New guaiane sesquiterpenes from Artemisia rupestris and their inhibitory effects on nitric oxide production

Bioorg Med Chem Lett. 2014 Sep 15;24(18):4435-4438. doi: 10.1016/j.bmcl.2014.08.004. Epub 2014 Aug 8.

Abstract

Phytochemical investigation of the ethanol extract of the aerial parts of Artemisia rupestris resulted in the isolation of three new guaiane sesquiterpenes, (1R,7R,10S)-1-hydroxy-3-oxoguaia-4,11(13)-dien-12-oic acid (1), (1R,7R,10S)-10-hydroxy-3-oxoguaia-4,11(13)-dien-12-oic acid (2), pechueloic acid 12-O-β-d-glucopyranoside (3), together with 12 known compounds (4-15). The structures of these new compounds were established on the basis of extensive spectroscopic analysis and electronic circular dichroism (ECD) calculation. All isolates were evaluated for their in vitro inhibitory effects on nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages cells, and the structure-activity relationships were also discussed.

Keywords: Artemisia rupestris; Asteraceae; Guaiane sesquiterpenes; Nitric oxide inhibition.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Artemisia / chemistry*
  • Cell Line
  • Dose-Response Relationship, Drug
  • Lipopolysaccharides / antagonists & inhibitors
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects
  • Macrophages / metabolism
  • Mice
  • Molecular Structure
  • Nitric Oxide / biosynthesis*
  • Sesquiterpenes, Guaiane / chemistry
  • Sesquiterpenes, Guaiane / isolation & purification
  • Sesquiterpenes, Guaiane / pharmacology*
  • Structure-Activity Relationship

Substances

  • Lipopolysaccharides
  • Sesquiterpenes, Guaiane
  • Nitric Oxide