Bioactive constituents from Chinese natural medicines. XXIII. Absolute structures of new megastigmane glycosides, sedumosides A(4), A(5), A(6), H, and I, and hepatoprotective megastigmanes from Sedum sarmentosum.
The methanol-eluted fraction of the hot water extract from the whole plant of Sedum sarmentosum (Crassulaceae) was found to show hepatoprotective effect on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes. From the active fraction, five new megastigmane glycosides, sedumosides A(4), A(5), A(6), H, and I, were isolated together with 22 megastigmane constituents. Their absolute stereostructures were elucidated on the basis of chemical and physicochemical evidence. Among them, sedumoside F(1) (IC(50)=47 microM), (3S,5R,6S,9R)-megastigmane-3,9-diol (61 microM), and myrsinionosides A (52 microM) and D (62 microM) were found to show the strong hepatoprotective activity.
Ninomiya
Kiyofumi
K
Kyoto Pharmaceutical University, Kyoto, Japan.
Morikawa
Toshio
T
Zhang
Yi
Y
Nakamura
Seikou
S
Matsuda
Hisashi
H
Muraoka
Osamu
O
Yoshikawa
Masayuki
M
D000818:Animals; D002478:Cells, Cultured; D055598:Chemical Phenomena; D056486:Chemical and Drug Induced Liver Injury / Q000517:prevention & control*; D002627:Chemistry, Physical; D002851:Chromatography, High Pressure Liquid; D003512:Cyclohexanones / Q000737:chemistry* / Q000494:pharmacology*; D005688:Galactosamine / Q000037:antagonists & inhibitors / Q000633:toxicity; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D005960:Glucosides / Q000737:chemistry* / Q000494:pharmacology*; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D022781:Hepatocytes / Q000187:drug effects; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D045792:Norisoprenoids / Q000737:chemistry* / Q000494:pharmacology*; D031963:Sedum / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
D003512:Cyclohexanones; D005960:Glucosides; D006027:Glycosides; D045792:Norisoprenoids; C413264:megastigmane; D005688:Galactosamine; D005944:Glucosamine