Synthesis and anti-nociceptive and anti-inflammatory effects of gaultherin and its analogs

J Asian Nat Prod Res. 2011 Sep;13(9):817-25. doi: 10.1080/10286020.2011.596830.

Abstract

The synthesis of gaultherin (1) and its analogs was carried out to provide 11 glycosides under phase-transfer catalytic conditions. The activities of all synthesized compounds were evaluated by nitric oxide production inhibitory assay in vitro. Methyl 2-O-(4-O-β-d-galactopyranosyl)-β-d-glucopyranosylbenzoate (5f) showed significantly anti-nociceptive and anti-inflammatory effects by the evaluation in vivo. Structure-activity relationships within these compounds were discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Analgesics / chemical synthesis*
  • Analgesics / chemistry
  • Analgesics / pharmacology*
  • Animals
  • Anti-Inflammatory Agents / chemical synthesis*
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / pharmacology*
  • Croton Oil / pharmacology
  • Disaccharides / chemical synthesis*
  • Disaccharides / chemistry
  • Disaccharides / pharmacology*
  • Edema / chemically induced
  • Edema / drug therapy
  • Macrophages / drug effects
  • Mice
  • Nitric Oxide / biosynthesis
  • Salicylates / chemical synthesis*
  • Salicylates / chemistry
  • Salicylates / pharmacology*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Analgesics
  • Anti-Inflammatory Agents
  • Disaccharides
  • Salicylates
  • methyl 2-O-(4-O-beta-D-galactopyranosyl)-beta-D-glucopyranosylbenzoate
  • Nitric Oxide
  • 2-((6-O-beta-D-Xylopyranosyl-beta-D-glucopyranosyl)oxy) benzoic acid methyl ester
  • Croton Oil