Chiral HPLC separation and CD spectra of the C-2 diastereomers of naringin in grapefruit during maturation.
Naringin is the chief flavanone glycoside of grapefruit (Citrus paradisi). It is responsible for part of the bitter taste of the fruit and can cause the inhibition of some cytochrome P450s. The direct separation of (2R)- and (2S)-naringin in the albedo of grapefruits was obtained in normal phase HPLC mode using Chiralcel OD as chiral stationary phase and n-hexane/ethanol with 0.1% of TFA as mobile phase. Chiralpak AD was almost ineffective in the separation. This procedure was used to evaluate the stereochemistry at C-2 during maturation of the grapefruit. The CD curves of (2R)- and (2S)-naringin isolated by semipreparative chiral HPLC were determined and the elution order of the chromatographic peaks was related to the absolute C-2 configuration. Partial resolution of the C-2 diastereomers of narirutin was obtained on Chiralpak AD.
Caccamese
Salvatore
S
Dipartimento di Scienze Chimiche, Università di Catania, Catania, Italy. scaccamese@dipchi.unict.it
Manna
Luigi
L
Scivoli
Giovanna
G
D000975:Antioxidants / Q000737:chemistry* / Q000302:isolation & purification; D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D032083:Citrus paradisi / Q000254:growth & development* / Q000378:metabolism*; D044950:Flavanones / Q000737:chemistry* / Q000302:isolation & purification; D015203:Reproducibility of Results; D013237:Stereoisomerism
D000975:Antioxidants; D044950:Flavanones; C005274:naringin