title: High-performance liquid chromatography separation of enantiomers of flavanone and 2'-hydroxychalcone under reversed-phase conditions.
abstract: A reversed-phase high-performance liquid chromatography (HPLC) method was developed for evaluating the chiral discrimination ability of Chiralpak IA chiral stationary phase (CSP) towards flavanone. The effect of the nature and pH buffer as well as nature of alcohol modifier on enantioselectivity was investigated. Comparative study of enantioseparation in reversed-phase and polar organic conditions indicated a significative improvement in resolution when aqueous-based eluents were used. The developed reversed-phase chromatographic method was able to separate the enantiomers of flavanone from its isomeric form, the 2'-hydroxychalcone. The stereochemical stability of flavanone was studied by classical off-column HPLC kinetic procedures in aqueous and non-aqueous media. It was clearly demonstrated that the 2'-hydroxychalcone was involved as intermediate in the on-column and off-column enantiomerization process of flavanone.
authors: Istituto Superiore di Sanità, Dipartimento del Farmaco, Viale Regina Elena 299, 00161 Rome, Italy. rcirilli@iss.it <rcirilli@iss.it>
authors: Roberto
authors: R
authors: Cirilli
authors: Rosella
authors: R
authors: Ferretti
authors: Emiliana
authors: E
authors: De Santis
authors: Bruno
authors: B
authors: Gallinella
authors: Leo
authors: L
authors: Zanitti
authors: Francesco
authors: F
authors: La Torre
mesh_terms: D047188:Chalcones / Q000302:isolation & purification*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D044950:Flavanones / Q000302:isolation & purification*; D006863:Hydrogen-Ion Concentration; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
chemical_list: D047188:Chalcones; D044950:Flavanones; C013031:2'-hydroxychalcone; C028610:flavanone