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(20S)-Protopanaxatriol

CAS# 34080-08-5

(20S)-Protopanaxatriol

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Chemical structure

(20S)-Protopanaxatriol

3D structure

Chemical Properties of (20S)-Protopanaxatriol

Cas No. 34080-08-5 SDF Download SDF
PubChem ID 161798 Appearance White powder
Formula C30H52O4 M.Wt 476.7
Type of Compound Triterpenoids Storage Desiccate at -20°C
Synonyms 20(S)-APPT; g-PPT
Solubility DMSO : ≥ 47 mg/mL (98.59 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name (3S,5R,6S,8R,9R,10R,12R,13R,14S,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-3,6,12-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-PHFGEWBZSA-N
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 (20S)-Protopanaxatriol

The roots of Panax ginseng C. A. Mey.

Biological Activity of (20S)-Protopanaxatriol

Description(20S)-Protopanaxatriol is a metabolite of ginsenoside, works through the glucocorticoid receptor (GR) and oestrogen receptor (ER), and is also a LXRα inhibitor. (20S)-Protopanaxatriol shows strong and selective antimicrobial activity, it also has anti-oxidant activity. (20S)-Protopanaxatriol exerts cardioprotective effects against myocardial ischemic injury, by enhancing the anti-free-radical actions of heart tissues.
TargetsAntifection | Glucocorticoid receptor | Oestrogen receptor | LXRα
In vivo

Effect of 20(S)-protopanaxatriol and its epimeric derivatives on myocardial injury induced by isoproterenol.[Pubmed: 21528638]

Arzneimittelforschung. 2011;61(3):148-52.

It was reported Panax ginseng had diverse components and multifaceted pharmacological functions. This study aims to investigate the effect of (20S)-Protopanaxatriol (PT, CAS 179799-20-3) and its epimeric derivatives (20S, 24R-epoxy-dammarane-3beta, 6alpha, 12beta, 25-tetraol, PTD1 and 20S, 24S-epoxy-dammarane-3beta, 6alpha, 12beta, 25-tetraol, PTD2) on myocardial injury induced by isoproterenol in rats.
METHODS AND RESULTS:
Male Wistar rats were administered orally 20(S)-protopanaxatriol or its epimeric derivatives for 7 days. Four days after treatment, all rats, except those in the control group, were subcutaneously injected with isoproterenol (20 mg/kg) for 3 consecutive days. Two hours after the last isoproterenol injection, the rats were anaesthetized and sacrificed. The biochemical parameters were assayed and pathological examination of the heart tissues was performed. Administration of PT and PTD1 resulted in a reduction in creatine kinase and lactate dehydrogenase. PT and PTD1 Inhibited not only the elevation of malondialdehyde content, but also the reduction of superoxide dismutase activity, glutathione peroxidase and total antioxIdant capacity. The pathohistological changes induced by isoproterenol were also ameliorated by PT and PTD1.
CONCLUSIONS:
The present findings suggest that PT and PTD1 exerted cardioprotective effects against myocardial ischemic injury by enhancing the anti-free-radical actions of heart tissues. Furthermore the results indicated that the configuration of C-24 of the funan ring was involved in the phannacological action of the epimeric derivatives of 20(S)-protopanaxatriol.

Protocol of (20S)-Protopanaxatriol

Structure Identification
J Pharm Biomed Anal. 2014 Jan;88:497-508.

Identification of 20(S)-protopanaxatriol metabolites in rats by ultra-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry and nuclear magnetic resonance spectroscopy.[Pubmed: 24184656]

