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Ginsenosides
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. The leaves and s ...
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Ginsenoside Rg1
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. The leaves an ...
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American Ginseng
American ginseng (''Panax quinquefolius'') is a species of flowering plant in the ivy family (biology), family Araliaceae. It is native to eastern North America and has been introduced into China. The specific epithet ''quinquefolius'' means "five-leaved", which refers to the typical number of leaflets per leaf. It is one of a group of Taxon, taxa known as "ginseng". Europeans first became aware of American ginseng near Montreal in 1716. It has been wild-harvested and exported to Asia since 1720. Billions of plants were wild-harvested in the 19th century alone. To control international trade and prevent global extinction of the species, the United States Fish and Wildlife Service implements a CITES Export Program that authorizes 19 states and one tribe to export American ginseng from the United States. From 1978 to 2019, the bulk of exports have come from southern Appalachian states, especially Kentucky, West Virginia, and Tennessee. The NatureServe conservation status, cons ...
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Glycoside
In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzymatic, enzyme hydrolysis, which causes the sugar part to be broken off, making the chemical available for use. Many such plant glycosides are used as medications. Several species of ''Heliconius'' butterfly are capable of incorporating these plant compounds as a form of chemical defense against predators. In animals and humans, poisons are often bound to sugar molecules as part of their elimination from the body. In formal terms, a glycoside is any molecule in which a sugar group is bonded through its anomeric carbon to another group via a glycosidic bond. Glycosides can be linked by an O- (an ''O-glycoside''), N- (a ''glycosylamine''), S-(a ''thioglycoside''), or C- (a ''C-glycoside'') glycosidic bond. Accord ...
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Triterpene Saponin
Saponins (Latin ''sapon'', 'soap' + ''-in'', 'one of') are bitter-tasting, usually toxic plant-derived secondary metabolites. They are organic chemicals that become foamy when agitated in water and have high molecular weight. They are present in a wide range of plant species throughout the bark, leaves, stems, roots and flowers but particularly in soapwort (genus '' Saponaria''), a flowering plant, the soapbark tree (''Quillaja saponaria''), common corn-cockle (''Agrostemma githago'' L.), baby's breath ( ''Gypsophila'' spp.) and soybeans (''Glycine max'' L.). They are used in soaps, medicines (e.g. drug adjuvants), fire extinguishers, dietary supplements, steroid synthesis, and in carbonated beverages (for example, being responsible for maintaining the head on root beer). Saponins are both water and fat soluble, which gives them their useful soap properties. Some examples of these chemicals are glycyrrhizin (licorice flavoring) and quillaia (alt. quillaja), a bark extract used ...
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Pseudoginsenoside F11
Pseudoginsenoside F11 is a chemical natural product found in American ginseng American ginseng (''Panax quinquefolius'') is a species of flowering plant in the ivy family (biology), family Araliaceae. It is native to eastern North America and has been introduced into China. The specific epithet ''quinquefolius'' means "fiv ... (''Panax quinquefolius'') but not in ginseng, Asian ginseng (''Panax ginseng''), although it has similar properties to the Asian ginseng compound ginsenoside, ginsenoside Rf. The molecule is a triterpenoid saponin member of the dammarane family and contains a four-polycyclic compound, ring rigid skeleton. Compounds in the ginsenoside family are found almost exclusively in plants of the genus ''Panax''. A wide variety of difficult-to-characterize ''in vitro'' effects have been reported for the compounds in isolation. Pseudoginsenoside F11 and its derivatives are sometimes referred to as having an ''ocotillol''-type skeleton structure. Studies in laboratory ...
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Protopanaxadiol
Protopanaxadiol (PPD) is an organic compound that is an aglycone of ginsenosides, a group of steroid glycosides. It is a dammarane-type tetracyclic terpene sapogenin found in ginseng (''Panax ginseng'') and in notoginseng (''Panax pseudoginseng''). The health effect of protopanaxadiol inside the human body is still unclear. One study suggests it has rapid, non-genomic effects on endothelial cells, binding to the glucocorticoid and oestrogen beta receptors. The study also showed an increase in intracellular calcium ion concentration. Shanghai Innovative Research Center of Traditional Chinese Medicine (SIRC-TCM) is trying to develop an antidepressant based on this substance under the brand name ''Yoxintine''. The drug has finished phase II trials as of May 2023. Results were published in November 2024. A pharmacokinetic study done on phase IIa human volunteers reports the relationship between oral dose and blood plasma concentration, but no data is given for oral bioavailbilit ...
