Identity, Synthesis, and Cytotoxicity of Forchlorfenuron Metabolites in Kiwifruit.

Abstract

Forchlorfenuron (CPPU) is a plant growth regulator widely used in kiwifruit production. Although research on the toxicological and environmental effects of CPPU is well-established, the nature and toxicological properties of its metabolites are much less well-known. Using high resolution mass spectrometry and nuclear magnetic resonance, the CPPU previously unidentified metabolites in Xuxiang and Jinyan kiwifruit were identified as N-(2-chloro-4-pyridinyl)-N'-(2-hydroxy-4-methoxyphenyl)-urea (metabolite 1) and N-phenyl-N'-4-pyridinylurea (metabolite 2, CAS: 1932-35-0). Their structures were confirmed by synthesis (metabolite 1) and by comparison with a commercial standard (metabolite 2). Quantitative studies demonstrate that CPPU and its metabolites are mainly retained in the kiwifruit peel, while the content is dependent on the nature of the peel surface, with the smoother peel of Jinyan kiwifruit retaining smaller amounts of the compound. Cell viability experiments in Caco2 and Lo2 cells show that the metabolites may have a lower cytotoxicity compared to the parent compound CPPU.