Enantioselective fate of dinotefuran from tomato cultivation to home canning for refining dietary exposure

Highlights: • R-dinotefuran preferentially degraded and resulted in relative enrichment of S-dinotefuran in tomato. • (−)-UF was metabolized preferentially and was more persistent than (+)-UF in tomato by foliage uptake pathway. • Uptake pathways can affect the enantioselective dissipation and metabolism of dinotefuran in tomato. • Peeling played the key role in reducing S-dinotefuran and R-dinotefuran in tomato. • Simmering was the most effective way to remove UF enantiomers by elevated temperature. Understanding the enantioselective fate of chiral neonicotinoid dinotefuran is of vital importance for accurate dietary exposure assessment and food safety regulation. The study investigated the enantioselectivity in respect to dissipation, metabolism, and removal, of dinotefuran from tomato cultivation to tomato paste processing. The chiral analytical method of dinotefuran, UF and DN was developed in tomato using ultrahigh performance supercritical fluid chromatography/tandem mass spectrometry. Under greenhouse cultivation R-dinotefuran preferentially degraded (T_1/2, 9.1−12.6 days), resulting in relative enrichment of S-dinotefuran (T_1/2, 10.3−13.3 days) by foliage and root uptake pathways. (−)-UF generated at a faster rate and was more persistent than its antipode in tomato by foliage treatment. Furthermore, changes in the enantiomeric removal and enantioselectivity orientation of dinotefuran and metabolites were evaluated during home canning of tomato paste, including washing, peeling, homogenization, simmering, and sterilization. Peeling played the key role in reducing S-dinotefuran by 67.3% and R-dinotefuran by 69.9% with processing factor of 0.313 and 0.287, respectively. Simmering was the most effective way to remove UF enantiomers (Pf, 0.336–0.421) by elevated temperature. This study sheds light on the chiral profiles of the fate of dinotefuran from cultivation to processing, providing scientific importance to protect human health from hazardous effects.