Dictamnine

CAS# 484-29-7

Dictamnine

Catalog No. BCN1273----Order now to get a substantial discount!

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Quality Control of Dictamnine

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Chemical structure

Dictamnine

3D structure

Chemical Properties of Dictamnine

Cas No. 484-29-7 SDF Download SDF
PubChem ID 68085 Appearance White powder
Formula C12H9NO2 M.Wt 199.21
Type of Compound Alkaloids Storage Desiccate at -20°C
Synonyms Dictamnine; Dectamine
Solubility DMSO : 50 mg/mL (250.99 mM; Need ultrasonic)
Chemical Name 4-methoxyfuro[2,3-b]quinoline
SMILES COC1=C2C=COC2=NC3=CC=CC=C31
Standard InChIKey WIONIXOBNMDJFJ-UHFFFAOYSA-N
Standard InChI InChI=1S/C12H9NO2/c1-14-11-8-4-2-3-5-10(8)13-12-9(11)6-7-15-12/h2-7H,1H3
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 Dictamnine

1 Casimiroa sp. 2 Dictamnus sp. 3 Ptelea sp. 4 Ruta sp. 5 Skimmia sp. 6 Zanthoxylum sp.

Biological Activity of Dictamnine

DescriptionDictamnine shows anticholinesterase, anti-inflammatory, mutagenic, and has antimicrobial activity against bacteria and fungi. It has the ability to exert cytotoxicity in human cervix, colon, and oral carcinoma cells, it at higher concentrations(≥100uM) has potential hepatotoxicity because of the cell membrane damage and mitochondrial membrane damage.
TargetsAntifection
In vitro

Anticholinesterase activity evaluation of alkaloids and coumarin from stems of Conchocarpus fontanesianus[Reference: WebLink]

Rev. Bras. Farmacogn., 2012, 22(2):374-80.


METHODS AND RESULTS:
Conchocarpus fontanesianus (A. St.-Hill.) Kallunki & Pirani, Rutaceae, popularly known as pitaguará, is a native and endemic tree from São Paulo and Rio de Janeiro States, Brazil. Based in the information that anticholinesterasic derivatives could act as new prototypes to treatment of Alzheimer disease, this work describes the fractionation guided by evaluation of the anticholinesterase activity of the ethanolic stems extract from C. fontanesianus.
CONCLUSIONS:
This procedure afforded the alkaloids Dictamnine (1), γ-fagarine (2), skimianine (3), and 2-phenyl-1-methyl-4-quinolone (4), as well as the coumarin marmesin (5).

Global gene expression profile of Saccharomyces cerevisiae induced by dictamnine.[Pubmed: 18727144]

Yeast. 2008 Sep;25(9):631-41.

Dictamnine, a natural plant product, has been reported to have antimicrobial activity against bacteria and fungi; however, the Dictamnine response mechanisms of microorganisms are still poorly understood.
METHODS AND RESULTS:
We have shown that Dictamnine has antimicrobial activities against the model fungus Saccharomyces cerevisiae, with a minimum inhibitory concentration (MIC) value of 64 microg/ml. Commercial oligonucleotide microarrays were used to determine the global transcriptional response of S. cerevisiae triggered by treatment with Dictamnine. We interpreted our microarray data using the hierarchical clustering tool, T-profiler. Several major transcriptional responses were induced by Dictamnine. The first was the induced environmental stress response, mainly under the control of the Msn2p and Msn4p transcription factors, and the repressed environmental stress response in genes containing the PAC (RNA polymerase A and C box) and rRPE (ribosomal RNA processing element) motifs. The second was the Upc2p-mediated response involved in lipid biosynthesis. The third comprised the PDR3- and RPN4-mediated responses involved in multidrug resistance (MDR). Finally, the TBP-mediated response was induced with Dictamnine treatment.
CONCLUSIONS:
TBP is an essential general transcription factor involved in directing the transcription of genes. Quantitative real-time RT-PCR was performed on selected genes to verify the microarray results. Furthermore, morphological transitions during Dictamnine exposure to S. cerevisiae L1190 (MATa/alpha) were examined, using confocal laser microscopy.

Study on in Vitro Antifungal Activity of Dictamnine against Candida albicans.[Reference: WebLink]

Chinese Agricultural Science Bulletin, 2009, 25(16): 21-4.

Candida albicans (C. albicans) and other fungi important human and veterinary pathogens.
METHODS AND RESULTS:
The minimal inhibitory concentration (MIC) of Dictamnine alone and in combination with fluconazole (FLC) against clinical 22 clinical Candida albicans were tested, and checkerboard assay was used to analyze the ractional inhibitory concentration index (FICI) of the combination of Dictamnine and FLC.
CONCLUSIONS:
The result showed that Dictamnine had good antifungal activity alone and in combination with FLC against Candida albicans.

In vivo

Isolation and Anti-inflammatory Effect of Dictamnine Extracted from Dictamni Cortex.[Reference: WebLink]

Chinese Journal of Experimental Traditional Medical Formulae, 2012, 18(14):128-31.

