Enzymatic biosynthesis of novel neobavaisoflavone glucosides via Bacillus UDP-glycosyltransferase.
10.1016/S1875-5364(17)30045-6
- Author:
Tao MA
1
;
Yi-Qun DAI
1
;
Nan LI
1
;
Qiang HUO
1
;
Hong-Mei LI
1
;
Yu-Xin ZHANG
2
;
Zheng-Hao PIAO
3
;
Cheng-Zhu WU
4
Author Information
1. School of Pharmacy, Bengbu Medical College, Bengbu 233030, China.
2. Department of Biochemistry, Bengbu Medical College, Bengbu 233030, China.
3. Department of Basic Medical Science, School of Medicine, Hangzhou Normal University, Hangzhou 321004, China.
4. School of Pharmacy, Bengbu Medical College, Bengbu 233030, China. Electronic address: wuchengzhu0611@foxmail.com.
- Publication Type:Journal Article
- Keywords:
Cytotoxicity;
Glycosylation;
Neobavaisoflavone;
UDP-glycosyltransferase;
Water-solubility
- MeSH:
Antineoplastic Agents;
metabolism;
pharmacology;
Bacillus;
enzymology;
Cell Line, Tumor;
Colorimetry;
Drug Screening Assays, Antitumor;
Glucosides;
biosynthesis;
chemistry;
Glycosyltransferases;
metabolism;
Humans;
Isoflavones;
biosynthesis;
chemistry;
Molecular Structure;
Solubility
- From:
Chinese Journal of Natural Medicines (English Ed.)
2017;15(4):281-287
- CountryChina
- Language:English
-
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 IC values ranging from 63.47 to 72.81 µmol·L. These results suggest that in vitro enzymatic glycosylation is a powerful approach to structural modification, improving water-solubility.
