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Evocarpine

$538

  • Brand : BIOFRON

  • Catalogue Number : BD-P1007

  • Specification : 98.0%(HPLC)

  • CAS number : 15266-38-3

  • Formula : C23H33NO

  • Molecular Weight : 339.51

  • PUBCHEM ID : 5317303

  • Volume : 25mg

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Catalogue Number

BD-P1007

Analysis Method

HPLC,NMR,MS

Specification

98.0%(HPLC)

Storage

2-8°C

Molecular Weight

339.51

Appearance

Oil

Botanical Source

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

CCCCC=CCCCCCCCC1=CC(=O)C2=CC=CC=C2N1C

Synonyms

4(1H)-Quinolinone, 1-methyl-2-(8-tridecenyl)-, (Z)-/4(1H)-Quinolinone, 1-methyl-2-[(8Z)-8-tridecen-1-yl]-/1-Methyl-2-[(8Z)-8-tridecen-1-yl]-4(1H)-quinolinone/evocarpine

IUPAC Name

1-methyl-2-[(Z)-tridec-8-enyl]quinolin-4-one

Applications

Density

1.0±0.1 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

156.1±18.1 °C

Boiling Point

456.2±45.0 °C at 760 mmHg

Melting Point

34-38℃

InChl

InChI=1S/C23H33NO/c1-3-4-5-6-7-8-9-10-11-12-13-16-20-19-23(25)21-17-14-15-18-22(21)24(20)2/h6-7,14-15,17-19H,3-5,8-13,16H2,1-2H3/b7-6-

InChl Key

HWFYWIVOYBPLQU-SREVYHEPSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:15266-38-3) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

25604161

Abstract

AIMS:
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.

SIGNIFICANCE AND IMPACT OF THE STUDY:
This study gives a striking example of antagonism between compounds present in the same plant extract which should be considered in natural product based screening projects.

© 2015 The Society for Applied Microbiology.

KEYWORDS

Euodia; antagonism; evocarpine; evodiamine; modelling; mycobacteria; rutaecarpine

Title

Antagonistic effects of indoloquinazoline alkaloids on antimycobacterial activity of evocarpine.

Author

Hochfellner C1, Evangelopoulos D, Zloh M, Wube A, Guzman JD, McHugh TD, Kunert O, Bhakta S, Bucar F.

Publish date

2015 Apr

PMID

24497124

Abstract

Fructus Euodiae is used in traditional Chinese medicine to treat infection. In this study, four of the quinolone alkaloids isolated from Fructus Euodiae showed activity against methicillin-resistant Staphylococcus aureus (MRSA). The minimum inhibitory concentrations (MIC) were 8-128 µg/mL, which were equivalent to or lower than the control antibiotics, oxacillin, erythromycin and tetracycline (MIC ≥128 µg/mL). Among these isolated quinolone alkaloids, evocarpine with a 13 carbon alkenyl chain substituent at position-2 showed the best activity against MRSA. This study has demonstrated the potential of quinolone alkaloids from Fructus Euodiae as anti-MRSA compounds and supports the traditional use of the fruit as a treatment for bacterial infections.

Copyright © 2013 John Wiley & Sons, Ltd.

KEYWORDS

Evocarpine; MIC; MRSA; antibacterial; minimum inhibitory concentration

Title

Quinolone alkaloids from Fructus Euodiae show activity against methicillin-resistant Staphylococcus aureus.

Author

Pan X1, Bligh SW, Smith E.

Publish date

2014 Feb

PMID

10987208

Abstract

Evocarpine, an isoquinolone alkaloid isolated from the fruit of Evodia rutaecarpa, was found to induce apoptotic cell death in promyelocytic leukaemia HL-60 cells in dose- and time-dependent manners. We investigated the involvement of protein kinase A during the evocarpine-induced apoptotic cell death. Evocarpine-induced apoptosis was markedly inhibited by treatment of the cells with dibutyryl-cyclic adenosine monophosphate. Similar results were obtained with other commonly used cyclic adenosine monophosphate analogues, chlorophenylthio-cyclic adenosine monophosphate and the intracellular cyclic adenosine monophosphate-elevating agent, forskolin. In contrast, pretreatment of HL-60 cells with KT5720, an inhibitor of cyclic adenosine monophosphate-dependent protein kinase A, abrogated the protective effects of cyclic adenosine monophosphate analogues and forskolin on evocrpine-induced apoptosis. These findings suggest that cyclic adenosine monophosphate-dependent activation of protein kinase A plays a crucial role in protecting HL-60 cells from the evocarpine-induced apoptotic cell death.

Title

Cyclic adenosine monophosphate inhibits quinolone alkaloid evocarpine-induced apoptosis via activation of protein kinase A in human leukaemic HL-60 cells.

Author

Kim NY1, Pae HO, Kang TH, Kim YC, Lee HS, Chung HT.

Publish date

2000 Jul;