Hepatoprotective constituents from zedoariae rhizoma: absolute stereostructures of three new carabrane-type sesquiterpenes, curcumenolactones A, B, and C

Bioorg Med Chem. 2001 Apr;9(4):909-16. doi: 10.1016/s0968-0896(00)00306-0.

Abstract

New carabrane-type sesquiterpene lactones, curcumenolactones A, B, and C, were isolated from the 80% aqueous acetone extract of Zedoariae Rhizoma (Zingiberaceae), together with 41 sesquiterpenes and two diarylheptanoids. The absolute stereostructures of curcumenolactones A, B, and C were determined on the basis of physicochemical evidence, which included nuclear Overhauser effect (NOE) and circular dichroic (CD) spectroscopic analyses. Curcumenone, a principal carabrane-type sesquiterpene from Zedoariae Rhizoma, was found to show potent protective effect on D-galactosamine/lipopolysaccharide-induced acute liver injury in mice. In addition, curcumenolactones A and B and the other constituents showed protective effect on D-galactosamine-induced cytotoxicity in primary cultured rat hepatocytes.

MeSH terms

  • Animals
  • Chemical and Drug Induced Liver Injury / prevention & control*
  • Dose-Response Relationship, Drug
  • Galactosamine / antagonists & inhibitors
  • Galactosamine / toxicity
  • Hepatocytes / drug effects
  • Lactones / chemistry
  • Lactones / isolation & purification
  • Lactones / pharmacology*
  • Lipopolysaccharides / antagonists & inhibitors
  • Lipopolysaccharides / toxicity
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Conformation
  • Plants, Medicinal / chemistry*
  • Rats
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / pharmacology*
  • Spectrophotometry, Ultraviolet

Substances

  • Lactones
  • Lipopolysaccharides
  • Sesquiterpenes
  • curcumenolactone A
  • curcumenolactone B
  • curcumenolactone C
  • Galactosamine