63223-86-9 , Ginsenoside Rh1
Cas:63223-86-9
C36H62O9 / 638.89
MFCD09951797
Natural triterpenoid saponin. Various pharmacological effects. Inactivates ERK, JNK, and p38. Weakly estrogenic. Inhibits TNF-α. Shows anti-inflammatory and hypoallergenic effects in vivo. Orally active.
Ginsenoside Rh1 is a steroid glycoside and saponin that has been found in red ginseng and has diverse biological activities. It inhibits expression of matrix metalloproteinase-1 (MMP-1), MMP-3, and MMP-9 induced by phorbol 12-myristate 13-acetate (PMA;) in U87MG and U373MG human astroglioma cells in a concentration-dependent manner. Ginsenoside Rh1 (300 μM) also inhibits PMA-induced invasion and migration of these cell lines in Matrigel™ invasion and wound healing assays, respectively. It inhibits LPS-induced increases in nitrite accumulation, prostaglandin E2 (PGE2;) synthesis, and inducible nitric oxide synthase (iNOS) protein levels in RAW 264.7 cells and inhibits histamine release induced by compound 48/80 in rat peritoneal mast cells (IC50 = 37 μM). Ginsenoside Rh1 (25 mg/kg, i.p.) inhibits IgE-induced passive cutaneous anaphylaxis reactions in mice by 87%. Ginsenoside Rh1 is also a metabolite of ginsenoside Re and ginsenoside Rg1 formed by intestinal microflora.
Ginsenoside Rh1 analytical standard provided with w/w absolute assay, to be used for quantitative titration.
Ginsenoside RH1, also known as sanchinoside B2, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Ginsenoside RH1 is considered to be a practically insoluble (in water) and relatively neutral molecule. Within the cell, ginsenoside RH1 is primarily located in the membrane (predicted from logP) and cytoplasm. Outside of the human body, ginsenoside RH1 can be found in tea. This makes ginsenoside RH1 a potential biomarker for the consumption of this food product.
Ginsenoside Rh1 is an active compound of ginseng, which belongs to the group of saponins. It has been shown to have significant cytotoxicity against HL-60 cells and K562 cells in vitro. Ginsenoside Rh1 inhibits energy production by inhibiting mitochondrial membrane potential, leading to cell death by apoptosis. This compound also stimulates the expression of toll-like receptor 4 and induces the production of inflammatory mediators. Ginsenoside Rh1 has been shown to inhibit tumor growth in an experimental model. The molecular structure of this active compound has been determined using NMR spectroscopy and X-ray crystallography.
CAS Number | 63223-86-9 |
Product Name | Ginsenoside Rh1 |
IUPAC Name | 2-[[3,12-dihydroxy-17-(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-6-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol |
Molecular Formula | C36H62O9 |
Molecular Weight | 638.89 g/mol |
InChI | InChI=1S/C36H62O9/c1-19(2)10-9-13-36(8,43)20-11-15-34(6)26(20)21(38)16-24-33(5)14-12-25(39)32(3,4)30(33)22(17-35(24,34)7)44-31-29(42)28(41)27(40)23(18-37)45-31/h10,20-31,37-43H,9,11-18H2,1-8H3 |
InChI Key | RAQNTCRNSXYLAH-OUEXKMQZSA-N |
SMILES | CC(=CCCC(C)(C1CCC2(C1C(CC3C2(CC(C4C3(CCC(C4(C)C)O)C)OC5C(C(C(C(O5)CO)O)O)O)C)O)C)O)C |
Solubility | Soluble in DMSO |
Synonyms | ginsenoside Rh1; HY-N0604; HYN0604; HY N0604; CS-3834; CS3834; CS 3834 |
Canonical SMILES | CC(=CCCC(C)(C1CCC2(C1C(CC3C2(CC(C4C3(CCC(C4(C)C)O)C)OC5C(C(C(C(O5)CO)O)O)O)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(C[C@@H]([C@@H]4[C@@]3(CC[C@@H](C4(C)C)O)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C)O)C)O)C |
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