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Papers In Press, published online ahead of print September 20, 2006
Linus Pauling Institute, Oregon State University, Corvallis, OR 97331
Corresponding Author: balz.frei{at}oregonstate.edu
Flavonoids have been suggested to exert human health benefits by anti-oxidant and anti-inflammatory mechanisms. In this study, we investigated whether–and by what mechanisms–dietary flavonoids inhibit expression of cellular adhesion molecules, which is relevant to inflammation and atherosclerosis. We found that the capacity of flavonoids to inhibit TNF(alpha)-induced adhesion molecule expression in human aortic endothelial cells was dependent on specific structural features of the flavonoids. The 5,7-dihydroxyl substitution of a flavonoid’s A-ring and 2,3-double bond and 4-keto group of the C-ring were the main structural requirements for inhibition of adhesion molecule expression. In striking contrast, hydroxyl substitutions of the B- and C-rings but not the A-ring were essential for antioxidant activity. Hence, only hydroxyl flavones, such as apigenin and chrysin, and flavonols, such as galangin, kaempferol, and quercetin, were able to inhibit endothelial adhesion molecule expression, whereas flavone, chromone, the flavanone, naringenin, and the flavanol, (-)-epicatechin, were ineffectual. At low concentrations, the active flavonoids significantly attenuated expression of E-selectin and intercellular adhesion molecule-1 (ICAM-1) but not vascular cell adhesion molecule-1. In addition, exposure of apigenin and kaempferol to cultured hepatocytes, mimicking first-pass metabolism, greatly diminished the flavonoids’ inhibitory effect on endothelial ICAM-1 expression. We conclude that the effect of dietary flavonoids on endothelial adhesion molecule expression depends on their molecular structure, concentration, and metabolic transformation but not their antioxidant activity.
J. Biol. Chem, 10.1074/jbc.M606804200
Submitted on July 17, 2006
Revised on September 14, 2006
Accepted on September 20, 2006
Dietary flavonoids attenuate TNF
-induced adhesion molecule expression in human aortic endothelial cells: Structure-function relationships and activity after first-pass metabolism
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