title: [Biosynthesis of a new psoralidin glucoside by enzymatic glycosylation].
abstract: OBJECTIVE
  To modify the structure of psoralidin using in vitro enzymatic glycosylation to improve its water solubility and stability.
  
  
  METHODS
  A new psoralidin glucoside (1) was obtained by enzymatic glycosylation using a UDP- glycosyltransferase. The chemical structure of compound 1 was elucidated by HR-ESI-MS and nuclear magnetic resonance (NMR) analysis. The high-performance liquid chromatography (HPLC) peaks were integrated and sample solution concentrations were calculated. MTT assay was used to detect the cytotoxicity of the compounds against 3 cancer cell lines in vitro. Results Based on the spectroscopic data, the new psoralidin glucoside was identified as psoralidin-6',7-di-O-β-D- glucopyranoside (1), whose water solubility was 32.6-fold higher than that of the substrate. Analyses of pH and temperature stability demonstrated that compound 1 was more stable than psoralidin at pH 8.8 and at high temperatures. Only psoralidin exhibited a moderate cytotoxicity against 3 human cancer cell lines. Conclusion In vitro enzymatic glycosylation is a powerful approach for structural modification and improving water solubility and stability of compounds.
authors: Faculty of Pharmacy, Bengbu Medical College, Bengbu 233030, China. E-mail: lijing2828@126.com.
authors: Jing
authors: J
authors: Li
authors: Nan
authors: N
authors: Li
authors: Yu-Ru
authors: YR
authors: Zhao
authors: Yi-Qun
authors: YQ
authors: Dai
authors: Qiang
authors: Q
authors: Huo
authors: Tao
authors: T
authors: Ma
authors: Hong-Mei
authors: HM
authors: Li
authors: Cheng-Zhu
authors: CZ
authors: Wu
mesh_terms: D000970:Antineoplastic Agents / Q000378:metabolism; D001572:Benzofurans / Q000378:metabolism*; D045744:Cell Line, Tumor; D002851:Chromatography, High Pressure Liquid; D003374:Coumarins / Q000378:metabolism*; D005960:Glucosides / Q000096:biosynthesis*; D006031:Glycosylation; D016695:Glycosyltransferases / Q000378:metabolism*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D012995:Solubility
chemical_list: D000970:Antineoplastic Agents; D001572:Benzofurans; D003374:Coumarins; D005960:Glucosides; D016695:Glycosyltransferases; C102768:psoralidin