(20S)-Protopanaxatriol (PPT), one of the aglycones of ginsenosides, has been shown to exert cardioprotective effects against myocardial ischemic injury. However, studies on PPT metabolism have rarely been reported.
METHODS AND RESULTS:
This study is the first to investigate the in vivo metabolism of PPT following oral administration by ultra-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UPLC-Q/TOF-MS) and nuclear magnetic resonance (NMR) spectroscopy. The structures of the metabolites were identified based on the characteristics of their MS data, MS(2) data, and chromatographic retention times. A total of 22 metabolites, including 17 phase I and 5 phase II metabolites, were found and tentatively identified by comparing their mass spectrometry profiles with those of PPT. Two new monooxygenation metabolites, (20S,24S)-epoxy-dammarane-3,6,12,25-tetraol and (20S,24R)-epoxy-dammarane-3,6,12,25-tetraol, were chemicallly synthesized and unambiguously characterized according to the NMR spectroscopic data. The metabolic pathways of PPT were proposed accordingly for the first time. Results revealed that oxidation of (1) double bonds at Δ((24,25)) to form 24,25-epoxides, followed by rearrangement to yield 20,24-oxide forms; and (2) vinyl-methyl at C-26/27 to form corresponding carboxylic acid were the predominant metabolic pathways. Phase II metabolic pathways were proven for the first time to consist of glucuronidation and cysteine conjugation.
CONCLUSIONS:
This study provides valuable and new information on the metabolism of PPT, which is indispensable for understanding the safety and efficacy of PPT, as well as its corresponding ginsenosides.

(20S)-Protopanaxatriol Dilution Calculator

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Preparing Stock Solutions of (20S)-Protopanaxatriol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.0978 mL 10.4888 mL 20.9776 mL 41.9551 mL 52.4439 mL
5 mM 0.4196 mL 2.0978 mL 4.1955 mL 8.391 mL 10.4888 mL
10 mM 0.2098 mL 1.0489 mL 2.0978 mL 4.1955 mL 5.2444 mL
50 mM 0.042 mL 0.2098 mL 0.4196 mL 0.8391 mL 1.0489 mL
100 mM 0.021 mL 0.1049 mL 0.2098 mL 0.4196 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 (20S)-Protopanaxatriol

(20S)-Protopanaxatriol is a metabolite of ginsenoside, works through the glucocorticoid receptor (GR) and oestrogen receptor (ER), and is also a LXRα inhibitor and a PPARγ activator.

In Vitro:(20S)-Protopanaxatriol works through the glucocorticoid receptor (GR) and oestrogen receptor (ER) in human umbilical vein endothelial cells (HUVECs). (20S)-Protopanaxatriol (g-PPT) increases [Ca2+]i with an EC50 of 482 nM in HUVECs. (20S)-Protopanaxatriol (1 µM) elevates NO production via ERβ[1]. (20S)-Protopanaxatriol (PPT) inhibits the autonomous transactivation of Gal4-LXRα LBD, the T0901317-dependent transcription of SREBP-1c and its promoter. (20S)-Protopanaxatriol (10 μg/mL) blocks the recruitment of RNA polymerase II to the LXRE region of SREBP-1c. (20S)-Protopanaxatriol also inhibits T0901317-dependent transcription of LXRα target genes related to lipogenesis, and reduces T0901317-induced cellular triglyceride (TG) accumulation in primary hepatocytes, but does not alter transcription of ABCA1, also an LXRα target gene[2]. (20S)-Protopanaxatriol (1, 5, 10, 25 μM) increases GAL4/PPARγ transactivating activitys in COS-7 cells. (20S)-Protopanaxatriol (10 μM) induces adipogenesis via expression of aP2, LPL, and PEPCK via PPARγ activation. (20S)-Protopanaxatriol (10, 25 μM) also upregulates GLUT4 expression[3].

References:
[1]. Leung KW, et al. Protopanaxadiol and protopanaxatriol bind to glucocorticoid and oestrogen receptors in endothelial cells. Br J Pharmacol. 2009 Feb;156(4):626-37. [2]. Oh GS, et al. 20(S)-protopanaxatriol inhibits liver X receptor α-mediated expression of lipogenic genes in hepatocytes. J Pharmacol Sci. 2015 Jun;128(2):71-7. [3]. Han KL, et al. Ginsenoside 20S-protopanaxatriol (PPT) activates peroxisome proliferator-activated receptor gamma (PPARgamma) in 3T3-L1 adipocytes. Biol Pharm Bull. 2006 Jan;29(1):110-3.

