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(+)-Praeruptorin A

CAS# 73069-27-9

(+)-Praeruptorin A

Catalog No. BCN4989----Order now to get a substantial discount!

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Chemical structure

(+)-Praeruptorin A

3D structure

Chemical Properties of (+)-Praeruptorin A

Cas No. 73069-27-9 SDF Download SDF
PubChem ID 38347607 Appearance Powder
Formula C21H22O7 M.Wt 386.4
Type of Compound Coumarins Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name [(9S,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-NXIDYTHLSA-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.
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 A

The roots of Peucedanum praeruptorum Dunn.

Biological Activity of (+)-Praeruptorin A

Description(+)-Praeruptorin A exerts distinct relaxant effects on isolated rat aorta rings, which may be mainly attributed to nitric oxide synthesis catalyzed by endothelial nitric oxide synthase.
TargetsNOS | Calcium Channel
In vitro

(+/-)-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.


METHODS AND RESULTS:
(+)-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).
CONCLUSIONS:
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 Dilution Calculator

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Preparing Stock Solutions of (+)-Praeruptorin A

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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References on (+)-Praeruptorin A

(+/-)-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.

Description

Praeruptorin A is a main bioactive constituent of Peucedanum praeruptorum (also known as Bai-Hua Qian Hu). Praeruptorin A exerts anti-inflammatory effects in vitro through inhibition of NF-κB activation.

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