Journal
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS
Volume 469, Issue 2, Pages 209-219Publisher
ELSEVIER SCIENCE INC
DOI: 10.1016/j.abb.2007.10.012
Keywords
catechol-O-methyltransferase; endothelial; epicatechin; flavonoid metabolites; HUVEC; isorhamnetin; NADPH oxidase; procyanidin dimers; structure-activity relationship
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The dietary flavan-3-ol (-)-epicatechin improves the bioactivity of nitric oxide in arterial vessels in vivo. Moreover, it effectively protects cultured vascular endothelial cells from signs of oxidative stress and elevates intracellular nitric oxide in vitro. We addressed the effects of (-)-epicatechin, its metabolic conversion products and structurally related compounds on NADPH oxidase activity in intact human umbilical vein endothelial cells (HUVEC) and in cell lysates. (-)-Epicatechin proved to be an O-2(center dot-)-scavenger but did not inhibit NADPH oxidase activity, whereas the converse pattern was observed for the metabolites 3'- and 4'-O-methyl epicatechin. The dimer procyanidin B2 and (-)-epicatechin glucuronide were O-2(center dot-)-scavengers and inhibited NADPH oxidase. Analysis of structure-activity relations with 45 compounds suggests an apocynin-like mode of NADPH oxidase inhibition. Notably, HUVEC converted (-)-epicatechin to NADPH oxidase-inhibitory methyl ethers. These data identify endothelial NADPH oxidase as candidate target of dietary flavonoids and particularly of their metabolites. (C) 2007 Elsevier Inc. All rights reserved.
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