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(20R)-Protopanaxdiol

CAS# 7755-01-3

(20R)-Protopanaxdiol

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Quality Control of (20R)-Protopanaxdiol

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Chemical structure

(20R)-Protopanaxdiol

3D structure

Chemical Properties of (20R)-Protopanaxdiol

Cas No. 7755-01-3 SDF Download SDF
PubChem ID 3080644 Appearance White powder
Formula C30H52O3 M.Wt 460.74
Type of Compound Triterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (3S,8R,9R,10R,12R,13R,14S,17S)-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]phenanthrene-3,12-diol
SMILES CC(=CCCC(C)(C1CCC2(C1C(CC3C2(CCC4C3(CCC(C4(C)C)O)C)C)O)C)O)C
Standard InChIKey PYXFVCFISTUSOO-OIORDRSNSA-N
Standard InChI InChI=1S/C30H52O3/c1-19(2)10-9-14-30(8,33)20-11-16-29(7)25(20)21(31)18-23-27(5)15-13-24(32)26(3,4)22(27)12-17-28(23,29)6/h10,20-25,31-33H,9,11-18H2,1-8H3/t20-,21+,22?,23+,24-,25-,27-,28+,29-,30+/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.
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.
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.

Source of (20R)-Protopanaxdiol

The roots of Panax ginseng C. A. Mey.

Biological Activity of (20R)-Protopanaxdiol

DescriptionProtopanaxdiol is effective in preventing and healing obesity, fatty liver and hypertriglyceridemia in mice fed with a high-fat diet, it inhibits tumor interstitial microvascular density and its proliferation activity, finally inhibits tumor growth, it also inhibits expression of VEGF and bFGF protein. (20R)-Protopanaxdiol has protective effect on myocardial ischemia, which may be related to improving free radicals metabolism and myocardial metabolism, decreasing plasma TXA 2 levels.
Targetsp38MAPK | JNK | VEGFR | bFGF | ATF2
In vitro

Anti-Obesity effects of protopanaxdiol types of Ginsenosides isolated from the leaves of American ginseng (Panax quinquefolius L.) in mice fed with a high-fat diet.[Pubmed: 20627120]

Fitoterapia. 2010 Dec;81(8):1079-87.

Effects of protopanaxdiol (PDG) and protopanaxatriol (PTG) types of ginsenosides isolated from the leaves of American ginseng on porcine pancreatic lipase activity were determined in vitro.
METHODS AND RESULTS:
PDG inhibited the pancreatic lipase activity in a dose-dependent manner at the concentrations of 0.25-1mg/ml. It inhibited hydrolysis of about 83.2% of triolein at about 1mg/ml of PDG. However, PTG showed no inhibitory activity. Therefore, anti-obesity activity of PDG was evaluated in mice fed a high-fat diet.
CONCLUSIONS:
The results demonstrated that PDG was effective in preventing and healing obesity, fatty liver and hypertriglyceridemia in mice fed with a high-fat diet.

In vivo

Molecular mechanism of protopanaxadiol saponin fraction-mediated anti-inflammatory actions.[Pubmed: 25535478]

J Ginseng Res. 2015 Jan;39(1):61-8

Korean Red Ginseng (KRG) is a representative traditional herbal medicine with many different pharmacological properties including anticancer, anti-atherosclerosis, anti-diabetes, and anti-inflammatory activities. Only a few studies have explored the molecular mechanism of KRG-mediated anti-inflammatory activity.
METHODS AND RESULTS:
We investigated the anti-inflammatory mechanisms of the protopanaxadiol saponin fraction (PPD-SF) of KRG using in vitro and in vivo inflammatory models. PPD-SF dose-dependently diminished the release of inflammatory mediators [nitric oxide (NO), tumor necrosis factor-α, and prostaglandin E2], and downregulated the mRNA expression of their corresponding genes (inducible NO synthase, tumor necrosis factor-α, and cyclooxygenase-2), without altering cell viability. The PPD-SF-mediated suppression of these events appeared to be regulated by a blockade of p38, c-Jun N-terminal kinase (JNK), and TANK (TRAF family member-associated NF-kappa-B activator)-binding kinase 1 (TBK1), which are linked to the activation of activating transcription factor 2 (ATF2) and interferon regulatory transcription factor 3 (IRF3). Moreover, this fraction also ameliorated HCl/ethanol/-induced gastritis via suppression of phospho-JNK2 levels.
CONCLUSIONS:
These results strongly suggest that the anti-inflammatory action of PPD-SF could be mediated by a reduction in the activation of p38-, JNK2-, and TANK-binding-kinase-1-linked pathways and their corresponding transcription factors (ATF2 and IRF3).

Antimyocardial ischemic effects of Panax quinquefolium 20s-protopanaxdiol saponins (PQDS) and its mechanism[Reference: WebLink]

Journal of Chinese Pharmaceutical Sciences, 2002, 37(2):100-3.