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References on (20S)-Protopanaxatriol

Identification of 20(S)-protopanaxatriol metabolites in rats by ultra-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry and nuclear magnetic resonance spectroscopy.[Pubmed:24184656]

J Pharm Biomed Anal. 2014 Jan;88:497-508.

20(S)-Protopanaxatriol (PPT), one of the aglycones of ginsenosides, has been shown to exert cardioprotective effects against myocardial ischemic injury. However, studies on PPT metabolism have rarely been reported. This study is the first to investigate the in vivo metabolism of PPT following oral administration by ultra-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UPLC-Q/TOF-MS) and nuclear magnetic resonance (NMR) spectroscopy. The structures of the metabolites were identified based on the characteristics of their MS data, MS(2) data, and chromatographic retention times. A total of 22 metabolites, including 17 phase I and 5 phase II metabolites, were found and tentatively identified by comparing their mass spectrometry profiles with those of PPT. Two new monooxygenation metabolites, (20S,24S)-epoxy-dammarane-3,6,12,25-tetraol and (20S,24R)-epoxy-dammarane-3,6,12,25-tetraol, were chemicallly synthesized and unambiguously characterized according to the NMR spectroscopic data. The metabolic pathways of PPT were proposed accordingly for the first time. Results revealed that oxidation of (1) double bonds at Delta((24,25)) to form 24,25-epoxides, followed by rearrangement to yield 20,24-oxide forms; and (2) vinyl-methyl at C-26/27 to form corresponding carboxylic acid were the predominant metabolic pathways. Phase II metabolic pathways were proven for the first time to consist of glucuronidation and cysteine conjugation. This study provides valuable and new information on the metabolism of PPT, which is indispensable for understanding the safety and efficacy of PPT, as well as its corresponding ginsenosides.

Effect of 20(S)-protopanaxatriol and its epimeric derivatives on myocardial injury induced by isoproterenol.[Pubmed:21528638]

Arzneimittelforschung. 2011;61(3):148-52.

OBJECTIVE: It was reported Panax ginseng had diverse components and multifaceted pharmacological functions. This study aims to investigate the effect of 20(S)-protopanaxatriol (PT, CAS 179799-20-3) and its epimeric derivatives (20S, 24R-epoxy-dammarane-3beta, 6alpha, 12beta, 25-tetraol, PTD1 and 20S, 24S-epoxy-dammarane-3beta, 6alpha, 12beta, 25-tetraol, PTD2) on myocardial injury induced by isoproterenol in rats. METHODS: Male Wistar rats were administered orally 20(S)-protopanaxatriol or its epimeric derivatives for 7 days. Four days after treatment, all rats, except those in the control group, were subcutaneously injected with isoproterenol (20 mg/kg) for 3 consecutive days. Two hours after the last isoproterenol injection, the rats were anaesthetized and sacrificed. The biochemical parameters were assayed and pathological examination of the heart tissues was performed. RESULTS: Administration of PT and PTD1 resulted in a reduction in creatine kinase and lactate dehydrogenase. PT and PTD1 Inhibited not only the elevation of malondialdehyde content, but also the reduction of superoxide dismutase activity, glutathione peroxidase and total antioxIdant capacity. The pathohistological changes induced by isoproterenol were also ameliorated by PT and PTD1. CONCLUSION: The present findings suggest that PT and PTD1 exerted cardioprotective effects against myocardial ischemic injury by enhancing the anti-free-radical actions of heart tissues. Furthermore the results indicated that the configuration of C-24 of the funan ring was involved in the phannacological action of the epimeric derivatives of 20(S)-protopanaxatriol.

Description

(20S)-Protopanaxatriol is a metabolite of ginsenoside, works through the glucocorticoid receptor (GR) and oestrogen receptor (ER), and is also a LXRα inhibitor.

Keywords:

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