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Przewaquinone A

目录号 : GC68298

Przewaquinone A 是一种亲脂性二萜醌,到目前为止仅存在于 Salvia przewalskii 中,有效抑制血管收缩。

Przewaquinone A Chemical Structure

Cas No.:76843-23-7

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5mg
¥13,500.00
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产品描述

Przewaquinone A, a lipophilic diterpene quinone present only in Salvia przewalskii, induces a potent inhibitory action on vascular contraction[1].

[1]. Alan K S Wan, et al. Vascular effects of different lipophilic components of "Danshen", a traditional Chinese medicine, in the isolated porcine coronary artery. J Nat Prod. 2008 Nov;71(11):1825-8.

Chemical Properties

Cas No. 76843-23-7 SDF Download SDF
分子式 C19H18O4 分子量 310.34
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1 mM 3.2223 mL 16.1114 mL 32.2227 mL
5 mM 0.6445 mL 3.2223 mL 6.4445 mL
10 mM 0.3222 mL 1.6111 mL 3.2223 mL
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Research Update

PEG-amino acid-przewaquinone a conjugations: Synthesis, physicochemical properties and protective effect in a rat model of brain ischemia-reperfusion

Bioorg Med Chem Lett 2020 Jan 1;30(1):126780.PMID:31784321DOI:10.1016/j.bmcl.2019.126780.

A total of 21 PEG-przewaquinone A conjugations with high drug loading ability, good water solubility and in vivo slow-release quality were obtained by conjugating Przewaquinone A with PEG through amino acids and tripeptides spacers respectively. Notably, compound 3a can obviously reduce the brain ischemia-reperfusion damage dose-dependently in a rat model, which indicated the efficacy of our PEG prodrug strategy.

Vascular effects of different lipophilic components of "Danshen", a traditional Chinese medicine, in the isolated porcine coronary artery

J Nat Prod 2008 Nov;71(11):1825-8.PMID:18855446DOI:10.1021/np800119k.

"Danshen" has been used for the treatment of various cardiovascular diseases in the People's Republic of China for many years. Two different forms of "Danshen" exist, with the roots of Salvia miltiorrhiza being the traditional form and the roots of Salvia przewalskii being a surrogate used in the western areas of mainland China. The most abundant lipophilic diterpene quinones present in S. miltiorrhiza and S. przewalskii roots, tanshinone IIA (1) and cryptotanshinone (2), inhibited contraction of the isolated porcine coronary artery to the thromboxane A(2) analogue, U46619. Przewaquinone A (3), a lipophilic diterpene quinone present only in S. przewalskii, induced a similar but greater inhibitory action on vascular contraction than 1 and 2. This effect of 3 was endothelium-independent and reversible. The present results suggest that 3 is more potent than 1 and 2 and may contribute to a great extent to the ability of S. przewalskii roots to inhibit vascular contractions.

Simultaneous determination of tanshinone IIA and its three hydroxylated metabolites by liquid chromatography/tandem mass spectrometry

Rapid Commun Mass Spectrom 2006;20(5):815-22.PMID:16470728DOI:10.1002/rcm.2367.

A rapid and sensitive method based on liquid chromatography/tandem mass spectrometry (LC/MS/MS) for the simultaneous determination of tanshinone IIA and its three hydroxylated metabolites, tanshinone IIB, hydroxytanshinone IIA and Przewaquinone A, in a rat liver microsome was developed and fully validated. A single step of liquid-liquid extraction with ethyl acetate was utilized in this method. Chromatographic separation of the sample matrix from the analytes and the internal standard diazepam was performed using a Shim-pack VP-ODS analytical column. Detection was performed on a triple quadrupole tandem mass spectrometer equipped with an electrospray ionization source and operated in selected reaction monitoring (SRM) mode. The method was linear in the concentration range of 1-500 ng/mL for all analytes. The intra- and inter-day precisions (RSD %) were within 15% and deviations of the assay accuracies were within 15.0% for all analytes. The analytes proved to be stable during sample storage, preparation and analyses. This validated method was successfully applied to the enzyme kinetic study of tanshinone IIA in liver microsome. The elimination of tanshinone IIA and formation of tanshinone IIB and hydroxytanshinone IIA in the liver microsome all exhibited a sigmoidal kinetics profile. The formation of Przewaquinone A shows a typical hyperbolic profile. In addition, this method has now been applied in the analysis of other bio-samples including plasma, urine, bile and feces.

Profiling the metabolic difference of seven tanshinones using high-performance liquid chromatography/multi-stage mass spectrometry with data-dependent acquisition

Rapid Commun Mass Spectrom 2007;21(14):2211-26.PMID:17569103DOI:10.1002/rcm.3080.

Tanshinones are a class of bioactive constituents in the roots of Salvia miltiorrhiza named Dan-Shen in Chinese, which possess diverse pharmacological activities. In this study, we employed a sensitive high-performance liquid chromatography/multi-stage mass spectrometry (HPLC/MS(n)) method with data-dependent acquisition and a dynamic exclusion program for the identification of phase I metabolites of seven tanshinones in rat bile after intravenous administration. These seven tanshinones are tanshinone IIA, sodium tanshinone IIA sulfonate (abbreviated as STS, a water-soluble derivate of tanshinone IIA), cryptotanshinone, 15,16-dihydrotanshinone I, tanshinone IIB, Przewaquinone A and tanshinone I. Altogether 33 metabolites underwent monohydroxylation, dihydroxylation, dehydrogenation, D-ring hydrolysis or oxidation reactions in the C-4 or C-15 side chain which were characterized by analyzing the LC/MS(n) data. Different metabolic reactions for tanshinones were dependent on the degree of saturation and the substituent group in the skeleton. Dehydrogenation was the major metabolic modification for cryptotanshinone with saturated A and D rings. 15,16-Dihydrotanshinone I containing a saturated D ring was mainly metabolized through D-ring hydrolysis. For tanshinone IIA, possessing a saturated A ring, hydroxylation was the major metabolic pathway. When there was hydroxyl group substitution in the C-17 or C-18 position, such as Przewaquinone A and tanshinone IIB, or sulfonic group substitution in the C-16 position, such as STS, higher metabolic stability than that of tanshinone IIA was shown and only trace metabolites were generated. Oxidation in the C-4 or C-15 side chain was a characteristic reaction for tanshinone IIA and hydroxylated tanshinone IIA. For tanshinone I, bearing unsaturated A and D rings simultaneously, no metabolites were detected.

Identification of tanshinone IIA metabolites in rat liver microsomes by liquid chromatography-tandem mass spectrometry

J Chromatogr A 2006 Feb 3;1104(1-2):366-9.PMID:16405978DOI:10.1016/j.chroma.2005.12.047.

Tanshinone IIA, the major component extracted from Radix salvia miltiorrhiza, has been observed to possess various kinds of pharmacological activities including antioxidant, prevention of angina pectoris and myocardial infarction and anticancer. Tanshinone IIA was incubated with rat liver microsomes and the resulting metabolites were identified by liquid chromatography/tandem mass spectrometry. The results showed the formation of three main hydroxyl metabolites. The three hydroxyl metabolites of tanshinone IIA were proved to be tanshinone IIB, hydroxytanshinone IIA and Przewaquinone A by comparing the tandem mass spectra and the chromatographic retention time with that of the respective authentic compounds. Tanshinone IIB, hydroxytanshinone IIA and Przewaquinone A are all the chemical components of total tanshinones. It was reasonable to presume that the three hydroxy metabolites of tanshinone IIA were pharmacologically active the same as tanshinone IIA and the total tanshinones.