Rossi, M. J. Tabernero, L. Anzillotti, M. Chiarotti, and A. M. Bermejo, “Hygrine and Cuscohygrine as Possible Markers to Distinguish Coca Chewing from Cocaine Abuse in Workplace Drug Testing,” Forensic Science International, vol. 227, no. 1, pp. 60–63, Apr. 2013. doi: 10.1016/j.forsciint.2012.09.005. Abstract
     Cocaine abuse is widespread all over the world, and is performed generally by sniffing, injecting or smoking cocaine or crack. The distinction between the recreational use of cocaine from the practice of the so called “coqueo” is still an issue in those countries where this habit is diffused and where it is not considered an addiction, by this reason is necessary to develop a method for to distinguish the coca chewers and cocaine abusers. The use of an unique marker to distinguish between cocaine abuse and chewing of coca leaves is of fundamental importance in those countries where this habit is diffused. Certain alkaloids of the leaves of Erythroxylum coca are lost during the process of extraction/purification of cocaine and it is not possible to find them neither in seizures of chlorhidrate of cocaine nor urine samples of cocaine abusers. These markers are the hygrine and cuscohygrine that are present in the leaves of E. coca. A fast GC/MS method involving a liquid:liquid extraction procedure with tertbutylmethylether (TBME) is proposed for the determination of some alkaloids in cocaine leaves, cocaine seizures and biological samples. All specimens were alkalinized to pH 9 with a carbonate/bicarbonate buffer and then extracted with TBME. The analysis was carry out by GC/MS with electron impact at 70eV and in full scan mode. The results demonstrate that hygrine and cuscohygrine are not found neither in the urine of cocaine abusers nor in cocaine seizures. For this reason this compounds could be considered as markers of coca chewing. This developed method permits to distinguish coca chewing from cocaine abuse in workplace drug testing through the analysis of urine samples.
206. P. M. Rury and T. Plowman, “Morphological Studies of Archeological and Recent Coca Leaves (Erythroxylum Spp),” Botanical Museum Leaflets, Harvard University, vol. 29, no. 4, pp. 297–341, 1983. doi: 10.5962/p.168665.
207. P. M. Rury, “Systematic Anatomy of Erythroxylum P. Browne: Practical and Evolutionary Implications for the Cultivated Cocas,” Journal of Ethnopharmacology, vol. 3, no. 2, pp. 229–263, Mar. 1981. doi: 10.1016/0378-8741(81)90056-8. Abstract
     Preliminary study of the pantropical Erythroxylaceae indicates that anatomical features can provide valuable insight into the generic, infra-generic and specific affinities of unidentified specimens. Combinations of qualitative and quantitative anatomical data are most reliable when considered in conjunction with relevant ecological and plant morphological data. Extreme caution is advised in such taxonomic applications due to the intergrading patterns of anatomical variation exhibited within the family. Careful consideration must be given to the potential influence on anatomy of factors such as plant age, habit, leaf morphology and environmental conditions. Although a few species of Erythroxylum are identifiable solely on the basis of unique wood anatomical features, the majority of species can be identified only through a combination of morphological and vegetative anatomical features. Closely related species and species of similar habitats are often very similar in their wood and leaf structure. Anatomical differences are more subtle among the cultivated cocas and their closest neotropical relatives than among most taxa of Erythroxylaceae. A typological concept of foliar venation patterns among the cultivated cocas permits the varietal identification of isolated coca leaves. Several neotropical relatives of the cultivated cocas represent potential adulterants in commercial samples of coca leaf as a result of their striking similarity to genuine coca in leaf form, venation and anatomy. Due to the broad and overlapping range of leaf structural variation exhibited among the cultivated cocas and their nearest relatives, identifications of isolated leaves or leaf fragments are ill-advised in the absence of relevant ecological data. Patterns of wood and leaf anatomical variation within the Erythroxylaceae are most readily explicable as the result of evolutionary diversification in plant habit, leaf size, form and relative duration. Significant correlations among wood and leaf structure reveal various “adaptive strategies” among species of Erythroxylaceae. Redundant patterns of structural evolution, evident among the different species and genera of Erythroxylaceae, help to elucidate the probable evolutionary origins of the cultivated cocas. Comparative anatomical data support the hypothesis that Bolivian coca (E. coca) represents the most primitive of the cultivated cocas. The Colombian and Trujillo varieties of coca (E. novogranatense) appear to have been derived from a Bolivian-like ancestral coca as a result of long-term cultivation, geographic isolation and human selection for increased flavor, palatability and drought resistance.
208. V. H. S, R. D. C, and H. S. L, “Erythroxylum coca Lam.Vs. Uncaria tomentosa (Willd.), en la respuesta tisular de alveolos post-exodoncia en Cavia porcellus,” Revista Estomatologica del Altiplano, vol. 1, no. 1, pp. 1–1, 2014. https://dialnet.unirioja.es/servlet/articulo?codigo=8360787. Abstract
     Autorías: Vladimir Huacasi S., Rosalia Duran C., Haydee Sotelo L.. Localización: Revista Estomatologica del Altiplano. Nº. 1, 2014. Artículo de Revista en Dialnet.
209. J. Sáenz, A. J. Cortés, I. F. Calixto-Botía, S. Madriñán, and J. A. Sanchez, “Efectos del proceso de domesticación en la especiación y flujo genético de Erythroxylum coca y E. novogranatense en Colombia,” p. 16.
210. L. M. Sanchez Campo, “Determinación De Los Parámetros Fisicoquímicos Del Suelo, Degradados Por Cultivo De Coca (erythroxylum Coca) En El Caserio Bajo Chimbote, Distrito José Crespo Y Castillo, Huánuco - 2020,” PhD thesis, Universidad de Huánuco, 2021. http://repositorio.udh.edu.pe/handle/123456789/3061. Abstract
     La tesis fue de tipo y nivel aplicativo, con enfoque mixto, de diseño no experimental correlacional. Metodología: Para la etapa de campo se muestreo suelo, lo que consto de la obtención de la recolección de 5 muestras simples por parcela, con ello se forma una muestra compleja de 1 kg, aproximadamente por parcela; esto fue enviada a laboratorio de suelos de la UNAS para los análisis respectivos; cabe indicar que las parcelas se diferenciaban por años de antigüedad del cultivo de coca (Erythroxylum coca) estos fueron de 1 año, 2 años y 3 años de antigüedad del cultivo. Los resultados: obtenidos fueron: Análisis mecánico del suelo para M1 (1 año de cultivo) fue Franco arcillo arenoso; M2 (2 años de cultivo) fue Arcilloso; M3 (3 años de cultivo) Arcilloso; para materia orgánica fue de 26,44 y 41 % para M1, M2 y M3 respectivamente; El pH fue de 4.41 (M1), 4.35 (M2) y 4.35 (M3); conductividad eléctrica en (Μs/Cm): 0.132 M1, 0.88 M2 y 0.108 M3; M.O. (materia orgánica): 0.75 (M1), 1.66 (M2) y 2.01 (M3); para él % Nitrógeno (N): 0.04 (M1), 0.08 (M2) y 0.10 (M3); para Fosforo (P) en ppm: 1.67 (M1), 2.23 (M2) y 1.43 (M3); para Potasio (K) en ppm: 102 (M2), 79 (M2) y 97 (M3); para CICe: 9.92 (M1), 15.86 (M2) y 16.82 (M3); para Cd (cadmio) en ppm: 0.016 (M1), 0.014 (M2) y 0.004 (M3). Se concluye que el uso de agroquímicos en los cultivos de coca en el caserío bajo Chimbote, son los responsables de la acidificación y el bajo contenido de macronutrientes en los suelos muestreados.
