New sesquiterpene lactones from Laurus nobilis leaves as inhibitors of nitric oxide production

Planta Med. 2005 Aug;71(8):706-10. doi: 10.1055/s-2005-864191.

Abstract

Two new metabolites 5alphaH,7alphaH-eudesman-4alpha,6alpha,11,12-tetraol (1) and 1beta,15-dihydroxy-5alphaH,7alphaH-eudesma-3,11(13)-dien-12,6alpha-olide ( 2) have been isolated from the methanolic extract of Laurus nobilis L. leaves. Their structures were determined through analysis of their one- and two-dimensional NMR spectral data ((1)H- and (13)C-NMR, DEPT, COSY, HMQC, HMBC and ROESY). The relative stereochemistry is proposed on the basis of combined J-based configuration analysis and ROESY data. In addition, three known sesquiterpene lactones santamarine (3), reynosin (4) and costunolide (5) along with blumenol C (6) were isolated and identified by spectral means. The isolated compounds 1 - 6 were found to inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-activated murine macrophages. The most active compound 2 potently inhibited NO (2)(-) release with an IC (50) value of 0.8 microM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Inhibitory Concentration 50
  • Laurus*
  • Lipopolysaccharides
  • Macrophages / metabolism
  • Mice
  • Nitric Oxide / antagonists & inhibitors
  • Nitric Oxide / biosynthesis*
  • Phytotherapy*
  • Plant Extracts / administration & dosage
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology*
  • Plant Extracts / therapeutic use
  • Plant Leaves
  • Sesquiterpenes / administration & dosage
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / pharmacology
  • Sesquiterpenes / therapeutic use
  • Stereoisomerism

Substances

  • Lipopolysaccharides
  • Plant Extracts
  • Sesquiterpenes
  • Nitric Oxide