Cirilli Roberto, Ferretti Rosella, De Santis Emiliana, Gallinella Bruno, Zanitti Leo, La Torre Francesco
Istituto Superiore di Sanità, Dipartimento del Farmaco, Viale Regina Elena 299, 00161 Rome, Italy.
J Chromatogr A. 2008 May 9;1190(1-2):95-101. doi: 10.1016/j.chroma.2008.02.101. Epub 2008 Mar 6.
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.
建立了一种反相高效液相色谱（HPLC）方法，用于评估手性派克IA手性固定相（CSP）对黄烷酮的手性识别能力。研究了缓冲液的性质和pH值以及醇改性剂的性质对对映体选择性的影响。在反相和极性有机条件下对映体分离的比较研究表明，当使用水基洗脱剂时，分离度有显著提高。所建立的反相色谱方法能够将黄烷酮的对映体与其异构体形式2'-羟基查耳酮分离。通过经典的柱外HPLC动力学方法研究了黄烷酮在水性和非水性介质中的立体化学稳定性。结果清楚地表明，2'-羟基查耳酮是黄烷酮柱上和柱外对映体异构化过程中的中间体。