211. C. O. Sánchez, “Narcos alteran la coca para hacerla gigante e hiperresistente,” www.elcolombiano.com. 14:4:56. https://www.elcolombiano.com/colombia/narcos-manipulan-geneticamente-la-hoja-de-coca-para-tener-mas-cocaina-AL15873542. Abstract
     Plantas que miden más de 6 metros de altura, con hojas de hasta 12 centímetros de longitud, capacidad para adaptarse a varios tipos de clima e incluso...
212. D. C. Sands et al., “Characterization of a Vascular Wilt of Erythroxylum Coca Caused by Fusarium Oxysporum f. Sp. Erythroxyli Forma Specialis Nova,” Plant Disease, vol. 81, no. 5, pp. 501–504, May 1997. doi: 10.1094/PDIS.1997.81.5.501. Abstract
     A new forma specialis of Fusarium oxysporum (F. oxysporum f. sp. erythroxyli) pathogenic to Erythroxylum coca and E. novogranatense is described. The pathogen was isolated from the vascular tissue of diseased plants from an Erythroxylum plantation in Hawaii. This pathogen causes vascular wilt symptoms and death in both E. coca and E. novogranatense plants as soon as 7 weeks after soil infestation. The pathogenicity of seven isolates from the affected field was determined in field and growth-chamber studies. Genetic variation was not detected among the seven Hawaiian isolates, using arbitrarily primed polymerase chain reaction. The seven isolates could be differentiated from a strain isolated from a diseased E. coca plant from South America. All Hawaiian isolates and the South American isolate belonged to a single vegetative compatibility group.
213. M. E. Santoni and G. Torres, “La Coca (erythroxylum Coca),” p. 29.
214. M. Sauvain et al., “Estudio químico y botánico de las diferentes formas de erythroxylum coca var. coca cultivadas en Bolivia,” 1997. http://repositorio.umsa.bo/xmlui/handle/123456789/13062. Abstract
     La coca es una de las plantas de cultivo más antiguo de los pueblos de Sur américa, constituyendo uno de los más importantes de Bolivia. Una parte de la producción es consumida tradicionalmente por los campesinos (principalmente bajo la forma del acullicu) alrededor de 10.000 toneladas sobre las 60.000 a 80.000 toneladas producidas anualmente en el país (Carter y Mamani, 1986). Las preguntas que habitualmente se hace la población boliviana sobre las cualidades de la hoja de coca son las siguientes: ¿Existen distintas variedades de coca cultivadas en Bolivia? ¿La hoja de coca en su estado natural, tiene o no cocaína? ¿Cuántos compuestos diferentes están presentes en la hoja de coca? ¿Cuál es el compuesto responsable de sus propiedades medicinales?
215. M. Sauvain et al., “A Study of the Chemical Composition of Erythroxylum Coca Var. Coca Leaves Collected in Two Ecological Regions of Bolivia,” Journal of Ethnopharmacology, vol. 56, no. 3, pp. 179–191, May 1997. doi: 10.1016/S0378-8741(97)00030-5. Abstract
     Coca—Erythroxylum coca Lamarck var. coca—remains one of the most common plants of the folk medicine of Bolivia used as a general stimulant. Aymara and Quechua natives prefer to chew the sweeter coca leaves from the Yungas (tropical mountain forests of the eastern slopes of the Andes) rather than those from the Chapare lowlands. The contents in cocaine and minor constituents of leaf samples cultivated in these regions does not rationalize this choice.
216. L. M. Scarpetta RamírezA, “Reconocimiento Fitoquímico y etnobotánico de Erythroxylum coca en la población Nasa del Departamento del Cauca – Colombia,” Revista Criterio Libre Jurídico, vol. 14, no. 1, pp. 10–19, 2017. doi: 10.18041/1794-7200/criteriojuridico.2017.v14n1.1601. Abstract
     In the following article, research result, the relationship between the secondary metabolites in the Erythroxylum Coca var Coca plant and its medicinal use in the Nasa population of the department of Cauca- Colombia is established, based on the review of scientific literature. Initially, the general aspects of the plant Erythroxylum Coca var. Coca, which has different secondary metabolites such as alkaloids: Benzomethylecgonine (cocaine), cis and transinamilcocaine, B-truxilin, tropacocaine, benzoylecgonine, B-higrin, dihydrocuscohigrin; flavonoids such as O-conjugates of Eriodictyol and terpenes such as β-pinene (monoterpene), β-myrcene (monoterpene), nerolidol (sesquiterpene); in the essential oil is also found Stearic acid, phytol, methyl ester 7, 10, 13 hexadecatrienoic acid and nonacosane. Then the biogenesis of each major metabolite and the most important extraction forms of each of them is mentioned, according to laboratory techniques and ancestral techniques in the Nasa community and, finally, a relationship is made between ethnobotany and phytochemistry to understand the medicinal use. En el siguiente artículo, resultado de investigación, se establece la relación que hay entre los metabolitos secundarios en la planta de Erythroxylum Coca var  Coca y su uso medicinal en la población Nasa del departamento del Cauca- Colombia, basada en la revisión de literatura científica. Inicialmente se da a conocer los aspectos generales de la planta Erythroxylum Coca var. Coca, la cual posee diferentes metabolitos secundarios como los alcaloides: Benzometilecgonina (cocaína), cis y trans- cinamilcocaína, B- truxilina, tropacocaína, benzoilecgonina, B- higrina, dihidrocuscohigrina; flavonoides como los ~O-conjugados del Eriodictiol y terpenos como β- pineno (monoterpeno), β- mirceno (monoterpeno), nerolidol (sesquiterpeno); en el aceite esencial también se encuentra Ácido esteárico, fitol, ácido metil éster 7, 10, 13 hexadecatrienoico y nonacosano. Luego se menciona la biogénesis de cada metabolito principal y las formas de extracción más importantes de cada uno de ellos, de acuerdo a técnicas de laboratorio y técnicas ancestrales en la comunidad Nasa y, por último, se hace una relación entre la etnobotánica y la fitoquímica para comprender el uso medicinal. No seguinte artigo, resultado de pesquisa, é estabelecida a relação entre os metabólitos secundários na planta de Erythroxylum Coca var Coca e seu uso medicinal na população  Nasa do departamento Cauca - Colômbia, com base na revisão da literatura científica. Inicialmente, é dado a conhecer os aspectos gerais da planta Erythroxylum Coca var. Coca, que tem diferentes metabólitos secundários, como alcalóides: Benzometillecgonina (cocaína), cis e trans-cinamilocaína, B-truxilina, tropacocaína, benzoilecgonina, B-higrina, dihidrococihigrina; flavonóides tais como O-conjugados de  Eriodictyol e terpenos tais como β-pineno (monoterpeno), β -mirceno (monoterpeno), nerolidol (sesquiterpeno); no óleo essencial também encontra-se ácido esteárico, phytol, ácido metil éster  7, 10, 13  hexadecatrienoico e nonacosano. Após, é mencionada a biogênese de cada metabólito principal e as formas de extração mais importantes de cada um, de acordo com técnicas de laboratorio e técnicas ancestrais na comunidade Nasa e, finalmente, se faz uma relação entre etnobotânica e fitoquímica para compreender o uso medicinal.
