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Nigricanosides A and B, antimitotic glycolipids isolated from the green alga Avrainvillea nigricans collected in Dominica

TitleNigricanosides A and B, antimitotic glycolipids isolated from the green alga Avrainvillea nigricans collected in Dominica
Publication TypeJournal Article
Year of Publication2007
AuthorsWilliams, DE, Sturgeon, CM, Roberge, M, Andersen, RJ
JournalJournal of the American Chemical Society
Volume129
Pagination5822-+
Date PublishedMay
ISBN Number0002-7863
Abstract

The methyl esters 3 and 4 of the antimitotic glycolipids nigricanosides A (1) and B (2) have been isolated from extracts of the green alga Avrainvillea nigrans collected in Dominica. The structures of 3 and 4 were elucidated by detailed analysis of MS and NMR data. Nigricanoside A dimethyl ester 3 arrests human breast cancer MCF-7 cells in mitosis with an IC50 of 3 nM. Arrested cells have highly disorganized microtubule spindles, compared with the bipolar spindles of untreated metaphase cells. Ester 3 at 20 mu M stimulates the polymerization of pure tubulin in vitro and it inhibits the proliferation of both MCF-7 and human colon cancer HCT-116 cells with an IC50 approximate to 3 nM. The nigricanosides are the first examples of a new class of ether-linked glycoglycerolipids. The potent antimitotic activity of the nigricanosides and their ability to promote tubulin polymerization is without precedent among previously known glycoglycerolipids.

URL<Go to ISI>://000246180200019