Corrugoside, a new immunostimulatory alpha-galactoglycosphingolipid from the marine sponge Axinella corrugata

Bioorg Med Chem. 2008 Feb 15;16(4):2077-85. doi: 10.1016/j.bmc.2007.10.098. Epub 2007 Nov 4.

Abstract

Corrugoside (1a), a new immunostimulatory triglycosilated alpha-galactoglycosphingolipid, was isolated from the marine sponge Axinella corrugata, and its structure determined by spectral analysis and chemical degradation. Compound 1a activated murine NKT cells in vitro, with a potency of about 2 logs lower than that of alphaGalCer. Four stereoisomeric glycosphingolipids (2a-2d) were also obtained, beta-glucosylceramides bearing unusual endoperoxide and allylic hydroperoxide functionalities on the sphinganine chain. They were shown to be photooxidation artifacts of the known glycosphingolipids 3, also present in the sponge. A possible role of compound 3 as a singlet oxygen scavenger to protect the organism from oxidative damage is proposed.

Publication types

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

MeSH terms

  • Animals
  • Axinella / chemistry*
  • Cells, Cultured
  • Free Radical Scavengers / isolation & purification
  • Glycosphingolipids
  • Immunologic Factors / chemistry
  • Immunologic Factors / isolation & purification*
  • Immunologic Factors / pharmacology
  • Killer Cells, Natural / drug effects*
  • Mice
  • Molecular Structure
  • Singlet Oxygen
  • Trihexosylceramides / chemistry
  • Trihexosylceramides / isolation & purification
  • Trihexosylceramides / pharmacology*

Substances

  • Free Radical Scavengers
  • Glycosphingolipids
  • Immunologic Factors
  • Trihexosylceramides
  • corrugoside
  • Singlet Oxygen