Lundurines A–D, cytotoxic indole alkaloids incorporating a cyclopropyl moiety from Kopsia tenuis and revision of the structures of tenuisines A–C

The leaf extract of the Borneo Kopsia, K. tenuis, provided several new indoles with a novel hexacyclic carbon skeleton, incorporating a cyclopropyl moiety. Two of these, displayed appreciable in vitro cytotoxicity against B16 melanoma cells, as well as the circumvention of drug-resistance in drug-re...

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Bibliographic Details
Published in:Tetrahedron 2004-11, Vol.60 (47), p.10739-10745
Main Authors: Kam, Toh-Seok, Lim, Kuan-Hon, Yoganathan, K., Hayashi, Masahiko, Komiyama, Kanki
Format: Article
Language:English
Subjects:
Alkaloids
NMR
Plants
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Summary:The leaf extract of the Borneo Kopsia, K. tenuis, provided several new indoles with a novel hexacyclic carbon skeleton, incorporating a cyclopropyl moiety. Two of these, displayed appreciable in vitro cytotoxicity against B16 melanoma cells, as well as the circumvention of drug-resistance in drug-resistant KB cells. The structures of tenuisines A–C were revised from a dimeric to a monomeric structure, based on new LSIMS data, and in conjunction with the preparation of the methyl iodide salt of tenuisine A. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.08.091