217. G. W. Schmidt et al., “The Last Step in Cocaine Biosynthesis Is Catalyzed by a BAHD Acyltransferase,” Plant Physiology, vol. 167, no. 1, pp. 89–101, Jan. 2015. doi: 10.1104/pp.114.248187. Abstract
     The esterification of methylecgonine (2-carbomethoxy-3β-tropine) with benzoic acid is the final step in the biosynthetic pathway leading to the production of cocaine in Erythoxylum coca. Here we report the identification of a member of the BAHD family of plant acyltransferases as cocaine synthase. The enzyme is capable of producing both cocaine and cinnamoylcocaine via the activated benzoyl- or cinnamoyl-Coenzyme A thioesters, respectively. Cocaine synthase activity is highest in young developing leaves, especially in the palisade parenchyma and spongy mesophyll. These data correlate well with the tissue distribution pattern of cocaine as visualized with antibodies. Matrix-assisted laser-desorption ionization mass spectral imaging revealed that cocaine and cinnamoylcocaine are differently distributed on the upper versus lower leaf surfaces. Our findings provide further evidence that tropane alkaloid biosynthesis in the Erythroxylaceae occurs in the above-ground portions of the plant in contrast with the Solanaceae, in which tropane alkaloid biosynthesis occurs in the roots.
218. B. M. da S. e Silva, C. de Oliveira, F. Cesarino, and R. D. Vieira, “Armazenamento e germinação de sementes de coca (Erythroxylum squamatum Sw.),” Revista Trópica: Ciências Agrárias e Biológicas, vol. 8, no. 1, Dec. 2014. doi: 10.0000/rtcab.v8i1.1358. Abstract
     The objective this work was to evaluate the effect of the temperature on seeds storage and germination of the Erythroxylum squamatum Sw.. To develop this research, seeds were placed in plastic boxes contained wetted paper with nistatina (0,2%) and kept at 15, 20, 25, 30, 35 and 40ºC, during the photoperiod of 12 hours. In the storage, seeds were placed in paper bags and kept to ambient and refrigerator temperature. Monthly, the seeds germination were evaluated. The minimum temperature, ideal germination temperature and maximum temperature range for “coca” seeds were between 15 and 20ºC, 25 and 30ºC and 35 and 40ºC, respectively. The coca seeds storage for long time was impracticable in paper bag at (10ºC ± 2) refrigerator and (27ºC ± 5) ambient temperature. Probably, the “coca” seeds are intolerants to desiccation.
219. B. M. da S. e Silva, F. Cesarino, R. Sader, and J. D. Lima, “Germinação e armazenamento de sementes de COCA (Erythroxylum ligustrinum DC. - Erythroxylaceae),” Revista Brasileira de Sementes, vol. 30, pp. 25–29, 2008. doi: 10.1590/S0101-31222008000300004. Abstract
     O objetivo deste trabalho foi avaliar o efeito da temperatura sobre a germinação e o armazenamento de sementes de Erythroxylum ligustrinum DC. As sementes foram colocadas germinar caixas de plásticas sobre duas folhas de papel, umedecidas com Nistatina 0, 2%, mantidas em germinadores nas temperaturas constantes de 5, 10, 15, 20, 25, 30, 35, 40 e 45ºC e com fotoperíodo de 12 horas. Para o armazenamento, as sementes foram colocadas em sacos de papel, mantidos à temperatura ambiente e em geladeira. Em seguida, mensalmente, foi avaliada a germinação das sementes. A temperatura mínima, a faixa de temperatura ideal e a temperatura máxima para germinação de sementes de coca estão entre 10 e 15ºC, 25 e 30ºC e 40 e 45ºC, respectivamente. O armazenamento de sementes coca por longo período é inviável em embalagens de papel na geladeira (10ºC ± 2) e em temperatura ambiente (27ºC ± 5).
220. “Erythroxylum Species,” in Secondary Metabolites of Medicinal Plants: Ethnopharmacological Properties, Biological Activity and Production Strategies, vol. 3, John Wiley & Sons, Ltd, 2020, pp. 473–483. doi: 10.1002/9783527825578.c02-38. Abstract
     This chapter discusses the ethnopharmacological properties, phytochemistry, and culture conditions of the Erythroxylum species. Erythroxylum monogynum Roxb. (Fam. – Erythroxylaceae) is used in traditional system of medicine and found in southern parts of India. The crude extract of E. laurifolium possesses in vivo hypoglycemia effects. The methanolic extract of from E. pulchrum leaves shows antibacterial activity against Bacillus subtilis, Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Streptococcus sanguinis, Streptococcus salivarius, Streptococcus mutans, and Streptococcus species. The shoot cultures of E. coca were established on Murashige and Skoog culture medium from excised embryos as explants on semi-solid medium. The highest level of tropane alkaloids (cocaine) along with amino acids (arginine, glutamate, proline, and phenylalanine) and chlorogenic acid was reported in Anderson’s Rhododendron medium.
221. K. R. Solomon, E. J. P. Marshall, and G. Carrasquilla, “Human Health and Environmental Risks from the Use of Glyphosate Formulations to Control the Production of Coca in Colombia: Overview and Conclusions,” Journal of Toxicology and Environmental Health, Part A, vol. 72, no. 15-16, pp. 914–920, Aug. 2009. doi: 10.1080/15287390902929659.
