The anti-inflammatory secoiridoid glycosides from Gentianae Scabrae Radix: the root and rhizome of Gentiana scabra

Abstract

Gentianae Scabrae Radix is a well-known traditional medicine that is used for the treatment of hepatitis, cholecystitis and inflammatory diseases. It consists mainly of secoiridoid glycosides, with representatives of gentiopicroside, sweroside and swertiamarin. In the present study, a chemical investigation of the CHCl3 extract of Gentianae Scabrae Radix derived from Gentiana scabra Bunge yielded seven new (17) and ten known (817) secoiridoid glycosides. Their structures were elucidated by extensive spectroscopic analyses and comparison with literature data. All 17 compounds were evaluated for their inhibitory effects against NO, IL-6 and TNF-α productions induced by lipopolysaccharide (LPS) in RAW264 cells. Among them, 8-epi-kingiside derivatives 13; kingiside derivatives 4, 5 and 10; and a sweroside derivative 6 showed inhibition activity against IL-6 production with IC50 values of 51.70–61.10 μM, whereas sweroside derivatives 12 and 1517 and a swertiamarin derivative 13 showed inhibition effects on both NO and IL-6 productions with IC50 values of 64.74–94.95 and 48.91–75.45 μM, respectively. All the compounds exhibited weak inhibitory activity (IC50 > 100 μM) in a TNF-α bioassay. Finally, a primary structure–activity relationship of these secoiridoid glycosides is discussed.

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Acknowledgments

The authors would like to thank Dr. Shengli Wei from the School of Chinese Pharmacy, Beijing University of Chinese Medicine, Beijing, China, for helping with sample collection. They are also grateful to Dr. Feng Li from Joint Usage/Research Center for Science-Based Natural Medicine Research Promotion Office, Institute of Natural Medicine, University of Toyama, Toyama, Japan, for assistance with 2D-NMR experimental acquisition and troubleshooting. This work was supported by JSPS KAKENHI Grant Number 24406005.

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Correspondence to Katsuko Komatsu.

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He, YM., Zhu, S., Ge, YW. et al. The anti-inflammatory secoiridoid glycosides from Gentianae Scabrae Radix: the root and rhizome of Gentiana scabra . J Nat Med 69, 303–312 (2015). https://doi.org/10.1007/s11418-015-0894-8

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Keywords

  • Secoiridoid glycosides
  • Gentiana scabra
  • Gentianaceae
  • Anti-inflammatory activity
  • 8-epi-kingiside derivative
  • Kingiside derivative