六氯菌素的结构与绝对立体化学，一种肌动蛋白组装的强效刺激剂。

Structure and absolute stereochemistry of hectochlorin, a potent stimulator of actin assembly.

作者信息

Marquez Brian L, Watts Karl Shawn, Yokochi Alexandre, Roberts Mary Ann, Verdier-Pinard Pascal, Jimenez Jorge I, Hamel Ernest, Scheuer Paul J, Gerwick William H

机构信息

College of Pharmacy, Oregon State University, Corvallis, Oregon 97331, USA.

出版信息

J Nat Prod. 2002 Jun;65(6):866-71. doi: 10.1021/np0106283.

DOI:10.1021/np0106283

PMID:12088429

Abstract

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.

摘要

从牙买加赫克托湾以及巴拿马博卡斯德尔托罗省博卡德尔德拉戈海滩采集的大鞘丝藻海洋分离物中分离出了海克氯素（1）。通过一维和二维核磁共振光谱推断出其平面结构。利用X射线晶体学确定了海克氯素的绝对立体化学构型为2S，3S，14S，22S。海克氯素在促进肌动蛋白聚合的能力方面与茉莉素（5）相当，但与茉莉素不同的是，它无法从聚合的肌动蛋白中置换出荧光鬼笔环肽类似物。此外，通过COMPARE算法，海克氯素显示出独特的细胞毒性特征，并且对白色念珠菌具有强大的抑制活性。在结构上，海克氯素类似于多拉贝林以及最近报道的鞘丝藻贝林类化合物。