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- Title
Stereospecificity of Ginsenoside Rg<sub>3</sub> Action on Ion Channels.
- Authors
Sang Min Jeong; Jun-Ho Lee; Jong-Hoon Kim; Byung-Hwan Lee; In-Soo Yoon; Joon-Hee Lee; Dong-Hyun Kim; Hyewhon Rhim; Yangmee Kim; Seung-Yeol Nah
- Abstract
Ginsenosides, active ingredients of Panax ginseng, exist as stereoisomers depending on the position of the hydroxyl group on carbon-20; i.e. 20(R)-ginsenoside and 20(S)-ginsenoside are epimers. We have shown previously that the mixture of 20(R)- and 20(S)-ginsenosides regulates ion channel activity. However, it was not clear which epimer was responsible. We investigated the structure- activity relationship of the ginsenoside Rg3 stereoisomers, 20-R-protopanaxatriol-3-[O-β-D-glucopyranosyl (1→2)-β-glucopyranoside], (20(R)-Rg3) and 20-S-protopanaxatriol- 3-[O-β-D-glucopyranosyl (1→2)-β-glucopyranoside], (20(S)-Rg3) in regulating voltage-dependent Ca2+, K+ or Na+ channel currents and 5-HT3A and α3β4 nicotinic acetylcholine (nACh) receptor channel currents expressed in Xenopus oocytes. 20(S)-Rg3 but not 20(R)-Rg3 inhibited the Ca2+, K+ and Na+ channel currents in a dose- and voltage-dependent manner. The fact that only 20(S)-Rg3 is active indicates that its hydroxyl group may be geometrically better aligned with the hydroxyl acceptor group in the ion channels than that of 20(R)-Rg3. However, both Rg3 stereoisomers inhibited 5- HT3A and α3β4 nACh receptor channel currents. These results indicate that the selectivity of action of the Rg3 stereoisomers differs between voltage-dependent and ligand-gated ion channels.
- Publication
Molecules & Cells (Springer Nature), 2004, Vol 18, Issue 3, p383
- ISSN
1016-8478
- Publication type
Article
- DOI
10.1016/s1016-8478(23)13128-1