Characterization of the interaction between boscalid and tannic acid and its effect on the antioxidant properties of tannic acid

• Published in: Journal of food science 2023-04, Vol.88 (4), p.1325-1335
• Main Authors: Fu, Xiaoyan, Yuan, Shaofeng, Yang, Fangwei, Yu, Hang, Xie, Yunfei, Guo, Yahui, Yao, Weirong
• Format: Article
• Language: English
• Subjects: antioxidant properties; Antioxidants; binding interaction; boscalid; Calorimetry; Computational chemistry; Computer applications; Food; Food contamination; Fourier transforms; Fruits; Hydrogen bonding; Hydrogen bonds; Hydrophobicity; Infrared spectroscopy; Magnetic Resonance Spectroscopy; Molecular docking; Molecular Docking Simulation; Molecular modelling; NMR; Nuclear magnetic resonance; Pesticide Residues; Pesticides; Phenols; Residues; Tannic acid; Tannins - chemistry; Thermodynamics; Titration; Titration calorimetry
• ISSN: 0022-1147; 1750-3841
• DOI: 10.1111/1750-3841.16488

The binding of pesticide residues and fruit components may have a profound impact on pesticide dissipation and the functional characteristics of the corresponding components. Therefore, the interaction between boscalid and tannic acid (TA, a representative phenolic in fruit) was systematically investigated using spectroscopic, thermodynamic, and computational chemistry methods. A separable system was designed to obtain the boscalid–TA complex. Fourier transform infrared and 1H‐NMR spectroscopies indicated the formation of hydrogen bonds in the complex. Isothermal titration calorimetry showed that the complex bound spontaneously through hydrophobic interactions (ΔG  0, ΔS > 0), with a binding constant of 6.0 × 105 M−1 at 298 K. The molecular docking results further confirmed the formation of hydrogen bonds and hydrophobic interactions in the complex at the molecular level, with a binding energy of −8.43 kcal mol−1. In addition, the binding of boscalid to TA significantly decreased the antioxidant activity of TA. The binding of boscalid residue to TA was characterized at the molecular level, which significantly reduced the in vitro antioxidant properties of TA. Practical Application This study provides a reference for the molecular mechanisms of the interaction between pesticide residues and food matrices, as well as a basis for regulating bound‐state pesticide residues in food.