Chiral Separation of Several Flavanones by Liquid Chromatography

The HPLC enantiomeric separation of thirteen flavanones was accomplished in the normalphase mode using six polysaccharide-based chiral stationary phases namely, Chiralcel® OD-H, Chiralcel ® OD, Chiralcel® OJ, Chiralpak® AD, Chiralpak® IA and Chiralpak® IB and various n- alkane/ alcohol mobile phases. The enantioseparation of flavanone and its eight mono substituted derivatives is reported including four methoxylatedflavanones in positions; 4’, 5, 6 and 7, respectively, and four hydroxylated in positions 2’, 4’, 6 and 7, respectively. Furthermore, the enantioseparation of the two aglyconeshesperetin, naringenin and the diasteriomeric separation of their flavanone glycosides hesperidin and naringin were achieved. The chiral recognition mechanism of each stationary phase is suggested based on the chemical structure and conformation of the chiral selector.