A-Type proanthocyanidin trimers from cranberry that inhibit adherence of uropathogenic P-fimbriated Escherichia coli.
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).
Foo
L Y
LY
Industrial Research, Gracefield Research Center, PO Box 31-310, Lower Hutt, New Zealand. y.foo@irl.cri.nz
Lu
Y
Y
Howell
A B
AB
Vorsa
N
N
D000872:Anthocyanins / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D001422:Bacterial Adhesion / Q000187:drug effects*; D044946:Biflavonoids; D002392:Catechin; D004926:Escherichia coli / Q000166:cytology / Q000187:drug effects*; D005638:Fruit / Q000737:chemistry*; D006801:Humans; D015394:Molecular Structure; D044945:Proanthocyanidins; D001743:Urinary Bladder / Q000382:microbiology*; D014552:Urinary Tract Infections / Q000382:microbiology
D000872:Anthocyanins; D044946:Biflavonoids; D044945:Proanthocyanidins; C013221:proanthocyanidin; C479580:procyanidin B2; D002392:Catechin