Nigricanosides A and B, antimitotic glycolipids isolated from the green alga Avrainvillea nigricans collected in Dominica.
Nigricanosides A and B, antimitotic glycolipids isolated from the green alga Avrainvillea nigricans collected in Dominica.
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Nigricanosides A 和 B，是从多米尼加收集的绿藻 Avrainvillea nigricans 中分离出来的抗有丝分裂糖脂。
DOI：
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发表时间：
2007
影响因子：
15
通讯作者：
R. Andersen
中科院分区：
文献类型：
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作者：
David E. Williams;Christopher M. Sturgeon;M. Roberge;R. Andersen
抗有丝分裂糖脂黑苷A（1）和B（2）的甲酯3和4已从多米尼加采集的绿色Avrainvillea nigrans的提取物中分离出来。化合物3和4的结构通过MS和NMR数据的详细分析确定。黑果苷A二甲酯3在有丝分裂中抑制人乳腺癌MCF-7细胞，IC 50为3 nM。与未处理的中期细胞的双极纺锤体相比，停滞的细胞具有高度紊乱的微管纺锤体。20 μM的酯3在体外刺激纯微管蛋白的聚合，并抑制MCF-7和人结肠癌HCT-116细胞的增殖，IC 50为≤ 3 nM。黑果苷是一类新的醚连接糖甘脂的第一个例子。黑果苷的有效抗有丝分裂活性及其促进微管蛋白聚合的能力在先前已知的糖甘油脂中是没有先例的。
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.