Enzymatic Synthesis of Novel Bavachinin Glucoside by UDP‐glycosyltransferase

Abstract

Bavachinin, a member of the flavanone subclass of flavonoids, has long been considered to have various biological activities. Here, the synthesis of novel bavachinin glucoside by the in vitro glycosylation reaction was successfully achieved using a UDP-glucosyltransferase YjiC, from Bacillus licheniformis DSM-13. The chemical structure of bavachinin glucoside was characterized based on spectroscopic techniques as bavachinin-4¢-O-b-D-glucopyranoside (1). The water-solubility of bavachinin-4¢-O-b-Dglucopyranoside was found to be 9.96 mM, about 10 times higher than bavachinin. In addition, compound 1 showed moderate anti-proliferative activity against four human tumor cell lines, with IC 50 values ranging from 48.5 to 61.4 mM.

Biosynthesis of Novel Shikonin Glucosides by Enzymatic Glycosylation

“…YjiC transfers a sugar moiety from nucleoside diphosphate (NDP)-sugar to an acceptor substrate and has recently been used to biosynthesize many novel glycosides from natural products, such as apigenin, phloretin, bavachinin, anthraquinone, and resveratrol both in vitro and in vivo. [12][13][14][15][16][17] In this study, we report the successful enzymatic biosynthesis of the novel shikonin glucosides shikonin-1′,8-di-O-β-Dglucopyranoside (1) and shikonin-1′-O-β-D-glucopyranoside (2), and their water solubility, chemical stability, and cytotoxicity across six cancer cell lines (Fig. 1).…”