To study the antimyocardial ischemic effects of Panax quinquefolium 20 s-protopanaxdiolsaponins (PQDS) extracted from the leaves of Panax quinquefolium and its mechanism.
METHODS AND RESULTS:
The changes of myocardial infarct size, the serum creatine phosphokinase(CK), lactate dehydrogenase (LDH), superoside dismutase(SOD), catalase(CAT) and glutathione peroxidase(GSH-Px) activity, the serum lipid peroxidation(LPO) and myocardial free fatty acid(FFA), lactic acid(LA) content and plasma prostacycline(PGI2) and thromboxane (TXA2) level were determined in rats with acute myocardial infarct model induced by ligating the left anterior descending coronary artery(LAD). After treated by PQDS(in a dosage of 12.5~50 mg · kg-1 iv at the same time of operation and 6 h later), the sizes of acute myocardial infarction were significantly reduced. The serum CK, LDH activity, the plasma TXA2 levels and myocardial FFA and LA contents were declined, while PGI2/TXA2 was increased significantly. In addition, serum LPO content was declined, SOD, CAT and GSH-Px levels were increased markedly.
CONCLUSIONS:
PQDS had protective effect on myocardial ischemia, which may be related to improving free radicals metabolism and myocardial metabolism, decreasing plasma TXA2 levels. Therefore, PQDS may be an effective drug for the treatment of myocardial ischemia.

Protocol of (20R)-Protopanaxdiol

Animal Research

Influences of Protopanaxdiol to vascular endothelial growth factor and basofibroblast growth factor protein expression of liver[Reference: WebLink]

Chinese Journal of Clinical Hepatology, 2008, 24(1):42-3.

To discuss influences of Protopanaxdiol to vascular endothelial growth factor and basofibroblast growth factor protein expression of liver.
METHODS AND RESULTS:
To construct liver cancer animal models and the expermental animals are divided into five groups.Each group includes ten animals.That is control group,CTX group,Protopanaxdiol 25mg/kg,50mg/kg,100mg/kg groups.After two weeks,all the expertimental animals will be killed.We'll determine tumor volume and weight,then deal it into tissue spices for immunohistochemistry. In Protoanaxdiol groups,bFGF and VEGF protein expression is lower than that control group,its tumor volume and weight is lower distinguishly.
CONCLUSIONS:
It suggests that Ppd inhibites expression of VEGF and bFGF protein,finally inhibites tumor growth.

(20R)-Protopanaxdiol Dilution Calculator

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Preparing Stock Solutions of (20R)-Protopanaxdiol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.1704 mL 10.8521 mL 21.7042 mL 43.4084 mL 54.2605 mL
5 mM 0.4341 mL 2.1704 mL 4.3408 mL 8.6817 mL 10.8521 mL
10 mM 0.217 mL 1.0852 mL 2.1704 mL 4.3408 mL 5.4261 mL
50 mM 0.0434 mL 0.217 mL 0.4341 mL 0.8682 mL 1.0852 mL
100 mM 0.0217 mL 0.1085 mL 0.217 mL 0.4341 mL 0.5426 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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References on (20R)-Protopanaxdiol

Anti-Obesity effects of protopanaxdiol types of Ginsenosides isolated from the leaves of American ginseng (Panax quinquefolius L.) in mice fed with a high-fat diet.[Pubmed:20627120]

Fitoterapia. 2010 Dec;81(8):1079-87.

Effects of protopanaxdiol (PDG) and protopanaxatriol (PTG) types of ginsenosides isolated from the leaves of American ginseng on porcine pancreatic lipase activity were determined in vitro. PDG inhibited the pancreatic lipase activity in a dose-dependent manner at the concentrations of 0.25-1mg/ml. It inhibited hydrolysis of about 83.2% of triolein at about 1mg/ml of PDG. However, PTG showed no inhibitory activity. Therefore, anti-obesity activity of PDG was evaluated in mice fed a high-fat diet. The results demonstrated that PDG was effective in preventing and healing obesity, fatty liver and hypertriglyceridemia in mice fed with a high-fat diet.

Molecular mechanism of protopanaxadiol saponin fraction-mediated anti-inflammatory actions.[Pubmed:25535478]

J Ginseng Res. 2015 Jan;39(1):61-8.

BACKGROUND: Korean Red Ginseng (KRG) is a representative traditional herbal medicine with many different pharmacological properties including anticancer, anti-atherosclerosis, anti-diabetes, and anti-inflammatory activities. Only a few studies have explored the molecular mechanism of KRG-mediated anti-inflammatory activity. METHODS: We investigated the anti-inflammatory mechanisms of the protopanaxadiol saponin fraction (PPD-SF) of KRG using in vitro and in vivo inflammatory models. RESULTS: PPD-SF dose-dependently diminished the release of inflammatory mediators [nitric oxide (NO), tumor necrosis factor-alpha, and prostaglandin E2], and downregulated the mRNA expression of their corresponding genes (inducible NO synthase, tumor necrosis factor-alpha, and cyclooxygenase-2), without altering cell viability. The PPD-SF-mediated suppression of these events appeared to be regulated by a blockade of p38, c-Jun N-terminal kinase (JNK), and TANK (TRAF family member-associated NF-kappa-B activator)-binding kinase 1 (TBK1), which are linked to the activation of activating transcription factor 2 (ATF2) and interferon regulatory transcription factor 3 (IRF3). Moreover, this fraction also ameliorated HCl/ethanol/-induced gastritis via suppression of phospho-JNK2 levels. CONCLUSION: These results strongly suggest that the anti-inflammatory action of PPD-SF could be mediated by a reduction in the activation of p38-, JNK2-, and TANK-binding-kinase-1-linked pathways and their corresponding transcription factors (ATF2 and IRF3).

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