High-performance liquid chromatographic separation and chiroptical properties of the enantiomers of naringenin and other flavanones

被引:51
作者
Caccamese, S [1 ]
Caruso, C [1 ]
Parrinello, N [1 ]
Savarino, A [1 ]
机构
[1] Univ Catania, Dipartimento Sci Chim, I-95125 Catania, Italy
关键词
pharmacologically active flavanones; Citrus lipophilic flavanoids; polysaccharide chiral stationary phases; circular dichroism detectors; absolute configuration;
D O I
10.1016/j.chroma.2005.04.024
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
The HPLC enantiomeric separation of naringenin, eriodictyol, hesperetin and pinocembrin was accomplished in the normal-phase mode using two polysaccharide-derived chiral stationary phases (Chiralcel OD-H and Chiralpak AS-H) and various n-hexane/alcohol mobile phases. The 3',4' substituents pattern affect the enantioselectivity of these phases. Single enantiomers of naringenin were isolated by sernipreparative HPLC and their CD spectra were measured and related to the absolute configuration by the exciton-coupling method. Online coupling HPLC/spectropolarimeter afforded the CD sign of the eluted peaks at a single wavelength, and the complete CD spectra of the eluted enantiomers were obtained by trapping them in the spectropolarimeter cell through a switching valve. © 2005 Elsevier B.V. All rights reserved.
引用
收藏
页码:155 / 162
页数:8
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