78214-33-2 , Ginsenoside Rh2
Cas:78214-33-2
C36H62O8 / 622.87
MFCD00800712
Ginsenoside Rh2 is a natural compound derived from the root of Panax ginseng. It has been shown to have anti-inflammatory properties and may be effective in treating bowel disease. Ginsenoside Rh2 inhibits nitrate reductase, which is an enzyme that converts nitric oxide into nitrous oxide. It also inhibits toll-like receptor 4 (TLR4) expression that leads to inflammatory cytokine production, such as IL-1β and IL-6. Ginsenoside Rh2 also binds to Bcl-2 protein, which prevents its degradation by the proteasome. This inhibition leads to the activation of the caspase cascade and apoptosis of cells.
Ginsenoside Rh2 is a steroid glycoside found in plants of the genus Panax that has diverse biological activities. It inhibits release of β-hexosaminidase from RBL-2H3 cells (IC50 = 100 μM) and inhibits the IgE-dependent passive cutaneous anaphylaxis reaction in mice at a dose of 25 mg/kg. It inhibits growth of HRA ovarian and BxPC-3 pancreatic cancer cells in a dose-dependent manner. In vivo, ginsenoside Rh2 decreases immobility time in the forced swim test in a mouse model of colorectal carcinoma. Ginsenoside Rh2 also reduces infarct volume in a rat model of ischemia-reperfusion-induced brain injury.
Ginsenoside Rh2 analytical standard provided with w/w absolute assay, to be used for quantitative titration.
Ginsenoside Rh2 is an active component of Red P. ginseng. It is reported to be obtained as a metabolite of ginsenoside Rg3, when anaerobically incubated with human fecal microflora.
(20S)-ginsenoside Rh2 is a ginsenoside found in Panax species that is dammarane which is substituted by hydroxy groups at the 3beta, 12beta and 20 pro-S positions, in which the hydroxy group at position 3 has been converted to the corresponding beta-D-glucopyranoside, and in which a double bond has been introduced at the 24-25 position. It has a role as a plant metabolite, an antineoplastic agent, an apoptosis inducer, a cardioprotective agent, a bone density conservation agent and a hepatoprotective agent. It is a beta-D-glucoside, a 12beta-hydroxy steroid, a ginsenoside, a tetracyclic triterpenoid and a 20-hydroxy steroid. It derives from a hydride of a dammarane.
CAS Number | 78214-33-2 |
Product Name | Ginsenoside Rh2 |
IUPAC Name | (2R,3R,4S,5S,6R)-2-[[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-hydroxy-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol |
Molecular Formula | C36H62O8 |
Molecular Weight | 622.9 g/mol |
InChI | InChI=1S/C36H62O8/c1-20(2)10-9-14-36(8,42)21-11-16-35(7)27(21)22(38)18-25-33(5)15-13-26(32(3,4)24(33)12-17-34(25,35)6)44-31-30(41)29(40)28(39)23(19-37)43-31/h10,21-31,37-42H,9,11-19H2,1-8H3/t21-,22+,23+,24-,25+,26-,27-,28+,29-,30+,31-,33-,34+,35+,36-/m0/s1 |
InChI Key | CKUVNOCSBYYHIS-XMJKKTSFSA-N |
SMILES | CC(=CCCC(C)(C1CCC2(C1C(CC3C2(CCC4C3(CCC(C4(C)C)OC5C(C(C(C(O5)CO)O)O)O)C)C)O)C)O)C |
Solubility | Soluble in DMSO |
Synonyms | Ginsenoside Rh2; HY-N0605; HY N0605; HYN0605 AR-1A4936; AR1A4936; AR 1A4936 |
Canonical SMILES | CC(=CCCC(C)(C1CCC2(C1C(CC3C2(CCC4C3(CCC(C4(C)C)OC5C(C(C(C(O5)CO)O)O)O)C)C)O)C)O)C |
Isomeric SMILES | CC(=CCC[C@@](C)([C@H]1CC[C@@]2([C@@H]1[C@@H](C[C@H]3[C@]2(CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C)C)O)C)O)C |
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