222. S. Sonkar, A. K. Singh, and A. Husen, “Convolvulus Pluricaulis (Shankhpushpi) and Erythroxylum Coca (Coca Plant),” in Herbs, Shrubs, and Trees of Potential Medicinal Benefits, CRC Press, 2022. Abstract
     Plants with therapeutic and medicinal characteristics have been used by mankind since ancient times. However, the introduction and use of contemporary synthetic medicines by the local people has resulted in the loss of traditional knowledge. As a result, it is essential to chronicle the knowledge of plant uses for the treatment of various diseases before it is lost to future generations. The present study discusses the general description, traditional knowledge, chemical derivatives, and potential benefits to mankind of the plants, Convolvulus pluricaulis and Erythroxylum coca. This study also looks at the advantages of C. pluricaulis and E. coca as alternative medicines for a variety of illnesses. The potential benefits and uses of these plants have been thoroughly discussed, providing references to studies that have been done utilizing these plants.
223. M. M. Soto, C. R. Monroy, J. C. Contreras-Velásquez, S. Y. Wilches-Duran, M. E. Graterol-Rivas, and A. M. Díaz, “Approximation of a R+D+I Program for the Agro-Industry of Stevia Rebaudiana (Bertoni), as a Substitution Alternative of Erythroxylum Coca (Lam) for the Post-Conflict in Catatumbo, Colombia,” in Global Partnerships for Development and Engineering Education: Proceedings of the 15th LACCEI International Multi-Conference for Engineering, Education and Technology,July 19-21, 2017, Boca Raton, FL, United States, 2017, ISBN 978-0-9993443-0-9, 2017, p. 324. https://dialnet.unirioja.es/servlet/articulo?codigo=7352957. Abstract
     Autorías: Moisés Martínez Soto, Carlos Rodríguez Monroy, Julio C. Contreras-Velásquez, Sandra Y. Wilches-Duran, Modesto E. Graterol-Rivas, Anne Morris Díaz. Localización: Global Partnerships for Development and Engineering Education: Proceedings of the 15th LACCEI International Multi-Conference for Engineering, Education and Technology,July 19-21, 2017, Boca Raton, FL, United States, 2017. Artículo de Libro en Dialnet.
224. V. B. Stolberg, “The Use of Coca: Prehistory, History, and Ethnography,” Journal of Ethnicity in Substance Abuse, vol. 10, no. 2, pp. 126–146, Apr. 2011. doi: 10.1080/15332640.2011.573310. Abstract
     The purpose of this article is to review the use of the natural mild stimulant coca, which is a story that originates with the prehistory of coca, evolves through its following historical uses, and leads up to the eventual development of cocaine. This discussion will begin with the botanical background of the coca plant, followed by a review of some of the prehistoric, historic and ethnographic evidence of coca use, which indicates the extensive antiquity and pervasiveness of coca use in South and Central America. The diverse roles that coca played among the Inca and other indigenous peoples led to the early adoption of coca in the West and, in turn, to the resultant discovery of cocaine and its assorted early applications, particularly for medicinal purposes.
225. P. Subash and K. Srinivasa Rao, “In Silico Molecular Docking Analysis for Potential Anti-Alzheimer’s Compounds from the Methanolic Leaf Extract of Erythroxylum Monogynum Using Gas Chromatography–Mass Spectrometry,” Journal of Saudi Chemical Society, vol. 25, no. 8, p. 101285, Aug. 2021. doi: 10.1016/j.jscs.2021.101285. Abstract
     Background Alzheimer’s disease is the major cause of dementia by two main factors includes an accumulation of acetylcholinesterase enzyme at cholinergic synapse and deposition of β-amyloid protein at neurofibrillary tangles. The present investigation explores the binding affinities of phytoconstituents present in the methanolic leaf extract of Erytrhroxylum monogynum identified by gas chromatography-mass spectrometry against selected targets, i.e., β-amyloid and acetylcholinesterase. Objectives The main objective of present study was to explore anti-Alzheimer’s potential of phytoconstituents from methanolic leaf extract of Erytrhroxylum monogynum. Methods Erytrhroxylum monogynum leaf material was subjected to Soxhlet extraction by three different solvents, namely n-hexane, chloroform and methanol. The methanolic leaf extract was subjected to Gas chromatography–mass spectrometric analysis for identification of novel phytoconstituents and chromatogram revealed the presence of 45 novel phytoconstituents. These phytoconstituents were not reported earlier from any part of this plant material. These phytoconstituents were explored for their anti-Alzheimer’s potential by iGEMDOCK software against selected targets, namely recombinant human acetylcholinesterase (protein data bank ID: 3LII) and β-amyloid (protein data bank ID: 2LMN). Results From the results of docking analysis, the top five phytoconstituents with the highest binding affinity towards the selected targets were further subjected to ADMET prediction by in silico admetSAR web portal. Conclusions Molecular docking analysis revealed the presence of 7 phytoconstituents are having the highest binding affinity towards the selected targets when compared to their respective standard compounds namely 9, 12-octa-decadienoic acid, methyl ester, (E, E); octadecanoic acid, methyl ester; hexadecanoic acid, 2-hydroxy-1-(hydroxymethyl) ethyl ester; 3, 6-ditigloyloxy-7-hydroxytropane; 3, 7,11, 15-tetramethyl-2-hexa-decen-1-ol; neophytadiene and phytol. The lead hits were further subjected to LigPlot analysis to understand their intermolecular interactions. Thus the result collectively obtained from the in silico studies using computational approaches may become prospective novel lead compounds against the selected targets of Alzheimer’s disease.
226. L. K. P. D. Taveira, M. A. P. da Silva, and M. I. B. Loiola, “Allelopathy in Five Species of Erythroxylum,” Acta Scientiarum. Agronomy, vol. 35, pp. 325–331, Sep. 2013. doi: 10.4025/actasciagron.v35i3.16016. Abstract
     The objective of this study was to determine the allelopathic potential of Erythroxylum rosuliferum O.E. Schulz; Erythroxylum stipulosum; Erythroxylum cuneifolium (Mart) O.E. Schulz; Erythroxylum vacciniifolium Mart. and Erythroxylum barbatum O.E. Schulz. Bioassays were performed to examine the seed germination and initial growth of seedlings of Lycopersicum esculentum Mill (tomato) and Allium cepa L. (onion) in Petri dishes following exposure to an ethanolic extract of fresh leaves from the test species at various concentrations. The growth of the tomato and onion seedlings was inhibited with the extracts of the species tested, and significant alterations in the development of the shoots and primary roots were observed. These results suggest that the five species that were evaluated have allelopathic properties.
227. Terremoto, “Botanical Readings: Erythroxylum Coca by Ximena Garrido-Lecca,” Terremoto. . https://terremoto.mx/en/producto/lecturas-botanicas-erythroxylum-coca/. Abstract
     2022 Spanish / English 192 pages Soft cover, printed in color 15 x 23 cm ISBN: 978-607-98750-5-3 Botanical Readings: Erythroxylum Coca is an installation by the artist Ximena Garrido-Lecca (Peru, 1980), presented at proyectoamil in Lima, 2019. The piece was composed by a hydroponic structure for the cultivation of coca plants, whose leaves—and their divinatory...
