Glycosidase inhibitory phenolic compounds from the seed of Psoralea corylifolia

Abstract

The seeds of Psoralea corylifolia were extracted into five different polar solvents: chloroform, 50% ethanol in water, ethanol, methanol and water. All extracts were evaluated for glycosidase inhibitory activity. The chloroform extract (CE) showed the lowest IC50 values against alpha-glucosidase (82.9 mu g/ml) and alpha-mannosidase (132 mu g/ml). Chromatography of CE yielded nine phenolic compounds which were identified as isovabachalcone (1), 4'-O-methylbavachalcone (2), isobavachromene (3), corylifolin (4), bavachinin (5), psoralidin (6). neobavaisoflavone (7), corylifol A (8), and bakuchiol (9). All isolated compounds, apart from compound 5, possessed alpha-glucosidase inhibitory activities. Among them, compounds 6-8 exhibited potent inhibition with IC(50)s of 13.7, 27.7 and 11.3 mu M, respectively. Furthermore, compounds 2 and 6 showed alpha-mannosidase inhibitory activity. Mechanistic analysis of their inhibition modes against alpha-glucosidase showed that compounds (6 and 7) were noncompetitive, whereas compound 8 was mixed. Furthermore, the most active glycosidase inhibitors (2,6-8) were proven to be present in the native seed in high quantities by an HPLC chromatogram. (C) 2010 Elsevier Ltd. All rights reserved.