Variation of Alkaloid Content in Erythroxylum coca Leaves from Leaf Bud to Leaf Drop

Johnson, Emanuel L.; Emche, Stephen D.

doi:10.1006/anbo.1994.1081

Cited by 33 publications

(18 citation statements)

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“…Según trabajos publicados por la Oficina de las Naciones Unidas contra la Droga y el Delito (UNODC) (10) , Galindo y Fernández (26) ; y Johnson y Emche (27) , en la hoja de coca se encuentran compuestos principales como la cocaína (>1% en peso), compuestos accesorios (<1% en peso) y compuestos en trazas (<1% en peso); entre los compuestos principales y accesorios están la cinamoilcocaína, metilecgonina, benzoilecgonina, ecgonina, norcocaína, N-formilnorcocaína (10,26) higrina, tropinona, trans-cinnamoilcocaina, cis-cinnamoilcocaina, cuscohigrina y tropacocaina (27) . Esto se confirmó en nuestro estudio al encontrarse cocaína y benzoilecgonina en la determinación de alcaloides.…”

Section: Discussionunclassified

“…Por ejemplo, el trabajo de Johnson y Emche (27) monitoreó el contenido de alcaloides de la hoja de coca, desde el brote hasta hoja seca, en un período de 36 semanas. Así, se observó que el contenido de alcaloides fue aumentado hasta los 7 días en promedio, al llegar al período de hoja seca y su posterior desprendimiento de la planta, los niveles de alcaloides presentan un decaimiento.…”

Section: Discussionunclassified

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Metabolitos en las hojas de Erythroxylum coca Lam y Erithroxylum novogranatense (Morris) Vieron y evaluacion de sus propiedades biologicas mediante bioensayos.

Ochoa¹,

R²,

S³

et al. 2018

Rev. per. med. integr.

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Objetivo. Realizar el screening fitoquimico y determinar la actividad antioxidante y antibacteriana de los flavonoides y alcaloides aislados de extractos etanolicos de las hojas de Erythroxylum coca Lam y Erythroxylum novogranatense (Morris) Hieron. Materiales y Metodos. La capacidad antioxidante de los flavonoides y alcaloides aislados fue evaluada mediante el ensayo de DPPH, utilizando como control positivo a la vitamina C, y la actividad antibacteriana mediante el calculo del halo de inhibicion (mm) ante S. epidermidis, P. aeruginosa, S. aureus y E. coli. Resultados. Los alcaloides de E. coca presentaron mayor actividad antibacteriana frente a S. epidermidis y P. aeruginosa, y los flavonoides de E. novogranatense tuvieron mayor actividad frente a S. epidermidis, P. aeruginosa y S. aureus. E. novogranatense mostroun EC50 de 271,20 µg/mL para extracto crudo y 250,29 µg/mL para flavonoides, mientras que E. coca presento un EC50 de 172,59 µg/mL para extracto crudo y 611,29 µg/mL para flavonoides. Conclusion. En ambas especies se identificaron alcaloides (cocaina y benzoilecgonina), flavonoides (chalconas y flavonoles), fenoles y carbohidratos. Los flavonoides de Erythroxylum novogranatense (Morris) Hieron, y el extracto de Erythroxylum coca Lam presentaron mayor actividad antioxidante. El extracto de Erythroxylum coca Lam mostro mayor actividad antibacteriana frente a S. aureus, S. epidermidis y E. coli, excepto para P. aeruginosa. Los alcaloides de Erythroxylum coca Lam, exhibieron buena actividad frente a S. epidermidis y P. aeruginosa; excepto para E. coli, donde Erythroxylum novogranatense (Morris) Hieron tuvo mejor desempeño. Los flavonoides aislados de Erythroxylum novogranatense (Morris) Hieron mostraron actividad frente a S. epidermidis.

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Section: Discussionunclassified

Metabolitos en las hojas de Erythroxylum coca Lam y Erithroxylum novogranatense (Morris) Vieron y evaluacion de sus propiedades biologicas mediante bioensayos.

Ochoa¹,

R²,

S³

et al. 2018

Rev. per. med. integr.

