Enantiomer Separation of the Four Stereoisomers of 1-(4-Hydroxy-3-Methoxy)-Phenyl-2-[4-(1,2,3-Trihydroxy-Propyl)-2-Methoxy]-Phenoxy-1,3-Propandiol from Hydnocarpus annamensis by Capillary Zone Electrophoresis with HP-β-CD as Chiral Selector

Abstract

A capillary zone electrophoresis method with HP-β-CD as chiral selector was established for the chiral separation of four stereoisomers of 1-(4-hydroxy-3-methoxy)-phenyl-2-[4-(1,2,3-trihydroxy-propyl)-2-methoxy]-phenoxy-1,3-propandiol for the first time, which were isolated from Hydnocarpus annamensis. The effects of chiral selector type and concentration, buffer composition, pH and concentration, and cartridge temperature on the enantioseparation were investigated. A baseline separation of the four stereoisomers was achieved in less than 18 min under the optimized conditions: 40 mmol L⁻¹ Borax–NaOH buffer (pH 10.02) in the presence of 100 mmol L⁻¹ HP-β-CD at 15°C and 30 kV. The experimental results showed that the method by capillary zone electrophoresis for the separation of four stereoisomers is powerful, sensitive and fast, requires less amounts of reagents, and can be employed as a reliable alternative to other methods.