Chinese Journal of Magnetic Resonance ›› 2017, Vol. 34 ›› Issue (4): 465-473.doi: 10.11938/cjmr20152418

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NMR Characterization of Flavanone Naringenin 7-O-Glycoside Diastereomer

SUN Li-juan1, HU Xiao-fang1, CHENG Xun1, LUO Li-ting2, LIU Hong-bing2, CHEN Lei2   

  1. 1. Hubei Province Key Laboratory of Biotechnology of Chinese Traditional Medicine, Hubei Collaborative Innovation Center for Green Transformation of Bio-Resources, Hubei University, Wuhan 430062, China;
    2. State Key Laboratory of Magnetic Resonance and Atomic and Molecular Physics, National Center for Magnetic Resonance in Wuhan(Wuhan Institute of Physics and Mathematics, Chinese Academy of Sciences), Wuhan 430071, China
  • Received:2015-03-11 Revised:2017-10-24 Online:2017-12-05 Published:2017-11-29

Abstract: To discriminate R and S flavanone glycoside using NMR, the mixture of R and S naringenin 7-O-glycoside was first isolated from Gleditsia sinensis. 1H and 13C NMR data of the mixture were recorded with 1H NMR, 13C NMR, 1H-1H COSY, 1H-13C HSQC and 1H-13C HMBC in DMSO-d6 solution. The two diastereomers were then separated with chiral chromatographic isolation, with their absolute configurations determined by circular dichroism. To avoid the disturbance of protons from glucose residues to dihydroflavonoid, 1H NMR spectra were acquired for pure R and S naringenin 7-O-glycoside and their mixture in CD3CN. The two diastereomers showed the largest proton chemical shift differences at the end group of glucose residue (H-1") with a chemical shift difference of 9.4 Hz. The OH-5 proton showed a chemical shift difference of 5.8 Hz. The chemical shift of the three protons on ring C were all influenced by configuration.

Key words: NMR, naringenin 7-O-glycoside, diastereomer, circular dichroism, structure analysis

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