Enantioseparation with chiral recognition mechanism of eight coumarin enantiomers and determination of Oxypeucedanin hydrate enantiomers in Angelica dahurica by QuEChERS-HPLC

Oxypeucedanin hydrate is a bioactive coumarin component from Angelica dahurica (A.dahurica), which has two enantiomers possessing distinct pharmacological activities. In the present research, Oxypeucedanin hydrate and seven analogs including Byakangelicin, Byakangelicol, Praeruptorin A, Oxypeucedanin, Decursin, Nodakenin and Marmesin were enantioseparated on the cellulose tris-(3,5-dichlorophenylcarbamate) (CDCPC)-based chiral stationary phase (CSP) in the normal phase mode. The influences of polar modifier type, the acid additives type, the flow rate, the proportion of organic modifiers were systematically evaluated. As a result, seven enantiomers were completely separated and partial chiral separation for Oxypeucedanin was found on CDCPC. To gain further mechanistic understanding of enantioselective recognition, molecular docking simulations were systematically performed to investigate the intermolecular interactions between CDCPC and eight analytes. In conclusion, the chiral separation of coumarin compounds on CDCPC was governed by a synergistic interplay of multiple interactions, including hydrogen bonding, hydrophobic interactions, and steric influences. Finally, the modified QuEChERS method was developed to extract and purify samples. Combined with the optimized method, the chiral content of Oxypeucedanin hydrate enantiomers was determined in A.dahurica.