Separation of the enantiomers of naringenin and eriodictyol by amylosebased chiral reversed-phase high-performance liquid chromatography

Abstract

Naringenin and eriodictyol are chiral flavanones widely present in citrus fruits and herbal products. Pharmacological interest in the two flavanones is well known. Due to the chiral carbon atom, the compounds always exist in the racemic form. The present study reported a stereospecific HPLC method for the enantioseparation of naringenin and eriodictyol, which was performed on an amylosebased chiral stationary phase (CSP), Chiralpak AD-RH, in the reversed-phase mode. The effects of the mobile phase on retention, enantioseparation, and elution order were investigated. The different 3',4' substituent pattern of the two compounds affected the enantioselectivity. An online coupling HPLC-CD method was used for elution order determination. Both the CD sign of the eluted peaks at a single wavelength and complete CD spectra of the eluted enantiomers were obtained by the method.

Chemical Constituents from Ficus sagittifolia Stem Bark and Their Antimicrobial Activities

“…Therefore, the intensity of the CD bands is lower than it would be in case of pure 1. The CD data are in full agreement with the presence of the R-enantiomer [16] (see also main text). 1 H-NMR (600 MHz, (CD 3 OD) δ (ppm): 6.94 (1H, dd, J = 1.52 Hz, 0.85, H-5 ), 6.81 (2H, d, J = 0.75 Hz, H-2 , H-6 ), 5.93 (1H, d, J = 2.12 Hz, H-8), 5.91 (1H, d, J = 2.18 Hz, H-6), 5.31 (1H, dd, J = 12.75 Hz, 3.05 Hz, H-2), 3.10 (1H, dd, J = 17.06 Hz, 12.77 Hz, H-3ax), 2.73 (1H, dd, J = 17.12 Hz, 3.08 Hz, H-3eq); 13 -8).…”

“…Chromatographic separation of the ethylacetate fraction of an ethanol extract obtained from F. sagittifolia stem bark afforded seven known compounds (1-7; Figure 1). They were identified via detailed spectroscopic analysis and comparison of their spectroscopic data with those reported in the literature as (2R)-eriodictyol (1) [15][16][17], 2 -hydroxygenistein (2) [18,19], erycibenin A (3) [20,21], genistein (4) [22,23], moracin P (5) [24], peucedanol (6) [25][26][27], and dihydrophaseic acid (7) [28,29]. Compounds 1 and 2 as well as 4 and 5 were obtained as mixtures.…”

Eriodictyol and naringenin inhibit the formation of AGEs: An in vitro and molecular interaction study

“…Eriodictyol and naringenin are chiral molecules with an asymmetric center at the position C‐2 and can occur in two enantiomeric forms, R‐eriodictyol and S‐eriodictyol, R‐naringenin and S‐naringenin, respectively. Because of a chiral carbon atom in the position C‐2, eriodictyol and naringenin always exist in racemic form . In the present study, we evaluated the antiglycation ability of different concentrations of eriodictyol and naringenin by bovine serum albumin (BSA)–MGO model.…”

R-eriodictyol and S-eriodictyol exhibited comparable effect against H2O2-induced oxidative stress in EA.hy926 cells

“…For the separation of enantiomers of eriodictyol, a couple of methods have been previously reported, such as capillary electrophoresis (14), micellar electrokinetic chromatography (15), and chiral HPLC (16). In our previous papers, we also described the resolution of enantiomers of some fl avanones by chromatography on a chiral phase, and we reported the absolute confi guration determination by CD spectra (17). However, no bioactivity study was carried out using pure enantiomers of eriodictyol.…”