Biotransformation of glycyrrhizin to 18beta-glycyrrhetinic acid-3-O-beta-D-glucuronide by Streptococcus LJ-22, a human intestinal bacterium

Biol Pharm Bull. 1999 Mar;22(3):320-2. doi: 10.1248/bpb.22.320.

Abstract

By human intestinal bacteria, glycyrrhizin (18beta-glycyrrhetinic acid-3-O-[beta-D-glucuronopyranosyl-(1-->2)-betaD-glucuro nopyranoside], GL) was metabolized to 18beta-glycyrrhetinic acid (GA): the main pathway metabolized GL to GA by glucuronidases of Bacteroides J-37 and Eubacterium sp. GLH and the minor pathway metabolized GL to 18beta-glycyrrhetinic acid-3-O-beta-D-glucuronide (GAMG) by beta-glucuronidase of Streptococcus LJ-22. Beta-Glucuronidase from Streptococcus LJ-22 hydrolyzed GL to GAMG (not GA). The molecular weight and optimal pH of the enzyme were 240 kDa and 5-6.

MeSH terms

  • Animals
  • Biotransformation
  • Cattle
  • Glucuronidase / metabolism*
  • Glycyrrhetinic Acid / analogs & derivatives*
  • Glycyrrhetinic Acid / metabolism
  • Glycyrrhizic Acid / pharmacokinetics*
  • Humans
  • Hydrogen-Ion Concentration
  • Intestines / microbiology*
  • Molecular Weight
  • Rats
  • Streptococcus / metabolism*
  • Substrate Specificity
  • Sweetening Agents / metabolism*

Substances

  • Sweetening Agents
  • glycyrrhetyl 3-monoglucuronide
  • Glycyrrhizic Acid
  • Glucuronidase
  • Glycyrrhetinic Acid