A-Type proanthocyanidin trimers from cranberry that inhibit adherence of uropathogenic P-fimbriated Escherichia coli

J Nat Prod. 2000 Sep;63(9):1225-8. doi: 10.1021/np000128u.

Abstract

Three proanthocyanidin trimers possessing A-type interflavanoid linkages, epicatechin-(4beta-->6)-epicatechin-(4beta-->8, 2beta-->O-->7)-epicatechin (4), epicatechin-(4beta-->8, 2beta-->O-->7)-epicatechin-(4beta-->8)-epicatechin (5), and epicatechin-(4beta-->8)-epicatechin-(4beta-->8, 2beta-->O-->7)-epicatechin (6), were isolated from the ripe fruits of Vaccinium macrocarpon (cranberry) and prevented adherence of P-fimbriated Escherichia coli isolates from the urinary tract to cellular surfaces containing alpha-Gal(1-->4)beta-Gal receptor sequences similar to those on uroepithelial cells. The structure of 4 was elucidated by a combination of spectroscopic methods and acid-catalyzed degradation with phloroglucinol. Also isolated were the weakly active epicatechin-(4beta-->8, 2beta-->O-->7)-epicatechin (procyanidin A2) (3) and the inactive monomer epicatechin (1) and the inactive dimer epicatechin-(4beta-->8)-epicatechin (procyanidin B2) (2).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anthocyanins / chemistry
  • Anthocyanins / isolation & purification
  • Anthocyanins / pharmacology*
  • Bacterial Adhesion / drug effects*
  • Biflavonoids*
  • Catechin*
  • Escherichia coli / cytology
  • Escherichia coli / drug effects*
  • Fruit / chemistry*
  • Humans
  • Molecular Structure
  • Proanthocyanidins*
  • Urinary Bladder / microbiology*
  • Urinary Tract Infections / microbiology

Substances

  • Anthocyanins
  • Biflavonoids
  • Proanthocyanidins
  • proanthocyanidin
  • procyanidin B2
  • Catechin