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Enzymatic synthesis of novel isobavachalcone glucosides via a UDP-glycosyltransferase

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Abstract

Glycosylation is often used to improve a natural product’s properties such as water solubility, chemical stability, pharmacological potency, and structure diversification. In this study, we studied the enzymatic synthesis of novel isobavachalcone glucosides using a UDP-glycosyltransferase (YjiC) from Bacillus licheniformis DSM-13. The chemical structures of compounds 1 and 2 were elucidated by spectroscopic techniques, including LC–MS, MS, and NMR. Meanwhile, the parameters of glycosylation reaction such as incubation time, UDP-glucose concentration, and pH of buffer were also optimized during this study. Furthermore, the compounds 1 and 2 exhibited weak anti-proliferative activities against five human cancer cell lines, with IC50 values ranging from 58.6 to 86.6 μM.

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Acknowledgments

This work was financially supported by the National Natural Science Foundation of China under Grant (81302671); the Natural Science Foundation of Anhui Province under Grant (1408085QH162); the Foundation for Young Talents in College of Anhui Province under Grant (2013SQRL048ZD). This work was also supported in part by a grant from the KRIBB Research Initiative Program.

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Correspondence to Young-Soo Hong or Cheng-Zhu Wu.

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Hong-Mei Li and Jae Kyoung Lee have contributed equally to the work.

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Li, HM., Lee, J.K., Nie, LJ. et al. Enzymatic synthesis of novel isobavachalcone glucosides via a UDP-glycosyltransferase. Arch. Pharm. Res. 38, 2208–2215 (2015). https://doi.org/10.1007/s12272-015-0658-8

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  • DOI: https://doi.org/10.1007/s12272-015-0658-8

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