Caffeic acid assists microwave heating to inhibit the formation of mutagenic and carcinogenic PhIP

Nana Zhang; Yanfang Chen; Yueliang Zhao; Daming Fan; Lijie Li; Bowen Yan; Guanjun Tao; Jianxin Zhao; Hao Zhang; Mingfu Wang

doi:10.1016/j.foodchem.2020.126447

Caffeic acid assists microwave heating to inhibit the formation of mutagenic and carcinogenic PhIP

Food Chem. 2020 Jul 1:317:126447. doi: 10.1016/j.foodchem.2020.126447. Epub 2020 Feb 19.

Authors

Nana Zhang¹, Yanfang Chen², Yueliang Zhao³, Daming Fan⁴, Lijie Li⁵, Bowen Yan⁵, Guanjun Tao⁶, Jianxin Zhao⁷, Hao Zhang⁷, Mingfu Wang⁸

Affiliations

¹ State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi, China; School of Biological Sciences, The University of Hong Kong, Pokfulam Road, Hong Kong Special Administrative Region; School of Food Science and Technology, Jiangnan University, Wuxi, China.
² State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi, China; School of Food Science and Technology, Shanghai Ocean University, Shanghai, China.
³ School of Biological Sciences, The University of Hong Kong, Pokfulam Road, Hong Kong Special Administrative Region; School of Food Science and Technology, Shanghai Ocean University, Shanghai, China.
⁴ State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi, China; National Engineering Research Center for Functional Food, Jiangnan University, Wuxi, China; School of Food Science and Technology, Jiangnan University, Wuxi, China. Electronic address: fandm@jiangnan.edu.cn.
⁵ State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi, China; School of Food Science and Technology, Jiangnan University, Wuxi, China.
⁶ State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi, China.
⁷ State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi, China; National Engineering Research Center for Functional Food, Jiangnan University, Wuxi, China; School of Food Science and Technology, Jiangnan University, Wuxi, China.
⁸ School of Biological Sciences, The University of Hong Kong, Pokfulam Road, Hong Kong Special Administrative Region.

PMID: 32092610
DOI: 10.1016/j.foodchem.2020.126447

Abstract

The inhibitory effect of caffeic acid on the formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b] pyridine (PhIP) was investigated in chemical model systems under microwave heating (MW). A mechanistic study was subsequently carried out to identify the inhibitory mechanism. The results showed that both for conductive heating (CV) and MW, the inhibition of PhIP increased with the concentration of caffeic acid but decreased with the prolongation of heating time. The inhibition on PhIP under MW was always higher than under CV, which were dominated by the difference in dielectric loss (ε″). UPLC-MS analysis showed that caffeic acid releases a CO₂ molecule to produce 4-vinylcatechol which can form adducts with phenylacetaldehyde, thus reducing its availability for PhIP formation. The structure of adduct was characterized as 3-(3,4-dihydroxyphenyl)-2-phenylbutanal with a molecular weight of 256. The findings indicate that trapping of phenylacetaldehyde by 4-vinylcatechol is a key mechanism of caffeic acid in inhibiting PhIP formation.

Keywords: 4-Vinylcatechol; Caffeic acid; Dielectric loss; Microwave heating; PhIP.

MeSH terms

Acetaldehyde / analogs & derivatives
Acetaldehyde / chemistry
Caffeic Acids / chemistry*
Carcinogens / chemistry
Chromatography, Liquid
Electromagnetic Phenomena
Heating
Imidazoles / chemistry*
Mass Spectrometry
Microwaves*
Mutagens / chemistry
Time Factors

Substances

Caffeic Acids
Carcinogens
Imidazoles
Mutagens
2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine
Acetaldehyde
caffeic acid
phenylacetaldehyde