Journal
JOURNAL OF FOOD SCIENCE
Volume 81, Issue 8, Pages C1908-C1913Publisher
WILEY
DOI: 10.1111/1750-3841.13381
Keywords
PhIP (2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine); alkoxy radical; flavonoids; quantitative structure-activity relationship
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Funding
- National Natural Science Foundation of China [31471669]
- Ministry of Science and Technology of the People's Republic of China [2011AA100806]
- Special Fund for Agro-scientific Research in the Public Interest [201203069]
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The inhibitory effect of 10 flavonoids on the formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in a creatinine-phenylalanine model system was investigated through electronic spin resonance and a quantitative structure-activity relationship. Alkoxy radicals were observed during the heating process, providing evidence for a radical pathway in the formation of PhIP. The alkoxy radical scavenging capability of the flavonoids was proportional to their inhibition of PhIP formation (IC50). We deduced that flavonoid inhibition of PhIP generation occurs via scavenging of alkoxy radicals during the heating process. Multiple linear regression and partial least squares models were used to elucidate the relationship between PhIP inhibition activity and structure characteristics of the flavonoids. The lipo-hydro partition coefficient and molecular fractional polar surface area of the flavonoids were found to be predictive of the inhibition effect.
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