Cepharanthine

CAS# 481-49-2

Cepharanthine

2D Structure

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Cepharanthine

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Chemical Properties of Cepharanthine

Cas No. 481-49-2 SDF Download SDF
PubChem ID 10206 Appearance Off-white powder
Formula C37H38N2O6 M.Wt 606.71
Type of Compound Alkaloids Storage Desiccate at -20°C
Synonyms O-Methylcepharanoline
Solubility DMSO : 125 mg/mL (206.03 mM; Need ultrasonic)
SMILES CN1CCC2=CC3=C(C4=C2C1CC5=CC=C(C=C5)OC6=C(C=CC(=C6)CC7C8=CC(=C(C=C8CCN7C)OC)O4)OC)OCO3
Standard InChIKey YVPXVXANRNDGTA-WDYNHAJCSA-N
Standard InChI InChI=1S/C37H38N2O6/c1-38-13-11-24-18-31(41-4)33-20-27(24)28(38)16-23-7-10-30(40-3)32(17-23)44-26-8-5-22(6-9-26)15-29-35-25(12-14-39(29)2)19-34-36(37(35)45-33)43-21-42-34/h5-10,17-20,28-29H,11-16,21H2,1-4H3/t28-,29+/m1/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 Cepharanthine

The roots of Stephania japonica (Thunb.) Miers

Biological Activity of Cepharanthine

DescriptionCepharanthine has anti-plasmodial, anti-tumor , anti-inflammatory, antiallergic, antioxidant, and immunomodulatory activities in vivo, and it is a highly potent inhibitor of HIV-1 replication in a chronically infected monocytic cell line. Cepharanthine inhibits the HIV-1 entry process by reducing plasma membrane fluidity, and the plasma membrane is therefore an identical target to prevent viral infection.
TargetsROS | PARP | Bcl-2/Bax | Caspase | p65 | TNF-α | NF-kB | IkB | IL Receptor | LTR | HIV | IKK
In vitro

In vitro antiplasmodial activity of cepharanthine.[Pubmed: 25145413]

Malar J. 2014 Aug 22;13:327.

New classes of anti-malarial drugs are needed to control the alarming Plasmodium falciparum resistance toward current anti-malarial therapy. The ethnopharmacological approach allows the discovery of original chemical structures from the vegetable biodiversity. Previous studies led to the selection of a bisbenzylisoquinoline, called Cepharanthine and isolated from a Cambodian plant: Stephania rotunda. Cepharanthine could exert a mechanism of action different from commonly used drugs. Potential plasmodial targets are reported here.
METHODS AND RESULTS:
To study the mechanism of action of Cepharanthine, a combined approach using phenotypic and transcriptomic techniques was undertaken. Cepharanthine blocked P. falciparum development in ring stage. On a culture of synchronized ring stage, the comparisons of expression profiles showed that the samples treated with 5 μM of Cepharanthine (IC90) were significantly closer to the initial controls than to the final ones. After a two-way ANOVA (p-value < 0.05) on the microarray results, 1,141 probes among 9,722 presented a significant differential expression.A gene ontology analysis showed that the Maurer's clefts seem particularly down-regulated by Cepharanthine. The analysis of metabolic pathways showed an impact on cell-cell interactions (cytoadherence and rosetting), glycolysis and isoprenoid pathways. Organellar functions, more particularly constituted by apicoplast and mitochondrion, are targeted too.
CONCLUSIONS:
The blockage at the ring stage by Cepharanthine is described for the first time. Transcriptomic approach confirmed that Cepharanthine might have a potential innovative antiplasmodial mechanism of action. Thus, Cepharanthine might play an ongoing role in the progress on anti-malarial drug discovery efforts.

Antioxidant activity of bisbenzylisoquinoline alkaloids from Stephania rotunda: cepharanthine and fangchinoline.[Pubmed: 20030508 ]

J Enzyme Inhib Med Chem. 2010 Feb;25(1):44-53.


METHODS AND RESULTS:
In the present study, we determined the antioxidant activity of Cepharanthine and fangchinoline from Stephania rotunda by performing different in vitro antioxidant assays, including 1,1-diphenyl-2-picryl-hydrazyl (DPPH) free radical scavenging, 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) radical scavenging, N,N- dimethyl-p-phenylenediamine dihydrochloride (DMPD) radical scavenging, superoxide anion (O2*-) radical scavenging, hydrogen peroxide scavenging, total antioxidant activity, reducing power, and ferrous ion (Fe2+) chelating activities. Cepharanthine and fangchinoline showed 94.6 and 93.3% inhibition on lipid peroxidation of linoleic acid emulsion at 30 microg/mL concentration, respectively. On the other hand, butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), alpha-tocopherol, and trolox indicated inhibitions of 83.3, 92.2, 72.4, and 81.3% on peroxidation of linoleic acid emulsion at the same concentration (30 microg/mL), respectively.
CONCLUSIONS:
According to the results, Cepharanthine and fangchinoline have effective antioxidant and radical scavenging activity.

In vivo

Cepharanthine inhibited HIV-1 cell-cell transmission and cell-free infection via modification of cell membrane fluidity.[Pubmed: 24704028]

Bioorg Med Chem Lett. 2014 May 1;24(9):2115-7.

