来自包被根盘海绵的根盘鞘脂C和D。一种罕见的苏式鞘脂以及确定α,ω-双官能化酮鞘脂中羰基位置的简便方法。

Rhizochalins C and D from the sponge Rhizochalina incrustata. A rare threo-sphingolipid and a facile method for determination of the carbonyl position in alpha,omega-bifunctionalized ketosphingolipids.

作者信息

Makarieva Tatyana N, Dmitrenok Pavel S, Zakharenko Alexander M, Denisenko Vladimir A, Guzii Alla G, Li Ronghua, Skepper Colin K, Molinski Tadeusz F, Stonik Valentin A

机构信息

Laboratory of MaNaPro Chemistry, Pacific Institute of Bioorganic Chemistry of the Russian Academy of Sciences, 690022, Vladivostok-22, Russian Federation.

出版信息

J Nat Prod. 2007 Dec;70(12):1991-8. doi: 10.1021/np0704811. Epub 2007 Dec 6.

DOI:10.1021/np0704811

PMID:18052325

Abstract

Rhizochalins C and D ( 1, 2), new representatives of two-headed glycosphingolipids, were isolated from the sponge Rhizochalina incrustata. Rhizochalin D is an unexpected C 29 homologue of the canonical C 28 dimeric sphingolipid structures. Their structures including absolute configurations were established using spectroscopic data, micromolar-scale Baeyer-Villiger oxidation, and LCMS interpretation of the products. Application of the latter method leads to a revision of the structure of oceanapiside and placement of the keto group at C-18 rather than C-11.

摘要

从海绵包被根枝海绵（Rhizochalina incrustata）中分离出了双头糖鞘脂的新代表物——根枝菌素C和D（1, 2）。根枝菌素D是典型的C28二聚鞘脂结构中意想不到的C29同系物。利用光谱数据、微摩尔级的拜耳-维利格氧化反应以及产物的液相色谱-质谱解析确定了它们包括绝对构型在内的结构。后一种方法的应用导致了海洋糖苷结构的修订，并将酮基置于C-18而非C-11处。