Praeruptorin ACAS# 73069-25-7 |
- (-)-Praeruptorin A
Catalog No.:BCN7664
CAS No.:14017-71-1
- (+)-Praeruptorin A
Catalog No.:BCN4989
CAS No.:73069-27-9
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
Cas No. | 73069-25-7 | SDF | Download SDF |
PubChem ID | 38347601 | Appearance | White powder |
Formula | C21H22O7 | M.Wt | 386.40 |
Type of Compound | Coumarins | Storage | Desiccate at -20°C |
Solubility | Soluble in chloroform; sparingly soluble in water | ||
Chemical Name | [(9R,10S)-10-acetyloxy-8,8-dimethyl-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)C | ||
Standard InChIKey | XGPBRZDOJDLKOT-CIRUDOSSSA-N | ||
Standard InChI | InChI=1S/C21H22O7/c1-6-11(2)20(24)27-19-18(25-12(3)22)16-14(28-21(19,4)5)9-7-13-8-10-15(23)26-17(13)16/h6-10,18-19H,1-5H3/b11-6-/t18-,19+/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 | Praeruptorin A exerts neuroprotective, anti-osteoclastogenic, anti-inflammatory, distinct relaxant effects, it is beneficial to facilitate nestin expression in myocarditis,and suitable in treatment of early myocarditis. Praeruptorin A can significantly up-regulate UGT1A1 expression in HepG2 cells partially via the CAR-mediated pathway. Praeruptorin A inhibited p38/Akt-c-Fos-NFATc1 signaling and PLCγ-independent Ca2+ oscillation. |
Targets | Calcium Channel | p38MAPK | Akt | NO | IL Receptor | TNF-α | NF-kB | IkB | Bcl-2/Bax | SOD | IKK |
In vitro | Praeruptorin a inhibits in vitro migration of preosteoclasts and in vivo bone erosion, possibly due to its potential to target calmodulin.[Pubmed: 25734761]J Nat Prod. 2015 Apr 24;78(4):776-82.Excessive activity and/or increased number of osteoclasts lead to bone resorption-related disorders. Here, we investigated the potential of Praeruptorin A to inhibit migration/fusion of preosteoclasts in vitro and bone erosion in vivo. Anti-osteoclastogenic activity of praeruptorin A via inhibition of p38/Akt-c-Fos-NFATc1 signaling and PLCγ-independent Ca2+ oscillation.[Pubmed: 24586466]PLoS One. 2014 Feb 21;9(2):e88974.A decrease of bone mass is a major risk factor for fracture. Several natural products have traditionally been used as herbal medicines to prevent and/or treat bone disorders including osteoporosis. Praeruptorin A is isolated from the dry root extract of Peucedanum praeruptorum Dunn and has several biological activities, but its anti-osteoporotic activity has not been studied yet.
Praeruptorin A inhibits lipopolysaccharide-induced inflammatory response in murine macrophages through inhibition of NF-κB pathway activation.[Pubmed: 20842678 ]Phytother Res. 2011 Apr;25(4):550-6.Praeruptorin A (PA) is a pyranocoumarin compound isolated from the dried root of Peucedanum praeruptorum Dunn (Umbelliferae). However, the antiinflammatory effect of PA has not been reported. |
In vivo | Praeruptorin A upregulates expression of nestin in experimental autoimmune myocarditis of rats[Reference: WebLink]Pharmacology & Clinics of Chinese Materia Medica, 2007, 23(3):21-3.To investigate the influence of dl-Praeruptorin A(Pd-Ia) on expression of intermediate filament protein nestin and its cardioprotective actions in myocarditis.[WT5"HZ] |
Cell Research | (+/-)-Praeruptorin A enantiomers exert distinct relaxant effects on isolated rat aorta rings dependent on endothelium and nitric oxide synthesis.[Pubmed: 20433815 ]Induction of UGT1A1 expression by praeruptorin A and praeruptorin C through hCAR pathway.[Pubmed: 23888707]Yao Xue Xue Bao. 2013 May;48(5):794-8.This study is purposed to investigate the effects of Praeruptorin A (PA) and praeruptorin C (PC) on UGT1A1 in HepG2 cells through hCAR pathway.
Chem Biol Interact. 2010 Jul 30;186(2):239-46.Praeruptorin A (PA) is a pyranocoumarin compound isolated from the dried root of Peucedanum praeruptorum Dunn (Umbelliferae). However, the antiinflammatory effect of PA has not been reported. The present study investigated the antiinflammatory effect of PA in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophage cells. |
Animal Research | Effects of dl-praeruptorin A on interleukin-6 level and Fas, bax, bcl-2 protein expression in ischemia-reperfusion myocardium.[Pubmed: 12230942]Acta Pharmacol Sin. 2002 Sep;23(9):769-74.To investigate the effects of dl-praeruptorin (Pd-Ia) on interleukin-6 (IL-6) level and apoptosis-related protein expression in ischemia-reperfusion myocardium.
