Selective β-Mono-Glycosylation of a C15-Hydroxylated Metabolite of the Agricultural Herbicide Cinmethylin Using Leloir Glycosyltransferases.

ABSTRACT: Cinmethylin is a well-known benzyl-ether derivative of the natural terpene 1,4-cineole that is used industrially as a pre-emergence herbicide in grass weed control for crop protection. Cinmethylin detoxification in plants has not been reported, but in animals, it prominently involves hydroxylation at the benzylic C15 methyl group. Here, we show enzymatic β-glycosylation of synthetic 15-hydroxy-cinmethylin to prepare a putative phase II detoxification metabolite of the cinmethylin in plants. We examined eight Leloir glycosyltransferases for reactivity with 15-hydroxy cinmethylin and revealed the selective formation of 15-hydroxy cinmethylin β-d-glucoside from uridine 5'-diphosphate (UDP)-glucose by the UGT71E5 from safflower (Carthamus tinctorius). The UGT71E5 showed a specific activ

SUBMITTER: Jung J 

PROVIDER: S-EPMC8278484 | biostudies-literature | 2021 May

REPOSITORIES: biostudies-literature