Antimutagenicity of Maillard reaction products from amino acid/sugar model systems against 2-amino-3-methylimidazo[4,5-f]quinoline

The role of pyrazines

S. N. Jenq, S. J. Tsai, H. Lee

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

The antimutagenicity of dichloromethane extracts from eight amino acid/sugar model systems was determined using Salmonella typhimurium TA98 against 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) in the presence of Aroclor 1254-induced rat hepatic S9. The Maillard reaction products in the dichloromethane extracts were then quantified and qualified by capillary gas chromatography and gas chromatography-mass spectrometry, respectively. Pyrazines and furans were found to be the major Maillard reaction products yielded in the extracts. Moreover, the antimutagenicity of dichloromethane extracts correlated positively with the total amounts of pyrazines and furans. To elucidate the mechanism of antimutagenicity of dichloromethane extracts, the inhibitory effect of pyrazines on ethoxycoumarin deethylase activity in Aroclor 1254-induced hepatic microsomes was examined. We also studied the effects of pyrazines on IQ metabolism by Aroclor 1254-induced microsomes using high-performance liquid chromatography. The antimutagenicity of pyrazines correlated positively with both the inhibition of cytochrome P-450 IA2-linked ethoxycoumarin deethylase in hepatic microsomes and the inhibition of N-hydroxy-IQ formation from IQ metabolism by hepatic microsomes. Thus we concluded that pyrazines in dichloromethane extracts from eight amino acid/sugar model systems play an important role in the antimutagenicity of IQ. Moreover, we concluded that the modifying effect of pyrazines on the mutagenicity of IQ is mediated through interaction with microsomal activating enzymes to inhibit the major active metabolite in N-hydroxy-IQ formation.

Original languageEnglish
Pages (from-to)483-488
Number of pages6
JournalMutagenesis
Volume9
Issue number5
Publication statusPublished - 1994
Externally publishedYes

Fingerprint

2-amino-3-methylimidazo(4,5-f)quinoline
Amino Sugars
Pyrazines
Maillard Reaction
Dichloromethane
Sugars
Reaction products
Amino Acids
Amino acids
Gas Chromatography
Methylene Chloride
Metabolism
Chlorodiphenyl (54% Chlorine)
Microsomes
7-Alkoxycoumarin O-Dealkylase
Furans
Gas chromatography
High-performance Liquid Chromatography
Mass Spectrometry
Liver

ASJC Scopus subject areas

  • Genetics
  • Health, Toxicology and Mutagenesis
  • Genetics(clinical)
  • Toxicology
  • Statistics, Probability and Uncertainty
  • Applied Mathematics

Cite this

Antimutagenicity of Maillard reaction products from amino acid/sugar model systems against 2-amino-3-methylimidazo[4,5-f]quinoline : The role of pyrazines. / Jenq, S. N.; Tsai, S. J.; Lee, H.

In: Mutagenesis, Vol. 9, No. 5, 1994, p. 483-488.

Research output: Contribution to journalArticle

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