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

被引：130

作者：

Marquez, BL

Watts, KS

Yokochi, A

Roberts, MA

Verdier-Pinard, P

Jimenez, JI

Hamel, E

Scheuer, PJ

Gerwick, WH ^{[1
]}

机构：

[1] Oregon State Univ, Coll Pharm, Corvallis, OR 97331 USA

[2] Oregon State Univ, Dept Biochem & Biophys, Corvallis, OR 97331 USA

[3] Oregon State Univ, Dept Chem, Corvallis, OR 97331 USA

[4] NCI, Screening Technol Branch, Dev Therapeut Program, Div Canc Treatment & Diag,NIH, Frederick, MD 21702 USA

[5] Univ Hawaii Manoa, Dept Chem, Honolulu, HI 96822 USA

来源：

JOURNAL OF NATURAL PRODUCTS | 2002年 / 65卷 / 06期

关键词：

D O I：

10.1021/np0106283

中图分类号：

Q94 [植物学];

学科分类号：

071001 [植物学];

摘要：

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.

引用

页码：866 / 871

页数：6

共 26 条

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