Inhibition effects of flavonoids on 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline and 2-amino-3,7,8-trimethylimidazo[4,5-f]quinoxaline formation and alkoxy radical scavenging capabilities of flavonoids in a model system.

Abstract

Heterocyclic aromatic amines (HAAs) have been considered as carcinogenic and mutagenic chemicals generated during thermal processing of protein-rich foods that can be inhibited by some flavonoids. Free radical scavenging is a major characteristic of flavonoids. The half-maximal inhibitory concentration (IC50 ) values of nine flavonoids were determined by evaluating their capacity to inhibit 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) and 2-amino-3,7,8-trimethylimidazo[4,5-f]quinoxaline (7,8-DiMeIQx) formation in a model system. The results of the 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) test validated that MeIQx and 7,8-DiMeIQx formed via a free radical pathway. Electron spin resonance (ESR) spectroscopic analysis with spin trapping (α-(4-pyridyl N-oxide)-N-tert-butylnitrone (POBN) spin adduct, aN = 15.2 G and aH = 2.7 G) revealed that an alkoxy radical was the generated intermediate. The scavenging capacities of the nine flavonoids on alkoxy radicals were then evaluated based on the ESR spectra of the POBN spin adducts. The weak correlation between the alkoxy radical scavenging capacities and IC50 of the flavonoids suggested that their inhibitory activity against MeIQx and 7,8-DiMeIQx formation operates by a more complex mechanism than simply scavenging alkoxy radicals. © 2017 Society of Chemical Industry.