Moandaensine,a dimeric indole alkaloid from Strychnos moandaensis (Loganiaceae) |
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| Authors: | Robert Verpoorte Michel Frédérich Clément Delaude Luc Angenot Georges Dive Philippe Thépenier Marie-José Jacquier Monique Zèches-Hanrot Catherine Lavaud Jean-Marc Nuzillard |
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| Institution: | 1. Department of Pharmacognosy, Section Metabolomics, IBL, Leiden University, PO Box 502, 2300RA Leiden, The Netherlands;2. Université de Liège, Laboratoire de Pharmacognosie, Centre Interfacultaire de Recherche sur le Médicament (CIRM), Département de Pharmacie, Université de Liège, B36, B-4000 Liège, Belgium;3. Centre d’Ingénérie des Protéines, Université de Liège, Sart-Tilman, B-4000 Liège, Belgium;4. Institut de Chimie Moléculaire de Reims, CNRS UMR 6229, IFR 53 Biomolécules, Université de Reims Champagne-Ardenne, BP 1039, 51687 Reims Cedex 02, France |
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| Abstract: | The chemical investigation of the liana Strychnos moandaensis De Wild. led to the isolation of moandaensine, a novel dimeric indole alkaloid. The structure was elucidated by a thorough analysis of the spectroscopic data and by molecular modeling. Moandaensine, or methyl (2S)-2-(2R,3E,12bS)-3-ethylidene-2,4,6,7,12,12b-hexahydro-1H-indolo2,3-a]quinolizin-2-yl]-3-(2S,3R)-3-ethyl-2-(1R)-1-(hydroxymethyl)-2-methoxy-2-oxo-ethyl]-1,2,3,4-tetrahydroindolo2,3-a]quinolizin-5-ium-7-yl]propanoate, contains a rare anhydronium base subunit. It presents a moderate antiplasmodial activity with IC50 values of 11.2 and 9.2 μM against, respectively, the chloroquine sensitive FCA 20 GHA and chloroquine resistant W2 strains of Plasmodium falciparum. |
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