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Chem Res Toxicol. 2008 Feb;21(2):282-7. Epub 2008 Jan 5.
Effect of methyl substitution on the antioxidative property and
genotoxicity of resveratrol.
Fukuhara K, Nakanishi I, Matsuoka A, Matsumura T, Honda S, Hayashi M,
Ozawa T, Miyata N, Saito S, Ikota N, Okuda H.
Division of Organic Chemistry, National Institute of Health Sciences,
Setagaya-ku, Tokyo 158-8501, Japan. fukuh...@nihs.go.jp
Resveratrol ( trans-3,4',5-trihydroxystilbene) is a natural
phytoalexin with various biological activities including inhibition of
lipid peroxidation and free radical scavenging properties. In addition
to its beneficial effects, resveratrol also has significant
genotoxicity that leads to a high frequency of chromosome aberration
together with micronucleus and sister chromatid exchanges. To enhance
the radical scavenging activities and to reduce the genotoxicity of
resveratrol, we designed 4'-methyl resveratrol analogues where a
methyl group was introduced at the ortho position relative to the 4'-
hydroxy group, which is responsible for both antioxidative activities
and genotoxicity of resveratrol. These synthesized methyl analogues of
resveratrol showed increased antioxidative activities against
galvinoxyl radical as an oxyl radical species. Furthermore, the methyl
analogues also surprisingly showed reduced in vitro genotoxicities,
suggesting that methyl substitution may improve resveratrol efficacy.
PMID: 18177016 [PubMed - indexed for MEDLINE]