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Praeruptorin A Dilution Calculator
Praeruptorin A Molarity Calculator
1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
1 mM | 2.588 mL | 12.94 mL | 25.8799 mL | 51.7598 mL | 64.6998 mL |
5 mM | 0.5176 mL | 2.588 mL | 5.176 mL | 10.352 mL | 12.94 mL |
10 mM | 0.2588 mL | 1.294 mL | 2.588 mL | 5.176 mL | 6.47 mL |
50 mM | 0.0518 mL | 0.2588 mL | 0.5176 mL | 1.0352 mL | 1.294 mL |
100 mM | 0.0259 mL | 0.1294 mL | 0.2588 mL | 0.5176 mL | 0.647 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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Anti-osteoclastogenic activity of praeruptorin A via inhibition of p38/Akt-c-Fos-NFATc1 signaling and PLCgamma-independent Ca2+ oscillation.[Pubmed:24586466]
PLoS One. 2014 Feb 21;9(2):e88974.
BACKGROUND: A decrease of bone mass is a major risk factor for fracture. Several natural products have traditionally been used as herbal medicines to prevent and/or treat bone disorders including osteoporosis. Praeruptorin A is isolated from the dry root extract of Peucedanum praeruptorum Dunn and has several biological activities, but its anti-osteoporotic activity has not been studied yet. MATERIALS AND METHODS: The effect of Praeruptorin A on the differentiation of bone marrow-derived macrophages into osteoclasts was examined by phenotype assay and confirmed by real-time PCR and immunoblotting. The involvement of NFATc1 in the anti-osteoclastogenic action of Praeruptorin A was evaluated by its lentiviral ectopic expression. Intracellular Ca(2+) levels were also measured. RESULTS: Praeruptorin A inhibited the RANKL-stimulated osteoclast differentiation accompanied by inhibition of p38 and Akt signaling, which could be the reason for Praeruptorin A-downregulated expression levels of c-Fos and NFATc1, transcription factors that regulate osteoclast-specific genes, as well as osteoclast fusion-related molecules. The anti-osteoclastogenic effect of Praeruptorin A was rescued by overexpression of NFATc1. Praeruptorin A strongly prevented the RANKL-induced Ca(2+) oscillation without any changes in the phosphorylation of PLCgamma. CONCLUSION: Praeruptorin A could exhibit its anti-osteoclastogenic activity by inhibiting p38/Akt-c-Fos-NFATc1 signaling and PLCgamma-independent Ca(2+) oscillation.
(+/-)-Praeruptorin A enantiomers exert distinct relaxant effects on isolated rat aorta rings dependent on endothelium and nitric oxide synthesis.[Pubmed:20433815]
Chem Biol Interact. 2010 Jul 30;186(2):239-46.
Praeruptorin A is a coumarin compound naturally occurring in the roots of Peucedanum praeruptorum Dunn., a commonly used traditional Chinese medicine for the treatment of certain respiratory diseases and hypertension. Although previous studies indicated the relaxant effects of (+/-)-Praeruptorin A on tracheal and arterial preparations, little is known about the functional characteristics of the enantiomers. In the present study, the two enantiomers were successfully isolated and identified by using a preparative Daicel Chiralpak AD-H column, and their relaxant effects on aorta rings were observed and compared. (+)-Praeruptorin A showed more potent relaxation than (-)-Praeruptorin A against KCl- and phenylephrine-induced contraction of rat isolated aortic rings with intact endothelium. Removal of the endothelium remarkably reduced the relaxant effect of (+)-Praeruptorin A but not that of (-)-Praeruptorin A. Pretreatment of aortic rings with N(omega)-nitro-L-arginine methyl ester (L-NAME, an inhibitor of nitric oxide synthase) or methylene blue (MB, a soluble guanylyl cyclase inhibitor) resulted in similar changes of the relaxant effects of the two enantiomers to endothelium removal. Molecular docking studies also demonstrated that (+)-Praeruptorin A was in more agreement to nitric oxide synthase pharmacophores than (-)-Praeruptorin A. On the other hand, the two enantiomers of Praeruptorin A could slightly attenuate the contraction of rat aortic rings induced by internal Ca(2+) release from sarcoplasmic reticulum (SR). These findings indicated that (+)-Praeruptorin A and (-)-Praeruptorin A exerted distinct relaxant effects on isolated rat aorta rings, which might be mainly attributed to nitric oxide synthesis catalyzed by endothelial nitric oxide synthase.
Praeruptorin A inhibits lipopolysaccharide-induced inflammatory response in murine macrophages through inhibition of NF-kappaB pathway activation.[Pubmed:20842678]
Phytother Res. 2011 Apr;25(4):550-6.