228. A. R. Toppozada et al., “Evaluation of a Fiber Optic Immunosensor for Quantitating Cocaine in Coca Leaf Extracts,” Biosensors and Bioelectronics, vol. 12, no. 2, pp. 113–124, Jan. 1997. doi: 10.1016/S0956-5663(97)87057-1. Abstract
     A fiber optic evanescent fluoroimmunosensor was used to rapidly detect and quantitate coaca alkaloids as cocaine equivalents in leaf extracts of five Erythroxylum species. A monoclonal antibody (mAb) made against benzoylecgonine (BE), a major metabolite of cocaine, was immobilized covalently on quartz fibers and used as the biological sensing element in the portable fluorometer. Benzoylecgonine-fluorescein (BE-FL) was used as the optical signal generator when it bound to the fiber. If present, cocaine competed for the mAb and interfered with the binding of BE-FL, thereby reducing the fluorescence transmitted by the fiber. Calibration curves were prepared by measuring (over 30 s) the rates of fluorescence increase in the absence, or presence of cocaine. Ethanol or acid extracts of dry coca leaves were assayed by this fiber optic biosensor, gas chromatography and fluorescent polarization immune assay. Biosensor values of cocaine content of leaves from five Erythroxylum species were not significantly different from gas chromatography values, but had higher variance. The biosensor assay was rapid and did not require cleanup of the crude leaf extracts. Cocaine in acid extracts was reduced significantly after 4 weeks at 23°C and after 3 weeks at 37°C. Fibers (mAb-coated), stored at 37°C in phosphate-buffered solution (0.02% NaN3), gave stable responses for 14 days.
229. M. Toyne, “The Transformation of Coca to Cocaine: An Overview of Traditional Drug Use and Modern Drug Abuse,” p. 11.
230. C. J. Tunjano Huerta and D. J. Calvo Valencia, “Evaluación de sustancias fitoprotectoras usadas como estrategia de neutralización de la acción del glifosato sobre cultivos de erythroxylum coca,” Revista Logos, Ciencia & Tecnología, vol. 2, no. 2, Jan. 2011. doi: 10.22335/rlct.v2i2.79. Abstract
     They are multiple the strategies used by the cocaleros to resist to the programs of eradication. The study had as objective to evaluate 3 treatments used by the farmers of coca to neutralize the action of the glifosato, for such an effect he/she settled down a to cultivate of coca Erythroylum coca and by means of experimental design in blocks the consistent treatments were applied at random in aspersions to totally established mature plants of (8 months of age) compound in 3 types of substances dissolved in water: Molasses 0.1g/ml., Milk 1g/ml, Soap detergente10g/l, by means of inspection based on the scale of ALAM was determined the toxicity signs and the effectiveness fitoprotectora of the used substances being the inefficacy of the strategies.
231. D. Tunque Huamaní, “Formulación y elaboración de un pan de molde enriquecido con coca (Erythroxylum coca), camote (Ipomea batata) y quinua (Chenopodium quinoa Willd) aplicando superficie de respuesta,” Universidad Nacional de San Cristóbal de Huamanga, 2017. http://repositorio.unsch.edu.pe/handle/UNSCH/3326. Abstract
     Se elaboró un pan de molde enriquecidos con harina de coca (Erythroxylum coca), harina de quinua (Chenopodium quinoa willd) y pulpa de camote (Ipomea batata), se evaluó de la formulación óptima del pan de molde las propiedades nutritivas y sensoriales se obtuvo un mejor contenido proteico, color y sabor. El diseño de mezclas aplicado fue el software D-optimal desing, que se estableció en dieciséis mezclas. Se encontró que: 1) las propiedades sensoriales de color y sabor de las dieciséis formulaciones evaluadas cumplieron con las normas y fueron aceptadas, 2) la formulación óptima del pan de molde fue 1% de harina de coca, 8,95% de harina de quinua, 10,05% de pulpa de camote y 80% de harina de trigo, 3) el pan de molde optimizado tuvo la siguiente composición química: 26,59% de humedad, 13,07% de proteína, 2,25% de grasa, 57,18% de carbohidratos y 0,91% de cenizas. El modelo de mezclas obtenidas en el programa Design Expert a través del diseño D-optimal se representó por medio del uso de gráficos de contorno, superficie de respuesta e interacción y resultaron ser efectivos para el estudio e interpretación de los resultados obtenidos. Para evaluar la aceptación del producto final se evaluó mediante el test hedónico con 30 panelistas no entrenados que evaluaron la aceptación del pan.
232. C. E. Turner, C. Y. Ma, and M. A. Elsohly, “Constituents in Erythroxylum Coca I: Gas Chromatographic Analysis of Cocaine from Three Locations in Peru,” Bulletin on narcotics, vol. 31, no. 1, pp. 71–76, Jan. 1979. Abstract
     A method for the determination of cocaine content in coca leaves (Erythroxylum coca) has been developed. The procedure involves refluxing the powdered leaves in 95% ethanol for 15 minutes, followed by acid-base partitioning with chloroform and a GLC assay. The recovery of cocaine was quantitative. This procedure was applied to determine cocaine content in three samples of Erythroxylum coca Lam. collected from different geographic locations in Peru. Using androst-4-ene-3,17-dione as the internal standard the calibration curve was linear over a factor of 0.5 to 10 fold cocaine concentration relative to internal standard. The slope (b) was 0.733, the coefficient of determination (r2) was 1.00 and the average precision was 3.9%.
233. C. E. Turner, C. Y. Ma, and M. A. Elsohly, “Constituents of Erythroxylon Coca II. Gas-Chromatographic Analysis of Cocaine and Other Alkaloids in Coca Leaves,” Journal of Ethnopharmacology, vol. 3, no. 2, pp. 293–298, Mar. 1981. doi: 10.1016/0378-8741(81)90059-3. Abstract
     A gas-chromatographic procedure is outlined for the analysis of cocaine and cis- and trans-cinnamoylcocaines in coca leaves. The procedure was applied to the determination of these alkaloids in coca leaves collected from three different locations in Peru. The extraction of alkaloids from plant material was accomplished following the procedure we previously outlined. Recovery of cinnamoylcocaines was quantitative and the average coefficient of variation was 6.8%. Using androst-4-ene-3,17-dione as the internal standard, the correlation coefficient (r2) as determined from the calibration curve of frans-cinnamoylcocaine was 0.99 and the response factor 0.72. Observable differences in relative proportions of cis and trans isomers of cinnamoylcocaine were found among samples from different locations. In addition, the relative proportions of the total cinnamoylcocaine concentration to cocaine varied with sample origin. We have also examined coca extracts using a nitrogen detector and by gas chromatography-mass spectrometry. The nature and identity of other nitrogenous peaks in the chromatograms are also discussed.
