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Praeruptorin C

CAS# 72463-77-5

Praeruptorin C

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Chemical structure

Praeruptorin C

3D structure

Chemical Properties of Praeruptorin C

Cas No. 72463-77-5 SDF Download SDF
PubChem ID 5320692 Appearance Powder
Formula C24H28O7 M.Wt 428.48
Type of Compound Coumarins Storage Desiccate at -20°C
Synonyms 83382-71-2
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name [(9R,10R)-8,8-dimethyl-10-(3-methylbutanoyloxy)-2-oxo-9,10-dihydropyrano[2,3-f]chromen-9-yl] (Z)-2-methylbut-2-enoate
SMILES CC=C(C)C(=O)OC1C(C2=C(C=CC3=C2OC(=O)C=C3)OC1(C)C)OC(=O)CC(C)C
Standard InChIKey UFUVJROSOIXJGR-IULGZIFLSA-N
Standard InChI InChI=1S/C24H28O7/c1-7-14(4)23(27)30-22-21(29-18(26)12-13(2)3)19-16(31-24(22,5)6)10-8-15-9-11-17(25)28-20(15)19/h7-11,13,21-22H,12H2,1-6H3/b14-7-/t21-,22-/m1/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 Praeruptorin C

The roots of Peucedanum praeruptorum Dunn.

Biological Activity of Praeruptorin C

DescriptionPraeruptorin C has been widely used as an antioxidant and a calcium antagonist to treat diseases, it partially protects cortical neurons by inhibiting the expression of GluN2B-containing NMDA receptors and regulating the Bcl-2 family. It has cardioprotective effect , it can reduce vascular hypertrophy in isolated rat hypertrophied smooth muscle cells, is important in prevention and treatment of vascular hyperplastic disease.
TargetsCalcium Channel | Bcl-2/Bax | NMDAR | CYP3A
In vitro

The neuroprotective effect of praeruptorin C against NMDA-induced apoptosis through down-regulating of GluN2B-containing NMDA receptors.[Pubmed: 23313464]

Toxicol In Vitro. 2013 Mar;27(2):908-14.

Praeruptorin C (Pra-C), one of the principal bioactive components derived from the root of Peucedanum praeruptorum Dunn, has been widely used as an antioxidant and a calcium antagonist to treat diseases. The present study investigated the protective effect of Pra-C on cultured cortical neuron injury induced by glutamate.
METHODS AND RESULTS:
After challenge with 200μM N-methyl-d-aspartate (NMDA) for 30min, loss of cell viability and excessive apoptotic cell death were observed in cultured cortical neurons. Pra-C conferred protective effects against loss of cellular viability in a concentration-dependent manner. Pra-C also significantly inhibited neuronal apoptosis induced by NMDA exposure by reversing intracellular Ca(2+) overload and balancing Bcl-2 and Bax expression. Furthermore, Pra-C significantly reversed the upregulation of GluN2B-containing NMDA receptors by exposure to NMDA but did not affect the expression of GluN2A-containing NMDA receptors.
CONCLUSIONS:
These findings suggest that Pra-C partially protects cortical neurons by inhibiting the expression of GluN2B-containing NMDA receptors and regulating the Bcl-2 family.

Inhibitory effects of praeruptorin C on cattle aortic smooth muscle cell proliferation.[Pubmed: 11866872]

Acta Pharmacol Sin. 2002 Feb;23(2):129-32.

To study the effects of Praeruptorin C (pra-C) on proliferation of cattle aortic smooth muscle cells (SMC).
METHODS AND RESULTS:
The DNA synthesis of SMC was measured using the incorporation of [3H]thymidine([3H]TdR). Cell cycle phase was evaluated by flow cytometry and cytotoxicity was evaluated by measuring lactic dehydrogenase (LDH) activity. Whether or not treated with angiotensin II (Ang-II), SMC proliferation was suppressed by pra-C in a concentration-dependent manner at range from 0.001 micromol/L to 10 micromol/L. The inhibitory effects appeared to be related to G1-S block in cell cycle traverse while the LDH activities did not change dramatically.
CONCLUSIONS:
Pra-C can completely inhibit SMC proliferation induced by Ang II and partly inhibit the growth of SMC- induced by bovine serum, which is important in prevention and treatment of vascular hyperplastic disease.

Effects of praeruptorin C on myocardial plasma membrane calcium handling proteins during ischemia/reperfusion[Reference: WebLink]

Chinese Heart Journal, 2008(5):513-6.

