title: Novel polyacetylene derivatives and their inhibitory activities on acetylcholinesterase obtained from Panax ginseng roots.
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.
authors: Faculty of Pharmacy, Kindai University, 3-4-1 Kowakae, Higashiosaka, Osaka, 577-8502, Japan.
authors: Kazuya
authors: K
authors: Murata
authors: Faculty of Pharmacy, Kindai University, 3-4-1 Kowakae, Higashiosaka, Osaka, 577-8502, Japan.
authors: Daiki
authors: D
authors: Iida
authors: Faculty of Pharmacy, Kindai University, 3-4-1 Kowakae, Higashiosaka, Osaka, 577-8502, Japan.
authors: Yoshihiro
authors: Y
authors: Ueno
authors: Faculty of Medicine, Osaka City University, 1-4-3 Asahimachi, Abenoku, Osaka, 545-8585, Japan.
authors: Keiichi
authors: K
authors: Samukawa
authors: Sakai City Medical Center, 1-1-1 Ebaraji-cho, Nishi-ku, Sakai, Osaka, 593-8304, Japan.
authors: Toshihiko
authors: T
authors: Ishizaka
authors: Faculty of Pharmacy, Kindai University, 3-4-1 Kowakae, Higashiosaka, Osaka, 577-8502, Japan.
authors: Takeshi
authors: T
authors: Kotake
authors: Faculty of Pharmacy, Kindai University, 3-4-1 Kowakae, Higashiosaka, Osaka, 577-8502, Japan. murata@phar.kindai.ac.jp.
authors: Hideaki
authors: H
authors: Matsuda
mesh_terms: D000110:Acetylcholinesterase / Q000737:chemistry*; D002091:Butyrylcholinesterase / Q000737:chemistry*; D005894:Panax / Q000737:chemistry*; D010936:Plant Extracts / Q000737:chemistry*; D018517:Plant Roots / Q000737:chemistry*; D053279:Polyynes / Q000032:analysis / Q000737:chemistry*
chemical_list: D010936:Plant Extracts; D053279:Polyynes; D000110:Acetylcholinesterase; D002091:Butyrylcholinesterase
keywords: Acetylcholinesterase; Butyrylcholinesterase; Panax ginseng; Polyacetylene