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20(R)-Protopanaxatriol

CAS# 1453-93-6

20(R)-Protopanaxatriol

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Quality Control of 20(R)-Protopanaxatriol

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Chemical structure

20(R)-Protopanaxatriol

3D structure

Chemical Properties of 20(R)-Protopanaxatriol

Cas No. 1453-93-6 SDF Download SDF
PubChem ID 9847853 Appearance White powder
Formula C30H52O4 M.Wt 476.73
Type of Compound Triterpenoids Storage Desiccate at -20°C
Synonyms 20(R)-APPT; 20(R)-Protopanaxatriol
Solubility DMSO : ≥ 32 mg/mL (67.12 mM);
Chemical Name (3S,5R,6S,8R,9R,10R,12R,13R,14R,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-3,6,12-triol
SMILES CC(=CCCC(C)(C1CCC2(C1C(CC3C2(CC(C4C3(CCC(C4(C)C)O)C)O)C)O)C)O)C
Standard InChIKey SHCBCKBYTHZQGZ-DLHMIPLTSA-N
Standard InChI InChI=1S/C30H52O4/c1-18(2)10-9-13-30(8,34)19-11-15-28(6)24(19)20(31)16-22-27(5)14-12-23(33)26(3,4)25(27)21(32)17-29(22,28)7/h10,19-25,31-34H,9,11-17H2,1-8H3/t19-,20+,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 20(R)-Protopanaxatriol

The roots of Panax ginseng C. A. Mey.

Biological Activity of 20(R)-Protopanaxatriol

Description20(R)-Protopanaxatriol shows anti-hyperglycaemic, and anti-cancer activities.Protopanaxatriol has inhibitory effects on the enzyme catalytic activities of cyclooxygenases-1 and -2 (COX-1 and -2).
TargetsCOX | PPAR
In vitro

Cyclooxygenase inhibitory activity of ginsenosides from heat-processed ginseng.[Reference: WebLink]

Food Chem., 2012, 133(3):998-1000.

Ginsenosides, from heat-processed ginseng, and sapogenins were evaluated for their inhibitory effects on the enzyme catalytic activities of cyclooxygenases-1 and -2 (COX-1 and -2).
METHODS AND RESULTS:
The ginsenosides, 20(S)-Rg3, Rg5, and Rk1, inhibited COX-2 activity, but did not affect the enzyme activity of COX-1. Protopanaxatriol (PPT) moderately inhibited both COX-1 and -2. The ginsenosides, 20(R)-Rg3, Re, and protopanaxadiol (PPD) showed a minimal effect on COX-1 and -2 activities.
CONCLUSIONS:
Taken together, ginsenosides Rg3 (20S-form), Rg5 and Rk1 showed selective inhibitory activity on COX-2 by behaving as an inhibitor of the enzyme–substrate reaction.

Semisynthesis and cytotoxicity evaluation of a series of ocotillol type saponins and aglycones from 20(S)-ginsenoside Rg2, Rh1, protopanaxatriol and their 20(R)-epimers[Reference: WebLink]

Chemical Research in Chinese Universities, 2016, 32(1): 1-6.

With the oxidation treatment, eighteen compounds were separated from 20(S)-ginsenoside Rg2, Rh1, protopanaxatriol(PPT) and their 20(R)-epimers in total and cytotoxicity of most of them was evaluated against three human cancer cell lines HeLa, A549 and MCF-7 by 3-(4,5-dimetylthiazol-z-yl)-2,5-diphenyltetrazolium bromide(MTT) assay.
METHODS AND RESULTS:
Their structures were confirmed by means of nuclear magnetic resonance(NMR) and mass spectrometry and the results were compared with those of previous literature. In this study, we systematically semisynthesized all four ocotillol type saponins, i.e., (20S, 24S), (20S, 24R), (20R, 24S) and (20R, 24R). All the configurations at C20 kept the same with their starting materials. Meanwhile a pair of C24 epimers was generated in terms of ocotillol type saponins. In addition, seven compounds(4―8, 13 and 14) were reported firstly.
CONCLUSIONS:
The cytotoxic results distinguished the ocotillol type products(6, 7, 13 and 14) from 20(R)-Protopanaxatriol and 20(R)-ginsenoside Rh1, which possessed better cytotoxicities than their correspondents from 20(S)-epimers against HeLa cells, and the carbonyl group at C3 can improve the cytotoxicity, which helped us to gain deeper insight into Ocotillol type saponins.

Protocol of 20(R)-Protopanaxatriol

Structure Identification
J. Funct. Foods, 2016, 23:188-97.

The inhibition of α-glycosidase and protein tyrosine phosphatase 1B (PTP1B) activities by ginsenosides from Panax ginseng C.A. Meyer and simultaneous determination by HPLC-ELSD.[Reference: WebLink]

