Nigricanosides A and B, Antimitotic Glycolipids Isolated from the Green Alga Avrainvillea nigricans Collected in Dominica
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- 作者：David E. Williams ; Christopher M. Sturgeon ; Michel Roberge ; Raymond J. Andersen
- 刊名：Journal of the American Chemical Society
- 出版年：2007
- 出版时间：May 9, 2007
- 年：2007
- 卷：129
- 期：18
- 页码：5822 - 5823
- 全文大小：87K
- 年卷期：v.129,no.18(May 9, 2007)
- ISSN：1520-5126
文摘
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 
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 
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.
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 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.