PREPARATIVE ISOLATION AND PURIFICATION OF PRENYLATED ISOFLAVONOIDS FROM CUDRANIA TRICUSPIDATA FRUITS USING CENTRIFUGAL PARTITION CHROMATOGRAPHY

Abstract

Prenylated isoflavonoids such as 6,8-diprenylorobol, 6,8-diprenylgenistein and 4′-O-methylalpinumisoflavone were purified from n-hexane extract of C. tricuspidata fruits using centrifugal partition chromatography (CPC) with a n-hexane-ethyl acetate-methanol-water (7:3:6:4, v/v, ascending mode) solvent system in a one-step within 200 min. One-step preparative CPC yielded 22.4 mg of 6,8-diprenylorobol and 26.7 mg of 6,8-diprenylgenistein with 95% and 85% purity, respectively, from 350 mg of crude hexane extract. Further purification by crystallization in methanol yielded 4′-O-methylalpinumisoflavone (9.3 mg) at over 95% purity based on the HPLC analysis. The chemical structures of purified compounds were elucidated by ¹H, ¹³C NMR, and ESI-MS.

Keywords:

• 4′-O-methylalpinumisoflavone
• 6,8-diprenylgenistein
• 6,8-diprenylorobol
• centrifugal partition chromatography
• Cudrania tricuspidata
• prenylated isoflavonoids