234. L. M. Valdez, J. Taboada, and J. E. Valdez, “Ancient Use of Coca Leaves in the Peruvian Central Highlands,” Journal of Anthropological Research, vol. 71, no. 2, pp. 231–258, Jun. 2015. doi: 10.3998/jar.0521004.0071.204. Abstract
     Coca, of the genus Erythroxylum, is a stimulant and painkiller that played key roles within the Inka state. As reported by the early Spanish chroniclers, coca was the most important plant offering during public rituals. Likewise, important landmarks within the Inka domain regularly received offerings of this precious leaf. Its high value is indicated by the fact that not only the living chewed the leaves on a regular basis, but also the dead carried coca leaves in their mouths. We still do not know when coca leaves were first used in the Peruvian central highlands. This uncertainty is largely due to the lack of coca leaves recovered from highland archaeological sites. Several leaves recently found at Convento in the northern part of the Ayacucho Valley are the first direct evidence from an archaeological context that, based on ceramic stylistic grounds, dates to sometime between the end of the Early Intermediate Period (ca. 1–550 ce) and the beginning of the Middle Horizon Period (ca. 550–1100 ce). The botanical identification also indicates that the source of the coca was the Pacific coast. This paper reports this unique finding and discusses its implications.
235. A. R. van der Hoogte and T. Pieters, “From Javanese Coca to Java Coca: An Exemplary Product of Dutch Colonial Agro-Industrialism, 1880-1920,” Technology and Culture, vol. 54, no. 1, pp. 90–116, 2013. doi: 10.1353/tech.2013.0045. Abstract
     In 1875 the Botanical Garden of Buitenzorg introduced two coca plants on the island of Java, which was then part of the Netherlands East Indies. Within a thirty-year period, starting in 1892, Java succeeded in becoming the world's leading
236. M. van der Merwe, J. Christina, and M. Rossetto, “Microsatellite Loci for a New Australian Endemic Plant Species Erythroxylum Sp. ‘Cholmondely Creek’ (J.R.Clarkson 9367) (Erythroxylaceae),” Conservation Genetics Resources, vol. 1, no. 1, pp. 329–331, Dec. 2009. doi: 10.1007/s12686-009-9076-x. Abstract
     A population of a recently discovered Australian endemic plant species in the genus Erythroxylum (Erythroxylaceae), previously thought only to occur on the Cape York Peninsula, was found at Gove in the Northern Territory. As the only population in the Northern Territory it is likely to be listed as critically endangered within the state. Unlike the other populations it was found to produce mainly vegetatively. To investigate levels of clonality in comparison to non-clonal populations and the spatial distribution of genotypes we developed microsatellite markers. Following an enrichment protocol 10 loci were found to be polymorphic after screening twenty plants from a sexually reproducing population. Number of alleles varied from 3 to 11 while expected heterozygosity ranged between 0.14 and 0.84. While these markers will form a valuable part of an ongoing investigation into the conservation of the isolated population, successful cross species amplification indicates their potential use in other studies.
237. S. Vázquez-Santana, C. A. Domínguez, and J. Márquez-Guzmán, “Embriología de Erythroxylum havanense Jacq. (Erythroxylaceae),” Botanical Sciences, no. 59, pp. 25–33, Dec. 1996. doi: 10.17129/botsci.1503. Abstract
     We studied the development of reproductive structures in pin and thrum morphs of Erythroxylum havanense. The young anther wall consists of an epidermis, endothecium , 1-3 middle layers anda binucleate secretory tapetum. The mature anther wall has only two layers: epidermis and endothecium. Microspore tetrads are tetrahedral or isobilateral. Mature pollen grains are tricolporate, bicellular and contain starch grains. Exine sculpturing is verrugate in thrum pollen and reticulate in pin pollen. The ovule is sessile, pendulous, anatropous, bitegmic and crassinucellate. The embryo sac is heptacellular. An endothelium is differentiated. The endosperm development is nuclear, and the basal part of the nucellus persists during early endosperm development. Both integuments form the seed coat.
238. G. L. Vee, G. B. Fink, and G. H. Constantine, “Anorexic Activity of Cocaine and Coca Extract in Naive and Cocaine Tolerant Rats,” Pharmacology Biochemistry and Behavior, vol. 18, no. 4, pp. 515–517, Apr. 1983. doi: 10.1016/0091-3057(83)90273-3. Abstract
     Dose response curves for reducing limited access food consumption were determined for cocaine HC1 IP, cocaine HC1 PO, and whole Erythroxylum coca extract PO. The ED50’s for cocaine HC1 in drug naive rats were 19.6 mg/kg (IP) and 34.6 mg/kg (PO). When the dose of E. coca extract was expressed in terms of cocaine HC1 content, the ED50 was 52.6 mg/kg (PO). When dose response curves were determined in rats that had received cocaine (45 mg/kg, PO) for 30 days, a shift to the right in the cocaine HC1 curve (an ED50 of 98.4 mg/kg PO) indicated tolerance. However, the shift to the right was less for E. coca extract than for cocaine HCI. Although the anorexic activity of E. coca extract was less than that of an equivalent amount of cocaine in naive rats it was often more than that of equivalent doses of cocaine HC1 in tolerant rats. Interaction with other constituents of E. coca extract appears to alter the potency of the cocaine content of the extract in different directions in naive and tolerant rats.
239. G. L. Vee, “A Study of Bioactive Substances from Erythroxylum Coca (Lin.) and Vancouveria Hexandra (Morr. and Decne.),” Doctor of Philosophy, Oregon State University, 1983. Abstract
     Thegoalofthisresearchwastouseproceduresto assayforbiologicalactivitesandthentoutilizethese proceduresintheevaluationorpurificationofthe activenaturalproducts. Cocaandcocainewereevaluatedusingbioassayto developdoseresponsecurves. Doseresponsecurvesfor reducinglimitedaccessfoodconsumptionweredetermined forcocaineHC1IP,cocaineHC1P0,andwhole Erythroxylumcoca(Lin.) extractP0. TheED50’sfor cocaineHC1indrugnaiveratswere19.6mg/kg(IP)an 34.6mg/kg(P0). WhenthedoseofE. cocaextractwas expressedintermsofcocaineHC1content,theED50was 52.6mg/kg(P0). Whendoseresponsecurveswere determinedinratsthathadreceivedcocaine(45mg/kg, P0)for30days,ashifttotherightinthecocaineHC1 curve(anED50of98.4mg/kg,P0)indicatedtolerance. However,theshifttotherightwaslessforE. coca extractthanforcocaineHC1. Althoughtheanorexic activityofE. cocaextractwaslessthanthatofan equivalentamountofcocaineinnaiveratsitwasoften morethanthatofequivalentdosesofcocaineHC1in tolerantrats. InteractionwithotherconstituentsofE. cocaextractappearstoalterthepotencyofthecocaine contentoftheextractindifferentdirectionsinnaive andtolerantrats. Thesecondplantstudiedusingbioassayand phytochemicaltechniqueswastheInside-Outplant, Vancouveriabexandra(Morr. andDecne.). Duringa phytochemicalinvestigationofK. bexandraforalkaloids itwasnotedthatcertainfractionsposessed vasoconstrictoractivity. Aquaternaryalkaloidwas isolatedwhichwasnotresponsibleforthe vasoconstrictoreffect. Amethanolextract,through chromatographictechniques,yieldedanactiveprinciple. Theactiveprinciplewasshowntobeicariinthrough comparisonwithanauthenticsampleandconversionto knownderivatives. Icariinwasfoundtohaveinvivovasoconstrictor activitywhichwasconsiderablylessactivethan norepinephrine. Howeverthevasoconstrictoractivityof icariinwasnotreducedbyphentolamine,anadrenergic blocker. Thusicariinappearstoactdirectlyonthe smoothmuscleoftheartery.
