Sinularioside, a triacetylated glycolipid from the Indonesian soft coral Sinularia sp., is an inhibitor of NO release

Bioorg Med Chem Lett. 2012 Apr 15;22(8):2723-5. doi: 10.1016/j.bmcl.2012.02.102. Epub 2012 Mar 8.

Abstract

Chemical analysis of the Indonesian soft coral Sinularia sp. (order Alcyonacea, family Alcyoniidae) afforded a known glucosylcerebroside of the sarcoehrenoside-type and sinularioside (2), a new naturally triacetylated glycolipid containing two α-D-arabinopyranosyl residues and a myristyl alcohol unit. Their complete stereostructures were solved by interpretation of MS and NMR data along with CD analysis of degradation products. Sinularioside proved to moderately inhibit LPS-induced NO release, providing interesting clues into the poorly understood structure-activity relationships for anti-inflammatory glycolipids.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anthozoa / chemistry*
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / pharmacology
  • Circular Dichroism
  • Enzyme Activation / drug effects
  • Enzyme Inhibitors / pharmacology
  • Glycolipids / chemistry*
  • Glycolipids / pharmacology*
  • Indonesia
  • Inflammation / prevention & control
  • Macrophages / metabolism
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Nitric Oxide / antagonists & inhibitors*
  • Nitric Oxide / metabolism
  • Structure-Activity Relationship

Substances

  • Anti-Inflammatory Agents
  • Enzyme Inhibitors
  • Glycolipids
  • sinularioside
  • Nitric Oxide