20(R)-Ginsenoside Rh2CAS# 112246-15-8 |
2D Structure
- 20(S)-Ginsenoside Rh2
Catalog No.:BCN1070
CAS No.:78214-33-2
Quality Control & MSDS
3D structure
Package In Stock
Number of papers citing our products
Cas No. | 112246-15-8 | SDF | Download SDF |
PubChem ID | 54580480 | Appearance | Powder |
Formula | C36H62O8 | M.Wt | 622.88 |
Type of Compound | Triterpenoids | Storage | Desiccate at -20°C |
Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
Chemical Name | (2R,3R,4S,5S,6R)-2-[[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-hydroxy-17-[(2R)-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 | ||
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 | ||
Standard InChIKey | CKUVNOCSBYYHIS-SUEBGMEDSA-N | ||
Standard 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 | ||
General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. |
Description | 20(R)-Ginsenoside Rh2, a minor stereoisomer of ginsenoside Rh2, possesses matrix metalloproteinase inhibitory. 20(R)-Ginsenoside Rh2 has anticancer, anti- proliferation, anti-inflammatory and antioxidative activities, it also shows selective osteoclastgenesis inhibitory activity. 20(R)-Ginsenoside Rh2 reduce apoptotic rate significantly, enhance the activity of caspase-3 and induces apoptosis in human lung adenocarcinoma A549 cells. |
Targets | NO | PGE | MMP(e.g.TIMP) | ROS | TNF-α | Caspase |
In vitro | Effects of 20 (S) -ginsenoside Rh2 and 20 (R) -ginsenoside Rh2 on proliferation and apoptosis of human lung adenocarcinoma A549 cells.[Pubmed: 22007558]Zhongguo Zhong Yao Za Zhi. 2011 Jun;36(12):1670-4. To evaluate and explore the effects of 20(S)-ginsenoside Rh2 and 20(R)-Ginsenoside Rh2 on the cytotoxicity, proliferation and the apoptosis of human lung adenocarcinoma A549 cells, and to illustrate the structure-activity relationship and possible mechanisms of anti-tumor active ingredients of ginseng. 20(R)-ginsenoside Rh2, not 20(S), is a selective osteoclastgenesis inhibitor without any cytotoxicity.[Pubmed: 19428246]Bioorg Med Chem Lett. 2009 Jun 15;19(12):3320-3.Increased osteoclastic bone resorption plays a central role in the pathogenesis of many bone diseases, and osteoclast inhibitors are the most widely used treatments for these diseases. Ginsenosides, the main component of ginseng, have been known for their medicinal effects such as anti-inflammatory and anti-proliferative activities. |
Kinase Assay | Anti-inflammatory, antioxidative and matrix metalloproteinase inhibitory properties of 20(R)-ginsenoside Rh2 in cultured macrophages and keratinocytes.[Pubmed: 23278699]J Pharm Pharmacol. 2013 Feb;65(2):310-6.This work aimed to assess the matrix metalloproteinase inhibitory and related pharmacological actions of 20(R)-Ginsenoside Rh2 (20(R)-Rh2) in cultured macrophages and keratinocytes. |
20(R)-Ginsenoside Rh2 Dilution Calculator
20(R)-Ginsenoside Rh2 Molarity Calculator
1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
1 mM | 1.6054 mL | 8.0272 mL | 16.0545 mL | 32.1089 mL | 40.1361 mL |
5 mM | 0.3211 mL | 1.6054 mL | 3.2109 mL | 6.4218 mL | 8.0272 mL |
10 mM | 0.1605 mL | 0.8027 mL | 1.6054 mL | 3.2109 mL | 4.0136 mL |
50 mM | 0.0321 mL | 0.1605 mL | 0.3211 mL | 0.6422 mL | 0.8027 mL |
100 mM | 0.0161 mL | 0.0803 mL | 0.1605 mL | 0.3211 mL | 0.4014 mL |
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. |
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20(R)-ginsenoside Rh2, not 20(S), is a selective osteoclastgenesis inhibitor without any cytotoxicity.[Pubmed:19428246]
Bioorg Med Chem Lett. 2009 Jun 15;19(12):3320-3.
Increased osteoclastic bone resorption plays a central role in the pathogenesis of many bone diseases, and osteoclast inhibitors are the most widely used treatments for these diseases. Ginsenosides, the main component of ginseng, have been known for their medicinal effects such as anti-inflammatory and anti-proliferative activities. In this study, we investigated the inhibitory effects of ginsenosides (ginsenoside 20(R)-Rh2 and ginsenoside 20(S)-Rh2) on osteoclastgenesis using RAW264 cells in vitro. Only ginsenoside 20(R)-Rh2 showed selective osteoclastgenesis inhibitory activity without any cytotoxicity up to 100 microM. These results implied that the stereochemistry of the hydroxyl group at C-20 may play an important role in selective osteoclastgenesis inhibitory activity.
