Antioxidative and Prooxidative Action of Stilbene Derivatives

Abstract

The effects of stilbene derivatives, including resveratrol, diethylstilboestrol and stilbene, as antioxidants or prooxidants were examined. Resveratrol and diethylstilboestrol, but not stilbene, strongly inhibited NADPH-and adenosine 5ø-diphosphate (ADP)-Fe 3π -dependent lipid peroxidation at the initial and propagation stages. In addition, phenolic stilbenes also inhibited ultraviolet light-induced lipid peroxidation. Resveratrol and diethylstilboestrol efficiently scavenged 2,2ø-azobis-(2-amidinopropane)-dihydrochloride peroxyl radicals. However, 2,2ø-diphenyl-p-picrylhydrazyl radicals were trapped only by resveratrol, but not by diethylstilboestrol. These results suggest that the inhibitory effect of phenolic stilbenes on lipid peroxidation was due to their scavenging ability of lipid peroxyl and/or carbon-cantered radicals. Resveratrol efficiently reduced ADP-Fe . The strand breaks of DNA were stimulated during the interaction of resveratrol with ADP-Fe 3π in the presence of H 2 O 2 . These results suggest that phenolic stilbenes act as antioxidants of membrane lipids and that resveratrol has a prooxidative effect DNA damage during interaction with ADP-Fe 3π in the presence of H 2 O 2 .

Involvement of the Nrf2 Pathway in the Regulation of Pterostilbene-Induced Apoptosis in HeLa Cells via ER Stress

“…We observed a rapid enhancement in ROS production (Pte from 0 to 160 mM) and GSH depletion (Pte from 80 to 160 mM) as a preliminary effect of Pte-induced HeLa cell apoptosis, in agreement with previously published pro-apoptotic reports in other cell lines (21,45,46). Stilbenes, including Pte, have also been reported to generate ROS and electrophilic molecules (19,21,47). Nevertheless, other research has revealed that Pte shows highly efficient anti-oxidative activities against several types of ROS (48).…”

Antioxidant effects of resveratrol in cardiovascular, cerebral and metabolic diseases

“…Oxidation of LDL cholesterol is strongly associated with risk of CVD (Holvoet, 2004). In this regard, resveratrol was found in rat liver microsomes to inhibit iron-induced, as well as ultraviolet-irradiated, lipid peroxidation and to prevent LDL oxidation by copper (Fauconneau et al, 1997;Miura et al, 2000); moreover, Rocha et al found a reduction in oxidized LDL in rats fed on a high fat diet when treated with resveratrol for 45 days at a dose of 1 mg/kg BW/day .…”

Dose-Dependency of Resveratrol in Providing Health Benefits

“…Iron plays a crucial role in free radical reactions leading to iron-oxygen complexes that remove hydrogen atoms from the polyunsaturated fatty acid membrane (Minotti and Aust 1989;Sotomatsu et al, 1990;Rice-Evans and Burdon 1993). Miura et al (2000) found that resveratrol possesses both antioxidant and pro-oxidant effects. Resveratrol promoted the reduction of Fe 3+ by increasing the formation of hydroxyl radicals through the Fenton reaction producing hydroxyl radicals and iron species (Yamazaki and Piette 1990).…”