To explore the cardioprotective mechanism of Praeruptorin C(Pra-C)during ischemia/reperfusion.METHODS Cultured rat neonatal cardiomyocytes were randomly divided into 3 groups: ischemia/reperfusion group(9 h ischemia followed by 1 h reperfusion,I/R),Pra-C pretreatment group(pretreated with Pra-C for 1 h before I/R) and control group.The leakage of intracellular lactate dehydrogenase(LDH) in various groups was determined by biochemical autoanalyzer.Activity of natrium-calcium exchanger(NCX) was indicated by Na+-dependent 45Ca2+ uptake tested by liquid scintillation counting.Semi-quantitative RT-PCR was employed to detect the mRNA level of NCX.Activity of plasma membrane calcium ATPase(PMCA) was determined by microcolorimetrg of inorganic phosphorus. Compared with that in I/R group,the LDH leakage in Pra-C pretreatment group was significantly reduced(P0.01).The Na+-dependent 45Ca2+ uptake was significantly increased in I/R group(P0.01) compared with that in control group.This increase could be significantly attenuated in Pra-C pretreatment group.The level of NCX mRNA in I/R group was also significantly increased(P0.01) compared with that in control group and this increase could be significantly attenuated in Pra-C pretreatment group(P0.01).No significant change of PMCA activity was observed between various groups.
CONCLUSIONS:
NCX mediates the cardioprotective effect of Pra-C during ischemia/reperfusion in the neonatal rat cardiomyocytes I/R model.

In vivo

Effects of praeruptorin C on blood pressure and expression of phospholamban in spontaneously hypertensive rats.[Pubmed: 24075213]

Phytomedicine. 2014 Feb 15;21(3):195-8.

The traditional Chinese medicine Praeruptorin C (Pra-c) has many physiological and pharmacological effects, including antagonistic effects on blood pressure and calcium levels, maintenance of cellular calcium homeostasis, and improved cardiac systolic and diastolic function. It is potentially a novel and versatile drug for the treatment and prevention of cardiovascular diseases. To explore the possible impact of Praeruptorin C on blood pressure in SHR and its mechanism of action.
METHODS AND RESULTS:
SHR treated with Praeruptorin C for 8 weeks had a lower systolic pressure than untreated SHR (p<0.05), two measures of cardiac damage, the heart mass index and left ventricle mass index (HMI and LVMI, respectively) were improved, and the level of PLB mRNA expression was lower in the untreated SHR group (p<0.05).
CONCLUSIONS:
With continuous hypertension, SHR gradually formed or developed cardiac hypertrophy and fibrosis. Praeruptorin C had a clear effect on blood pressure in SHR, and reversed SHR ventricular remodeling by upregulating the gene expression of sarcoplasmic reticulum PLB.

Protocol of Praeruptorin C

Cell Research

PXR-Mediated Upregulation of CYP3A Expression by Herb Compound Praeruptorin C from Peucedanum praeruptorum Dunn.[Pubmed: 24379885]

Effects of praeruptorin-C on cytosolic free calcium in cultured rat heart cells[Pubmed: 7516604]

Yao Xue Xue Bao. 1993;28(10):728-31.

The negative inotropic effect of Praeruptorin C(Pra-C) was supposed to be related to the blocking of extracellular calcium influx but direct evidence is not known.
METHODS AND RESULTS:
We, therefore, examined the effects of Pra-C on [Ca2+]i in isolated rat ventricular myocytes using the fluorescent Ca(2+)-indicator Fura-2/AM. It was found that Pra-C inhibited the elevation of [Ca2+]i induced by potassium-depolarization, high extracellular calcium and calcium agonist Bay K 8644 in a dose-dependent manner. At 1.0 mumol.L-1, it decreased the [Ca2+]i at the presence of 75 mmol.L-1 KCl, 10 mol.L-1 CaCl and 3 mumol.L-1 Bay K 8644 by 50, 31 and 42% respectively. No significant effect on ouabain evoked [Ca2+]i increase was found, showing that it does not affect sarcolemmal Na(+)-Ca2+ exchange.
CONCLUSIONS:
These results further indicate that Pra-C may decrease the [Ca2+]i of myocyte by blocking voltage-dependent calcium channels.

Evid Based Complement Alternat Med. 2013;2013:156574.

