Methionine thioether reduces the content of 4-hydroxy-2-nonenal in high-temperature soybean oil by preventing the radical chain reaction

Nanyu Zhao; Zhihua Song; Xue Zhang; Xinlei Shi; Lijun Wang; Ziyue Chen; Jianhua Huang; Xingguo Wang

doi:10.1016/j.foodchem.2025.142811

Methionine thioether reduces the content of 4-hydroxy-2-nonenal in high-temperature soybean oil by preventing the radical chain reaction

Food Chem. 2025 Jan 7:471:142811. doi: 10.1016/j.foodchem.2025.142811. Online ahead of print.

Authors

Nanyu Zhao¹, Zhihua Song¹, Xue Zhang¹, Xinlei Shi¹, Lijun Wang¹, Ziyue Chen¹, Jianhua Huang², Xingguo Wang¹

Affiliations

¹ National Key Laboratory, School of Food Science and Technology, Jiangnan University, 1800 Lihu Road, Wuxi 214122, China.
² National Key Laboratory, School of Food Science and Technology, Jiangnan University, 1800 Lihu Road, Wuxi 214122, China. Electronic address: Huangjianhua1124@126.com.

PMID: 39793354
DOI: 10.1016/j.foodchem.2025.142811

Abstract

This study investigated how methionine (Met) reduced 4-hydroxy-2-nonenal (4-HNE) generation during the heating of soybean oil. The results showed that Met at 5 mM, 10 mM, 15 mM, 20 mM and 30 mM reduced the 4-HNE content by 0.67 %, 58.86 %, 66.35 %, 86.62 % and 82.39 %, respectively, as detected by liquid chromatography coupled to tandem mass spectrometry. Additionally, a decrease in the content of alkyl radicals, alkyl peroxyl radicals and alkoxyl radicals with increasing Met concentration was detected by electron spin resonance. Combined with the subsequent identification of the adducts of Met with the three radicals, it could be shown that Met reduces the 4-HNE content by preventing the free radical chain reaction. Finally, the kinetics simulations of the reaction between 4-HNE and Met indicated that adducts formed by the two cannot be stabilized in high-temperature systems. This study offers insights into safe oil processing and the antioxidant mechanisms of Met thioether.

Keywords: 4-hydroxy-2-nonenal; Free radicals; Lipid oxidation; Methionine; Soybean oil.