Dimeric bisindole alkaloids from the stem bark of Strychnos nux-vomica L.
Jonville, Marie-Caroline ; Dive, Georges ; Angenot, Luc et al
in Phytochemistry (2013), 87
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 ... [more ▼]
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. [less ▲]Detailed reference viewed: 71 (13 ULg)
Plantes Médicinales Antipaludiques de l'île de la Réunion
Frederich, Michel ; Jonville, Marie-Caroline ; et al
Conference (2012, November 06)Detailed reference viewed: 35 (3 ULg)