Inhibitory effects of hyperoside and quercitrin from Zanthoxylum bungeanum Maxim. leaf on 2-amino-1-methyl-6-phenylimidazo [4,5-b]pyridine formation by trapping phenylacetaldehyde

Abstract

Abstract2-amino-1-methyl-6-phenylimidazole[4,5-b]pyridine (PhIP) is one of the most abundant Heterocyclic amines (HAs) in meat products. Zanthoxylum bungeanum Maxim. leaf (ZML) extract has been shown to be rich in polyphenols, which are gaining increasing interest as efficient tools for inhibiting the formation of HAs. In the present work, the effects of ZML extract, major polyphenols, chlorogenic acid, hyperoside and quercitrin on the formation of PhIP in both roast beef patties and chemical model systems were investigated. UPLC-MS showed that ZML extract and those three polyphenols effectively inhibited PhIP formation. Additionally, GC-MS analysis showed that those three polyphenols significantly reduced the content of phenylacetaldehyde in the model systems, a key intermediate involved in PhIP formation. The subsequent UPLC-MS and TOF-MS/MS analysis found that hyperoside and quercitrin reacted with phenyacetaldehyde to form those four adducts, 8-C-(E-Phenylethenyl)hyperoside, 6-C-(E-Phenylethenyl)hyperoside, 8-C-(E-Phenylethenyl)quercitrin and 6-C-(E-Phenylethenyl)quercitrin, respectively. The results revealed that hyperoside and quercitrin could trap phenylacetaldehyde to form adducts, thereby, retarding the reaction of phenylacetaldehyde and creatinine, blocking the generation of PhIP.