We recently reported that Praeruptorin C effectively transactivated the mRNA, protein expression, and catalytic activity of CYP3A4 via the CAR-mediated pathway, but whether and how PC could affect the expression and catalytic activity of CYP3A4 via PXR pathway remains unknown.
METHODS AND RESULTS:
Therefore, in this study, the effect of PC on the CYP3A gene expression was investigated in mice primary hepatocytes after knockdown of PXR by transient transfection of PXR siRNA, and the gene expression, protein expression, and catalytic activity of CYP3A4 in the LS174T cells with PXR overexpression were determined by real-time PCR, western blot analysis, and LC-MS/MS-based CYP3A4 substrate assay, respectively. We found that the level of CYP3a11 gene expression in mouse primary hepatocytes was significantly increased by Praeruptorin C, but such an induction was suppressed after knockdown of pregnane X receptor by its siRNA. In PXR-overexpressed LS174T cells, PC significantly enhanced CYP3A4 mRNA, protein expression, and functional activity through PXR-mediated pathway; conversely, no such increase was found in the untransfected cells.
CONCLUSIONS:
These findings suggest that PC can significantly upregulate CYP3A level via the PXR-mediated pathway, and this should be taken into consideration to predict any potential herb-drug interactions between PC, Qianhu, and the other coadministered drugs.

Praeruptorin C Dilution Calculator

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Preparing Stock Solutions of Praeruptorin C

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.3338 mL 11.6692 mL 23.3383 mL 46.6766 mL 58.3458 mL
5 mM 0.4668 mL 2.3338 mL 4.6677 mL 9.3353 mL 11.6692 mL
10 mM 0.2334 mL 1.1669 mL 2.3338 mL 4.6677 mL 5.8346 mL
50 mM 0.0467 mL 0.2334 mL 0.4668 mL 0.9335 mL 1.1669 mL
100 mM 0.0233 mL 0.1167 mL 0.2334 mL 0.4668 mL 0.5835 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 Praeruptorin C

PXR-Mediated Upregulation of CYP3A Expression by Herb Compound Praeruptorin C from Peucedanum praeruptorum Dunn.[Pubmed:24379885]

Evid Based Complement Alternat Med. 2013;2013:156574.

We recently reported that Praeruptorin C effectively transactivated the mRNA, protein expression, and catalytic activity of CYP3A4 via the CAR-mediated pathway, but whether and how PC could affect the expression and catalytic activity of CYP3A4 via PXR pathway remains unknown. Therefore, in this study, the effect of PC on the CYP3A gene expression was investigated in mice primary hepatocytes after knockdown of PXR by transient transfection of PXR siRNA, and the gene expression, protein expression, and catalytic activity of CYP3A4 in the LS174T cells with PXR overexpression were determined by real-time PCR, western blot analysis, and LC-MS/MS-based CYP3A4 substrate assay, respectively. We found that the level of CYP3a11 gene expression in mouse primary hepatocytes was significantly increased by Praeruptorin C, but such an induction was suppressed after knockdown of pregnane X receptor by its siRNA. In PXR-overexpressed LS174T cells, PC significantly enhanced CYP3A4 mRNA, protein expression, and functional activity through PXR-mediated pathway; conversely, no such increase was found in the untransfected cells. These findings suggest that PC can significantly upregulate CYP3A level via the PXR-mediated pathway, and this should be taken into consideration to predict any potential herb-drug interactions between PC, Qianhu, and the other coadministered drugs.

[Effects of praeruptorin-C on cytosolic free calcium in cultured rat heart cells].[Pubmed:7516604]

Yao Xue Xue Bao. 1993;28(10):728-31.

The negative inotropic effect of Pra-C was supposed to be related to the blocking of extracellular calcium influx but direct evidence is not known. We, therefore, examined the effects of Pra-C on [Ca2+]i in isolated rat ventricular myocytes using the fluorescent Ca(2+)-indicator Fura-2/AM. It was found that Pra-C inhibited the elevation of [Ca2+]i induced by potassium-depolarization, high extracellular calcium and calcium agonist Bay K 8644 in a dose-dependent manner. At 1.0 mumol.L-1, it decreased the [Ca2+]i at the presence of 75 mmol.L-1 KCl, 10 mol.L-1 CaCl and 3 mumol.L-1 Bay K 8644 by 50, 31 and 42% respectively. No significant effect on ouabain evoked [Ca2+]i increase was found, showing that it does not affect sarcolemmal Na(+)-Ca2+ exchange. These results further indicate that Pra-C may decrease the [Ca2+]i of myocyte by blocking voltage-dependent calcium channels.

