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Ginsenoside Rh2

CAS No.:
78214-33-2
Catalog Number:
AG00393A
Molecular Formula:
C36H62O8
Molecular Weight:
622.8727
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥98%
1 week
United States
$111
- +
5mg
98%
1 week
United States
$140
- +
10mg
98%
1 week
United States
$182
- +
Product Description
Catalog Number:
AG00393A
Chemical Name:
Ginsenoside Rh2
CAS Number:
78214-33-2
Molecular Formula:
C36H62O8
Molecular Weight:
622.8727
MDL Number:
MFCD00800712
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
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-IRFFNABBSA-N
SMILES:
OCC1OC(OC2CCC3(C(C2(C)C)CCC2(C3CC(O)C3C2(C)CCC3C(CCC=C(C)C)(O)C)C)C)C(C(C1O)O)O
Properties
Complexity:
1070  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
15  
Defined Bond Stereocenter Count:
0
Exact Mass:
622.444g/mol
Formal Charge:
0
Heavy Atom Count:
44  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
6  
Isotope Atom Count:
0
Molecular Weight:
622.884g/mol
Monoisotopic Mass:
622.444g/mol
Rotatable Bond Count:
7  
Topological Polar Surface Area:
140A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
5.6  
Literature
Title Journal
Ginsenoside F1 suppresses astrocytic senescence-associated secretory phenotype. Chemico-biological interactions 20180301
Ginsenoside 20(s)-Rh2 as potent natural histone deacetylase inhibitors suppressing the growth of human leukemia cells. Chemico-biological interactions 20151205
Sulfated derivative of 20(S)-ginsenoside Rh2 inhibits inflammatory cytokines through MAPKs and NF-kappa B pathways in LPS-induced RAW264.7 macrophages. Inflammation 20121001
Key role of nuclear factor-κB in the cellular pharmacokinetics of adriamycin in MCF-7/Adr cells: the potential mechanism for synergy with 20(S)-ginsenoside Rh2. Drug metabolism and disposition: the biological fate of chemicals 20121001
In vitro studies on the oxidative metabolism of 20(s)-ginsenoside Rh2 in human, monkey, dog, rat, and mouse liver microsomes, and human liver s9. Drug metabolism and disposition: the biological fate of chemicals 20121001
Ginsenoside Rh2 inhibits osteoclastogenesis through down-regulation of NF-κB, NFATc1 and c-Fos. Bone 20120601
Microbial transformation of ginsenoside Rg3 to ginsenoside Rh2 by Esteya vermicola CNU 120806. World journal of microbiology & biotechnology 20120401
Structural modification of ginsenoside Rh(2) by fatty acid esterification and its detoxification property in antitumor. Bioorganic & medicinal chemistry letters 20120115
A dynamic study on reversal of multidrug resistance by ginsenoside Rh₂ in adriamycin-resistant human breast cancer MCF-7 cells. Talanta 20120115
Cellular pharmacokinetic mechanisms of adriamycin resistance and its modulation by 20(S)-ginsenoside Rh2 in MCF-7/Adr cells. British journal of pharmacology 20120101
Antihyperglycemic effect of ginsenoside Rh2 by inducing islet β-cell regeneration in mice. Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme 20120101
Stereoselective regulations of P-glycoprotein by ginsenoside Rh2 epimers and the potential mechanisms from the view of pharmacokinetics. PloS one 20120101
Ginsenoside Rh2(S) induces differentiation and mineralization of MC3T3-E1 cells through activation of the PKD/AMPK signaling pathways. International journal of molecular medicine 20111101
Co-treatment with ginsenoside Rh2 and betulinic acid synergistically induces apoptosis in human cancer cells in association with enhanced capsase-8 activation, bax translocation, and cytochrome c release. Molecular carcinogenesis 20111001
Enhancement of oral bioavailability of 20(S)-ginsenoside Rh2 through improved understanding of its absorption and efflux mechanisms. Drug metabolism and disposition: the biological fate of chemicals 20111001
[Effects of 20 (S) -ginsenoside Rh2 and 20 (R) -ginsenoside Rh2 on proliferation and apoptosis of human lung adenocarcinoma A549 cells]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20110601
