Caccamese Salvatore, Manna Luigi, Scivoli Giovanna
Dipartimento di Scienze Chimiche, Università di Catania, Catania, Italy.
Chirality. 2003 Oct;15(8):661-7. doi: 10.1002/chir.10262.
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.
柚皮苷是葡萄柚（Citrus paradisi）中的主要黄酮糖苷。它是果实部分苦味的来源，并且能够抑制某些细胞色素P450。使用Chiralcel OD作为手性固定相，以含0.1%三氟乙酸的正己烷/乙醇为流动相，在正相高效液相色谱模式下实现了葡萄柚白皮层中（2R）-和（2S）-柚皮苷的直接分离。Chiralpak AD在分离中几乎无效。该方法用于评估葡萄柚成熟过程中C-2位的立体化学。测定了通过半制备手性高效液相色谱分离得到的（2R）-和（2S）-柚皮苷的圆二色光谱曲线，色谱峰的洗脱顺序与C-2位的绝对构型相关。在Chiralpak AD上实现了橙皮苷C-2位非对映异构体的部分拆分。
