Transglycosylation of neolignans by enzymatic synthesis and evaluation of their antitumor activity.
- Author:
Hongmei LI
1
;
Jing LI
;
Wei JIN
;
Xing GUO
;
Nan LI
;
Tao MA
;
Qiang HUO
;
ChengZhu WU
Author Information
- Publication Type:Journal Article
- MeSH: Antineoplastic Agents, Phytogenic; chemistry; Biphenyl Compounds; chemistry; Cell Line, Tumor; Chromatography, High Pressure Liquid; Glucosides; chemistry; Glycosylation; Humans; Lignans; chemistry; Magnetic Resonance Spectroscopy; Mass Spectrometry
- From: Journal of Southern Medical University 2015;35(11):1570-1574
- CountryChina
- Language:Chinese
-
Abstract:
OBJECTIVETo improve the water solubility and biological activity of neoligans (magnolol and honokiol) and test the antitumor activity of the modified compounds.
METHODSThe glycosylated products of magnolol and honokiol were obtained by enzymatic synthesis using a UDP-glycosyltransferase (YjiC) from Bacillus. The products were characterized by high-performance liquid chromatography (HPLC), liquid chromatography-mass spectrometry (LC-MS), and nuclear magnetic resonance (NMR) analysis. MTT assay was used to detect the growth inhibition of 4 human cancer cell lines induced by the compounds.
RESULTSWe obtained two glucosides of neolignans (magnolol and honokiol) for the first time by enzymatic synthesis using a UDP-glycosyltransferase. Based on the spectroscopic data, the glucosides were identified as magnolol-2- O-β-D-glucopyranoside (1) and honokiol-4'-O-β-D-glucopyranoside (2). Compounds 1-4 exhibited moderate anti-proliferative activities against the 4 human cancer cell lines, with IC50 values ranging from 9.41 to 111.21 µmol/L.
CONCLUSIONThe glycoslated products show enhanced water solubility and drug sensitivity against SMMC7721 cells, suggesting their value as potential therapeutic drugs.
