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Enzymatic Synthesis of Novel Corylifol A Glucosides via a UDP-glycosyltransferase

Enzymatic Synthesis of Novel Corylifol A Glucosides via a UDP-glycosyltransferase

Nan Li, Jian Miao, Jing Li, Yu-Ru Zhao, Hong-Mei Li, Yi-Qun Dai, Qiang Huo, Cheng-Zhu Wu, Tao Ma

Carbohydr Res. 2017 Jun 29;446-447:61-67.

PMID: 28528234

Abstract:

Corylifol A, a member of the isoflavone subclass of isoflavonoids, has long been considered to have various biological activities. Here, we sought to synthesize corylifol A glucosides by the in vitro glucosylation reaction using the UDP-glycosyltransferase YjiC from Bacillus licheniformis DSM 13, and obtained two novel glucosides: corylifol A-4',7-di-O-beta-d-glucopyranoside (1) and corylifol A-4'-O-beta-d-glucopyranoside (2). To improve the yield of the products, the reaction time, concentration of UDP-glucose, and pH of the buffer were optimized. The Michaelis constant (Km) was calculated to be 2.88 mM, and the maximal velocity (Vmax) was calculated to be 77.32 nmol/min/mg for UDP-glycosyltransferase. Meanwhile, the water-solubility of compounds 1 and 2 was approximately 27.03 and 15.13 times higher, respectively, than that of their parent compound corylifol A. Additionally, the corylifol A glycosylated products exhibited the highest stability at pH 9.6 and better temperature stability than corylifol A at 40, 60, 80 and 100 °C. In addition, cytotoxicity activity assays against three human tumor cell lines, only corylifol A showed moderate anti-proliferative activity. Overall, this work demonstrates that glycosylation can enhance the water solubility and stability of promising compounds, with potential for further development and application.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP775351887	Corylifol A		775351-88-7	Price

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