NMR Characterization of Flavanone Naringenin 7-O-Glycoside Diastereomer

doi:10.11938/cjmr20152418

Abstract

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

CLC Number:

O482.53

SUN Li-juan, HU Xiao-fang, CHENG Xun, LUO Li-ting, LIU Hong-bing, CHEN Lei. NMR Characterization of Flavanone Naringenin 7-O-Glycoside Diastereomer[J]. Chinese Journal of Magnetic Resonance, 2017, 34(4): 465-473.

References

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