240. G. Ventura, “Chemical composition of essential oil Erythroxylum coca Lam var. coca (Coca) and evaluation of its antibacterial activity,” 2009.
241. G. Ventura, A. Castro, M. Roque, and J. Ruiz, “Composición química del aceite esencial de Erythroxylum coca Lam var. Coca (coca) y evalua­ción de su actividad antibacteriana,” Ciencia e Investigación, vol. 12, no. 1, pp. 24–28, Jun. 2009. doi: 10.15381/ci.v12i1.3382. Abstract
     The study was to evaluate the essential oil of Erythroxylum coca Lam. var. coca (Coca) - from Quillabamba province, Cusco region and determine its antibacterial activity, and elucidate the same chemical composition by Gas Chromatography / Mass Spectrometry (GC / MS). The plant part used the dried leaves were provided by the National Coca Company ENACO SA, which dealt with a system by steam distillation of water. The essential oil yield was 0.08% v/p and on that physicochemical tests were performed: Miscibility, density and refractive index. In the chemical composition found the following components: Guai-1(5),(11)-diene, t-cadinene, (2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecan-1 -ol, eudesm-4(14)-en-11-ol, hexahydrofarnesil ketone, hexadecanoic acid, phytol, cis-9-octadecenoic and octadecanoic acid. The study of antibacterial activity in vitro, using the method of excavation culture plate at concentrations of 10 and 50% of the oil showed greater activity to Staphylococcus aureus strain ATCC 25923, than against strains of Escherichia coli, Bacillus subtilis, Staphylococcus epidermidis and Pseudomonas aeruginosa ATCC 27853 strain. It was determined that the chemical components of essential oil of Erythroxylum coca Lam. Var coca (Coca) have antibacterial activity against Staphylococcus aureus.
242. J. Weil, “Beyond the Mystique of Cocaine: Coca in Andean Cultural Perspective,” in Plants and Indigenous Medicine and Diet, Routledge, 1986. Abstract
     The coca/cocaine distinction corresponds to a more general distinction, often blurred, whereby the balance between benefits and hazards of drugs shifts according to the circumstances surrounding their use. Cocaine is the only local anaesthetic which also acts as a vasoconstrictor. These dual effects have made it a drug of choice for surgery involving the mucous membranes of the nose, throat, and ear. A number of investigators believed that cocaine is ineffective when ingested orally because of hydrolysis, and it has been suggested that alkaloids other than cocaine—including arecoline, ecgonine, and nicotine—may account for some of the effects of coca leaf chewing. Cocaine and coca were in vogue in Europe and North America in the latter half of the 19th century. The migration of Andean peasants to new agricultural settlements on the eastern slopes to grow coca has led to their rapid integration into the national society and economy.
243. A. T. Weil, “Coca Leaf as a Therapeutic Agent,” The American Journal of Drug and Alcohol Abuse, vol. 5, no. 1, pp. 75–86, Jan. 1978. doi: 10.3109/00952997809029262. Abstract
     South American Indians have used coca leaf as a remedy for thousands of years. Coca might be useful as a treatment for gastrointestinal ailments and motion sickness, as a fast-acting antidepressant medication, as a substitute stimulant for coffee in certain cases, and as an adjunct in programs of weight reduction and physical fitness. In leaf form, coca does not produce toxicity or dependence. Its effects are distinct from those of cocaine, which is but one of a number of active compounds in the leaf. Coca can be administered as a chewing gum containing a whole extract of the leaf, including alkaloids, natural flavors, and several nutrients. Legal mechanisms exist for importing, distributing, and dispensing coca, and experimentation with it by interested physicians would be valuable.
244. D. M. White, L. Meinhardt, B. Bailey, and S. Pirro, “The Complete Genome Sequences of Erythroxylum Coca and Erythroxylum Novogranatense,” no. 11:457. F1000Research, Apr-2022. doi: 10.12688/f1000research.108549.1. Abstract
     The flowering plant genus Erythroxylum contains approximately 280 species, including the economically and socially consequential crops called coca. We present the genome sequences of Erythroxylum coca and E. novogranatense , two cultigens produced for medicinal and quotidian use in the Andes and Amazon regions of South America, as well as the international cocaine industry. Sequencing was performed on an Illumina X-Ten platform, and reads were assembled by a de novo method followed by finishing via comparison with several species from the same genus. The BioProject, raw and assembled data can be accessed in GenBank for E. coca (PRJNA676123; JAJMLV000000000) and E. novogranatense (PRJNA675212; JAJKBF000000000)
245. D. M. White, “A New Variety of Erythroxylum Ulei from the Cordillera Escalera of Peru (Archerythroxylum, Erythroxylaceae),” Phytotaxa, vol. 449, no. 3, pp. 279–286, Jun. 2020. doi: 10.11646/phytotaxa.449.3.6. Abstract
     Erythroxylum ulei var. escalerense is a new variety described from a single collection made in a remote region of the Cordillera Escalera in Loreto, Peru. It is an understory shrub exhibiting the erect lateral setae on the stipules and ovoid fruits characteristic of E. ulei, but with much smaller, narrowly elliptic to lanceolate leaves without bifacial coloration. Morphological comparison and phylogenetic relationships with similar Erythroxylum are presented and discussed, as well as implications for the current intrageneric classification system.
