Single-step separation of bioactive flavonol glucosides from Osteomeles schwerinae by high-speed counter-current chromatography.
Two bioactive flavonol glucosides, hyperoside and quercitrin, were successfully isolated in one step from the phytochemically unknown medicinal plant Osteomeles schwerinae by high-speed counter-current chromatography using a two-phase solvent system composed of n-hexane-ethyl acetate-methanol-water (0.5:5.5:1.5:4.5 v/v). From 160 mg of crude extract, 2.1 mg of hyperoside (98.6% purity, 83.3% recovery) and 4.5 mg of quercitrin (99.2% purity, 81.7% recovery) were separated and then their chemical structures were identified by (1)H and (13)C NMR analysis. In addition, the isolates were subjected to an in vitro bioassay to evaluate their inhibitory activity on rat lens aldose reductase. Both quercitrin and hyperoside showed excellent inhibitory activities toward rat lens aldose reductase with the IC(50) values of 0.16 and 4.33 microM, respectively, as compared with positive control, 3,3-tetramethyleneglutaric acid (28.7 microM). So far, chemical constituents and biological activities of O. schwerinae have never been reported. This is the first report on the chemical constituents and biological activity of this plant using semi-preparative high-speed counter-current chromatography separation technique.
Lee
Jun
J
Diabetic Complications Research Center, Division of Traditional Korean Medicine Integrated Research, Korea Institute of Oriental Medicine, Daejeon, Korea.
Jang
Dae Sik
DS
Yoo
Nam Hee
NH
Lee
Yun Mi
YM
Kim
Joo-Hwan
JH
Kim
Jin Sook
JS
D000449:Aldehyde Reductase / Q000037:antagonists & inhibitors*; D000818:Animals; D003377:Countercurrent Distribution; D044948:Flavonols / Q000737:chemistry* / Q000494:pharmacology; D005960:Glucosides / Q000737:chemistry* / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D007908:Lens, Crystalline / Q000187:drug effects*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009930:Organic Chemicals; D010936:Plant Extracts / Q000737:chemistry*; D018515:Plant Leaves / Q000737:chemistry; D018547:Plant Stems / Q000737:chemistry; D011794:Quercetin / Q000031:analogs & derivatives / Q000737:chemistry; D051381:Rats; D027824:Rosaceae / Q000737:chemistry*; D014867:Water / Q000737:chemistry
D044948:Flavonols; D005960:Glucosides; D009930:Organic Chemicals; D010936:Plant Extracts; D014867:Water; C012526:quercitrin; C021304:hyperoside; D011794:Quercetin; D000449:Aldehyde Reductase