Preparation of glycyrrhetic acid glycosides having various beta(1----2)-linked disaccharides and their cytoprotective effects on carbon tetrachloride-induced hepatic injury

Chem Pharm Bull (Tokyo). 1991 Sep;39(9):2333-9. doi: 10.1248/cpb.39.2333.

Abstract

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.

Publication types

  • Comparative Study

MeSH terms

  • Animals
  • Carbohydrate Sequence
  • Carbon Tetrachloride Poisoning / complications*
  • Chemical and Drug Induced Liver Injury
  • Disaccharides / chemical synthesis*
  • Disaccharides / therapeutic use
  • Glycosides / chemical synthesis*
  • Glycosides / pharmacology
  • Glycyrrhetinic Acid / analogs & derivatives*
  • Glycyrrhetinic Acid / therapeutic use
  • Glycyrrhizic Acid
  • Liver Diseases / prevention & control*
  • Molecular Sequence Data
  • Rats
  • Rats, Inbred Strains
  • Saponins / therapeutic use

Substances

  • Disaccharides
  • Glycosides
  • Saponins
  • Glycyrrhizic Acid
  • Glycyrrhetinic Acid