Preparation of glycyrrhetic acid glycosides having various beta(1----2)-linked disaccharides and their cytoprotective effects on carbon tetrachloride-induced hepatic injury.
Glycyrrhetic acid glycosides (1-7) having beta(1----2)-linked disaccharides such as 2-O-beta-D-glucopyranosyl-beta-D-galactopyranose, 2-O-beta-D-galactopyranosyl-beta-D-galactopyranose, 2-O-beta-D-glucuronopyranosyl-beta-D-galactopyranose, 2-O-beta-D-glucopyranosyl-beta-D-glucuronopyranose, 2-O-beta-D-galactopyranosyl-beta-D-glucuronopyranose, 2-O-beta-D-galactopyranosyl-beta-D-glucopyranose, 2-O-beta-D-glucuronopyranosyl-beta-D-glucopyranose, respectively, were synthesized by stepwise construction; from glycyrrhetic acid monoglycosides to the diglycosides. The cytoprotective activities of the glycosides 1-7 and 2-O-(beta-D-glucopyranosyl)-beta-D-glucopyranosyl-11-oxoolean-12-e n-30-oate (8) were compared with natural occurring glycyrrhizin (9). Among these glycosides 1-8, glycosides 3 and 7 having beta-D-glucuronopyranose (glcUA) as the only terminal sugar component were more effective materials against hepatic injury than glycyrrhizin 9.
Saito
S
S
Faculty of Pharmaceutical Sciences, Josai University, Saitama, Japan.
Kuroda
K
K
Hayashi
Y
Y
Sasaki
Y
Y
Nagamura
Y
Y
Nishida
K
K
Ishiguro
I
I
D000818:Animals; D002240:Carbohydrate Sequence; D002252:Carbon Tetrachloride Poisoning / Q000150:complications*; D056486:Chemical and Drug Induced Liver Injury; D004187:Disaccharides / Q000138:chemical synthesis* / Q000627:therapeutic use; D006027:Glycosides / Q000138:chemical synthesis* / Q000494:pharmacology; D006034:Glycyrrhetinic Acid / Q000031:analogs & derivatives* / Q000627:therapeutic use; D019695:Glycyrrhizic Acid; D008107:Liver Diseases / Q000517:prevention & control*; D008969:Molecular Sequence Data; D051381:Rats; D011919:Rats, Inbred Strains; D012503:Saponins / Q000627:therapeutic use
D004187:Disaccharides; D006027:Glycosides; D012503:Saponins; D019695:Glycyrrhizic Acid; D006034:Glycyrrhetinic Acid