Anti-inflammatory, antioxidative and matrix metalloproteinase inhibitory properties of 20(R)-ginsenoside Rh2 in cultured macrophages and keratinocytes.[Pubmed:23278699]
J Pharm Pharmacol. 2013 Feb;65(2):310-6.
OBJECTIVES: This work aimed to assess the matrix metalloproteinase inhibitory and related pharmacological actions of 20(R)-Ginsenoside Rh2 (20(R)-Rh2) in cultured macrophages and keratinocytes. METHODS: In-vitro anti-inflammatory activity of 20(R)-Rh2 was evaluated by analysing nitric oxide (NO) and prostaglandin E2 (PGE2) contents in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells. Its antioxidant activity was determined by measuring the level of reactive oxygen species (ROS) in the macrophage and keratinocyte cells. Matrix metalloproteinase-9 (MMP-9) and -2 (MMP-2) activity in the culture medium was detected using zymography. KEY FINDINGS: 20(R)-Rh2 was able to suppress NO, PGE2, ROS and pro-matrix metalloproteinase-9 (pro-MMP-9) levels that were enhanced in the LPS-stimulated murine RAW264.7 macrophage cells. 20(R)-Rh2 also exhibited inhibitory effects on the level of ROS and the activity of MMP-9 and -2 in human HaCat keratinocyte cells without stimulant exposure. 20(R)-Rh2 could suppress the gelatinolytic activity of MMP-9 enhanced by tumour necrosis factor-alpha in the keratinocytes. CONCLUSIONS: 20(R)-Rh2, a minor stereoisomer of ginsenoside Rh2, possesses matrix metalloproteinase inhibitory, anti-inflammatory and antioxidative activity.
[Effects of 20 (S) -ginsenoside Rh2 and 20 (R) -ginsenoside Rh2 on proliferation and apoptosis of human lung adenocarcinoma A549 cells].[Pubmed:22007558]
Zhongguo Zhong Yao Za Zhi. 2011 Jun;36(12):1670-4.
OBJECTIVE: To evaluate and explore the effects of 20(S)-ginsenoside Rh2 and 20(R)-Ginsenoside Rh2 on the cytotoxicity, proliferation and the apoptosis of human lung adenocarcinoma A549 cells, and to illustrate the structure-activity relationship and possible mechanisms of anti-tumor active ingredients of ginseng. METHOD: A549 cells were treated with different concentration gradient of ginsenoside Rh2 (S and R structure) and incubated for different time. Cell proliferation and cytotoxicity studies were detected by methyl thiazolyl tetrazolium (MTT) colorimetric assay, cell cycle and apoptotic was analyzed by PI stains and combination of Annexin V/Prop idium iodide double staining with flow cytometric analysis. The influences of activation on Caspase-3 were also detected by the immunofluorescence staining with fluorescence microscope. RESULT: MTT test indicated that ginsenoside Rh2 had a strong cytotoxicity activity to A549 cells. Ginsenoside Rh2 could obviously inhibit the cell proliferation in human lung adenocarcinoma cell line A549 at the effective doses of 25 mg x L(-1) treated with 48 h. The inhibition ratio and the value of IC50 for48 h of 20(R)-Rh2 and 20(S)-Rh2 were respectively 28.5%, 33.6% and 33.4, 28.5 mg x L(-1). The inhibition of ginsenoside Rh2 to A549 showed structure relationship significantly, time-dependent and concentration-dependent. Flow cytometric analysis (FACS) with PI stains analysis results showed that the proportion of A549 cells in G1 phase increased, while the number of cells in S phase decreased significantly and those in G2 phase reduced slightly. This result indicated structure relationship significantly, especially in the 20(S) -ginsenoside Rh2 inhibited the proliferation of A549 cell dramatically and retarded A549 cell cycle at G0/G1 phase. The immunofluorescent of combination with Annexin VFITC/PI by flow cytometric suggested ginsenoside Rh2 can induce inchoate apoptsis rate and late apoptosis rate of A549 cell significantly. All the results showed structure relationship significantly, especially in the 20(S)-ginsenoside Rh2. The immunofluorescent with fluorescence microscope suggested the activity of Caspase-3 were enhanced after ginsenoside Rh2 treated. CONCLUSION: 20 (R) and 20(S)-ginsenoside Rh2 had a significant inhibitory effect on the proliferation. Compared with 20(S)-ginsenoside Rh2, 20 (S)-ginsenoside Rh2 has been shown to have significant anticancer effects and to be capable of blocking cell proliferation and causing G1 phase arrest in human lung adenocarcinoma A549 cells. 20 (R) and 20(S)-ginsenoside Rh2 have been shown to have anticancer effects and to be capable of increasing inchoate apoptotic rate, reducing apoptotic rate significantly, enhancing the activity of Caspase-3 and inducing apoptosis in human lung adenocarcinoma A549 cells.