Effect of acrolein, a lipid oxidation product, on the formation of the heterocyclic aromatic amine 2-amino-1-methyl-6-phenylimidazo[4,5- b]pyridine (PhIP) in model systems and roasted tilapia fish patties

Meilin Jing; Qingqing Jiang; Yamin Zhu; Daming Fan; Mingfu Wang; Yueliang Zhao

doi:10.1016/j.fochx.2022.100315

Effect of acrolein, a lipid oxidation product, on the formation of the heterocyclic aromatic amine 2-amino-1-methyl-6-phenylimidazo[4,5- b]pyridine (PhIP) in model systems and roasted tilapia fish patties

Food Chem X. 2022 Apr 23:14:100315. doi: 10.1016/j.fochx.2022.100315. eCollection 2022 Jun 30.

Authors

Meilin Jing^{1

2}, Qingqing Jiang^{1

2}, Yamin Zhu^{1

2}, Daming Fan³, Mingfu Wang⁴, Yueliang Zhao^{1

2}

Affiliations

¹ College of Food Science and Technology, Shanghai Ocean University, Shanghai 201306, China.
² Laboratory of Quality and Safety Risk Assessment for Aquatic Products on Storage and Preservation (Shanghai), Ministry of Agriculture, Shanghai 201306, China.
³ School of Food Science and Technology, Jiangnan University, Wuxi, China.
⁴ Institute for Advanced Study, Shenzhen University, Shenzhen, China.

Abstract

The effect of acrolein on the formation of the 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) was investigated in a chemical model. Acrolein was found to increase PhIP formation at each tested addition level. 0-0.2 mmol of acrolein increased PhIP formation dose-dependently, while high levels of acrolein (>0.2 mmol) did not further increase PhIP formation. Mechanistic study showed that acrolein addition decreased the residue of phenylalanine and creatinine, but increased the content of some key intermediates. Further analysis indicated that acrolein can react with phenylalanine, creatinine, and PhIP to form adducts. These results suggested that acrolein was able to contribute to PhIP formation as a consequence of its comprehensive ability to facilitate Strecker degradation of phenylalanine and react with phenylalanine, creatinine, and PhIP. In addition, oxidation of the tilapia fish increased the PhIP formation in the roasted fish patties, further supporting the potential contribution role of lipid oxidation products to the formation of PhIP.

Keywords: Acrolein; Adduct; Intermediates; PhIP; Roasted tilapia fish.