Enzymatic synthesis of novel isobavachalcone glucosides via a UDP-glycosyltransferase

Arch Pharm Res. 2015 Dec;38(12):2208-15. doi: 10.1007/s12272-015-0658-8. Epub 2015 Sep 15.

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.

Keywords: Cytotoxicity; Diversification; Glycosylation; Isobavachalcone; YjiC.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Survival / drug effects
  • Cell Survival / physiology
  • Chalcones / biosynthesis*
  • Chalcones / isolation & purification
  • Chalcones / pharmacology
  • Glucosides / metabolism*
  • Glycosyltransferases / metabolism*
  • Hep G2 Cells
  • Humans
  • Plant Extracts / biosynthesis*
  • Plant Extracts / isolation & purification
  • Plant Extracts / pharmacology
  • Psoralea*

Substances

  • Chalcones
  • Glucosides
  • Plant Extracts
  • isobavachalcone
  • Glycosyltransferases