Radical-Scavenging Activity and Cytotoxicity of p-Methoxyphenol and p-Cresol Dimers 英文参考文献.docVIP

Molecules 2010, 15, 1103-1112; doi:10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Radical-Scavenging Activity and Cytotoxicity of p-Methoxyphenol and p-Cresol Dimers Yoshinori Kadoma 1, Yukio Murakami 2, Takako Ogiwara 2, Mamoru Machino 2, Ichiro Yokoe and Seiichiro Fujisawa 2,* 3 1 Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, Kanda- surugadai, Chiyoda-ku, Tokyo 101-0062 Japan; E-Mail: y-kadoma.fm@tmd.ac.jp (Y.K.) 2 Meikai University School of Dentistry, Sakado, Saitama 350-0283, Japan; E-Mails: ymura@dent.meikai.ac.jp (Y.M.); a-hirata@dent.meikai.ac.jp (T.O.); machino@dent.meikai.ac.jp (M.M.) 3 Faculty of Pharmaceutical Sciences, Josai University, Saitama 350-0295 Japan; E- Mail: yokoe@josai.ac.jp (I.Y.) * Author to whom correspondence should be addressed; E-Mail: fujisawa33@; Tel.: +81-049-285-5511; Fax: (+81)-49-287-6657. Received: 4 December 2009; in revised form: 21 February 2010 / Accepted: 21 February 2010 / Published: 26 February 2010 Abstract: Compounds with two phenolic OH groups like curcumin possess efficient antioxidant and anti-inflammatory activity. We synthesized p-cresol dimer (2,2-dihydroxy- 5,5-dimethylbiphenol, 2a) and p-methoxyphenol dimer (2,2-dihydroxy-5,5- dimethoxybiphenol, 2b) by ortho-ortho coupling reactions of the parent monomers, p- cresol (1a) and p-methoxyphenol (1b), respectively. Their antioxidant activity was determined using the induction period method, and their cytotoxicity towards RAW 264.7 cells was also investigated using a cell counting kit. The stoichiometric factors n (number of free radicals trapped by one mole of antioxidant moiety) for 2a and 2b were 3 and 2.8, respectively, being greater than those for 1a and 1b. The ratio of the rate constant of inhibition to that of propagation (kinh/kp) for 2a and 2b was similar to that for 2-t-butyl-4- methoxyphenol (BHA), a convention