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IUPAC name 20-[β-D-Glucopyranosyl-(1→6)-β-D-glucopyranosyloxy]-12β-hydroxydammar-24-en-3β-yl β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside | |
Systematic IUPAC name (12S,13R,14S,15S,16R,32R,33R,34S,35S,36R,51S,53aR,53bR,55aR,57S,59aR,59bR,511R,511aR,6S,82S,83R,84S,85S,86R,112R,113R,114S,115R,116R)-16,36,116-Tris(hydroxymethyl)-53a,53b,56,56,59a,6-hexamethyl-6-(4-methylpent-3-en-1-yl)hexadecahydro-51H-2,4,7,10-tetraoxa-1,11(2),3(3,2),8(2,6)-tetrakis(oxana)-5(7,1)-cyclopenta[a]phenanthrenaundecaphane-13,14,15,34,35,511,83,84,85,113,114,115-dodecol | |
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Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.050.466 |
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KEGG | |
PubChem CID | |
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Properties | |
C54H92O23 | |
Molar mass | 1109.307 g·mol−1 |
Hazards | |
GHS labelling: | |
Warning | |
H302, H312, H332 | |
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Ginsenoside Rb1 (or Ginsenoside Rb1 or GRb1 or GRb1) is a chemical compound belonging to the ginsenoside family.
Like other ginsenosides, it is found in the plant genus Panax (ginseng), and has a variety of potential health effects including anticarcinogenic, immunomodulatory, anti‐inflammatory, antiallergic, antiatherosclerotic, antihypertensive, and antidiabetic effects as well as antistress activity and effects on the central nervous system. [3]
A 1998 study by Seoul National University reported that GRb1 and GRg3 (ginsenosides Rb1 and Rg3) significantly attenuated glutamate-induced neurotoxicity by inhibiting the overproduction of nitric oxide synthase among some other findings regarding their neuroprotective properties. [4]
In 2002, the Laboratory for Cancer Research in Rutgers University showed that GRb1 and GRg1 have neuroprotective effect for spinal cord neurons, while ginsenoside Re did not exhibit any activity. GRb1 and GRg1 are proposed to represent potentially effective therapeutic agents for spinal cord injuries. [5]
The protection that GRg1 (ginsenoside Rg1) and GRb1 offer against Alzheimer’s disease symptoms in mice was first published by researchers in 2015. The GRg1 affected three metabolic pathways: the metabolism of lecithin, amino acids and sphingolipids, while GRb1 treatment affected lecithin and amino acid metabolism. [6]
It was reported in 2017 that GRb1 improved cardiac function and remodelling in heart failure in mice. The treatment of H-ginsenoside Rb1 potentially attenuated cardiac hypertrophy and myocardial fibrosis. [7]
The biosynthesis of GRb1 in Panax ginseng starts from farnesyl diphosphate (FPP), which is converted to squalene with squalene synthase (SQS), then to 2,3-oxidosqualene with squalene epoxidase (SE).
The 2,3-oxidasqualene is then converted to dammarenediol-II by cyclization, with dammarenediol-II synthase (DS) as the catalyst. The dammarenediol-II is converted to protopanaxadiol and then to ginsenoside Rd.
Finally, GRb1 is synthesized from ginsenoside Rd, catalysed by UDPG:ginsenoside Rd glucosyltransferase (UGRdGT), a biosynthetic enzyme of GRb1 first discovered in 2005. [8] [9] [10]
Ginseng is the root of plants in the genus Panax, such as Korean ginseng, South China ginseng, and American ginseng, typically characterized by the presence of ginsenosides and gintonin. Ginseng is most commonly used in the cuisines and medicines of China and Korea.
The Panax (ginseng) genus belongs to the Araliaceae (ivy) family. Panax species are characterized by the presence of ginsenosides and gintonin. Panax is one of approximately 60 plant genera with a classical disjunct east Asian and east North American distribution. Furthermore, this disjunct distribution is asymmetric as only two of the ~18 species in genus are native to North America.
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). An estimated 12% of bodily squalene in humans is found in sebum. Squalene has a role in topical skin lubrication and protection.
Gingerol ([6]-gingerol) is a phenolic phytochemical compound found in fresh ginger that activates spice receptors on the tongue. It is normally found as a pungent yellow oil in the ginger rhizome, but can also form a low-melting crystalline solid. This chemical compound is found in all members of the Zingiberaceae family and is high in concentrations in the grains of paradise as well as an African Ginger species.
Neuroprotection refers to the relative preservation of neuronal structure and/or function. In the case of an ongoing insult the relative preservation of neuronal integrity implies a reduction in the rate of neuronal loss over time, which can be expressed as a differential equation. It is a widely explored treatment option for many central nervous system (CNS) disorders including neurodegenerative diseases, stroke, traumatic brain injury, spinal cord injury, and acute management of neurotoxin consumption. Neuroprotection aims to prevent or slow disease progression and secondary injuries by halting or at least slowing the loss of neurons. Despite differences in symptoms or injuries associated with CNS disorders, many of the mechanisms behind neurodegeneration are the same. Common mechanisms of neuronal injury include decreased delivery of oxygen and glucose to the brain, energy failure, increased levels in oxidative stress, mitochondrial dysfunction, excitotoxicity, inflammatory changes, iron accumulation, and protein aggregation. Of these mechanisms, neuroprotective treatments often target oxidative stress and excitotoxicity—both of which are highly associated with CNS disorders. Not only can oxidative stress and excitotoxicity trigger neuron cell death but when combined they have synergistic effects that cause even more degradation than on their own. Thus limiting excitotoxicity and oxidative stress is a very important aspect of neuroprotection. Common neuroprotective treatments are glutamate antagonists and antioxidants, which aim to limit excitotoxicity and oxidative stress respectively.
