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微酰胺和关岛酰胺:来自海洋蓝藻席藻属一种的细胞毒性生物碱。

Micromide and guamamide: cytotoxic alkaloids from a species of the marine cyanobacterium Symploca.

作者信息

Williams Philip G, Yoshida Wesley Y, Moore Richard E, Paul Valerie J

机构信息

Department of Chemistry, University of Hawaii at Manoa, Honolulu, HI 96822, USA.

出版信息

J Nat Prod. 2004 Jan;67(1):49-53. doi: 10.1021/np030215x.

DOI:10.1021/np030215x
PMID:14738385
Abstract

Two new cytotoxins have been isolated from a species of marine cyanobacterium belonging to the genus Symploca that was collected in Guam. These new compounds, micromide (1) and guamamide (2), were accompanied by the known lipopeptides apramides A (3), B (4), and G (5). The planar structures of both alkaloids were elucidated by standard 2D NMR techniques, and the configurations of the amino acid-derived units in 1 were determined by chiral HPLC. The stereochemistry of the beta-methoxyhexanoic acid in 1 was determined by derivatization with methyl d-mandelate, after acid hydrolysis, and comparison with synthetic standards.

摘要

从关岛采集的一种席藻属海洋蓝藻中分离出了两种新的细胞毒素。这些新化合物,即微酰胺(1)和关岛酰胺(2),与已知的脂肽阿普拉酰胺A(3)、B(4)和G(5)一同被发现。两种生物碱的平面结构通过标准二维核磁共振技术得以阐明,化合物1中氨基酸衍生单元的构型通过手性高效液相色谱法确定。化合物1中β-甲氧基己酸的立体化学结构是在酸水解后用d-扁桃酸甲酯进行衍生化,并与合成标准品进行比较后确定的。

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