title: Dimeric bisindole alkaloids from the stem bark of Strychnos nux-vomica L.
abstract: 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 (13)C 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.
authors.affiliation: Laboratoire de Pharmacognosie, Drug Research Center (CIRM), Université de Liège, Liège, Belgium. MC.Jonville@ulg.ac.be
authors.forename: Marie-Caroline
authors.initials: MC
authors.lastname: Jonville
authors.forename: Georges
authors.initials: G
authors.lastname: Dive
authors.forename: Luc
authors.initials: L
authors.lastname: Angenot
authors.forename: Joanne
authors.initials: J
authors.lastname: Bero
authors.forename: Monique
authors.initials: M
authors.lastname: Tits
authors.forename: Evelyne
authors.initials: E
authors.lastname: Ollivier
authors.forename: Michel
authors.initials: M
authors.lastname: Frédérich
mesh_terms: D000470:Alkaloids / Q000737:chemistry* / Q000494:pharmacology*; D000818:Animals; D000962:Antimalarials / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D024301:Plant Bark / Q000737:chemistry*; D018547:Plant Stems / Q000737:chemistry*; D010963:Plasmodium falciparum / Q000187:drug effects; D031461:Strychnos nux-vomica / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D000962:Antimalarials