Ambrein is a triterpene alcohol that is the chief constituent of ambergris, a secretion from the digestive system of the sperm whale, and has been suggested as the possible active component producing the supposed aphrodisiac effects of ambergris. Although ambrein itself is odorless, it serves as the biological precursor for a number of aromatic derivatives such as ambroxan and is thought to possess fixative properties for other odorants.
Xylan is a type of hemicellulose, a polysaccharide consisting mainly of xylose residues. It is found in plants, in the secondary cell walls of dicots and all cell walls of grasses. Xylan is the third most abundant biopolymer on Earth, after cellulose and chitin.
Triterpenes are a class of terpenes composed of six isoprene units with the molecular formula C30H48; they may also be thought of as consisting of three terpene units. Animals, plants and fungi all produce triterpenes, including squalene, the precursor to all steroids.
Squalene synthase (SQS) or farnesyl-diphosphate:farnesyl-diphosphate farnesyl transferase is an enzyme localized to the membrane of the endoplasmic reticulum. SQS participates in the isoprenoid biosynthetic pathway, catalyzing a two-step reaction in which two identical molecules of farnesyl pyrophosphate (FPP) are converted into squalene, with the consumption of NADPH. Catalysis by SQS is the first committed step in sterol synthesis, since the squalene produced is converted exclusively into various sterols, such as cholesterol, via a complex, multi-step pathway. SQS belongs to squalene/phytoene synthase family of proteins.
Squalene monooxygenase is a eukaryotic enzyme that uses NADPH and diatomic oxygen to oxidize squalene to 2,3-oxidosqualene. 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.
Panax notoginseng is a species of the genus Panax, and it is commonly referred to in English as Chinese ginseng or notoginseng. In Chinese it is called tiánqī, tienchi ginseng, sānqī or sanchi, three-seven root, and mountain plant. P. notoginseng belongs to the same scientific genus as Panax ginseng. In Latin, the word panax means "cure-all", and the family of ginseng plants is one of the best-known herbs.
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.
Zaragozic acids are a family of natural products produced by fungi. The first characterized zaragozic acids, A, B, and C were isolated from an unidentified sterile fungal culture, Sporormiella intermedia, and L. elatius, respectively. just outside the European city Zaragoza, Spain on the Jalón river. This family of natural products possesses a unique 4,8-dioxabicyclo[3.2.1]octane core, and vary in their 1-alkyl and their 6-acyl side chains.
Salidroside (rhodioloside) is a glucoside of tyrosol found in the plant Rhodiola rosea. It has been studied, along with rosavin, as one of the potential compounds responsible for the putative antidepressant and anxiolytic actions of this plant. Salidroside may be more active than rosavin, even though many commercially marketed Rhodiola rosea extracts are standardized for rosavin content rather than salidroside.
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 and in notoginseng.
American ginseng 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 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.
The amyrins are three closely related natural chemical compounds of the triterpene class. They are designated α-amyrin (ursane skeleton), β-amyrin (oleanane skeleton) and δ-amyrin. Each is a pentacyclic triterpenol with the chemical formula C30H50O. They are widely distributed in nature and have been isolated from a variety of plant sources such as epicuticular wax. In plant biosynthesis, α-amyrin is the precursor of ursolic acid and β-amyrin is the precursor of oleanolic acid. All three amyrins occur in the surface wax of tomato fruit. α-Amyrin is found in dandelion coffee.
The squalene/phytoene synthase family represents proteins that catalyze the head-to-head condensation of C15 and C20 prenyl units (i.e. farnesyl diphosphate and genranylgeranyl diphosphate). This enzymatic step constitutes part of steroid and carotenoid biosynthesis pathway. Squalene synthase EC (SQS) and Phytoene synthase EC (PSY) are two well-known examples of this protein family and share a number of functional similarities. These similarities are also reflected in their primary structure. In particular three well conserved regions are shared by SQS and PSY; they could be involved in substrate binding and/or the catalytic mechanism. SQS catalyzes the conversion of two molecules of farnesyl diphosphate (FPP) into squalene. It is the first committed step in the cholesterol biosynthetic pathway. The reaction carried out by SQS is catalyzed in two separate steps: the first is a head-to-head condensation of the two molecules of FPP to form presqualene diphosphate; this intermediate is then rearranged in a NADP-dependent reduction, to form squalene:
Dammarenediol II synthase (EC 4.2.1.125, dammarenediol synthase, 2,3-oxidosqualene (20S)-dammarenediol cyclase, DDS, (S)-squalene-2,3-epoxide hydro-lyase (dammarenediol-II forming)) is an enzyme with systematic name (3S)-2,3-epoxy-2,3-dihydrosqualene hydro-lyase (dammarenediol-II forming). This enzyme catalyses the following chemical reaction
Pseudoginsenoside F11 is a chemical natural product found in American ginseng but not in Asian 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.