@article{oai:repo.qst.go.jp:00044511,
 author = {Fukuhara, Kiyoshi and Nagakawa, Maki and Nakanishi, Ikuo and Ohkubo, Kei and Imai, Kohei and Urano, Shiro and Fukuzumi, Shunichi and Ozawa, Toshihiko and Ikota, Nobuo and Mochizuki, Masataka and Miyata, Naoki and Okuda, Haruhiro and 中西 郁夫 and 小澤 俊彦 and 伊古田 暢夫},
 issue = {5},
 journal = {Bioorganic & Medicinal Chemistry},
 month = {Mar},
 note = {Resveratrol (3,5,4'-trihydroxy-trans-stilbene), a polyphenol found in grapes and other food products, is known as an antioxidant and cancer chemopreventive agent.   However, resveratrol was shown to induce genotoxicity through a high frequency of micronucleus and sister chromatid exchange in vitro and DNA-cleaving activity in the presence of Cu(II).  The present study was designed to explore the structure-activity relationship of resveratrol in DNA strand scission and to characterize the substrate specificity for Cu(II) and DNA binding.  When pBR322DNA was incubated with resveratrol or its analogues differing in the number and positions of hydroxyl groups in the presence of Cu(II), the ability of 4-hydroxystilbene analogues to induce DNA strand scission is much stronger than that of 3-hydroxy analogues.  The high binding affinity with both Cu(II) and DNA was also observed  by 4-hydroxystilbene analogues.  The reduction of Cu(II) which is essential for activation of molecular oxygen proceeded by addition of resveratrol to the solution of the Cu(II)-DNA complex, while such reduction was not observed with the addition of isoresveratrol, in which the 4-hydroxy group of resveratrol is changed to the 3-position. The results show that the 4-hydroxystilbene structure of resveratrol is a major determinant of generation of reactive oxygen species that was responsible for DNA strand scission.},
 pages = {1437--1443},
 title = {Structural Basis for DNA-Cleaving Activity of Resveratrol in the Presence of Cu(II)},
 volume = {14},
 year = {2006}
}