Specific inhibition of human beta-D-glucuronidase and alpha-L-iduronidase by a trihydroxy pipecolic acid of plant origin

FEBS Lett. 1984 Oct 15;176(1):61-4. doi: 10.1016/0014-5793(84)80911-4.

Abstract

The glucuronic acid analogue of 1-deoxynojirimycin, 2(S)-carboxy-3(R), 4(R), 5(S)-trihydroxypiperidine, recently isolated from seeds of Baphia racemosa, is a novel specific inhibitor of human liver beta-D-glucuronidase and alpha-L-iduronidase. No other glycosidases are inhibited. The inhibition of beta-D-glucuronidase is competitive, with a Ki of 8 X 10(-5) M and is pH-dependent. This inhibitor may be useful to induce a mucopolysaccharidosis or to investigate the function of microsomal beta-D-glucuronidase.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Binding, Competitive
  • Glucuronidase / antagonists & inhibitors*
  • Glycoside Hydrolases / antagonists & inhibitors*
  • Humans
  • Hydrogen-Ion Concentration
  • Iduronidase / antagonists & inhibitors*
  • Liver / enzymology*
  • Molecular Conformation
  • Pipecolic Acids / pharmacology*
  • Seeds / analysis
  • Structure-Activity Relationship

Substances

  • 2-carboxy-3,4,5-trihydroxypiperidine
  • Pipecolic Acids
  • Glycoside Hydrolases
  • Glucuronidase
  • Iduronidase