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
Journal of Natural Products2007Vol. 70(12), pp. 1991–1998
Citations Over TimeTop 13% of 2007 papers
Tatyana N. Makarieva, Pavel S. Dmitrenok, Alexander M. Zakharenko, В. А. Денисенко, Alla G. Guzii, Ronghua Li, Colin K. Skepper, Tadeusz F. Molinski, Valentin A. Stonik
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.
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