Chiral resolution of four major flavanones in post-administrative urine of chinese herbal medicines by HPLC on macroporous silica gel coated with cellulose tris(3,5-dimethylphenylcarbamate)

Direct chiral resolution of four major flavanones recovered from post-administrative urine of the traditional Chinese medicines Daisaiko-to and Shosaiko-to was achieved by high-performance liquid chromatography (HPLC) on macroporous silica gel coated with cellulose tris(3,5-dimethylphenylcarbamate), Chiralcel OD. Chromatographic conditions were optimized so as to attain satisfactory enantiomeric resolution of the polysubstituted flavanones. Urinary liquiritigenin and naringenin were considerable mixtures of R and S-enantiomers, while S-enantiomers of dihydrowogonin and dihydrooroxylin A were predominantly excreted. Our chiral HPLC techniques can be applied to pharmacokinetical evaluation of the chiral flavanone enantiomers following oral administration of the herbal medicines.