title: Effect of methyl substitution on the antioxidative property and genotoxicity of resveratrol.
abstract: 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.
authors.affiliation: Division of Organic Chemistry, National Institute of Health Sciences, Setagaya-ku, Tokyo 158-8501, Japan. fukuhara@nihs.go.jp
authors.forename: Kiyoshi
authors.initials: K
authors.lastname: Fukuhara
authors.forename: Ikuo
authors.initials: I
authors.lastname: Nakanishi
authors.forename: Atsuko
authors.initials: A
authors.lastname: Matsuoka
authors.forename: Tomohiro
authors.initials: T
authors.lastname: Matsumura
authors.forename: Sachiko
authors.initials: S
authors.lastname: Honda
authors.forename: Mikiko
authors.initials: M
authors.lastname: Hayashi
authors.forename: Toshihiko
authors.initials: T
authors.lastname: Ozawa
authors.forename: Naoki
authors.initials: N
authors.lastname: Miyata
authors.forename: Shinichi
authors.initials: S
authors.lastname: Saito
authors.forename: Nobuo
authors.initials: N
authors.lastname: Ikota
authors.forename: Haruhiro
authors.initials: H
authors.lastname: Okuda
mesh_terms: D000818:Animals; D000975:Antioxidants / Q000737:chemistry* / Q000633:toxicity; D002460:Cell Line; D002869:Chromosome Aberrations / Q000139:chemically induced; D006224:Cricetinae; D003412:Cricetulus; D004305:Dose-Response Relationship, Drug; D008745:Methylation; D009153:Mutagens / Q000737:chemistry* / Q000633:toxicity; D000077185:Resveratrol; D013267:Stilbenes / Q000737:chemistry* / Q000633:toxicity; D013329:Structure-Activity Relationship
chemical_list: D000975:Antioxidants; D009153:Mutagens; D013267:Stilbenes; D000077185:Resveratrol