Dimeric bisindole alkaloids from the stem bark of Strychnos nux-vomica L.

[en] Strychnos nux-vomica L. (Loganiaceae) is famous for its monomeric alkaloid content, such as strychnine, a convulsant poison. The stem bark of the tree is traditionally used to treat intermittent fever in South East Asia. In various studies, it appeared that dimeric indolo-monoterpenic alkaloids possess a promising activity on Plasmodium falciparum. Three bisindolomonoterpenic alkaloids together with strychnochrysine, previously identified in the root bark of S. nux-vomica, were isolated from the stem bark. The structures of these compounds were established using NMR spectroscopy and mass spectrometry. Stereochemistry of the compounds was confirmed by molecular modelling. This then allowed the structural determination of strychnoflavine, a coloured bisindole alkaloid previously isolated from the root bark of the tree. Moreover, the conformational inversion in alkaloids possessing an ether bond in the strychnane moiety could be easily predicted by specific δ 13C NMR values. These longicaudatine-type alkaloids were found to display in vitro antiplasmodial activity against a chloroquine resistant strain and a chloroquine sensitive strain. The most interesting was strychnochrysine showing an IC 50 value at around 10 μM. © 2012 Elsevier Ltd. All rights reserved.

Disciplines :

Pharmacy, pharmacology & toxicology

Author, co-author :

Jonville, Marie-Caroline ; Université de Liège - ULiège > Département de pharmacie > Pharmacognosie

Dive, Georges ; Université de Liège - ULiège > Centre d'ingénierie des protéines

Angenot, Luc ; Université de Liège - ULiège > Département de pharmacie > Département de pharmacie

Bero, J.; Louvain Drug Research Institute, Université Catholique de Louvain, UCL 7230, 72 Avenue E. Mounier, 1200 Brussels, Belgium

Tits, Monique ; Université de Liège - ULiège > Département de pharmacie > Phytochimie et phytothérapie

Ollivier, E.; Laboratoire de Pharmacognosie et Ethnopharmacologie, UMR MD3, Faculté de Pharmacie, 27 Boulevard Jean Moulin, Cs 30064, 13385 Marseille Cedex 5, France

Frederich, Michel ; Université de Liège - ULiège > Département de pharmacie > Pharmacognosie

Language :

English

Title :

Dimeric bisindole alkaloids from the stem bark of Strychnos nux-vomica L.

Publication date :

2013

Journal title :

Phytochemistry

ISSN :

0031-9422

eISSN :

1873-3700

Publisher :

Elsevier, Netherlands

Volume :

Pages :

157-163

Peer reviewed :

Peer Reviewed verified by ORBi

Available on ORBi :

since 11 December 2012

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