Ginsenoside Rh2 inhibits glioma cell proliferation by targeting microRNA-128. Acta pharmacologica Sinica 20110301
Ginsenoside Rh2 induces apoptosis and paraptosis-like cell death in colorectal cancer cells through activation of p53. Cancer letters 20110227
Ginsenoside Rh2 induces Bcl-2 family proteins-mediated apoptosis in vitro and in xenografts in vivo models. Journal of cellular biochemistry 20110101
20(S)-ginsenoside Rh2 noncompetitively inhibits P-glycoprotein in vitro and in vivo: a case for herb-drug interactions. Drug metabolism and disposition: the biological fate of chemicals 20101201
Cholesterol-dependent induction of dendrite formation by ginsenoside Rh2 in cultured melanoma cells. International journal of molecular medicine 20101201
Stereospecificity of hydroxyl group at C-20 in antiproliferative action of ginsenoside Rh2 on prostate cancer cells. Fitoterapia 20101001
Rh2 or its aglycone aPPD in combination with docetaxel for treatment of prostate cancer. The Prostate 20100915
Intestinal absorption mechanisms of ginsenoside Rh2: stereoselectivity and involvement of ABC transporters. Xenobiotica; the fate of foreign compounds in biological systems 20100901
Induction of apoptosis by the ginsenoside Rh2 by internalization of lipid rafts and caveolae and inactivation of Akt. British journal of pharmacology 20100701
[Effect of ginsenoside Rh2 on the development of transferred tumors and chemotherapy efficiency]. Eksperimental'naia i klinicheskaia farmakologiia 20100401
Improving enzymatic production of ginsenoside Rh2 from Rg3 by using nonionic surfactant. Applied biochemistry and biotechnology 20100201
[Research on the mechanism of ginsenoside Rh2 reversing the resistance of lung adenocarcinoma cells to cisplatin]. Zhonghua yi xue za zhi 20100126
Pre-clinical evaluation of Rh2 in PC-3 human xenograft model for prostate cancer in vivo: formulation, pharmacokinetics, biodistribution and efficacy. Cancer chemotherapy and pharmacology 20091101
Ginsenoside Rh2-mediated G1 phase cell cycle arrest in human breast cancer cells is caused by p15 Ink4B and p27 Kip1-dependent inhibition of cyclin-dependent kinases. Pharmaceutical research 20091001
Ginsenoside Rh2 ameliorates scopolamine-induced learning deficit in mice. Biological & pharmaceutical bulletin 20091001
Pharmacokinetic characterization of ginsenoside Rh2, an anticancer nutrient from ginseng, in rats and dogs. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20090901
Ginsenoside Rh2 induces ligand-independent Fas activation via lipid raft disruption. Biochemical and biophysical research communications 20090724
20(R)-ginsenoside Rh2, not 20(S), is a selective osteoclastgenesis inhibitor without any cytotoxicity. Bioorganic & medicinal chemistry letters 20090615
Anxiolytic-like effects of ginsenosides Rg3 and Rh2 from red ginseng in the elevated plus-maze model. Planta medica 20090601
Increase of adipogenesis by ginsenoside (Rh2) in 3T3-L1 cell via an activation of glucocorticoid receptor. Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme 20090401
[Effect of ginsenoside Rh2 on transplanted-tumor and expression of JAM in mice]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20080901
20(S)-protopanaxadiol and the ginsenoside Rh2 inhibit Na+ channel-activated depolarization and Na+ channel-dependent amino acid neurotransmitter release in synaptic fractions isolated from mammalian brain. Comparative biochemistry and physiology. Toxicology & pharmacology : CBP 20080401
Role of pituitary adenylate cyclase-activating polypeptide (PACAP) in the action of ginsenoside Rh2 against beta-amyloid-induced inhibition of rat brain astrocytes. Neuroscience letters 20080321
20(S)-25-methoxyl-dammarane-3beta, 12beta, 20-triol, a novel natural product for prostate cancer therapy: activity in vitro and in vivo and mechanisms of action. British journal of cancer 20080226
