Unusual amino acids and monofluoroacetate from Dichapetalum michelsonii (Umutambasha), a toxic plant from Rwanda.

Abstract:

:In the course of our investigations on Umutambasha in order to identify its convulsant principles, small quantities of monofluoroacetate were observed in stem bark, leaves, and fruits of this plant newly identified as Dichapetalum michelsonii Hauman. Conclusive evidence for a monofluoroacetate presence came from its isolation from the freeze-dried extract of stem bark. Three free unusual amino acids, named N-methyl-α-alanine, N-methyl-β-alanine, and 2,7-diaminooctan-1,8-dioic acid, described for the first time in a plant, and known trigonelline were also isolated from the stem bark of D. michelsonii. Structure elucidations were mainly achieved by spectroscopic methods (1H-NMR, 2D-NMR, MS) and by comparison with authentic references. These unusual amino acids were detected by a fast, reliable TLC analysis in all our batches of Umutambasha, suggesting that they could be used for identification purposes in case of human or livestock intoxications. Finally, EEG recordings and behavioural observations performed in mice suggested that the convulsive patterns produced by Umutambasha are the consequence of monofluoroacetate presence in D. michelsonii.

journal_name

Planta Med

journal_title

Planta medica

authors

Esters V,Karangwa C,Tits M,Francotte P,Pirotte B,Servais AC,Fillet M,Crommen J,Robbrecht E,Minet A,Grisar T,Angenot L,Frederich M

doi

10.1055/s-0032-1328283

subject

Has Abstract

pub_date

2013-03-01 00:00:00

pages

334-7

issue

5

eissn

0032-0943

issn

1439-0221

journal_volume

79

pub_type

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