The 4'-hydroxy group is responsible for the in vitro cytogenetic activity of resveratrol.
We previously reported that 3,5,4'-trihydroxy-trans-stilbene (resveratrol), a polyphenolic phytoalexin found in grapes, induces a high frequency of sister chromatid exchanges (SCEs) in vitro. In this study, to investigate structure activity relationships, we synthesized six analogues of resveratrol differing in number and position of hydroxy groups, and we investigated their activity in chromosomal aberration (CA), micronucleus (MN) and sister chromatid exchange (SCE) tests in a Chinese hamster cell line (CHL). Two of the six analogues (3,4'-dihydroxy-trans-stilbene and 4-hydroxy-trans-stilbene) showed clear positive responses in a concentration-dependent manner in all three tests. Both were equal to or stronger than resveratrol in genotoxicity. The 4'-hydroxy (OH) analogue had the simplest chemical structure and was the most genotoxic. The other analogues did not have a 4'-hydroxy group. These results suggested that a 4'-hydroxy group is essential to the genotoxicity of stilbenes.
Matsuoka
Atsuko
A
Division of Medical Devices, National Institute of Health Sciences, 1-18-1 Kamiyoga, Setagaya-ku, Tokyo 158-8501, Japan. matsuoka@nihs.go.jp
Takeshita
Kenji
K
Furuta
Ayumi
A
Ozaki
Masayasu
M
Fukuhara
Kiyoshi
K
Miyata
Naoki
N
D000818:Animals; D002460:Cell Line; D002869:Chromosome Aberrations; D006224:Cricetinae; D003412:Cricetulus; D020732:Cytogenetic Analysis; D004305:Dose-Response Relationship, Drug; D015162:Micronucleus Tests; D009152:Mutagenicity Tests / Q000379:methods; D000077185:Resveratrol; D012854:Sister Chromatid Exchange; D013267:Stilbenes / Q000737:chemistry* / Q000494:pharmacology* / Q000633:toxicity*; D013329:Structure-Activity Relationship
C578987:3,4'-dihydroxystilbene; D013267:Stilbenes; C064297:4-hydroxystilbene; D000077185:Resveratrol