Anti-obesity effects of ginsenoside Rh2 are associated with the activation of AMPK signaling pathway in 3T3-L1 adipocyte. Biochemical and biophysical research communications 20071228
Repression of matrix metalloproteinase gene expression by ginsenoside Rh2 in human astroglioma cells. Biochemical pharmacology 20071203
Characterizing the mechanism for ginsenoside-induced cytotoxicity in cultured leukemia (THP-1) cells. Canadian journal of physiology and pharmacology 20071101
Determination of 25-OH-PPD in rat plasma by high-performance liquid chromatography-mass spectrometry and its application in rat pharmacokinetic studies. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20071015
[Effect of ginsenoside Rh2 on immunocompetence of alveolar macrophages in patients with non-small cell lung cancer]. Zhong nan da xue xue bao. Yi xue ban = Journal of Central South University. Medical sciences 20071001
Bifidus fermentation increases hypolipidemic and hypoglycemic effects of red ginseng. Journal of microbiology and biotechnology 20070701
Ginsenosides compound K and Rh(2) inhibit tumor necrosis factor-alpha-induced activation of the NF-kappaB and JNK pathways in human astroglial cells. Neuroscience letters 20070621
Ginsenoside Rh2 is one of the active principles of Panax ginseng root to improve insulin sensitivity in fructose-rich chow-fed rats. Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme 20070501
Ginsenoside-Rh2-induced mitochondrial depolarization and apoptosis are associated with reactive oxygen species- and Ca2+-mediated c-Jun NH2-terminal kinase 1 activation in HeLa cells. The Journal of pharmacology and experimental therapeutics 20061201
Quantitative determination of ginsenoside Rh2 in rat biosamples by liquid chromatography electrospray ionization mass spectrometry. Analytical and bioanalytical chemistry 20061201
Inhibitory effects of Korean red ginseng and its genuine constituents ginsenosides Rg3, Rf, and Rh2 in mouse passive cutaneous anaphylaxis reaction and contact dermatitis models. Biological & pharmaceutical bulletin 20060901
[Determination of ginsenoside Rd and its metabolites in rat urine by LC-MS]. Yao xue xue bao = Acta pharmaceutica Sinica 20060801
Ginsenosides Rg3 and Rh2 inhibit the activation of AP-1 and protein kinase A pathway in lipopolysaccharide/interferon-gamma-stimulated BV-2 microglial cells. Planta medica 20060601
Rh2 synergistically enhances paclitaxel or mitoxantrone in prostate cancer models. The Journal of urology 20060501
In vitro assessment of plasma protein binding of 20(R)-ginsenoside Rh2 by equilibrium dialysis and LC-MS analysis: a case of species differences. Biological & pharmaceutical bulletin 20060501
20(S)-ginsenoside Rh2, a newly identified active ingredient of ginseng, inhibits NMDA receptors in cultured rat hippocampal neurons. European journal of pharmacology 20060424
Ginsenoside Rh(2) enhances antitumour activity and decreases genotoxic effect of cyclophosphamide. Basic & clinical pharmacology & toxicology 20060401
[Determination of 20 (S)-ginsengnoside Rh2 in the alkali-hydrolysis product of saponins from leaves of Panax qinquefolium by RP-HPLC]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20060301
Natural products from ginseng inhibit [3H]batrachotoxinin A 20-alpha-benzoate binding to Na+ channels in mammalian brain. European journal of pharmacology 20060113
Increase of insulin secretion by ginsenoside Rh2 to lower plasma glucose in Wistar rats. Clinical and experimental pharmacology & physiology 20060101
Mediation of beta-endorphin by ginsenoside Rh2 to lower plasma glucose in streptozotocin-induced diabetic rats. Planta medica 20060101
Caspase-3-dependent protein kinase C delta activity is required for the progression of Ginsenoside-Rh2-induced apoptosis in SK-HEP-1 cells. Cancer letters 20051218
Hepatoprotective effect of 20(S)-ginsenosides Rg3 and its metabolite 20(S)-ginsenoside Rh2 on tert-butyl hydroperoxide-induced liver injury. Biological & pharmaceutical bulletin 20051001
