Rhizochalins C and D from the sponge Rhizochalina incrustata.: A rare threo-sphingolipid and a facile method for determination of the carbonyl position in α,ω-bifunctionalized ketosphingolipids
Rhizochalins C and D from the sponge Rhizochalina incrustata.: A rare threo-sphingolipid and a facile method for determination of the carbonyl position in α,ω-bifunctionalized ketosphingolipids
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DOI：
10.1021/np0704811
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发表时间：
2007-12-01
影响因子：
5.1
通讯作者：
Stonik, Valentin A.
中科院分区：
文献类型：
--
作者：
Makarieva, Tatyana N.;Dmitrenok, Pavel S.;Stonik, Valentin A.
从皱皮海绵（Rhizochalinacrustata）中分离得到两个新的双头鞘糖脂的代表化合物--皱皮海绵糖脂C和D（1，2）。大黄素D是典型C-28二聚鞘脂结构的意外C-29同系物。使用光谱数据、微摩尔尺度Baeyer-Villiger氧化和产物的LCMS解释建立了它们的结构，包括绝对构型。后一种方法的应用导致oceanapiside的结构的修订和酮基在C-18而不是C-11的位置。
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.