Investigation of the transformation and toxicity of trichlorfon at the molecular level during enzymic hydrolysis of apple juice

Changjian Li; Huimin Zhu; Yahui Guo; Yunfei Xie; Yuliang Cheng; Hang Yu; He Qian; Weirong Yao

doi:10.1016/j.foodchem.2020.128653

Investigation of the transformation and toxicity of trichlorfon at the molecular level during enzymic hydrolysis of apple juice

Food Chem. 2021 May 15:344:128653. doi: 10.1016/j.foodchem.2020.128653. Epub 2020 Nov 18.

Authors

Changjian Li¹, Huimin Zhu¹, Yahui Guo¹, Yunfei Xie¹, Yuliang Cheng¹, Hang Yu², He Qian¹, Weirong Yao³

Affiliations

¹ State Key Laboratory of Food Science and Technology, Jiangnan University, No.1800 Lihu Avenue, Wuxi, Jiangsu Province 214122, China; School of Food Science and Technology, Jiangnan University, No.1800 Lihu Avenue, Wuxi, Jiangsu Province 214122, China.
² State Key Laboratory of Food Science and Technology, Jiangnan University, No.1800 Lihu Avenue, Wuxi, Jiangsu Province 214122, China; School of Food Science and Technology, Jiangnan University, No.1800 Lihu Avenue, Wuxi, Jiangsu Province 214122, China; Qingdao Special Food Research Institute, Qingdao, Shandong Province, 266109, China.
³ State Key Laboratory of Food Science and Technology, Jiangnan University, No.1800 Lihu Avenue, Wuxi, Jiangsu Province 214122, China; School of Food Science and Technology, Jiangnan University, No.1800 Lihu Avenue, Wuxi, Jiangsu Province 214122, China; Qingdao Special Food Research Institute, Qingdao, Shandong Province, 266109, China. Electronic address: yaoweirongcn@jiangnan.edu.cn.

PMID: 33229164
DOI: 10.1016/j.foodchem.2020.128653

Abstract

Trichlorfon is one of the most widely used organophosphorus pesticides in agriculture. In this study, the extent of transformation of trichlorfon to dichlorvos (DDVP), during the polygalacturonase (PG) treatment of apple pulp was monitored. A transformation pathway is proposed for trichlorfon molecules, based on density functional theory (DFT) calculations. The transformation of trichlorfon involves hydroxyl substitution and cleavage, which was confirmed by molecular electrostatic potential (MEP) and frontier molecular orbital (FMO) theory. In addition, the toxicity of trichlorfon and its transformed products was analyzed using Ecological Structure Activity Relationships (ECOSAR) software. The binding sites of the two pesticides are located in the hydrophobic grooves of the acetylcholinesterase (AChE) active site region and both pesticides form hydrophobic interactions and hydrogen bonds with a large number of surrounding amino acid residues. DDVP binds more strongly with AChE, so it is a better AChE inhibitor and more toxic than trichlorfon.

Keywords: Apple juice; Binding mechanism; Toxicity; Trichlorfon.

MeSH terms

Acetylcholinesterase / metabolism*
Biotransformation
Density Functional Theory
Fruit and Vegetable Juices*
Hydrolysis
Malus / chemistry*
Pesticides / metabolism*
Pesticides / toxicity*
Trichlorfon / metabolism*
Trichlorfon / toxicity*

Substances

Pesticides
Trichlorfon
Acetylcholinesterase