Praeruptorin A (PA) is a pyranocoumarin compound isolated from the dried root of Peucedanum praeruptorum Dunn (Umbelliferae). However, the antiinflammatory effect of PA has not been reported. The present study investigated the antiinflammatory effect of PA in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophage cells. PA significantly inhibited the LPS-induced production of nitric oxide (NO), interleukin-1beta (IL-1beta) and tumor necrosis factor-alpha (TNF-alpha). The mRNA and protein expressions of inducible nitric oxide synthase (iNOS), IL-1beta and TNF-alpha were also suppressed by this compound. Further study showed that PA decreased the cytoplasmic loss of inhibitor kappaB-alpha (IkappaB-alpha) protein and inhibited the translocation of NF-kappaB from cytoplasm to nucleus. Taken together, the results suggest that PA may exert antiinflammatory effects in vitro in LPS-stimulated RAW 264.7 macrophages through inhibition of NF-kappaB signal pathway activation.
Praeruptorin A inhibits in vitro migration of preosteoclasts and in vivo bone erosion, possibly due to its potential to target calmodulin.[Pubmed:25734761]
J Nat Prod. 2015 Apr 24;78(4):776-82.
Excessive activity and/or increased number of osteoclasts lead to bone resorption-related disorders. Here, we investigated the potential of Praeruptorin A to inhibit migration/fusion of preosteoclasts in vitro and bone erosion in vivo. Praeruptorin A inhibited the RANKL-induced migration/fusion of preosteoclasts accompanied by the nuclear translocation of NFATc1, a master regulator of osteoclast differentiation. Antimigration/fusion activity of Praeruptorin A was also confirmed by evaluating the mRNA expression of fusion-mediating molecules. In silico binding studies and several biochemical assays further revealed the potential of Praeruptorin A to bind with Ca(2+)/calmodulin and inhibit its downstream signaling pathways, including the Ca(2+)/calmodulin-CaMKIV-CREB and Ca(2+)/calmodulin-calcineurin signaling axis responsible for controlling NFATc1. In vivo application of Praeruptorin A significantly reduced lipopolysaccharide-induced bone erosion, indicating its possible use to treat bone resorption-related disorders. In conclusion, Praeruptorin A has the potential to inhibit migration/fusion of preosteoclasts in vitro and bone erosion in vivo by targeting calmodulin and inhibiting the Ca(2+)/calmodulin-CaMKIV-CREB-NFATc1 and/or Ca(2+)/calmodulin-calcineurin-NFATc1 signaling axis.
Effects of dl-praeruptorin A on interleukin-6 level and Fas, bax, bcl-2 protein expression in ischemia-reperfusion myocardium.[Pubmed:12230942]
Acta Pharmacol Sin. 2002 Sep;23(9):769-74.
AIM: To investigate the effects of dl-praeruptorin (Pd-Ia) on interleukin-6 (IL-6) level and apoptosis-related protein expression in ischemia-reperfusion myocardium. METHODS: Left anterior descending coronary artery was subjected to 30 min ischemia followed by 120 min reperfusion in open-chest anesthetized rats. Serum IL-6 level was measured by radioimmunoassay. Apoptosis-related protein Fas, bax, and bcl-2 expression was detected by immunohistochemistry and computer image analysis system. Infiltration of neutrophils was observed using Hematoxylin-Eosin staining under optical microscope. RESULTS: Pd-Ia 2.0 mg/kg iv lowered serum IL-6 level and Fas, bax, bcl-2 expression under conditions with hypotension and without changes on heart rate, but increased the ratio of bcl-2/bax. There existed a close linearity and positive correlation between IL-6 level and Fas, bax, bcl-2 expression. Whereas, the infiltration of neutrophils was mild. CONCLUSION: Pd-Ia elicits a novel target in the therapeutic prevention of postischemic cardiomyocyte death. The reason might be associated with modulating the expression of some immediate-early genes including IL-6, Fas, bax, and bcl-2 in ischemia-reperfusion myocardium.
[Induction of UGT1A1 expression by praeruptorin A and praeruptorin C through hCAR pathway].[Pubmed:23888707]
Yao Xue Xue Bao. 2013 May;48(5):794-8.
This study is purposed to investigate the effects of Praeruptorin A (PA) and praeruptorin C (PC) on UGT1A1 in HepG2 cells through hCAR pathway. PA and PC were incubated with HepG2 cells for 24 h and 48 h, mRNA and protein expressions of UGT1A1 were determined by real-time PCR and Western blotting assays. Additionally, effects of PA and PC on UGT1A1 mRNA and protein expressions were also measured after transient transfection of a specific CAR siRNA for 72 h in HepG2 cells. UGT1A1 mRNA and protein expression levels were significantly increased by PA and PC after incubation for 48 h. Moreover, the mRNA and protein up-regulations of UGT1A1 were attenuated by transient transfection of a specific CAR siRNA, suggesting the induction was mediated by CAR. The results suggest that PA and PC can significantly up-regulate UGT1A1 expression partially via the CAR-mediated pathway.