GLYCOSYLATION OF 2-PHENYLPROPIONIC ACID AND ITS ETHYL ESTER IN SUSPENSION CULTURES OF NICOTIANA TABACUM, DIOSCOREOPHYLLUM CUMMINSII AND ACONITUM JAPONICUM

Article abstract of DOI:10.1016/S0031-9422(00)84576-8

Key Word Index-Nicotiana tabacum; Dioscoreophyllum cumminsii; Aconitum japonicum; cell suspension culture; biotransformation; glycosylation; 2-(RS)-phenylpropionic acid; glucosyl ester; gentiobiosyl ester; ethyl 6-O-<2-(RS)-phenylpropionyl>-β-D-glucopyranoside. Suspension cultures of Nicotiana tabacum and Dioscoreophyllum cumminsii converted 2-(RS)-phenylpropionic acid and its ethyl ester into 2-(RS)-phenylpropionyl β-D-glucopyranoside, 2-(RS)-phenylpropionyl 6-O-β-D-glucopyranosyl-β-D-glucopyranoside and 6-O-β-D-glucopyranosyl-2-O-<2-(RS)-phenylpropionyl>-D-glucose which accumulated in the cells.A suspension culture of Aconitum japonicum converted these substrates into ethyl 6-O-<2-(RS)-phenylpropionyl>-β-D-glucopyranoside which was mostly excreted into the medium.The diastereomeric mixture of the glucosyl esters of 2-(RS)-phenylpropionic acid was resolved by HPLC to show the ratio of R:S was 1:1.