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Ginsenoside (Molecule of the Month for October 2020)

Ginseng, Panaxosides



Ginsenosides or panaxosides are a class of natural product steroid glycosides and triterpene saponins. Compounds in this family are found almost exclusively in the plant genus Panax (ginseng), which has a long history of use in traditional medicine that has led to the study of pharmacological effects of ginseng compounds. As a class, ginsenosides exhibit a large variety of subtle and difficult-to-characterize biological effects when studied in isolation.

Ginsenosides can be isolated from various parts of the plant, though typically from the roots, and can be purified by column chromatography. The chemical profiles of Panax species are distinct; although Asian ginseng, Panax ginseng, has been most widely studied due to its use in traditional Chinese medicine, there are ginsenosides unique to American ginseng (Panax quinquefolius) and Japanese ginseng (Panax japonicus). Ginsenoside content also varies significantly due to environmental effects.

Most known ginsenosides are classified as members of the dammarane family. The structure of these dammarane ginsenosides consists of a 4-ring, steroid-like structure. To each ginsenoside is bound at least 2 or 3 hydroxyl groups at the carbon-3 and -20 positions or the carbon-3, -6, and -20 positions respectively. In protopanaxadiols, sugar groups attach to the 3-position of the carbon skeleton, while in comparison sugar groups attach to the carbon-6 position in protopanaxatriols. Well known protopanaxadiols include Rb1, Rb2, Rg3, Rh2, and Rh3. Well known protopanaxatriols include Rg1, Rg2, and Rh1. The picture is ginsenoside Rg1.

Formal Chemical Name (IUPAC)
(2R,3R,4S,5S,6R)-2-(((3S,5R,6S,8R,9R,10R,12R,13R,14R,17S)-3,12-dihydroxy-4,4,8,10,14-pentamethyl-17-((S)-6-methyl-2-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)hept-5-en-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-

References

https://en.wikipedia.org/wiki/Ginsenoside

Picture of Ginsenoside 3D model

click on the picture of  Ginsenoside above to interact
with the 3D model of the
Ginsenoside structure
(this will open a new browser window)

Picture of Ginsenoside

C42 H72 O14



Update by Karl Harrison
(Molecule of the Month for October 2020 )

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