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

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

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.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Glycolipids / chemistry*
  • Glycosphingolipids / chemistry*
  • Glycosphingolipids / isolation & purification*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Porifera / chemistry*

Substances

  • Glycolipids
  • Glycosphingolipids
  • oceanapiside
  • rhizochalin C
  • rhizochalin D