Journal of Natural Medicines

, Volume 71, Issue 1, pp 114–122 | Cite as

Novel polyacetylene derivatives and their inhibitory activities on acetylcholinesterase obtained from Panax ginseng roots

  • Kazuya Murata
  • Daiki Iida
  • Yoshihiro Ueno
  • Keiichi Samukawa
  • Toshihiko Ishizaka
  • Takeshi Kotake
  • Hideaki Matsuda
Original Paper

Abstract

In our research program to identify cholinesterase and β-secretase inhibitors, we investigated Ginseng (root of Panax ginseng), a crude drug described as a multifunctional drug in the ancient Chinese herbal book Shennong Ben Cao Jing. Results from hexane and methanol extracts showed moderate inhibitory activities. This suggests that ginseng roots may be effective for the prevention of and therapy for dementia. We then focused on hexane extracts of raw ginseng root and dried ginseng root since the determination of hexane extract constituents has not been studied extensively. Activity-guided fractionation and purification led to the isolation of 4 polyacetylene compounds; homopanaxynol, homopanaxydol, (9Z)-heptadeca-1, 9-diene-4,6-diyn-3-one, and (8E)-octadeca-1,8-diene-4,6-diyn-3,10-diol. The chemical structures of these compounds, including stereochemistry, were determined. This is the first study to identify the structure of homopanaxynol and homopanaxydol. Moreover, the modes of action of some compounds were characterized as competitive inhibitors. This study showed, for the first time, that polyacetylene compounds possess acetylcholinesterase inhibitory activities.

Keywords

Acetylcholinesterase Butyrylcholinesterase Panax ginseng Polyacetylene 

Notes

Acknowledgments

The authors are grateful to Professor T. Shinada at Osaka City University for MS measurements. This work was financially supported in part by the Japan Red Ginseng Research Association and the Kindai University Fund for the Antiaging Center Project.

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Copyright information

© The Japanese Society of Pharmacognosy and Springer Japan 2016

Authors and Affiliations

  • Kazuya Murata
    • 1
  • Daiki Iida
    • 1
  • Yoshihiro Ueno
    • 1
  • Keiichi Samukawa
    • 2
  • Toshihiko Ishizaka
    • 3
  • Takeshi Kotake
    • 1
  • Hideaki Matsuda
    • 1
  1. 1.Faculty of PharmacyKindai UniversityHigashiosakaJapan
  2. 2.Faculty of MedicineOsaka City UniversityAbenokuJapan
  3. 3.Sakai City Medical CenterSakaiJapan

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