Echinatine

CAS# 480-83-1

Echinatine

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Chemical structure

Echinatine

3D structure

Chemical Properties of Echinatine

Cas No. 480-83-1 SDF Download SDF
PubChem ID 10197 Appearance White powder
Formula C15H25NO5 M.Wt 299.37
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Freely soluble in methanol and water; sparingly soluble in acetone
Chemical Name [(7S,8S)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl 2-hydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoate
SMILES CC(C)C(C(C)O)(C(=O)OCC1=CCN2C1C(CC2)O)O
Standard InChIKey SFVVQRJOGUKCEG-RZUNFUDNSA-N
Standard InChI InChI=1S/C15H25NO5/c1-9(2)15(20,10(3)17)14(19)21-8-11-4-6-16-7-5-12(18)13(11)16/h4,9-10,12-13,17-18,20H,5-8H2,1-3H3/t10-,12-,13-,15?/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 Echinatine

The herbs of Eupatorium cannabinum L.

Biological Activity of Echinatine

Description1. Echinatin can inhibit DNP-ATPase activity while stimulating range latent ATPase activity in the low concentration, so echinatin can disturb the mitochondrial energy transfer reactions and membrane permeability. 2. Echinatin exerts a protective effect against ischemia/reperfusion (I/R)-induced myocardial injury on hearts, this effect may be attributed to the antioxidant and anti-inflammatory activities of this compound.
TargetsATPase | TNF-α | IL Receptor

Echinatine Dilution Calculator

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Echinatine Molarity Calculator

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Preparing Stock Solutions of Echinatine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.3403 mL 16.7017 mL 33.4035 mL 66.807 mL 83.5087 mL
5 mM 0.6681 mL 3.3403 mL 6.6807 mL 13.3614 mL 16.7017 mL
10 mM 0.334 mL 1.6702 mL 3.3403 mL 6.6807 mL 8.3509 mL
50 mM 0.0668 mL 0.334 mL 0.6681 mL 1.3361 mL 1.6702 mL
100 mM 0.0334 mL 0.167 mL 0.334 mL 0.6681 mL 0.8351 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 Echinatine

The effects of echinatin and its related compounds on the mitochondrial energy transfer reaction.[Pubmed:6221118]

J Toxicol Sci. 1982 Nov;7(4):245-54.

To investigate the mechanism by which various biological action of licorice root are brought about, the effects of echinatin as a small constituent of Glycyrrhiza echinata and several related compounds on mitochondrial energy transfer reactions were examined. The results obtained were as follows: 1) Echinatin, 4'-hydroxychalcone, chalcone and 3,4'-dihydroxychalcone at a low concentration cause deterioration of respiratory control and oxidative phosphorylation of isolated rat liver mitochondria. 2) Chalcone and 4'-hydroxychalcone stimulate both latent and DNP-ATPase activity of mitochondria. Echinatin inhibits DNP-ATPase activity while stimulating range latent ATPase activity in the low concentration. 3) Chalcone and 4'-hydroxychalcone induce a rapid potassium release from mitochondrial vesicles, while echinatin and 3,4'-dihydroxychalcone have lesser effect than the former two substances. From these results, it can be concluded that echinatin and several related compounds disturb the mitochondrial energy transfer reactions and membrane permeability.

Cardioprotection provided by Echinatin against ischemia/reperfusion in isolated rat hearts.[Pubmed:27246834]

BMC Cardiovasc Disord. 2016 May 31;16:119.

