The inhibitory effects of antioxidants of bamboo leaves (AOB) and flavonoids against 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) formation were investigated in creatinine and phenylalanine model systems. AOB and the tested flavonoids (orientin, homoorientin, vitexin, isovitex, apigenin, luteolin, isorhamnetin, fisetin, and hesperetin) had significant dose-dependent inhibition effects on PhIP formation with different IC50 values. The superoxide anion (O2(•-)) scavenging activities of these nine flavonoids were evaluated using the pyrogallol autoxidation system. The EC50 values of compounds that showed antioxidant activity were found to correlate well (R(2) = 0.8003) with the corresponding IC50 values representing their inhibition of PhIP formation. It was assumed that the inhibitory effects of flavonoids on PhIP formation were probably achieved by scavenging free radicals generated in the reaction system. These findings provide valuable information for the development of effective strategies to minimize heterocyclic amine content in thermally processed food.
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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