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      Enzymatic biosynthesis of novel neobavaisoflavone glucosides via Bacillus UDP-glycosyltransferase

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          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.

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          Most cited references 17

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          Comparison of in vitro anticancer-drug-screening data generated with a tetrazolium assay versus a protein assay against a diverse panel of human tumor cell lines.

          The National Cancer Institute (NCI) is implementing a large-scale in vitro drug-screening program that requires a very efficient automated assay of drug effects on tumor cell viability or growth. Many laboratories worldwide have adopted a microculture assay based on metabolic reduction of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT). However, because of certain technical advantages to use of the protein-binding dye sulforhodamine B (SRB) in a large-scale screening application, a detailed comparison of data generated by each type of assay was undertaken. The MTT and SRB assays were each used to test 197 compounds, on simultaneous days, against up to 38 human tumor cell lines representing seven major tumor categories. On subsequent days, 38 compounds were retested with the SRB assay and 25 compounds were retested with the MTT assay. For each of these three comparisons, we tabulated the differences between the two assays in the ratios of test group values to control values (T/C) for cell survival; calculated correlation coefficients for various T/C ratios; and estimated the bivariate distribution of the values for IC50 (concentration of drug resulting in T/C values of 50%, or 50% growth inhibition) for the two assays. The results indicate that under the experimental conditions used and within the limits of the data analyses, the assays perform similarly. Because the SRB assay has practical advantages for large-scale screening, however, it has been adopted for routine use in the NCI in vitro antitumor screen.
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            Enzymatic glycosylation of small molecules: challenging substrates require tailored catalysts.

            Glycosylation can significantly improve the physicochemical and biological properties of small molecules like vitamins, antibiotics, flavors, and fragrances. The chemical synthesis of glycosides is, however, far from trivial and involves multistep routes that generate lots of waste. In this review, biocatalytic alternatives are presented that offer both stricter specificities and higher yields. The advantages and disadvantages of different enzyme classes are discussed and illustrated with a number of recent examples. Progress in the field of enzyme engineering and screening are expected to result in new applications of biocatalytic glycosylation reactions in various industrial sectors. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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              Enzymatic methods for glyco(diversification/randomization) of drugs and small molecules.

              Glyco (randomization/diversification) is a term that encompasses strategies to diversify a core drug scaffold via enzymatic glycosylation to provide sets of analogs wherein the sole diversity element is a carbohydrate. This review covers the influence of glycosylation upon various drug properties, the classes of glycosyl-conjugating enzymes amenable to glyco(randomization/diversification) schemes, approaches to the synthesis of required substrates and specific examples of glycorandomized libraries utilizing both wild-type and engineered enzymes.
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                Author and article information

                Journal
                CJNM
                Chinese Journal of Natural Medicines
                Elsevier
                1875-5364
                20 April 2017
                : 15
                : 4
                : 281-287
                Affiliations
                1School of Pharmacy, Bengbu Medical College, Bengbu 233030, China
                2Department of Biochemistry, Bengbu Medical College, Bengbu 233030, China
                3Department of Basic Medical Science, School of Medicine, Hangzhou Normal University, Hangzhou 321004, China
                Author notes
                *Corresponding author: WU Cheng-Zhu, Tel: 86-552-3175232, Fax: 86-552-3171261, E-mail: wuchengzhu0611@ 123456foxmail.com .

                ΔCo-first author

                These authors have no conflicts of interest to declare.

                Article
                S1875-5364(17)30045-6
                10.1016/S1875-5364(17)30045-6
                Copyright © 2017 China Pharmaceutical University. Published by Elsevier B.V. All rights reserved.
                Funding
                Funded by: National Natural Science Foundation of China
                Award ID: 81302671
                Funded by: Education Department of Anhui Natural Science Research Project China
                Award ID: KJ2015A273
                Funded by: Zhejiang Provincial Natural Science Foundation of China
                Award ID: LY13H10004
                This work was financially supported by National Natural Science Foundation of China (No. 81302671), the Education Department of Anhui Natural Science Research Project China (No. KJ2015A273) and Zhejiang Provincial Natural Science Foundation of China (No. LY13H10004).

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