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Enzymatic Synthesis of Novel Bavachinin Glucoside by UDP‐glycosyltransferase
Author(s) -
Dai Yiqun,
Ma Tao,
Ge Min,
Li Jing,
Huo Qiang,
Li HongMei,
Zhang Xinyu,
Liu Hao,
Wu ChengZhu
Publication year - 2016
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.201500497
Subject(s) - chemistry , glucoside , glycosylation , flavanone , bacillus licheniformis , glycosyltransferase , glucosyltransferase , enzyme , stereochemistry , in vitro , biochemistry , flavonoid , bacillus subtilis , bacteria , medicine , alternative medicine , pathology , biology , genetics , antioxidant
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 ‐ß‐D‐glucopyranoside ( 1 ). The water‐solubility of bavachinin‐4′‐ O ‐ß‐D‐glucopyranoside was found to be 9.96 μM, 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 μM.