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“…In contrast, the mean ratio EME/COC is about one order of magnitude higher for coca chewers, and there is almost no overlap between the ranges of both groups. This should be caused both by its high content in coca leaves [13][14][15][16] and by the enhanced hydrolysis of cocaine to EME in the chewing process.…”

Section: Differentiation Between Coca Chewers and Cocaine Usersmentioning

confidence: 97%

“…As an example, in the investigation of samples from fields in Bolivia, Peru, Ecuador and Columbia and from a greenhouse at the US Department of Agriculture by Moore et al [13], it amounted to 29-63 % ecgonine methyl ester, 0.16-4.9 % tropacocaine, 5.8-53 % cis-cinnamoylcocaine, 2.9-170 % trans-cinnamoylcocaine, 1.4-24 % hygrine, 3.8-61 % cuscohygrine and 2.5-61 % total of isomeric truxillines. Furthermore, low concentrations of tropinone were described [14,15]. Benzoylecgonine (1-2 % related to cocaine in coca tea bags [16]) seems not to be a natural alkaloid in coca leaf but is formed by hydrolysis of cocaine [12].…”

Section: Introductionmentioning

confidence: 97%

“…The content of alkaloids in coca leaves was qualitatively and quantitatively investigated several times and varies with coca species, age of the plant and the leaf, position in the leaf, soil composition, altitude of cultivation, longitudinal location, environmental factors, the time lapse between leaf harvesting and analysis and the conditions of storage [11][12][13][14][15][16][17][18][19]. The cocaine content of dried coca leaves is usually 0.4-0.7 % (w/w).…”

Section: Introductionmentioning

confidence: 99%

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Possibilities for discrimination between chewing of coca leaves and abuse of cocaine by hair analysis including hygrine, cuscohygrine, cinnamoylcocaine and cocaine metabolite/cocaine ratios

Rubio¹,

Hastedt

Gonzalez³

et al. 2014

Int J Legal Med

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Contrary to the illegal use of any form of manufactured cocaine, chewing of coca leaves and drinking of coca tea are allowed and are very common and socially integrated in several South American countries. Because of this different legal state, an analytical method for discrimination between use of coca leaves and abuse of processed cocaine preparations is required. In this study, the applicability of hair analysis for this purpose was examined. Hair samples from 26 Argentinean coca chewers and 22 German cocaine users were analysed for cocaine (COC), norcocaine (NC), benzoylecgonine (BE), ecgonine methyl ester (EME), cocaethylene (CE), cinnamoylcocaine (CIN), tropacocaine (TRO), cuscohygrine (CUS) and hygrine (HYG) by hydrophilic interaction liquid chromatography (HILIC) in combination with triplequad mass spectrometry (MS/MS) and hybrid quadrupole time-of-flight mass spectrometry (QTOF-MS). The following concentrations (range, median, ng/mg) were determined in hair of the coca chewers: COC 0.085-75.5, 17.0; NC 0.03-1.15, 0.12; BE 0.046-35.5, 6.1; EME 0.014-6.0, 0.66; CE 0.00-13.8, 0.38; CIN 0.005-16.8, 0.79; TRO 0.02-0.16, 0.023; CUS 0.026-26.7, 0.31. In lack of a reference substance, only qualitative data were obtained for HYG, and two metabolites of CUS were detected which were not found in hair of the cocaine users. For interpretation, the concentrations of the metabolites and of the coca alkaloids in relation to cocaine were statistically compared between coca chewers and cocaine users. By analysis of variance (ANOVA) significant differences were found for all analytes (α = 0.000 to 0.030) with the exception of TRO (α = 0.218). The ratios CUS/COC, CIN/COC and EME/COC appeared to be the most suitable criteria for discrimination between both groups with the means and medians 5-fold to 10-fold higher for coca chewers and a low overlap of the ranges between both groups. The same was qualitatively found for HYG. However, these criteria cannot exclude cocaine use in addition to coca chewing. In this regard screening for typical cutting agents can be helpful and led to the detection of levamisole (21×), lidocaine (6×) and paracetamol (3×) in the 22 samples from German cocaine users, whereas no levamisole, lidocaine (3×) and paracetamol (1×) were found in hair from the Argentinean coca chewers. These criteria have to be confirmed for South American cocaine consumers including smokers of coca paste and may be different because of different composition of the drug and other use habits.

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Content and Distribution of Erythroxylum coca Leaf Alkaloids

Johnson¹

1995

Annals of Botany

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Variation of Alkaloid Content in Erythroxylum coca Leaves from Leaf Bud to Leaf Drop

Cited by 33 publications

References 0 publications

Metabolitos en las hojas de Erythroxylum coca Lam y Erithroxylum novogranatense (Morris) Vieron y evaluacion de sus propiedades biologicas mediante bioensayos.

Metabolitos en las hojas de Erythroxylum coca Lam y Erithroxylum novogranatense (Morris) Vieron y evaluacion de sus propiedades biologicas mediante bioensayos.

Possibilities for discrimination between chewing of coca leaves and abuse of cocaine by hair analysis including hygrine, cuscohygrine, cinnamoylcocaine and cocaine metabolite/cocaine ratios

Content and Distribution of Erythroxylum coca Leaf Alkaloids

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