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

David E. Williams; Christopher M. Sturgeon; Michel Roberge; Raymond J. Andersen

doi:10.1021/ja0715187

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

David E. Williams, Christopher M. Sturgeon, Michel Roberge, Raymond J. Andersen

Research output: Contribution to journal › Article › peer-review

60 Scopus citations

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 μM 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.

Original language	English
Pages (from-to)	5822-5823
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	129
Issue number	18
DOIs	https://doi.org/10.1021/ja0715187
State	Published - 9 May 2007
Externally published	Yes

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

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 μM 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.",

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AU - Williams, David E.

AU - Sturgeon, Christopher M.

AU - Roberge, Michel

AU - Andersen, Raymond J.

PY - 2007/5/9

Y1 - 2007/5/9

N2 - 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 μM 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.

AB - 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 μM 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.

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

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