Ginsenosides
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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. Classification G ...
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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. Classification G ...
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American Ginseng
American ginseng (''Panax quinquefolius'') is a herbaceous perennial plant in the ivy family, commonly used as an herb in traditional Chinese medicine. It is native to eastern North America, though it is also cultivated in China. Since the 18th century, American ginseng (''P. quinquefolius'') has been primarily exported to Asia, where it is highly valued for its cooling and sedative medicinal effects. It is considered to represent the cooling yin qualities, while Asian ginseng embodies the warmer aspects of yang. Description The aromatic root of American ginseng (''Panax quinquefolius'') resembles a small parsnip that forks as it matures. The plant grows tall, usually bearing three leaves, each with three to five leaflets, long. American ginseng can be found in much of the eastern and central United States and in part of southeastern Canada. It is found primarily in deciduous forests of the Appalachian and Ozark regions of the United States. American ginseng is found in full ...
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Pseudoginsenoside F11
Pseudoginsenoside F11 is a chemical natural product found in American ginseng (''Panax quinquefolius'') but not in Asian ginseng (''Panax ginseng''), although it has similar properties to the Asian ginseng compound ginsenoside Rf. The molecule is a triterpenoid saponin member of the dammarane family and contains a four-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 mice have identified antagonistic effects on the actions of other well-characterized drugs, such as scopolamine, morphine Morphine is a strong opiate that is found naturally in opium, a dark brown resin in poppies (''Papaver somniferum''). It is mainly used as a pain medication, and is also ...
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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 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. According to th ...
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Triterpene Saponin
Saponins (Latin "sapon", soap + "-in", one of), also selectively referred to as triterpene glycosides, are bitter-tasting usually toxic plant-derived organic chemicals that have a foamy quality when agitated in water. They are widely distributed but found particularly in soapwort (genus Saponaria), a flowering plant, the soapbark tree (''Quillaja saponaria'') and soybeans (''Glycine max'' L.). They are used in soaps, medicinals, fire extinguishers, speciously as dietary supplements, for synthesis of steroids, and in carbonated beverages (the head on a mug of root beer). Structurally, they are glycosides, sugars bonded to another organic molecule, usually a steroid or triterpene, a steroid building block. 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 in beverages. Uses The saponins are a subclass of terpenoids, the large ...
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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 this f ...
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Biosynthetic Pathway
Metabolism (, from el, μεταβολή ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cellular processes; the conversion of food to building blocks for proteins, lipids, nucleic acids, and some carbohydrates; and the elimination of metabolic wastes. These enzyme-catalyzed reactions allow organisms to grow and reproduce, maintain their structures, and respond to their environments. The word metabolism can also refer to the sum of all chemical reactions that occur in living organisms, including digestion and the transportation of substances into and between different cells, in which case the above described set of reactions within the cells is called intermediary (or intermediate) metabolism. Metabolic reactions may be categorized as ''catabolic'' – the ''breaking down'' of compounds (for example, of glucose to pyruvate by cel ...
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Isoprene
Isoprene, or 2-methyl-1,3-butadiene, is a common volatile organic compound with the formula CH2=C(CH3)−CH=CH2. In its pure form it is a colorless volatile liquid. Isoprene is an unsaturated hydrocarbon. It is produced by many plants and animals (including humans) and its polymers are the main component of natural rubber. C. G. Williams named the compound in 1860 after obtaining it from thermal decomposition (pyrolysis) of natural rubber; he correctly deduced the empirical formula C5H8. Natural occurrences Isoprene is produced and emitted by many species of trees (major producers are oaks, poplars, eucalyptus, and some legumes). Yearly production of isoprene emissions by vegetation is around 600 million metric tons, half from tropical broadleaf trees and the remainder primarily from shrubs. This is about equivalent to methane emissions and accounts for around one-third of all hydrocarbons released into the atmosphere. In deciduous forests, isoprene makes up approximately 80% o ...
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Squalene
Squalene is an organic compound. It is a triterpenoid 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). All plants and animals produce squalene as a biochemical intermediate to sterol biosynthesis. An estimated 12% of bodily squalene in humans is found in Sebaceous gland, sebum. Squalene has a role in topical skin lubrication and protection. Squalene is a precursor (chemistry), precursor for synthesis of all plant and animal sterols, including cholesterol and steroid hormones in the human body. Squalene is an important ingredient in some vaccine adjuvants: The Novartis and GlaxoSmithKline adjuvants are called MF59 and AS03, respectively. Role in steroid synthesis Squalene is the biochemical precursor to steroids. The squalene conversion begins with oxidation (via squalene monooxygenase) of one of its terminal double bonds, resulting in 2,3- ...
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Squalene Epoxidase
Squalene monooxygenase (also called squalene epoxidase) is a eukaryotic enzyme that uses NADPH and diatomic oxygen to oxidize squalene to 2,3-oxidosqualene (squalene epoxide). Squalene epoxidase catalyzes the first oxygenation step in sterol biosynthesis and is thought to be one of the rate-limiting enzymes in this pathway. In humans, squalene epoxidase is encoded by the ''SQLE'' gene. Several eukaryote genomes lack a squalene monooxygenase encoding gene, but instead encode an alternative squalene epoxidase that performs the same task. Mechanism The canonical squalene monooxygenase is a flavoprotein monooxygenase. Flavoprotein monooxygenase form flavin hydroperoxides at the enzyme active site, which then transfer the terminal oxygen atom of the hydroperoxide to the substrate. Squalene monooxygenase differs from other flavin monooxygenases in that the oxygen is inserted into the substrate as an epoxide rather than as a hydroxyl group. This enzyme contains a loosely bound FAD ...
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Protopanaxadiol
Protopanaxadiol (PPD) is an organic compound characterizing a group of ginsenosides. It is a dammarane-type tetracyclic terpene sapogenin found in ginseng (''Panax ginseng'') and in notoginseng (''Panax pseudoginseng''). Just what protopanaxadiol's metabolites do 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 of intracellular calcium ion concentration. See also * Protopanaxatriol Protopanaxatriol (PPT) is an organic compound characterizing a group of ginsenosides. It is a dammarane-type tetracyclic triterpene sapogenins found in ginseng (''Panax ginseng'') and in notoginseng (''Panax pseudoginseng''). See also * Panaxatr ... References Triterpenes Triols Steroids {{alcohol-stub ...
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