(20S)-ProtopanaxdiolCAS# 30636-90-9 |
- (20R)-Protopanaxdiol
Catalog No.:BCN1078
CAS No.:7755-01-3
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 30636-90-9 | SDF | Download SDF |
| PubChem ID | 11213350 | Appearance | White powder |
| Formula | C30H52O3 | M.Wt | 460.7 |
| Type of Compound | Triterpenoids | Storage | Desiccate at -20°C |
| Synonyms | 20-Epiprotopanaxadiol; 20(S)-APPD | ||
| Solubility | DMSO : ≥ 100 mg/mL (217.05 mM) H2O : < 0.1 mg/mL (insoluble) *"≥" means soluble, but saturation unknown. | ||
| Chemical Name | (3S,5R,8R,9R,10R,12R,13R,14R,17S)-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]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-HKUCOEKDSA-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. |
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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(S)-Protopanaxdiol may be a potential new P-gp inhibitor for cancer treatment, it may induce the apoptosis via the down-regulation of Bcl-2 protein and the up-regulation of γH2Ax protein expression; it may inhibit the proliferation of Siha cells via the up-regulating the expressions of p53, p21, and autophagy related gene Beclin 1and MAP1-LC3, and down-regulating the expression of cyclin-E. |
| Targets | p53 | p21 | Bcl-2/Bax | P-gp | Caspase | γH2Ax |
| In vitro | Inhibitory effect of 20(s)-protopanaxdiol on proliferation of Siha cells in vitro and its mechanism.[Reference: WebLink]Journal of Jilin University, 2013, 39(05):909-12.To observe the effect of (20S)-Protopanaxdiol(PPD)on the cell cycle of Siha cells in vitro and to detect the transcription and expressions of p53,p21and cyclin-E,and to clarify the mechanism of its inhibitory effect on proliferation of Siha cells.
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| Kinase Assay | 20S-protopanaxadiol inhibits P-glycoprotein in multidrug resistant cancer cells.[Pubmed: 19291609]Planta Med. 2009 Aug;75(10):1124-8.One of the major causes for cancer cells to resist current chemotherapy is attributed to the over-expression of P-glycoprotein (P-gp), resulting in insufficient drug delivery to the tumor sites. |
| Cell Research | Inductive effect of (20s)-proto-panaxdiol on apoptosis of human prostate cancer PC3 cells cultivated in vitro and its mechanism[Reference: WebLink]Journal of Jilin University Medicine Edition, 2012, 38(3):482-5.To study the effect of (20S)-Protopanaxdiol (PPD) on apoptosis of human prostate cancer PC3 cells cultivated in vitro, and to clarify the mechanism of its anticancer action.
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(20S)-Protopanaxdiol Dilution Calculator
(20S)-Protopanaxdiol Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.1706 mL | 10.853 mL | 21.7061 mL | 43.4122 mL | 54.2652 mL |
| 5 mM | 0.4341 mL | 2.1706 mL | 4.3412 mL | 8.6824 mL | 10.853 mL |
| 10 mM | 0.2171 mL | 1.0853 mL | 2.1706 mL | 4.3412 mL | 5.4265 mL |
| 50 mM | 0.0434 mL | 0.2171 mL | 0.4341 mL | 0.8682 mL | 1.0853 mL |
| 100 mM | 0.0217 mL | 0.1085 mL | 0.2171 mL | 0.4341 mL | 0.5427 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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(20S)-Protopanaxadiol (20-Epiprotopanaxadiol) is an aglycon metabolic derivative of the protopanaxadiol-type ginseng saponin; apoptosis inducer. IC50 value: Target: apoptosis inducer (20S)-Protopanaxadiol was used to induce cytotoxicity for two human glioma cell lines, SF188 and U87MG. For the SF188 cells, (20S)-Protopanaxadiol activated caspases-3, -8, -7, and -9 within 3 h and induced rapid apoptosis, which could be partially inhibited by a general caspase blocker and completely abolished when the caspase blocker was used in combination with an antioxidant. (20S)-Protopanaxadiol also induced cell death in U87MG cells but did not activate any caspases in these cells [1]. aPPD was able to inhibit P-gp activity as potently as verapamil on MDR cells. The blockage of P-gp activity was highly reversible as wash-out of aPPD resulted in an immediate recovery of P-gp activity. Unlike verapamil, aPPD did not affect ATPase activity of P-gp suggesting a different mechanism of action [2].
References:
[1]. Liu GY, et al. 20S-protopanaxadiol-induced programmed cell death in glioma cells through caspase-dependent and -independent pathways. J Nat Prod. 2007 Feb;70(2):259-64.
[2]. Zhao Y, et al. 20S-protopanaxadiol inhibits P-glycoprotein in multidrug resistant cancer cells. Planta Med. 2009 Aug;75(10):1124-8.
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20S-protopanaxadiol inhibits P-glycoprotein in multidrug resistant cancer cells.[Pubmed:19291609]
Planta Med. 2009 Aug;75(10):1124-8.
One of the major causes for cancer cells to resist current chemotherapy is attributed to the over-expression of P-glycoprotein (P-gp), resulting in insufficient drug delivery to the tumor sites. Protopanaxadiol ginsenosides Rg3 and Rh2 are known to induce apoptosis and significantly enhance the tumor inhibitory effects of chemotherapeutics in a synergistic fashion. One of the possible mechanisms is by blocking P-gp activity. The final deglycosylation metabolite of protopanaxadiols (PPDs) IN VIVO is 20S-protopapanaxadiol (aglycone PPD, aPPD), which has also shown anticancer activity and synergy with chemotherapy drugs. In the present study, P-gp over-expressing cancer cells were utilized to test whether aPPD also inhibits P-gp activity. We found that aPPD caused similar cytotoxicity in P388adr cells as their parental non-MDR cells, suggesting that aPPD may not be a substrate of P-gp. On the other hand, the calcein AM efflux assay showed that aPPD was able to inhibit P-gp activity as potently as verapamil on MDR cells. The blockage of P-gp activity was highly reversible as wash-out of aPPD resulted in an immediate recovery of P-gp activity. Unlike verapamil, aPPD did not affect ATPase activity of P-gp suggesting a different mechanism of action. The above results indicate that aPPD, unlike its precursor ginsenosides Rg3 and Rh2, is not a substrate of P-gp. It is also the first time that aPPD has showed a reversible nature of its P-gp inhibition. In addition to its pro-apoptotic nature, aPPD may be a potential new P-gp inhibitor for cancer treatment.