BACKGROUND: This study evaluated the protective effect of Echinatin against myocardial ischemia/reperfusion (I/R) injury in rats. METHODS: The effect of Echinatin on cardiac function in rats subjected to I/R was demonstrated through improved Langendorff retrograde perfusion technology. Adult Sprague-Dawley rats were randomly divided into five groups, and myocardial infarct size was macroscopically estimated through 2,3,5-triphenyltetrazolium chloride staining. The coronary effluent was analyzed for the release of lactate dehydrogenase (LDH) and creatine kinase (CK) to assess the degree of cardiac injury. The concentrations of malondialdehyde (MDA), interleukin-6 (IL-6), and tumor necrosis factor-alpha (TNF-alpha) were determined along with superoxide dismutase (SOD) activity using ELISA. Finally, cardiomyocyte apoptosis analysis was conducted with POD, an in situ cell death detection kit. RESULTS: Echinatin (0.5 and 2.5 mug/mL) pretreatment enhanced the maximum up/down rate of the left ventricular pressure (+/-dp/dtmax), improved the heart rate, increased the left ventricular developed pressure (LVDP), enhanced the coronary flow, and reduced the CK and LDH levels in the coronary flow of the treated group compared with the I/R group. Echinatin limited the contents of CK and LDH, improved the LVDP, reduced the contents of MDA, IL-6, and TNF-alpha, and increased the SOD activity. The infarct size and cell apoptosis in the hearts of the rats in the Echinatin-treated group were smaller and lower, respectively, than those in the hearts of the rats in the I/R control group. CONCLUSION: Echinatin exerts a protective effect against I/R-induced myocardial injury on hearts. This effect may be attributed to the antioxidant and anti-inflammatory activities of this compound.

Semi-automated separation of the epimeric dehydropyrrolizidine alkaloids lycopsamine and intermedine: preparation of their N-oxides and NMR comparison with diastereoisomeric rinderine and echinatine.[Pubmed:24816769]

Phytochem Anal. 2014 Sep-Oct;25(5):429-38.

INTRODUCTION: The diversity of structure and, particularly, stereochemical variation of the dehydropyrrolizidine alkaloids can present challenges for analysis and the isolation of pure compounds for the preparation of analytical standards and for toxicology studies. OBJECTIVE: To investigate methods for the separation of gram-scale quantities of the epimeric dehydropyrrolizidine alkaloids lycopsamine and intermedine and to compare their NMR spectroscopic data with those of their heliotridine-based analogues Echinatine and rinderine. METHODS: Lycopsamine and intermedine were extracted, predominantly as their N-oxides and along with their acetylated derivatives, from commercial samples of comfrey (Symphytum officinale) root. Alkaloid enrichment involved liquid-liquid partitioning of the crude methanol extract between dilute aqueous acid and n-butanol, reduction of N-oxides and subsequent continuous liquid-liquid extraction of free base alkaloids into CHCl3 . The alkaloid-rich fraction was further subjected to semi-automated flash chromatography using boronated soda glass beads or boronated quartz sand. RESULTS: Boronated soda glass beads (or quartz sand) chromatography adapted to a Biotage Isolera Flash Chromatography System enabled large-scale separation (at least up to 1-2 g quantities) of lycopsamine and intermedine. The structures were confirmed using one- and two-dimensional (1) H- and (13) C-NMR spectroscopy. Examination of the NMR data for lycopsamine, intermedine and their heliotridine-based analogues Echinatine and rinderine allowed for some amendments of literature data and provided useful comparisons for determining relative configurations in monoester dehydropyrrolizidine alkaloids. A similar NMR comparison of lycopsamine and intermedine with their N-oxides showed the effects of N-oxidation on some key chemical shifts. A levorotatory shift in specific rotation from +3.29 degrees to -1.5 degrees was observed for lycopsamine when dissolved in ethanol or methanol respectively. CONCLUSION: A semi-automated flash chromatographic process using boronated soda glass beads was standardised and confirmed as a useful, larger scale preparative approach for separating the epimers lycopsamine and intermedine. The useful NMR correlations to stereochemical arrangements within this specific class of dehydropyrrolizidine alkaloid cannot be confidently extrapolated to other similar dehydropyrrolizidine alkaloids. Published 2014. This article is a U.S. Government work and is in the public domain in the USA.

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