To detect the anti-inflammatory effects of ethanol extracts and Dictamnine extracted and isolated from Dictamni Cortex.
METHODS AND RESULTS:
High performance centrifugal partition chromatography method was used for separation of the essential Dictamnine,and anti-inflammatory effects of ethanol extracts and Dictamnine were investigated by xylene-induced aruical swelling in mice and the abdominal capillary permeability in mice.Separation was performed with a two-phase solvent system composed of hexane ethylacetate-ethanol-water(1∶1∶1∶1).The purity of Dictamnine obtained was 98% determined by high performance liquid chromatograph.The results showed that each dosage of ethanol extracts could significantly(P0.05) suppress the mouse auricle which caused by the xylene swelling(being 44.26%,52.46%,44.26%,respectively),as compared with the control group.The medium-dosage group of Dictamnine could obviously(P0.01) suppress the mouse auricle but the dosage was not increased significantly in abdominal capillary permeability in mice compared with control group.
CONCLUSIONS:
HPCPC is a recommendable method to prepare and purify the dictamnie with good separation and the method is simple,accurate and easy to operate.The results showed that ethanol extracts and Dictamnine showed different anti-inflammatory effect in variety of animal models of anti-inflammatory.

Protocol of Dictamnine

Cell Research

Cytotoxic effect of dictamnine on HepG2 cells and its possible mechanism[Reference: WebLink]

Chinese Journal of Pharmacology & Toxicology, 2013, 27(1):95-100.

To study the Dictamnine-induced hepatotoxicity in vitro and to explore its mechanism.
METHODS AND RESULTS:
HepG2 cells were exposed to Dictamnine 2.5-800 μmol·L-1 for 24 h,and cell viability was examined by MTT assay.Cell membrane injury was examined by detecting the release rate of lactate dehydrogenase(LDH),and the morphological changes were observed under a contrast microscope.The activities of alanine transaminase(ALT),aspartate aminotransferase(AST),glutathione S-transferase(GST) and glutamyltranspeptidase(GGT) in HepG2 cell cultures were measured using enzyme-labeled instrument,respectively.The mitochondrial membrane potential was measured by laser scanning confocal fluorescence microscope.RESULTS HepG2 cell viability was significantly reduced following exposure to Dictamnine 25-800 μmol·L-1 for 24 h in a concentration-dependent manner(r=0.965,P0.05),and IC50 value was(283±27)μmol·L-1.The LDH release rate of HepG2 cells was significantly increased after exposure to Dictamnine 12.5-50 μmol·L-1 for 24 h(P0.01).The morphology of HepG2 cells after 24 h exposure to Dictamnine 100 and 200 μmol·L-1 was changed greatly.The cells wrinkled up and dropped.Compared with control group,ALT and AST activities in HepG2 cell culture were significantly increased(P0.05) in a concentration-dependent manner(r=0.995,P0.05 and r=0.996,P0.05) following exposure to Dictamnine 100 and 200 μmol·L-1 for 24 h,and the mitochondrial membrane potential markedly declined(r=0.978,P0.05).After exposure to Dictamnine 100 and 200 μmol·L-1 for 4 h,GST activity in HepG2 cell culture was significantly increased(P0.05);and for 24 h,GST activity in Dictamnine 50,100 and 200 μmol·L-1 groups was also increased in a concentration-dependent manner(r=0.987,P0.05).After exposure to Dictamnine 200 μmol·L-1 for 48 h,GGT activity in HepG2 cell culture was increased(P0.05).
CONCLUSIONS:
Dictamnine at higher concentrations(≥100 μmol·L-1)has potential hepatotoxicity.The cell membrane damage and mitochondrial membrane damage may be involved in the Dictamnine-induced hepatotoxity mechanism.

Structure Identification
Mutat Res. 1985 Dec;144(4):221-5.

Mutagenic activities of dictamnine and gamma-fagarine from dictamni radicis cortex (Rutaceae).[Pubmed: 4069140]

A methanol extract of Dictamni Radicis Cortex exhibited a mutagenic effect on Salmonella typhimurium TA100 and TA98 with S9 mix.
METHODS AND RESULTS:
Two mutagenic compounds in Dictamni Radicis Cortex were isolated on a Sephadex LH 20 column and silica gel column chromatography and by preparative TLC. These were identified as Dictamnine and gamma-fagarine by UV, EI-Mass, 1H-NMR. Dictamnine and gamma-fagarine were mutagenic in strain TA100 and TA98 with S9 mix. The dose-response curves were linear in the range 10-40 micrograms.
CONCLUSIONS:
Dictamnine and gamma-fagarine had specific activities (His+/microgram) of about 50-70 revertant colonies in strain TA100, while in strain TA98 there were about 30-50 revertant colonies.

