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

Academic Article
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Overview

authors

  • Costantino, V.
  • Fattorusso, E.
  • Imperatore, C.
  • Mangoni, A.
  • Freigang, S.
  • Teyton, Luc

publication date

  • February 2008

journal

  • Bioorganic & Medicinal Chemistry  Journal

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.

subject areas

  • Animals
  • Axinella
  • Cells, Cultured
  • Free Radical Scavengers
  • Glycosphingolipids
  • Immunologic Factors
  • Killer Cells, Natural
  • Mice
  • Molecular Structure
  • Singlet Oxygen
  • Trihexosylceramides
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Identity

International Standard Serial Number (ISSN)

  • 0968-0896

Digital Object Identifier (DOI)

  • 10.1016/j.bmc.2007.10.098

PubMed ID

  • 18037298
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Additional Document Info

start page

  • 2077

end page

  • 2085

volume

  • 16

issue

  • 4

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