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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

LC-MS/MS Quantitative Determination of Tetrapterys mucronata Alkaloids, a Plant Occasionally used in Ayahuasca Preparation

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Author(s):
Queiroz, M. M. F. [1] ; Marti, G. [2] ; Queiroz, E. F. [2] ; Marcourt, L. [2] ; Castro-Gamboa, I. [1] ; Bolzani, V. S. [1] ; Wolfender, J. -L. [1]
Total Authors: 7
Affiliation:
[1] Univ Estadual Paulista UNESP, Inst Quim, Nucleo Bioensaios Biossintese & Ecofisiol Prod Na, Sao Paulo - Brazil
[2] Univ Lausanne, Univ Geneva, Sch Pharmaceut Sci Phytochem & Bioact Nat Prod, CH-1211 Geneva 4 - Switzerland
Total Affiliations: 2
Document type: Journal article
Source: Phytochemical Analysis; v. 26, n. 3, p. 183-188, MAY-JUN 2015.
Web of Science Citations: 8
Abstract

IntroductionTetrapterys mucronata Cav. (Malpighiaceae) is a plant used in some regions of Brazil in the preparation of ayahuasca. ObjectiveTo determine the content of the main tryptamine alkaloids in the stem bark of T. mucronata Cav. and assess their possible toxic and hallucinogenic properties based on the doses found in a water decoction that mimics the ayahuasca preparation. MethodsFour alkaloids previously described for their toxic and hallucinogenic properties were quantitated by multiple reaction monitoring HPLC combined with electrospray ionisation and tandem MS (HPLC-ESI/MS/MS) in the water decoction and ethanolic extracts from the bark of T. mucronata. ResultsExhaustive extraction of the stem barks with ethanol revealed the following alkaloid levels: bufotenine (1) 3.260.31mg/g, 5-methoxy-N-methyltryptamine (2) 0.880.08mg/g, 5-methoxy-bufotenine (3) 3.07 +/- 0.22mg/g and 2-methyl-6-methoxy-1,2,3,4-tetrahydro--carboline (4) 0.14 +/- 0.004mg/g. The water decoction presented slightly lower levels, ranging between 2.32 +/- 0.14, 0.50 +/- 0.04, 1.53 +/- 0.09 and 0.10 +/- 0.01mg/g for (1), (2), (3) and (4) respectively. ConclusionsThe HPLC-ESI/MS/MS quantitation revealed significant alkaloid levels, in particular for bufotenine and 5-methoxy-bufotenine. As such compounds are known for their toxic and hallucinogenic properties, these results indicate that the consumption of this plant as an ingredient in ayahuasca preparations may present a risk to consumers. Copyright (c) 2015 John Wiley \& Sons, Ltd. Tetrapterys mucronata Cav. (Malpighiaceae) is a plant occasionally used in some regions of Brazil in the preparation of ayahuasca. The water extract contains four known hallucinogenic alkaloids that have been quantitated by Multiple Reaction Monitoring HPLC-ESI-MS/MS. The quantitation revealed significant alkaloid levels in particular for bufotenine and 5-methoxy-bufotenine. Since such compounds are known for their toxic and hallucinogenic properties, these results indicate that the consumption of this plant as an ingredient in ayahuasca preparations may present a risk to consumers. (AU)

FAPESP's process: 10/09780-0 - Mass spectrometry and nuclear magnetic resonance in metabolomic assessment & identification of prototypes of AChE inhibitors in Banisteriopsis variabilis (b. gates) - Malpighiaceae
Grantee:Marcos Marçal Ferreira Queiroz
Support type: Scholarships in Brazil - Doctorate