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

Wei Wang,Junke Li,Xiaopu Ren,Yingjie Bao,Yawei Zhang,Zengqi Peng,Yuxia Zhu

doi:10.1007/s00217-020-03676-9

Abstract

2-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.

Highlights

Heterocyclic amines (HAs) are mutagenic and carcinogenic compounds which are formed from sugars, creatine, creatinine, and free amino acids during thermal processing of muscle foods [1, 2]
Similar results with a reduction of approx. 90% for PhIP using grape seed and rosemary extract in marinades were shown in a study of Gibis et al [10]. These results suggested that the Zanthoxylum bungeanum Maxim. leaf (ZML) extract was a potent inhibitor against
It was concluded that ZML extract, hyperoside and quercitrin significantly inhibit PhIP formation in both beef patties and chemical model systems

Summary

Introduction

Heterocyclic amines (HAs) are mutagenic and carcinogenic compounds which are formed from sugars, creatine, creatinine, and free amino acids during thermal processing of muscle foods [1, 2]. Leaf (ZML) has a unique flavor and rich nutrition. It is used as a medicine for the treatment of stomach ache, tooth ache and other diseases due to its alkaloids, polyphenols, and so on [13]. The effects of these phenolic acids on HAs formation have been evaluated, no report was found on the mechanism behind the inhibitory effects of chlorogenic acid, especially with reference to the natural ratios of ZML. As for flavonoids, naringenin, quercetin and EGCG have been proven to inhibit PhIP formation via trapping of phenylacetaldehyde to form adducts [12, 18, 19]. It is necessary to examine the inhibitory effects of ZML extract and its components on PhIP formation

Methods

Results

Conclusion