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突触苷A和A1,来自黄斑海参的含有3 - O - 甲基葡萄糖醛酸的三萜糖苷及其对肿瘤细胞的细胞毒性活性。

Synaptosides A and A1, triterpene glycosides from the sea cucumber Synapta maculata containing 3-O-methylglucuronic acid and their cytotoxic activity against tumor cells.

作者信息

Avilov Sergey A, Silchenko Alexandra S, Antonov Alexander S, Kalinin Vladimir I, Kalinovsky Anatoly I, Smirnov Alexey V, Dmitrenok Pavel S, Evtushenko Evgeny V, Fedorov Sergey N, Savina Alexandra S, Shubina Larisa K, Stonik Valentin A

机构信息

Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok, Russian Federation.

出版信息

J Nat Prod. 2008 Apr;71(4):525-31. doi: 10.1021/np070283+. Epub 2008 Feb 22.

DOI:10.1021/np070283+
PMID:18290630
Abstract

Two novel triterpene holostane glycosides, synaptosides A ( 1) and A 1 ( 2), have been isolated from the Vietnamese sea cucumber Synapta maculata (Synaptida, Apodida). Their structures were elucidated by spectroscopic methods (NMR and MS) and chemical transformations. Glycosides 1 and 2 have rare branched pentasaccharide carbohydrate chains featuring a 3- O-methylglucuronic acid residue not previously reported in glycosides from sea cucumbers and a 6- O-sulfated glucose. Glycoside 2 has an oxo group at C-7 and a 8(9)-double bond. All these structural features are unknown in glycosides from sea cucumbers. Glycoside 1 has moderate cytotoxic activity (IC 50 8.6 microg/mL) and glycoside 2 is inactive against HeLa tumor cells.

摘要

从越南海参黄斑疣海参(Synaptida,无足目)中分离出两种新型三萜类藿烷糖苷,即突触苷A(1)和A1(2)。通过光谱方法(核磁共振和质谱)以及化学转化对其结构进行了阐明。糖苷1和2具有罕见的分支五糖碳水化合物链,其特征在于海参糖苷中先前未报道的3 - O - 甲基葡萄糖醛酸残基和6 - O - 硫酸化葡萄糖。糖苷2在C - 7处有一个氧代基团和一个8(9) - 双键。所有这些结构特征在海参糖苷中都是未知的。糖苷1具有中等细胞毒性活性(IC50为8.6微克/毫升),而糖苷2对HeLa肿瘤细胞无活性。

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