Correlation of antimutagenic activity and suppression of CYP1A with the lipophilicity of alkyl gallates and other phenolic compounds

Qing Feng, Takeshi Kumagai, Yoshimasa Nakamura, Koji Uchida, Toshihiko Osawa

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Alkyl gallates are widely used as food antioxidants. Methyl, ethyl, propyl, lauryl, and cetyl gallates showed antimutagenicity to activated 2-aminoanthracene (2AA)-induced SOS responses in Salmonella typhimurium TA1535/pSK1002. They also exhibited a suppressive effect on 3-methylcholanthrene (3-MC)-induced cytochrome P450 1A (CYP1A) in human hepatoma HepG2 cells, as indexed by the 7-ethoxyresorufin-O-deethylase (EROD) activity, and on CYP1A protein level. Both antimutagenicity and suppression of CYP1A appeared to be dependent on alkyl chain lengths, which suggested lipophilicity dependence. Based on those results, we investigated 26 other phenolic compounds for their lipophilicity, antimutagenicity and inhibition of EROD activity. The lipophilicity correlated well with the inhibition of EROD activity (r=0.78), and the inhibition of EROD activity correlated with the antimutagenicity of those compounds (r=0.71). The results suggest that the lipophilicity of the phenolic compounds may be an important factor in their ability to inhibit EROD activity.

Original languageEnglish
Pages (from-to)101-108
Number of pages8
JournalMutation Research - Genetic Toxicology and Environmental Mutagenesis
Volume537
Issue number1
DOIs
Publication statusPublished - May 9 2003
Externally publishedYes

Keywords

  • Alkyl gallate
  • Antimutagenicity
  • CYP1A
  • Lipophilicity
  • Phenols

ASJC Scopus subject areas

  • Genetics
  • Health, Toxicology and Mutagenesis

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