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Protopanaxatriol
Protopanaxatriol (PPT) is an organic compound that is an aglycone of ginsenosides, a group of steroid glycosides. It is a dammarane-type tetracyclic triterpene sapogenins found in ginseng (''Panax ginseng'') and in notoginseng (''Panax pseudoginseng''). In rats, the oral bioavailability is about 3.7% and the half-life is 0.80 hours (when given as a PPD-PPT mixture). PPT is unstable in acid, showing 40% degradation after 4 hours at 37°C both in pH 1.2 buffer solution and rat stomach contents. It is extensively metabolized in mice. See also * Panaxatriol * Protopanaxadiol References

{{alcohol-stub Triterpenes Tetrols Steroids ...
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Hydroxyl
In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy groups. Both the negatively charged anion , called hydroxide, and the neutral radical , known as the hydroxyl radical, consist of an unbonded hydroxy group. According to IUPAC definitions, the term ''hydroxyl'' refers to the hydroxyl radical () only, while the functional group is called a ''hydroxy group''. Properties Water, alcohols, carboxylic acids, and many other hydroxy-containing compounds can be readily deprotonated due to a large difference between the electronegativity of oxygen (3.5) and that of hydrogen (2.1). Hydroxy-containing compounds engage in intermolecular hydrogen bonding increasing the electrostatic attraction between molecules and thus to higher boiling and melting points than found for compounds that lack thi ...
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Biosynthetic Pathway
In biochemistry, a metabolic pathway is a linked series of chemical reactions occurring within a cell. The reactants, products, and intermediates of an enzymatic reaction are known as metabolites, which are modified by a sequence of chemical reactions catalyzed by enzymes. In most cases of a metabolic pathway, the product of one enzyme acts as the substrate for the next. However, side products are considered waste and removed from the cell. Different metabolic pathways function in the position within a eukaryotic cell and the significance of the pathway in the given compartment of the cell. For instance, the electron transport chain and oxidative phosphorylation all take place in the mitochondrial membrane. In contrast, glycolysis, pentose phosphate pathway, and fatty acid biosynthesis all occur in the cytosol of a cell. There are two types of metabolic pathways that are characterized by their ability to either synthesize molecules with the utilization of energy ( anabolic pa ...
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2,3-oxidosqualene
(''S'')-2,3-Oxidosqualene ((''S'')-2,3-epoxysqualene) is an intermediate in the synthesis of the cell membrane sterol precursors lanosterol and cycloartenol, as well as saponins. It is formed when squalene is oxidized by the enzyme squalene monooxygenase. 2,3-Oxidosqualene is the substrate of various oxidosqualene cyclases, including lanosterol synthase, which produces lanosterol, a precursor to cholesterol Cholesterol is the principal sterol of all higher animals, distributed in body Tissue (biology), tissues, especially the brain and spinal cord, and in Animal fat, animal fats and oils. Cholesterol is biosynthesis, biosynthesized by all anima .... The stereoisomer (''R'')-2,3-oxidosqualene is an inhibitor of lanosterol synthase. References External links Oxidosqualene cyclase, PDB December 2007 Molecule of the Month {{DEFAULTSORT:Oxidosqualene, 2,3- Epoxides Triterpenes Polyenes ...
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Squalene
Squalene is an organic compound. It is a triterpene with the formula C30H50. It is a colourless oil, although impure samples appear yellow. It was originally obtained from shark liver oil (hence its name, as '' Squalus'' is a genus of sharks). An estimated 12% of bodily squalene in humans is found in sebum. Squalene has a role in topical skin lubrication and protection. Most plants, fungi, and animals produce squalene as biochemical precursor in sterol biosynthesis, including cholesterol and steroid hormones in the human body. It is also an intermediate in the biosynthesis of hopanoids in many bacteria. Squalene is an important ingredient in some vaccine adjuvants: The Novartis and GlaxoSmithKline adjuvants are called MF59 and AS03, respectively. Role in triterpenoid synthesis Squalene is a biochemical precursor to both steroids and hopanoids. For sterols, the squalene conversion begins with oxidation (via squalene monooxygenase) of one of its terminal double bonds, ...
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Dammarane
Dammarane is a tetracyclic triterpene found in sapogenins (forming triterpenoid saponins) like those of ginseng (ginsenosides: panaxatriol Panaxatriol is an organic compound that is an aglycone of ginsenosides, a group of steroid glycosides. It is a dammarane-type tetracyclic triterpene sapogenin found in ginseng (''Panax ginseng'') and in notoginseng (''Panax pseudoginseng''). It ... and protopanaxadiol). Compounds of the series were first isolated from and named after dammar resin, a natural resin from the tropical trees of the dipterocarp family. Mills J.S. (1956) "The Constitution of the Neutral, Tetracyclic Triterpenes of Dammar Resin" ''Journal of the Chemical Society'' 2196-2202 References External links Numbering of dammarane according to IUPAC Recommendations Steroids Triterpenes {{steroid-stub ...
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