[Effects of ginsenoside Rh2(GS-Rh2) on cell cycle of Eca-109 esophageal carcinoma cell line]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20051001
High performance liquid chromatographic-mass spectrometric determination of ginsenoside Rg3 and its metabolites in rat plasma using solid-phase extraction for pharmacokinetic studies. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20050425
Uptake and metabolism of ginsenoside Rh2 and its aglycon protopanaxadiol by Caco-2 cells. Biological & pharmaceutical bulletin 20050201
Liquid chromatography/tandem mass spectrometry for pharmacokinetic studies of 20(R)-ginsenoside Rg3 in dog. Rapid communications in mass spectrometry : RCM 20050101
Development of a HPLC-MS assay for ginsenoside Rh2, a new anti-tumor substance from natural product and its pharacokinetic study in dogs. European journal of drug metabolism and pharmacokinetics 20050101
Liquid chromatography/mass spectrometric analysis of rat samples for in vivo metabolism and pharmacokinetic studies of ginsenoside Rh2. Rapid communications in mass spectrometry : RCM 20050101
[Effect of telomerase on ginsenoside Rh2-induced differentiation of hepatocarcinoma cell line SMMC-7721]. Ai zheng = Aizheng = Chinese journal of cancer 20041201
[Effects of ginsenoside Rh2 on signal transduction in hepatocarcinoma SMMC-7721 cells]. Zhonghua gan zang bing za zhi = Zhonghua ganzangbing zazhi = Chinese journal of hepatology 20040901
[Induction of differentiation by ginsenoside Rh2 in hepatocarcinoma cell SMMC-7721]. Ai zheng = Aizheng = Chinese journal of cancer 20040801
Ginsenoside Rh2 induces apoptosis via activation of caspase-1 and -3 and up-regulation of Bax in human neuroblastoma. Archives of pharmacal research 20040801
Rh2, a compound extracted from ginseng, hypersensitizes multidrug-resistant tumor cells to chemotherapy. Canadian journal of physiology and pharmacology 20040701
Effects of ginsenosides Rg3 and Rh2 on the proliferation of prostate cancer cells. Archives of pharmacal research 20040401
Ginsenoside Rh2 reduces ischemic brain injury in rats. Biological & pharmaceutical bulletin 20040301
Ginsenosides 20(S)-protopanaxadiol and Rh2 reduce cell proliferation and increase sub-G1 cells in two cultured intestinal cell lines, Int-407 and Caco-2. Canadian journal of physiology and pharmacology 20040301
Transformation of ginseng saponins to ginsenoside Rh2 by acids and human intestinal bacteria and biological activities of their transformants. Archives of pharmacal research 20040101
Mechanistic studies on protopanaxadiol, Rh2, and ginseng (Panax quinquefolius) extract induced cytotoxicity in intestinal Caco-2 cells. Journal of biochemical and molecular toxicology 20040101
The c-Jun N-terminal kinase 1 activity is differentially regulated by specific mechanisms during apoptosis. The Journal of biological chemistry 20031212
In vitro induction of differentiation by ginsenoside Rh2 in SMMC-7721 hepatocarcinoma cell line. Pharmacology & toxicology 20031201
Antiallergic activity of ginsenoside Rh2. Biological & pharmaceutical bulletin 20031101
SEK1-dependent JNK1 activation prolongs cell survival during G-Rh2-induced apoptosis. Biochemical and biophysical research communications 20030502
Apoptotic effects of ginsenoside Rh2 on human malignant melanoma A375-S2 cells. Acta pharmacologica Sinica 20020401
[Saponins with low sugar chain from the leaves of Panax notoginseng (Burk) F. H. Chen]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20020301
Anticarcinogenic effect and enhancement of metastatic potential of BALB/c 3T3 cells by ginsenoside Rh(2). Japanese journal of cancer research : Gann 20011101
The antimetastatic and immunomodulating activities of ginseng minor glycosides. Doklady. Biochemistry and biophysics 20010101
Ginsenoside RH-2 induces apoptotic cell death in rat C6 glioma via a reactive oxygen- and caspase-dependent but Bcl-X(L)-independent pathway. Life sciences 19990101
Properties