Structure and absolute stereochemistry of hectochlorin, a potent stimulator of actin assembly
Structure and absolute stereochemistry of hectochlorin, a potent stimulator of actin assembly
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DOI：
10.1021/np0106283
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发表时间：
2002-06-01
影响因子：
5.1
通讯作者：
Gerwick, WH
中科院分区：
文献类型：
--
作者：
Marquez, BL;Watts, KS;Gerwick, WH
Hectochlorin(1)是从牙买加Hector Bay和巴拿马Bocas del Toro的Boca del Drago Beach的linggbya majuscula海洋分离株中分离得到的。通过一、二维核磁共振谱分析，推导出其平面结构。用x射线晶体学方法测定了五氯氯的绝对立体化学形态为2S、3S、14S、22S。在促进肌动蛋白聚合的能力上，七氯胺与茉莉烯内酯(5)是等价的，但与茉莉烯内酯不同的是，它不能从聚合的肌动蛋白中取代荧光的phalloidin类似物。此外，通过比较算法，己氯胺显示出独特的细胞毒性和对白色念珠菌的有效抑制活性。在结构上，七氯类似于美元和最近报道的lynbyabellin类化合物。
Hectochlorin (1) was isolated from marine isolates of Lyngbya majuscula collected from Hector Bay, Jamaica, and Boca del Drago Beach, Bocas del Toro, Panama. The planar structure was deduced by one-and two-dimensional NMR spectroscopy. X-ray crystallography was used to determine the absolute stereochemistry of hectochlorin as 2S,3S, 14S,22S. Hectochlorin is equipotent to jasplakinolide (5) in its ability to promote actin polymerization, but unlike jasplakinolide, is unable to displace a fluorescent phalloidin analogue from polymerized actin. In addition, hectochlorin shows both a unique profile of cytotoxicity by the COMPARE algorithm and potent inhibitory activity toward the fungus Candida albicans. Structurally, hectochlorin resembles dolabellin and the recently reported lyngbyabellin class of compounds.