High-performance liquid chromatography separation of enantiomers of flavanone and 2′-hydroxychalcone under reversed-phase conditions

被引：31
作者：
Cirilli, Roberto [1 ]
Ferretti, Rosella [1 ]
De Santis, Erniliana [1 ]
Gallinella, Bruno [1 ]
Zanitti, Leo [1 ]
La Torre, Francesco [1 ]
机构：
[1] Ist Super Sanita, Dipartimento Farmaco, I-00161 Rome, Italy
来源：
JOURNAL OF CHROMATOGRAPHY A | 2008年 / 1190卷 / 1-2期
关键词：
flavanone; 2'-hydroxychalcone; chiral stationary phase; Chiralpak IA; chiroptical properties; reversed-phase enantioseparation; configurational stability; racemization;
D O I：
10.1016/j.chroma.2008.02.101
中图分类号：
Q5 [生物化学];
学科分类号：
071010 ; 081704 ;
摘要：
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. (C) 2008 Elsevier B.V. All rights reserved.
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收藏
页码：95 / 101
页数：7
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