Resveratrol is a naturally occurring phytoalexin, present in grapes and other food products, with important antioxidant properties. Although still under debate, it is generally assumed that resveratrol has protective effects against heart diseases and probably tumor development. Lipoxygenase is a dioxygenase with peroxidase activity involved in the synthesis of mediators in inflammatory, atherosclerotic, and carcinogenic processes. Lipoxygenase activity is also involved in the generation of flavors and aromas in foods from animal or vegetal sources. The results presented here show that resveratrol was a potent inhibitor of the dioxygenase activity of lipoxygenase, with an IC(50) = 13 microM. Simultaneously, resveratrol was oxidized by the peroxidase activity of lipoxygenase with a V(max) = 0.28 microM min(-1) and a k(M) = 16.6 microM. Furthermore, oxidized resveratrol was as efficient a lipoxygenase inhibitor as in its reduced form. From the data obtained it can be concluded that both resveratrol and its oxidized form can act as inhibitors of the dioxygenase activity of lipoxygenase. In contrast, the hydroperoxidase activity of lipoxygenase was not inhibited by resveratrol. These results suggest that resveratrol may be used as an antioxidant food additive and as a pharmacological agent to prevent the generation of eicosanoids involved in pathological processes.
In this work the oxidative degradation of resveratrol catalyzed by lipoxygenase-1 (LOX-1) has been studied. The process has been characterized by spectroscopic and polarographic measurements. The oxidation of resveratrol was dependent on the concentration of resveratrol and the enzyme. When resveratrol was incubated in the presence of lipoxygenase at pH 9.0, the reaction displayed a k(M) value of 18.6 x 10(-)(6) M and a catalytic efficiency (k(cat)/k(M)) of 4.3 x 10(4) s(-)(1) M(-)(1). These values are close to those shown by the enzyme when linoleic acid is used as the substrate. The effect of lipoxygenase inhibitors on the lipoxygenase-catalyzed resveratrol oxidation was also evaluated. The rate of resveratrol oxidation was markedly decreased by the presence of NDGA in the incubation mixture. From HPLC measurements, it can be deduced that resveratrol is oxidatively decomposed to a complex mixture of products similar to those obtained when the molecule is oxidized by hydrogen peroxide.
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