Radical-scavenging activity and cytotoxicity of p-methoxyphenol and p-cresol dimers

Compoundswith 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...

Full description

Saved in:
Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2010-02, Vol.15 (3), p.1103-1112
Main Authors: Kadoma, Yoshinori, Murakami, Yukio, Ogiwara, Takako, Machino, Mamoru, Yokoe, Ichiro, Fujisawa, Seiichiro
Format: Article
Language:English
Subjects:
Animals
Anisoles - chemistry
Anisoles - pharmacology
antioxidant
Antioxidants
Calorimetry, Differential Scanning
Cell Line
Cell Survival - drug effects
Cresols - chemistry
Cresols - pharmacology
Cytotoxicity
Dimerization
Dose-Response Relationship, Drug
Free Radical Scavengers - chemistry
Free Radical Scavengers - pharmacology
Macrophages - cytology
Macrophages - drug effects
Magnetic Resonance Spectroscopy
Mice
p-cresol dimer
p-methoxyphenol dimer
Phenols
Polymerization
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Compoundswith 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 (k(inh)/k(p)) 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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules15031103