A novel potent inhibitor of 2-amino-1-methyl-6-phenylimidazo[4,5-b] pyridine (PhIP) formation from Chinese chive: Identification, inhibitory effect and action mechanism

Qi Wang; Weiwei Cheng; Yifeng Zhang; Qingzheng Kang; Vemana Gowd; Yuanyuan Ren; Feng Chen; Ka-Wing Cheng

doi:10.1016/j.foodchem.2020.128753

A novel potent inhibitor of 2-amino-1-methyl-6-phenylimidazo[4,5-b] pyridine (PhIP) formation from Chinese chive: Identification, inhibitory effect and action mechanism

Food Chem. 2021 May 30:345:128753. doi: 10.1016/j.foodchem.2020.128753. Epub 2020 Dec 1.

Authors

Qi Wang¹, Weiwei Cheng², Yifeng Zhang³, Qingzheng Kang², Vemana Gowd², Yuanyuan Ren¹, Feng Chen², Ka-Wing Cheng⁴

Affiliations

¹ Institute for Food and Bioresource Engineering, College of Engineering, Peking University, Beijing 100871, China; Shenzhen Key Laboratory of Marine Microbiome Engineering, Institute for Advanced Study, Shenzhen University, Shenzhen 518060, China; Institute for Innovative Development of Food Industry, Shenzhen University, Shenzhen 518060, China.
² Shenzhen Key Laboratory of Marine Microbiome Engineering, Institute for Advanced Study, Shenzhen University, Shenzhen 518060, China; Institute for Innovative Development of Food Industry, Shenzhen University, Shenzhen 518060, China.
³ Institute for Food and Bioresource Engineering, College of Engineering, Peking University, Beijing 100871, China.
⁴ Shenzhen Key Laboratory of Marine Microbiome Engineering, Institute for Advanced Study, Shenzhen University, Shenzhen 518060, China; Institute for Innovative Development of Food Industry, Shenzhen University, Shenzhen 518060, China. Electronic address: kwcheng@szu.edu.cn.

PMID: 33302112
DOI: 10.1016/j.foodchem.2020.128753

Abstract

Differential solvent extraction and phytochemical profiling of Chinse chive were employed to identify its principal PhIP-formation inhibitory constituents. Six compounds (mangiferin, isorhamnetin, luteolin, rosmarinic acid, 6-methylcoumarin, and cyanidin-3-glucoside) were further analyzed in a PhIP-producing chemical model to identify the dominant inhibitor. Its inhibitory mechanism was investigated by assessing the contribution of antioxidation and scavenging of key PhIP precursor/intermediate. No significant correlation was observed between PhIP inhibition rates and antioxidant activities. Further evaluation of the novel potent inhibitor mangiferin revealed a highly significant correlation between its dose-dependent inhibition of PhIP formation and phenylacetaldehyde scavenging. Finally, the proposed mechanism was corroborated through organic synthesis and structural elucidation of the mangiferin-phenylacetaldehyde adduct. This study has identified a potent novel inhibitor of the most abundant HA in heat-processed food and characterized its action mechanism. These findings may provide insight for future studies on mitigation of dietary exposure to toxic Maillard products by polyphenolic phytochemicals.

Keywords: Chinese chive; Inhibitory mechanism; Mangiferin; Mangiferin-phenylacetaldehyde adduct; PhIP-formation inhibitor.

MeSH terms

Animals
Antioxidants / pharmacology
Chive / drug effects*
Chive / metabolism
Imidazoles / antagonists & inhibitors*
Imidazoles / metabolism
Models, Chemical
Xanthones / pharmacology

Substances

Antioxidants
Imidazoles
Xanthones
mangiferin
2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine