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Enzymatic Biosynthesis of Novel Neobavaisoflavone Glucosides via Bacillus UDP-glycosyltransferase

Enzymatic Biosynthesis of Novel Neobavaisoflavone Glucosides via Bacillus UDP-glycosyltransferase

Tao Ma, Yi-Qun Dai, Nan Li, Qiang Huo, Hong-Mei Li, Yu-Xin Zhang, Zheng-Hao Piao, Cheng-Zhu Wu

Chin J Nat Med. 2017 Apr;15(4):281-287.

PMID: 28527513

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP41060155	Neobavaisoflavone		41060-15-5	Price

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