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.
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.
Laboratory of MaNaPro Chemistry, Pacific Institute of Bioorganic Chemistry of the Russian Academy of Sciences, 690022, Vladivostok-22, Russian Federation. makarieva@piboc.dvo.ru
Tatyana N
TN
Makarieva
Pavel S
PS
Dmitrenok
Alexander M
AM
Zakharenko
Vladimir A
VA
Denisenko
Alla G
AG
Guzii
Ronghua
R
Li
Colin K
CK
Skepper
Tadeusz F
TF
Molinski
Valentin A
VA
Stonik
D000818:Animals; D006017:Glycolipids / Q000737:chemistry*; D006028:Glycosphingolipids / Q000737:chemistry* / Q000302:isolation & purification*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry*
D006017:Glycolipids; D006028:Glycosphingolipids; C404387:oceanapiside; C527012:rhizochalin C; C527013:rhizochalin D