Enantioselective separation and simulation studies of five flavanone glycosides on a cellulose tris-(3,5-dichlorophenylcarbamate) chiral stationary phase

Abstract

In this study, the chiral separation of five flavanone glycosides was first examined on the cellulose tris-(3,5-dichlorophenylcarbamate) (CDCPC) chiral stationary phase (CSP) in the normal phase mode. The influence of acid additives, the type and proportion of organic modifiers, and column temperature were systematically evaluated and optimized. Under the optimum chromatographic conditions, hesperidin, eriocitrin, neohesperidin, naringin and narirutin enantiomers were completely or partially separated with resolutions of 2.56, 2.28, 1.84, 2.94 and 0.85. Moreover, to gain a better understanding of the chiral recognition mechanism, detailed computational simulations of CDCPC interacting with five pairs of enantiomers were carried out using molecular docking. The docking result demonstrated that the chiral recognition of analytes on CDCPC was an exothermic process which governed hydrogen bond, hydrophobic and unfavorable interaction. This work hoped to provide some guidance for the subsequent analysis of flavanone glycosides.