The neuroprotective effect of praeruptorin C against NMDA-induced apoptosis through down-regulating of GluN2B-containing NMDA receptors.[Pubmed:23313464]

Toxicol In Vitro. 2013 Mar;27(2):908-14.

Praeruptorin C (Pra-C), one of the principal bioactive components derived from the root of Peucedanum praeruptorum Dunn, has been widely used as an antioxidant and a calcium antagonist to treat diseases. The present study investigated the protective effect of Pra-C on cultured cortical neuron injury induced by glutamate. After challenge with 200muM N-methyl-d-aspartate (NMDA) for 30min, loss of cell viability and excessive apoptotic cell death were observed in cultured cortical neurons. Pra-C conferred protective effects against loss of cellular viability in a concentration-dependent manner. Pra-C also significantly inhibited neuronal apoptosis induced by NMDA exposure by reversing intracellular Ca(2+) overload and balancing Bcl-2 and Bax expression. Furthermore, Pra-C significantly reversed the upregulation of GluN2B-containing NMDA receptors by exposure to NMDA but did not affect the expression of GluN2A-containing NMDA receptors. These findings suggest that Pra-C partially protects cortical neurons by inhibiting the expression of GluN2B-containing NMDA receptors and regulating the Bcl-2 family.

Effects of praeruptorin C on blood pressure and expression of phospholamban in spontaneously hypertensive rats.[Pubmed:24075213]

Phytomedicine. 2014 Feb 15;21(3):195-8.

BACKGROUND: The traditional Chinese medicine Praeruptorin C (Pra-c) has many physiological and pharmacological effects, including antagonistic effects on blood pressure and calcium levels, maintenance of cellular calcium homeostasis, and improved cardiac systolic and diastolic function. It is potentially a novel and versatile drug for the treatment and prevention of cardiovascular diseases. OBJECTIVE: To explore the possible impact of Pra-c on blood pressure in SHR and its mechanism of action. MATERIALS AND METHODS: Twenty SHR were randomly divided into a Pra-c group [Pra-c was administered intragastrically, 20 mg kg(-1) d(-1), n=10] or an untreated control group (n=10), containing 10 age-matched SD rats. Each group of rats was followed for 8 weeks. Before and during the treatment, tail artery systolic blood pressure was measured using a tail-cuff every 2 weeks. After 8 weeks, the rats were sacrificed and RNA was extracted from homogenates of cardiac tissue. Tissue from the left ventricle was fixed, sectioned and H&E stained to assess possible changes in myocardial cell structure and morphology. Semi-quantitative RT-PCR was used to assess changes in phospholamban gene expression in treated and untreated rats. RESULTS: SHR treated with Pra-c for 8 weeks had a lower systolic pressure than untreated SHR (p<0.05), two measures of cardiac damage, the heart mass index and left ventricle mass index (HMI and LVMI, respectively) were improved, and the level of PLB mRNA expression was lower in the untreated SHR group (p<0.05). DISCUSSION AND CONCLUSION: With continuous hypertension, SHR gradually formed or developed cardiac hypertrophy and fibrosis. Pra-c had a clear effect on blood pressure in SHR, and reversed SHR ventricular remodeling by upregulating the gene expression of sarcoplasmic reticulum PLB.

Inhibitory effects of praeruptorin C on cattle aortic smooth muscle cell proliferation.[Pubmed:11866872]

Acta Pharmacol Sin. 2002 Feb;23(2):129-32.

AIM: To study the effects of Praeruptorin C (pra-C) on proliferation of cattle aortic smooth muscle cells (SMC). METHODS: The DNA synthesis of SMC was measured using the incorporation of [3H]thymidine([3H]TdR). Cell cycle phase was evaluated by flow cytometry and cytotoxicity was evaluated by measuring lactic dehydrogenase (LDH) activity. RESULTS: Whether or not treated with angiotensin II (Ang-II), SMC proliferation was suppressed by pra-C in a concentration-dependent manner at range from 0.001 micromol/L to 10 micromol/L. The inhibitory effects appeared to be related to G1-S block in cell cycle traverse while the LDH activities did not change dramatically. CONCLUSION: Pra-C can completely inhibit SMC proliferation induced by Ang II and partly inhibit the growth of SMC- induced by bovine serum, which is important in prevention and treatment of vascular hyperplastic disease.

Description

Praeruptorin C is a main bioactive constituent of Peucedanum praeruptorum (also known as Bai-Hua Qian Hu). Praeruptorin C is a calcium antagonist with pD2′ value of 5.7.

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