Guaiane-type sesquiterpenes from Curcuma phaeocaulis and their inhibitory effects on nitric oxide production

J Nat Prod. 2013 Jun 28;76(6):1150-6. doi: 10.1021/np400202f. Epub 2013 Jun 11.

Abstract

Ten new guaiane-type sesquiterpenes (1-10), phaeocaulisins A-J, and 18 known guaiane derivatives were isolated from rhizomes of Curcuma phaeocaulis. Their structures were established on the basis of extensive spectroscopic analyses, X-ray crystallographic analysis, and comparison with literature data. Compound 10 is the first example of a norsesquiterpene with this unusual skeleton isolated from the genus Curcuma. All of the isolated compounds were tested for inhibitory activity against LPS-induced nitric oxide production in RAW 264.7 macrophages. Compounds 1, 2, 20, and 22-24 inhibited nitric oxide production with IC50 values less than 2 μM. Preliminary structure-activity relationships for these compounds are discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Curcuma / chemistry*
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology*
  • Inhibitory Concentration 50
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects
  • Molecular Structure
  • Nitric Oxide / antagonists & inhibitors*
  • Nitric Oxide / biosynthesis*
  • Nuclear Magnetic Resonance, Biomolecular
  • Rhizome / chemistry
  • Sesquiterpenes, Guaiane / chemistry
  • Sesquiterpenes, Guaiane / isolation & purification*
  • Sesquiterpenes, Guaiane / pharmacology*
  • Structure-Activity Relationship

Substances

  • Drugs, Chinese Herbal
  • Lipopolysaccharides
  • Sesquiterpenes, Guaiane
  • Nitric Oxide