title: Separation and purification of α-glucosidase inhibitors from Polygonatum odoratum by stepwise high-speed counter-current chromatography combined with Sephadex LH-20 chromatography target-guided by ultrafiltration-HPLC screening.
abstract: Although Polygonatum odoratum has been widely used as medicinal plant and food supplement for treating diabetes, little is known regarding its bioactive components. In this study, ultrafiltration-HPLC based ligand screening was developed to screen α-glucosidase inhibitors from P. odoratum for the first time. Then bioactive components were target-guided separated by combining stepwise high-speed counter-current chromatography (HSCCC) using petroleum ether-ethyl acetate-methanol-water (1:4:0.8:4.2, v/v/v/v), (1:4:1.8:3.2, v/v/v/v) and (1:4:2.3:2.7, v/v/v/v) as solvent systems with Sephadex LH-20 chromatography eluted by MeCN-MeOH (1:1, v/v). Five phenethyl cinnamides, N-cis-feruloyloctopamine (1); N-trans-p-coumaroyloctopamine (2), N-trans-feruloyloctopamine (3), N-trans-p-coumaroyltyramine (4) and N-trans-feruloyltyramine (5), and four homoisoflavanones, (3R)-5,7-dihydroxyl-3-(2',4'-dihydroxylbenzyl)-chroman-4-one (6), (3R)-5,7-dihydroxyl-6-methyl-3-(4'-hydroxylbenzyl)-chroman-4-one (7), (3R)-5,7-dihydroxyl-6-methyl-8-methoxyl-3-(4'-hydroxylbenzyl)-chroman-4-one (8); and (3R)-5,7-dihydroxyl-6,8-dimethyl-3-(4'-hydroxylbenzyl)-chroman-4-one) (9), with purity over 98.5% were purified, and their structures were identified by UV, MS, and (1)H NMR. Notably, compounds 2 and 4 were first reported in genus Polygonatum, while compound 1 was first obtained from family Liliaceae. In addition, α-glucosidase inhibitory activities of compounds 1-9 were evaluated, and compounds 2 and 4 exhibited stronger α-glucosidase inhibitory activity with IC50 values of 2.3 and 2.7μM. The results suggested the potential medicinal use of P. odoratum, and the technology could be widely applied for rapid screening and preparative separation of a group of bioactive compounds from complex matrix.
authors: Hunan Academy of Forest Sciences, Changsha 410004, PR China; Key Laboratory of Hunan Tree Clones Breeding, Changsha 410004, PR China.
authors: Xiaoling
authors: X
authors: Zhou
authors: Hunan Academy of Forest Sciences, Changsha 410004, PR China; Key Laboratory of Hunan Tree Clones Breeding, Changsha 410004, PR China.
authors: Junsheng
authors: J
authors: Liang
authors: Hunan Academy of Forest Sciences, Changsha 410004, PR China; Key Laboratory of Hunan Tree Clones Breeding, Changsha 410004, PR China.
authors: Yi
authors: Y
authors: Zhang
authors: College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, PR China.
authors: Huading
authors: H
authors: Zhao
authors: Department of Clinical Pharmacology, Xiangya Hospital, Central South University, Changsha 410008, PR China.
authors: Ying
authors: Y
authors: Guo
authors: College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, PR China. Electronic address: shuyshi@gmail.com.
authors: Shuyun
authors: S
authors: Shi
mesh_terms: D002851:Chromatography, High Pressure Liquid / Q000379:methods; D003377:Countercurrent Distribution / Q000379:methods*; D003911:Dextrans; D065089:Glycoside Hydrolase Inhibitors / Q000302:isolation & purification*; D010936:Plant Extracts / Q000737:chemistry*; D031384:Polygonatum / Q000201:enzymology*; D014462:Ultrafiltration / Q000379:methods*
chemical_list: D003911:Dextrans; D065089:Glycoside Hydrolase Inhibitors; D010936:Plant Extracts; C025614:sephadex
keywords: HSCCC; Phenethyl cinnamide; Polygonatum odoratum; Sephadex LH-20; Ultrafiltration; α-Glucosidase inhibitor