Panax ginseng C.A. Meyer is extensively used as a food additive because of its medicinal and nutritional properties.
METHODS AND RESULTS:
This study investigated the inhibitory activity of eight ginsenosides against α-glycosidase and protein tyrosine phosphatase 1B (PTP1B). Results showed the anti-hyperglycaemic activities of the eight ginsenosides were in the order of 20(R)-dammarane-3β, 6α, 12β, 20, 25-pentol (25-OH-PPT) > 20(R)-25-methoxydammarane-3β, 12β, 20-tetrol (25-OCH3-PPT) > 20(R)-Protopanaxatriol (PPT) > 20(S)-panaxatriol (PT) > 20(R)-dammarane-3β, 12β, 20, 25-tetrol (25-OH-PPD) > 20(R)-25-methoxydammarane-3β, 12β, 20-triol (25-OCH3-PPD) > 20(R)-protopanaxadiol (PPD) > 20(S)-panaxadiol (PD), and 25-OH-PPT exerted stronger inhibitory activity than acarbose and Na3VO4. Meanwhile, simultaneous quantitative estimation results of eight ginsenosides suggested good linear regression within test ranges, precision, accuracy. 25-OH-PPT of the stems (leaves), flowers, and fruits contained 2.69, 3.31 and 7.20%, respectively.
CONCLUSIONS:
High performance liquid chromatography-evaporative light-scattering detector (HPLC-ELSD) method was proven to be simple, fast, and effective.

20(R)-Protopanaxatriol Dilution Calculator

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20(R)-Protopanaxatriol Molarity Calculator

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Preparing Stock Solutions of 20(R)-Protopanaxatriol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.0976 mL 10.4881 mL 20.9762 mL 41.9525 mL 52.4406 mL
5 mM 0.4195 mL 2.0976 mL 4.1952 mL 8.3905 mL 10.4881 mL
10 mM 0.2098 mL 1.0488 mL 2.0976 mL 4.1952 mL 5.2441 mL
50 mM 0.042 mL 0.2098 mL 0.4195 mL 0.839 mL 1.0488 mL
100 mM 0.021 mL 0.1049 mL 0.2098 mL 0.4195 mL 0.5244 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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Background on 20(R)-Protopanaxatriol

Protopanaxatriol is a natural PPARγ antagonist with an IC50 of 11.75 μM (Ki=4.2 μM).

In Vitro:Protopanaxatriol (PPT) does not show an inhibitory effect on other nuclear receptors involved in metabolic disorders, such as PPARα and PPARβ/σ, LXRα and LXRβ. A competitive binding assay using TR-FRET is performed. Protopanaxatriol is able to displace the Rosiglitazone from binding to PPARγ at an IC50 value of 11.75 μM (Ki=4.2 μM). Compared with unlabeled Rosiglitazone (Ki=43 nM), the PPARγ binding affinity of PPT is moderate[1]. To evaluate whether PPD, Protopanaxatriol (PPT), G-Rg3 and G-Rh2 regulate viability of lung cancer cells, the CCK-8 assay is performed to analysis the effect of these four compounds on the viability of A549 or SK-MES-1 cells. For A549 cells, all these compounds (PPD, Protopanaxatriol, G-Rg3 and G-Rh2) can notably inhibit the viability in a dosage-dependent manner (P<0.05, P<0.01 or P<0.001), especially at the concentration of 40 uM[2].

In Vivo:Protopanaxatriol, a novel PPARγ antagonist from Panax ginseng, alleviates steatosis in mice. onsistent with the increase of body temperature, the expression of uncoupling protein (UCP)-1, UCP-2 and UCP-3 genes, involved in energy dissipation and adoptive thermogenesis in brown adipose tissue (BAT), is enhanced in the brown adipose tissue (BAT) of PPT-treated mice. The other adipose tissue involving in the heat production and energy expenditure is beige adipose in WAT. The elevated expression of UCP-1 is a key feature for browning of WAT. Protopanaxatriol treatment increases the expression of UCP-1 in WAT[1].

References:
[1]. Zhang Y, et al. Protopanaxatriol, a novel PPARγ antagonist from Panax ginseng, alleviates steatosis in mice. Sci Rep. 2014 Dec 9;4:7375. [2]. Xu FY, et al. The antitumor activity study of ginsenosides and metabolites in lung cancer cell. Am J Transl Res. 2016 Apr 15;8(4):1708-18.

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References on 20(R)-Protopanaxatriol

Simultaneous determination of five active hydrolysis ingredients from Panax quinquefolium L. by HPLC-ELSD.[Pubmed:20737654]

Biomed Chromatogr. 2011 Jun;25(6):646-51.

An effective method for simultaneous determination of five hydrolysis products of 20 (R)-dammarane-3beta,6alpha,12beta,20,25-pentol, 24(R)-ocotillol, 20(R)-Protopanaxatriol, 20(S)-panaxatriol and 20(R)-dammarane-3beta,12beta,20,25-tetrol was developed using high-performance liquid chromatography with evaporative light scattering detection (HPLC-ELSD). The hydrolysis products from Panax quinquefolium L. in the stems and leaves, berries, flower buds and roots components were successfully separated on a Kromasil C(18) column using methanol and water (83:17, v/v) as mobile phase in 18 min. The parameter for the ELSD was set to a probe temperature of 40 degrees C and the nebulizer for nitrogen gas was adjusted to 3 L/min. All calibration curves showed good linear regression (r > 0.9975) within test ranges. The validation of the method included recovery, linearity, accuracy and precision (intra- and inter-day variation). The accuracy and precision were satisfactory, with the overall intra- and inter-day variation being less than 3.11%, and recoveries of this method were greater than 95.0%. This study developed an effective and rapid method for simultaneous determination of multiple hydrolysis components from Panax quinquefolium L.

Description

Protopanaxatriol, a major ginseng constituent, is a novel PPARγ antagonist.The inhibition of PPARγ activity could be a promising therapy for obesity and steatosis.

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