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  • Title: 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.
    Author: Makarieva TN, Dmitrenok PS, Zakharenko AM, Denisenko VA, Guzii AG, Li R, Skepper CK, Molinski TF, Stonik VA.
    Journal: J Nat Prod; 2007 Dec; 70(12):1991-8. PubMed ID: 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.
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