Evocarpine | CAS:15266-38-3 | Manufacturer ChemFaces

Evocarpine

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Description:

Evocarpine shows antimycobacterial, and vasorelaxant effects, it can inhibit Ca2+ influx through voltage-dependent calcium channels.

Targets:

Antifection | Calcium Channel | cAMP

In vitro:

J Appl Microbiol. 2015 Apr;118(4):864-72.

Antagonistic effects of indoloquinazoline alkaloids on antimycobacterial activity of evocarpine.[Pubmed: 25604161]

The interaction of quinolone and indoloquinazoline alkaloids concerning their antimycobacterial activity was studied.
METHODS AND RESULTS:
The antimycobacterial and modulating activity of evodiamine (1), rutaecarpine (2) and Evocarpine (3) was tested on mycobacteria including three multidrug-resistant (MDR) clinical isolates of Mycobacterium tuberculosis. Antagonistic effects were concluded from fractional inhibitory concentration (FICI) values. Interaction energies of the compounds were calculated using GLUE docking module implemented in GRID. 1 and 2 exhibited weak inhibition of rapidly growing mycobacteria, however, 1 was active against Myco. tuberculosis H37Rv (MIC = 10 mg l(-1) ) while 2 was inactive. Both 1 and 2 showed a marked antagonistic effect on the susceptibility of different mycobacterial strains to 3 giving FICI values between 5 and 9. The interaction energies between compounds 1 and 2 with compound 3 suggested the possibility of complex formation in solution.
CONCLUSIONS:
Indoloquinazoline alkaloids markedly reduce the antimycobacterial effect of the quinolone alkaloid Evocarpine. Complex formation may play a role in the attenuation of its antimycobacterial activity.

Planta Medica, 2012, 78(11):1142-1142.

Characterization of in vitro metabolites of evocarpine in rat liver microsomes and their influence on antibacterial activity[Reference: WebLink]

METHODS AND RESULTS:
After incubation of Evocarpine, the major bioactive compound of the n-hexane extract of the fruits of Evodiae fructus, with rat liver microsomes (S9 mix) nine metabolites were identified by their characteristic product ions using LC-PDA-ESI-MS analysis. The main biotransformation reactions observed were hydroxylation, hydration, dehydrogenation and N-demethylation. Comparison of incubation times between 1 and 72 hours showed no qualitative difference in biotransformation.
CONCLUSIONS:
In order to assess the influence of metabolism on the antibacterial activity of Evocarpine and the crude extract, the test solutions were pre-incubated with the S9 mix prior the determination of the minimum inhibitory concentration (MIC), which revealed a four-fold increase of the MIC against Mycobacterium smegmatis ATCC 14468 for pre-incubation times of 1, 24 and 72 hours for the crude extract and a sixteen-fold increase for Evocarpine for a pre-incubation time of 1 hour.

Evocarpine Description

Source:	The fruits of Evodiae fructus.
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage:	Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C). Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
After receiving:	The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.

Kinase Assay:

Eur J Pharmacol. 1988 Oct 11;155(1-2):139-43.

The vasorelaxant effect of evocarpine in isolated aortic strips: mode of action.[Pubmed: 2854068]

The effect of Evocarpine (EVO), a quinolone alkaloid isolated from Evodiae fructus, on Ca2+-blocking activity has been examined.
METHODS AND RESULTS:
In the isolated rat thoracic aorta Evocarpine significantly inhibited the contraction induced by 60 mM K+ with an IC50 of 9.8 microM, and that induced by external Ca2+ in the depolarized muscle in concentrations of 10-100 microM. The relaxant effect of Evocarpine and verapamil was antagonized by Bay K8644. The increase of 45Ca2+-influx induced by 60 mM K+ was significantly inhibited by 100 microM Evocarpine. In the isolated rabbit thoracic aorta 100 microM Evocarpine had no effect on the norepinephrine-induced contraction in normal medium or on the phasic contraction in Ca2+-free medium or on the transient relaxation induced by activation of the Na+ pump. The content of cyclic AMP or cyclic GMP was unchanged.
CONCLUSIONS:
These results suggest that Evocarpine inhibits Ca2+ influx through voltage-dependent calcium channels.

Product Name	Evocarpine
Price:
CAS No.:	15266-38-3
Catalog No.:	CFN96759
Molecular Formula:	C₂₃H₃₃NO
Molecular Weight:	339.52 g/mol
Purity:	>=98%
Type of Compound:	Alkaloids
Physical Desc.:	Oil
Source:	The fruits of Evodiae fructus.
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download:	COA MSDS
Similar structural:	Comparison (Web) (SDF)
Guestbook:

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Antibacterial Compound Library Vasorelaxation Compound Library Alkaloids Compound Library cAMP Inhibitor Library Calcium Channel Inhibitor Library Antifection Inhibitor Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	2.9453 mL	14.7267 mL	29.4533 mL	58.9067 mL	73.6334 mL
5 mM	0.5891 mL	2.9453 mL	5.8907 mL	11.7813 mL	14.7267 mL
10 mM	0.2945 mL	1.4727 mL	2.9453 mL	5.8907 mL	7.3633 mL
50 mM	0.0589 mL	0.2945 mL	0.5891 mL	1.1781 mL	1.4727 mL
100 mM	0.0295 mL	0.1473 mL	0.2945 mL	0.5891 mL	0.7363 mL

CFN96759	Evocarpine	15266-38-3	339.52	C₂₃H₃₃NO
CFN92786	Dihydroevocarpine	15266-35-0	341.5	C₂₃H₃₅NO
CFN91687	1-Methyl-2-[(6Z,9Z)-6,9-pentadecadiene]-4(1H)-quinolone	120693-52-9	365.6	C₂₅H₃₅NO
CFN90072	Kynurenic acid	492-27-3	189.17	C₁₀H₇NO₃
CFN97215	1,4-Dihydro-1,2-dimethyl-4-oxo-3-quinolinecarboxylic acid	73281-83-1	217.2	C₁₂H₁₁NO₃
CFN96756	Ifflaiamine	31520-95-3	243.30	C₁₅H₁₇NO₂
CFN97248	Mallorepine	767-98-6	134.1	C₇H₆N₂O
CFN98213	Antidesmone	222629-77-8	319.4	C₁₉H₂₉NO₃
CFN89240	1-Hydroxyacridone	65582-54-9	211.22	C₁₃H₉NO₂
CFN96973	1,7-Dihydroxyacridone	112649-95-3	227.21	C₁₃H₉NO₃