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

Three proanthocyanidin trimers possessing A-type interflavanoid linkages, epicatechin-(4 beta-->6)-epicatechin-(4 beta-->8; 2 beta-->O-->7)-epicatechin (4), epicatechin-(4 beta-->8, 2 beta-->O-->7)-epicatechin-(4 beta-->8)-epicatechin (5), and epicatechin (4 beta-->8)-epicatechin-(4 beta-->8, 2 beta-->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-(4 beta-->8, 2 beta-->O-->7)-epicatechin (procyanidin A2) (3) and the inactive monomer epicatechin (1) and the inactive dimer epicatechin-(4 beta-->8)-epicatechin (procyanidin B2) (2).