Dictamnine Dilution Calculator

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Preparing Stock Solutions of Dictamnine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 5.0198 mL 25.0991 mL 50.1983 mL 100.3966 mL 125.4957 mL
5 mM 1.004 mL 5.0198 mL 10.0397 mL 20.0793 mL 25.0991 mL
10 mM 0.502 mL 2.5099 mL 5.0198 mL 10.0397 mL 12.5496 mL
50 mM 0.1004 mL 0.502 mL 1.004 mL 2.0079 mL 2.5099 mL
100 mM 0.0502 mL 0.251 mL 0.502 mL 1.004 mL 1.255 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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Background on Dictamnine

Dictamnine (Dictamine) has the ability to exert cytotoxicity in human cervix, colon, and oral carcinoma cells; A natural plant product has been reported to have antimicrobial activity against bacteria and fungi. IC50 value: Target: Dictamnine has antimicrobial activities against the model fungus Saccharomyces cerevisiae, with a minimum inhibitory concentration (MIC) value of 64 microg/ml [1]. Dic induced S phase cell cycle arrest at low concentration and cell apoptosis at high concentration in which loss of mitochondrial membrane potential (Δψmm) was not involved. In addition, inhibition of caspase-3 using the specific inhibitor, z-DQMD-fmk, did not attenuate Dic-induced apoptosis, implying that Dic-induced caspase-3-independent apoptosis [2].

References:
[1]. Guo N, et al. Global gene expression profile of Saccharomyces cerevisiae induced by dictamnine. Yeast. 2008 Sep;25(9):631-41. [2]. An FF, et al. Dihydroartemisinine enhances dictamnine-induced apoptosis via a caspase dependent pathway in human lung adenocarcinoma A549 cells. Asian Pac J Cancer Prev. 2013;14(10):5895-900.

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References on Dictamnine

Further evidence for photoinduced genotoxicity of dictamnine as shown by prophage induction.[Pubmed:2684439]

Chem Biol Interact. 1989;72(1-2):105-11.

Photobiological activity of Dictamnine, a furoquinoline alkaloid, to induce lytic phage development in a lysogen of Escherichia coli was measured as a line of evidence for the photoinduced genotoxicity. Since Dictamnine forms the monoadducts to DNA but not the diadducts (DNA cross-links) by photoirradiation, the photobiological activity was compared with that of a cross-linking agent 5-methoxypsoralen, a structural analog, on the basis of relative quantum yield. The activity of Dictamnine with respect to both phage induction and photoinduced lethal activity was weaker than the psoralen derivative. Any lethal DNA damage including monoadducts and diadducts of 5-methoxypsoralen appeared to contribute to prophage induction at the same level of efficiency.

Global gene expression profile of Saccharomyces cerevisiae induced by dictamnine.[Pubmed:18727144]

Yeast. 2008 Sep;25(9):631-41.

Dictamnine, a natural plant product, has been reported to have antimicrobial activity against bacteria and fungi; however, the Dictamnine response mechanisms of microorganisms are still poorly understood. We have shown that Dictamnine has antimicrobial activities against the model fungus Saccharomyces cerevisiae, with a minimum inhibitory concentration (MIC) value of 64 microg/ml. Commercial oligonucleotide microarrays were used to determine the global transcriptional response of S. cerevisiae triggered by treatment with Dictamnine. We interpreted our microarray data using the hierarchical clustering tool, T-profiler. Several major transcriptional responses were induced by Dictamnine. The first was the induced environmental stress response, mainly under the control of the Msn2p and Msn4p transcription factors, and the repressed environmental stress response in genes containing the PAC (RNA polymerase A and C box) and rRPE (ribosomal RNA processing element) motifs. The second was the Upc2p-mediated response involved in lipid biosynthesis. The third comprised the PDR3- and RPN4-mediated responses involved in multidrug resistance (MDR). Finally, the TBP-mediated response was induced with Dictamnine treatment. TBP is an essential general transcription factor involved in directing the transcription of genes. Quantitative real-time RT-PCR was performed on selected genes to verify the microarray results. Furthermore, morphological transitions during Dictamnine exposure to S. cerevisiae L1190 (MATa/alpha) were examined, using confocal laser microscopy.

Mutagenic activities of dictamnine and gamma-fagarine from dictamni radicis cortex (Rutaceae).[Pubmed:4069140]

Mutat Res. 1985 Dec;144(4):221-5.

A methanol extract of Dictamni Radicis Cortex exhibited a mutagenic effect on Salmonella typhimurium TA100 and TA98 with S9 mix. Two mutagenic compounds in Dictamni Radicis Cortex were isolated on a Sephadex LH 20 column and silica gel column chromatography and by preparative TLC. These were identified as Dictamnine and gamma-fagarine by UV, EI-Mass, 1H-NMR. Dictamnine and gamma-fagarine were mutagenic in strain TA100 and TA98 with S9 mix. The dose-response curves were linear in the range 10-40 micrograms. Dictamnine and gamma-fagarine had specific activities (His+/microgram) of about 50-70 revertant colonies in strain TA100, while in strain TA98 there were about 30-50 revertant colonies.

Description

Dictamnine (Dictamine) has the ability to exert cytotoxicity in human cervix, colon, and oral carcinoma cells; A natural plant product has been reported to have antimicrobial activity against bacteria and fungi.

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