Enzymatic biosynthesis of novel neobavaisoflavone glucosides via Bacillus UDP-glycosyltransferase

Abstract

The present study was designed to perform structural modifications of of neobavaisoflavone (NBIF), using an in vitro enzymatic glycosylation reaction, in order to improve its water-solubility. Two novel glucosides of NBIF were obtained from an enzymatic glycosylation by UDP-glycosyltransferase. The glycosylated products were elucidated by LC-MS, HR-ESI-MS, and NMR analysis. The HPLC peaks were integrated and the concentrations in sample solutions were calculated. The MTT assay was used to detect the cytotoxic activity of compounds in cancer cell lines. Based on the spectroscopic analyses, the two novel glucosides were identified as neobavaisoflavone-4´- O- β-D-glucopyranoside ( 1) and neobavaisoflavone-4´, 7-di- O- β-D-glucopyranoside ( 2). Additionally, the water-solubilities of compounds 1 and 2 were approximately 175.1- and 4 031.9-fold higher than that of the substrate, respectively. Among the test compounds, only NBIF exhibited weak cytotoxicity against four human cancer cell lines, with IC50 values ranging from 63.47 to 72.81 μmol·L ^–1. These results suggest that in vitro enzymatic glycosylation is a powerful approach to structural modification, improving water-solubility.