Identification, Synthesis, and Safety Assessment of Thidiazuron [1-Phenyl-3-(1,2,3-thidiazol-5-yl)urea] and Its Metabolites in Kiwifruits

Abstract

The quality of kiwifruit became worse as a result of the abuse of plant growth regulators (PGRs). The safety of the fruits treated with PGRs also worried consumers. Therefore, the present study analyzed the structure of thidiazuron [TDZ, (1-phenyl-3-(1,2,3-thidiazol-5-yl)-urea)] (1) and its metabolites of biotransformation in kiwifruits using liquid chromatography hybrid ion trap time-of-flight mass spectrometry (LC-IT-TOF-MS). Standard compounds were also synthesized and used for structural identification of those metabolites. In addition, cytotoxicity of TDZ and its metabolites was tested through sulforhodamine B assays against normal Chinese hamster ovary (CHO) cells. Four metabolites were identified. They were 4-hydroxy-thidiazuron (2), 3-hydroxy-thidiazuron (3), thidiazuron-4-O-β-d-glucoside (4), and thidiazuron-3-O-β-d-glucoside (5). Values of IC₅₀ of compounds 1, 2, and 3 to CHO cells were 18.3 ± 1.8, 37.56 ± 1.5, and 23.36 ± 1.59 μM, respectively. Compounds 4 and 5 had no effect on CHO cells.

Keywords: LCMS−IT−TOF; metabolites; safety assessment; thidiazuron.