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HPLC separation of naringin, neohesperidin and their C-2 epimers in commercial samples and herbal medicines

2007; Elsevier BV; Volume: 46; Issue: 5 Linguagem: Inglês

10.1016/j.jpba.2007.04.004

1873-264X

Nahoko Uchiyama, Ik Hwi Kim, Ruri Kikura‐Hanajiri, Nobuo Kawahara, Tenji Konishi, Yukihiro Goda,

Bioactive natural compounds

Flavanone glycosides, such as naringin and neohesperidin, are distributed in some Citrus species and have a chiral center in the C-2 position of the flavanone moiety. Naringin and neohesperidin (2S-form) were separated from the corresponding C-2 epimers (2R-epi-form) by normal-phase HPLC using a polysaccaride-derived chiral stationary phases (CSPs), CHIRALPAK® IB. The analyses of commercial samples of naringin revealed that the relative ratios of naringin to the C-2 epimer were 29–89%. In the case of a commercial sample of neohesperidin, the relative ratio of the neohesperidin (2S-form) is 84%. The HPLC application to Citrus species used as crude drugs in Japan (Kijitsu, Kikoku and Tohi) showed that the relative ratios of naringin to the C-2 epimer were 75–93% in Kijitsu, 74–79% in Kikoku and 54–64% in Tohi. However, there is a quite small ratio of the (2R)-epi-neohesperidin in Citrus. This result suggested that the averages of relative ratio of (2S)-naringin in Citrus species reduced according to the maturity of fruits (Kijitsu < Kikoku < Tohi). Since the relative ratios of (2S)-naringin of dry extracts of 5 Kampo formulations (including Kijitsu or Kikoku) decreased to 42–54%, the conversion from naringin to the (2R)-epimer might be enhanced during the decoction process of the formulations.