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- Title
Radical-Scavenging Activity and Cytotoxicity of p-Methoxyphenol and p-Cresol Dimers.
- Authors
Kadoma, Yoshinori; Murakami, Yukio; Ogiwara, Takako; Machino, Mamoru; Yokoe, Ichiro; Fujisawa, Seiichiro
- 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, pcresol (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 conventional food antioxidant. The 50% inhibitory dose (ID50) declined in the order 1b > 1a >> 2b > 2a > BHA. The cytotoxicity for 2a and 2b was significantly greater than that for the parent monomers (p < 0.001), but smaller than that for BHA (p < 0.01). Compounds 2a and 2b may be useful as food antioxidants.
- Subjects
PHENOLS; DIMERS; ANTIOXIDANTS; CHEMICAL inhibitors; OLIGOMERS
- Publication
Molecules, 2010, Vol 15, Issue 3, p1103
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules15031103