246. D. M. White, J.-P. Huang, O. A. Jara-Muñoz, S. MadriñáN, R. H. Ree, and R. J. Mason-Gamer, “The Origins of Coca: Museum Genomics Reveals Multiple Independent Domestications from Progenitor Erythroxylum Gracilipes,” Systematic Biology, vol. 70, no. 1, pp. 1–13, Jan. 2021. doi: 10.1093/sysbio/syaa074. Abstract
     Abstract Coca is the natural source of cocaine as well as a sacred and medicinal plant farmed by South American Amerindians and mestizos. The coca crop comprises four closely related varieties classified into two species (Amazonian and Huánuco varieties within Erythroxylum coca Lam., and Colombian and Trujillo varieties within Erythroxylum novogranatense (D. Morris) Hieron.) but our understanding of the domestication and evolutionary history of these taxa is nominal. In this study, we use genomic data from natural history collections to estimate the geographic origins and genetic diversity of this economically and culturally important crop in the context of its wild relatives. Our phylogeographic analyses clearly demonstrate the four varieties of coca comprise two or three exclusive groups nested within the diverse lineages of the widespread, wild species Erythroxylum gracilipes; establishing a new and robust hypothesis of domestication wherein coca originated two or three times from this wild progenitor. The Colombian and Trujillo coca varieties are descended from a single, ancient domestication event in northwestern South America. Huánuco coca was domesticated more recently, possibly in southeastern Peru. Amazonian coca either shares a common domesticated ancestor with Huánuco coca, or it was the product of a third and most recent independent domestication event in the western Amazon basin. This chronology of coca domestication reveals different Holocene peoples in South America were able to independently transform the same natural resource to serve their needs; in this case, a workaday stimulant. [Erythroxylum; Erythroxylaceae; Holocene; Museomics; Neotropics; phylogeography; plant domestication; target-sequence capture.]
247. D. M. White, M. B. Islam, and R. J. Mason-Gamer, “Phylogenetic Inference in Section Archerythroxylum Informs Taxonomy, Biogeography, and the Domestication of Coca (Erythroxylum Species),” American Journal of Botany, vol. 106, no. 1, pp. 154–165, 2019. doi: 10.1002/ajb2.1224. Abstract
     Premise of the Study This investigation establishes the first DNA-sequence-based phylogenetic hypothesis of species relationships in the coca family (Erythroxylaceae) and presents its implications for the intrageneric taxonomy and neotropical biogeography of Erythroxylum. We also identify the closest wild relatives and evolutionary relationships of the cultivated coca taxa. Methods We focused our phylogenomic inference on the largest taxonomic section in the genus Erythroxylum (Archerythroxylum O.E.Schulz) using concatenation and gene tree reconciliation methods from hybridization-based target capture of 427 genes. Key Results We show that neotropical Erythroxylum are monophyletic within the paleotropical lineages, yet Archerythroxylum and all of the other taxonomic sections from which we sampled multiple species lack monophyly. We mapped phytogeographic states onto the tree and found some concordance between these regions and clades. The wild species E. gracilipes and E. cataractarum are most closely related to the cultivated E. coca and E. novogranatense, but relationships within this “coca” clade remain equivocal. Conclusions Our results point to the difficulty of morphology-based intrageneric classification in this clade and highlight the importance of integrative taxonomy in future systematic revisions. We can confidently identify E. gracilipes and E. cataractarum as the closest wild relatives of the coca taxa, but understanding the domestication history of this crop will require more thorough phylogeographic analysis.
248. K. R. Young, “A Geographical Perspective on Coca/Cocaine Impacts in South America,” in WorldMinds: Geographical Perspectives on 100 Problems: Commemorating the 100th Anniversary of the Association of American Geographers 1904–2004, D. G. Janelle, B. Warf, and K. Hansen, Eds. Dordrecht: Springer Netherlands, 2004, pp. 363–367. doi: 10.1007/978-1-4020-2352-1_59. Abstract
     Coca is the common name of a shrub, Erythroxylum coca, domesticated millennia ago in the Andes Mountains of South America. Its leaves are picked and transformed into various products, one of which is cocaine. The result is to spatially link the locations of coca cultivation in South America to the places in the world where demand for cocaine exists. There are only a handful of plants that directly affect both the welfare of millions of people and the world economy, including food species such as rice, wheat, and maize. The two globally significant plants that are transformed into important illicit drugs are poppy and coca. In this essay, I present a geographical perspective on the negative impacts associated with the latter.
249. M. Youssefi, R. G. Cooks, and J. L. McLaughlin, “Mapping of Cocaine and Cinnamoylcocaine in Whole Coca Plant Tissues by MIKES,” Journal of the American Chemical Society, vol. 101, no. 12, pp. 3400–3402, Jun. 1979. doi: 10.1021/ja00506a055.
250. B. Zanolari, D. Guilet, A. Marston, E. F. Queiroz, M. de Q. Paulo, and K. Hostettmann, “Tropane Alkaloids from the Bark of Erythroxylum Vacciniifolium,” Journal of Natural Products, vol. 66, no. 4, pp. 497–502, Apr. 2003. doi: 10.1021/np020512m. Abstract
     Eight new tropane alkaloids (1−8) were isolated from the bark of “catuaba”, a Brazilian endemic plant Erythroxylum vacciniifolium Martius. Their structures were determined by high-resolution mass spectrometry and multidimensional NMR spectroscopy.
251. R. Zapata and F. Villafrade, “Genome Size and Descriptors of Leaf Morphology as Indicators of Hybridization in Colombian Cultigens of Coca Erythroxylum Spp,” Master's thesis, Universidad de los Andes, Bogota D.C., Colombia, 2015. https://repositorio.uniandes.edu.co/handle/1992/13477. Abstract
     Recent biochemical and morphological data suggests that coca crops in Colombia are increasingly composed of hybrids coming from traditionally cultivated varieties of Erythroxylum coca and Erythroxylum novogranatense. Previous studies can not discriminate these cultigens on the basis of linear measurements of leaf morphology. The current study aims at measuring quantifiable differences in Fourier Elliptic Descriptors of leaf morphology and genome sizes among collected Colombian cultigens. Our current hypothesis is that hybrids must show intermediate morphologies and genome sizes of the parental varieties, and that these variables could be correlated. Given this scenario genome size and leaf morphology could be used as indicators of hybridization in cultivated coca populations, and used for the identification of further collected material. However no informative differences of leaf morphology or genome size were found between studied cultigens
252. J. A. S. Zuanazzi, V. Tremea, R. P. Limberger, M. Sobral, and A. T. Henriques, “Alkaloids of Erythroxylum (Erythroxylaceae) Species from Southern Brazil,” Biochemical Systematics and Ecology, vol. 29, no. 8, pp. 819–825, Aug. 2001. doi: 10.1016/S0305-1978(01)00022-9. Abstract
     A new alkaloid identified as 3β,6β-ditigloyloxynortropane as 3β,7β-ditigloyloxynortropane, 4-hydroxyhygrinic acid, methylecgonidine and tropacocaine have been isolated from the leaves of Erythroxylum argentinum. The new structure was established by means of spectroscopic techniques. Four other species E. deciduum, E. microphyllum, E. pelleterianum and E. cuneifolium collected in the state of Rio Grande do Sul were screened for methylecgonidine and tropacocaine by CG/MS. Two of these plants contain tropacocaine and two contain methylecgonidine. GC/MS analysis of all 5 species for cocaine proved fruitless. The chemotaxonomic significance of these results is discussed.