Hepatoprotective constituents from zedoariae rhizoma: absolute stereostructures of three new carabrane-type sesquiterpenes, curcumenolactones A, B, and C.
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.
Matsuda
H
H
Kyoto Pharmaceutical University, Japan.
Morikawa
T
T
Ninomiya
K
K
Yoshikawa
M
M
D000818:Animals; D056486:Chemical and Drug Induced Liver Injury / Q000517:prevention & control*; D004305:Dose-Response Relationship, Drug; D005688:Galactosamine / Q000037:antagonists & inhibitors / Q000633:toxicity; D022781:Hepatocytes / Q000187:drug effects; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D008070:Lipopolysaccharides / Q000037:antagonists & inhibitors / Q000633:toxicity; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D010946:Plants, Medicinal / Q000737:chemistry*; D051381:Rats; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D013056:Spectrophotometry, Ultraviolet
D007783:Lactones; D008070:Lipopolysaccharides; D012717:Sesquiterpenes; C436508:curcumenolactone A; C436509:curcumenolactone B; C436510:curcumenolactone C; D005688:Galactosamine