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

14 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

Fingerprint

Cytochrome P-450 CYP1A1
Cytochrome P-450 Enzyme System
Methylcholanthrene
Hep G2 Cells
Salmonella typhimurium
Hepatocellular Carcinoma
Antioxidants
Food
Proteins

Keywords

  • Alkyl gallate
  • Antimutagenicity
  • CYP1A
  • Lipophilicity
  • Phenols

ASJC Scopus subject areas

  • Health, Toxicology and Mutagenesis
  • Genetics

Cite this

Correlation of antimutagenic activity and suppression of CYP1A with the lipophilicity of alkyl gallates and other phenolic compounds. / Feng, Qing; Kumagai, Takeshi; Nakamura, Yoshimasa; Uchida, Koji; Osawa, Toshihiko.

In: Mutation Research - Genetic Toxicology and Environmental Mutagenesis, Vol. 537, No. 1, 09.05.2003, p. 101-108.

Research output: Contribution to journalArticle

@article{cce978ee08444b05921157b5659c08ad,
title = "Correlation of antimutagenic activity and suppression of CYP1A with the lipophilicity of alkyl gallates and other phenolic compounds",
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.",
keywords = "Alkyl gallate, Antimutagenicity, CYP1A, Lipophilicity, Phenols",
author = "Qing Feng and Takeshi Kumagai and Yoshimasa Nakamura and Koji Uchida and Toshihiko Osawa",
year = "2003",
month = "5",
day = "9",
doi = "10.1016/S1383-5718(03)00057-3",
language = "English",
volume = "537",
pages = "101--108",
journal = "Mutation Research - Genetic Toxicology and Environmental Mutagenesis",
issn = "1383-5718",
publisher = "Elsevier",
number = "1",

}

TY - JOUR

T1 - Correlation of antimutagenic activity and suppression of CYP1A with the lipophilicity of alkyl gallates and other phenolic compounds

AU - Feng, Qing

AU - Kumagai, Takeshi

AU - Nakamura, Yoshimasa

AU - Uchida, Koji

AU - Osawa, Toshihiko

PY - 2003/5/9

Y1 - 2003/5/9

N2 - 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.

AB - 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.

KW - Alkyl gallate

KW - Antimutagenicity

KW - CYP1A

KW - Lipophilicity

KW - Phenols

UR - http://www.scopus.com/inward/record.url?scp=0038396303&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0038396303&partnerID=8YFLogxK

U2 - 10.1016/S1383-5718(03)00057-3

DO - 10.1016/S1383-5718(03)00057-3

M3 - Article

C2 - 12742511

AN - SCOPUS:0038396303

VL - 537

SP - 101

EP - 108

JO - Mutation Research - Genetic Toxicology and Environmental Mutagenesis

JF - Mutation Research - Genetic Toxicology and Environmental Mutagenesis

SN - 1383-5718

IS - 1

ER -