Effects of structural characteristics of phenolic compounds on oxidation of glycerol trioleate: Action rule and mechanism

Hao-Xiang Gao; Nan Chen; Qiang He; Bi Shi; Wei-Cai Zeng

doi:10.1016/j.foodchem.2023.137361

Effects of structural characteristics of phenolic compounds on oxidation of glycerol trioleate: Action rule and mechanism

Food Chem. 2024 Feb 1:433:137361. doi: 10.1016/j.foodchem.2023.137361. Epub 2023 Sep 1.

Authors

Hao-Xiang Gao¹, Nan Chen¹, Qiang He², Bi Shi³, Wei-Cai Zeng⁴

Affiliations

¹ Antioxidant Polyphenols Team, Department of Food Engineering, Sichuan University, Chengdu 610065, PR China.
² The Key Laboratory of Food Science and Technology of Sichuan Province of Education, Sichuan University, Chengdu 610065, PR China.
³ Department of Biomass and Leather Engineering, Sichuan University, Chengdu 610065, PR China.
⁴ Antioxidant Polyphenols Team, Department of Food Engineering, Sichuan University, Chengdu 610065, PR China; The Key Laboratory of Food Science and Technology of Sichuan Province of Education, Sichuan University, Chengdu 610065, PR China. Electronic address: weicaizeng@qq.com.

PMID: 37688816
DOI: 10.1016/j.foodchem.2023.137361

Abstract

Effects of structural characteristics of phenolic compounds on the oxidation of glycerol trioleate were investigated, and the action rule and mechanism were further explored. By using thermal and multispectral analyses, all tested phenolic compounds significantly inhibited the oxidation of glycerol trioleate, and reduced the decomposition of CC and ester bonds of glycerol trioleate, which were attributed to their capability to inhibit the production of free radicals. Quercetin and gallic acid were the most effective among the condensed and hydrolyzable phenolic compounds in present study, respectively. For condensed phenolic compounds, the hydroxyl groups in B ring, substitution in C ring, and the structure of C ring played a crucial role in their inhibitory action. For hydrolyzable phenolic compounds, the amount of hydroxyl groups and their molecular weight had obvious effects on their inhibitory action. According to the measurement of molecular electrostatic potential and frontier molecular orbitals by density functional theory, the large maximum electrostatic potential and the small energy gap value were beneficial to enhance the inhibitory capability of phenolic compounds on the oxidation of glycerol trioleate. All present results suggested the potential action rule and molecular mechanism about the inhibitory effects of phenolic compounds on the oxidation of glycerol trioleate.

Keywords: Molecular mechanism; Oil; Oxidation; Phenolic compounds; Structural characteristics.