Effect and mechanism of polyphenols containing m-dihydroxyl structure on 2-amino-1-methyl-6-phenylimidazole [4, 5-b] pyridine (PhIP) formation in chemical models and roast pork patties

Abstract

2-amino-1-methyl-6-phenylimidazole [4, 5-b] pyridine (PhIP) is a prevalent heterocyclic amine (HAA) found in heated processed meat. This study investigated the inhibitory impact of eight different types of polyphenols containing m-dihydroxyl structure on PhIP formation through a chemical model system. The structure-activity relationship and potential sites of action of polyphenols containing m-dihydroxyl structure were also analyzed. Then, the mechanism of inhibiting PhIP formation by kaempferol, naringenin and quercetin was speculated by UPLC-MS. Results showed that 8 kinds of polyphenols containing m-dihydroxyl structure had significant (P < 0.05) inhibition on the formation of PhIP in the chemical model system in a dose-dependent manner. In addition, PhIP was most significantly inhibited by naringenin at the same concentration, followed by kaempferol and quercetin (83.27%, 80.81% and 79.26%, respectively). UPLC-MS results speculated that kaempferol, naringenin, and quercetin formed a new admixture via an electrophilic aromatic substitution reaction with the intermediate product phenylacetaldehyde, preventing the formation of PhIP.

Keywords

• 2-Amino-1-methyl-6-phenylimidazo [4, 5-b] pyridine (PhIP)
• Polyphenols containing m-dihydroxyl structure
• Generation pathway
• Inhibition mechanism