Inhibition of gastric H+, K(+)-ATPase by flavonoids: a structure-activity study

J Enzyme Inhib. 1999;14(2):151-66. doi: 10.3109/14756369909036551.

Abstract

Gastric H+, K(+)-ATPase plays a pivotal role in the final step of gastric acid secretion. Over 80 flavonoids, including flavones, flavanones, isoflavones and anthocyanidins were examined for their in vitro effect on gastric H+, K(+)-ATPase and some were found to be inhibitors of this enzyme. Kinetic studies showed that the inhibition of H+, K(+)-ATPase by flavonoids was competitive with respect to ATP, and non-competitive with respect to K+. Structure-activity analysis revealed the following: (1) The inhibitory potency of flavonoids depends on the number of hydroxyl groups up to four per molecule and that above this, no marked enhancement is seen; (2) The hydroxylation pattern is an important determinant of inhibitory potency. Two adjacent hydroxyl groups (catechol-type), three adjacent hydroxyl groups (pyrogallol-type) or hydroxyl groups at C-3, C-5 and C-7 are a minimum requirement for high potency inhibition; (3) Protection of the hydroxyl group(s) by glycosylation or methylation decreases potency; (4) Saturation of the C-2-C-3 double bond results in a decrease in potency; and (5) A ketone at C-4 is not essential for inhibition.

Publication types

  • Comparative Study

MeSH terms

  • Animals
  • Flavanones*
  • Flavonoids / pharmacology*
  • Glycosides / pharmacology
  • Isoflavones / pharmacology
  • Proton Pump Inhibitors*
  • Stomach / enzymology*
  • Structure-Activity Relationship
  • Swine

Substances

  • Flavanones
  • Flavonoids
  • Glycosides
  • Isoflavones
  • Proton Pump Inhibitors
  • flavanone