The anti-HIV-1 activity of Cepharanthine (CEP), a natural product derived from Stephania cepharantha Hayata, was evaluated.
METHODS AND RESULTS:
CEP stabilized plasma membrane fluidity and inhibited HIV-1 envelope-dependent cell-to-cell fusion of HIV-1-infected cells as well as cell-free infection.
CONCLUSIONS:
It is suggested that CEP inhibited the HIV-1 entry process by reducing plasma membrane fluidity, and the plasma membrane is therefore an identical target to prevent viral infection.

Protocol of Cepharanthine

Cell Research

Potent inhibition of HIV type 1 replication by an antiinflammatory alkaloid, cepharanthine, in chronically infected monocytic cells.[Pubmed: 9764907]

Cepharanthine induces apoptosis through reactive oxygen species and mitochondrial dysfunction in human non-small-cell lung cancer cells.[Pubmed: 25747710]

Biochem Biophys Res Commun. 2015 May 1;460(2):136-42.

Cepharanthine is a medicinal plant-derived natural compound which possesses potent anti-cancer properties. However, there is little report about its effects on lung cancer cells.
METHODS AND RESULTS:
In this study, we investigated the effects of Cepharanthine on the cell viability and apoptosis in human non-small-cell lung cancer H1299 and A549 cells. It was found that Cepharanthine inhibited the growth of H1299 and A549 cells in a dose-dependent manner which was associated with the generation of reactive oxygen species(ROS) and the dissipation of mitochondrial membrane potential (Δψm). These effects were markedly abrogated when cells were pretreated with N-acetylcysteine (NAC), a specific ROS inhibitor, indicating that the apoptosis-inducing effect of Cepharanthine in lung cancer cells was mediated by ROS. In addition, Cepharanthine triggered apoptosis in non-small lung cancer cells via the upregulation of Bax, downregulation of Bcl-2 and significant activation of caspase-3 and PARP.
CONCLUSIONS:
These results provide the rationale for further research and preclinical investigation of Cepharanthine's anti-tumor effect against human non-small-cell lung cancer.

AIDS Res Hum Retroviruses. 1998 Sep 20;14(14):1239-45.

Cepharanthine is a biscoclaurine alkaloid isolated from Stephania cepharantha Hayata and has been shown to have antiinflammatory, antiallergic, and immunomodulatory activities in vivo.
METHODS AND RESULTS:
As several inflammatory cytokines and oxidative stresses are involved in the pathogenesis of HIV-1 infection, we investigated the inhibitory effects of Cepharanthine on tumor necrosis factor alpha (TNF-alpha)- and phorbol 12-myristate 13-acetate (PMA)-induced HIV-1 replication in chronically infected cell lines. Two chronically HIV-1-infected cell lines, U1 (monocytic) and ACH-2 (T lymphocytic), were stimulated with TNF-alpha or PMA and cultured in the presence of various concentrations of the compound. HIV-1 replication was determined by p24 antigen level. The inhibitory effects of Cepharanthine on HIV-1 long terminal repeat (LTR)-driven gene expression and nuclear factor kappaB (NF-kappaB) activation were also examined. Cepharanthine dose dependently inhibited HIV-1 replication in TNF-alpha- and PMA-stimulated U1 cells but not in ACH-2 cells. Its 50% effective and cytotoxic concentrations were 0.016 and 2.2 microg/ml in PMA-stimulated U1 cells, respectively. Cepharanthine was found to suppress HIV-1 LTR-driven gene expression through the inhibition of NF-kappaB activation.
CONCLUSIONS:
These results indicate that Cepharanthine is a highly potent inhibitor of HIV-1 replication in a chronically infected monocytic cell line. Since biscoclaurine alkaloids, containing Cepharanthine as a major component, are widely used for the treatment of patients with various inflammatory diseases in Japan, Cepharanthine should be further pursued for its chemotherapeutic potential in HIV-1-infected patients.

Animal Research

Cepharanthine attenuates lipopolysaccharide-induced mice mastitis by suppressing the NF-κB signaling pathway.[Pubmed: 24062060]

Inflammation. 2014 Apr;37(2):331-7.

Cepharanthine (CEP), a biscoclaurine alkaloid isolated from Stephania cepharantha Hayata, has been reported to have potent anti-inflammatory properties. However, the anti-inflammatory effects of CEP on a mouse model of lipopolysaccharide (LPS)-induced mastitis and its underlying molecular mechanisms remain to be elucidated.
METHODS AND RESULTS:
The purpose of the present study was to investigate the effects of CEP on LPS-induced mouse mastitis. The mouse model of mastitis was induced by inoculation of LPS through the canals of the mammary gland. CEP was administered intraperitoneally at 1 h before and 12 h after induction of LPS. The results show that CEP significantly attenuates the infiltration of neutrophils, suppresses myeloperoxidase activity, and reduces the levels of TNF-α, IL-1β, and IL-6 in LPS-induced mouse mastitis. Furthermore, CEP inhibited the phosphorylation of NF-κB p65 subunit and the degradation of its inhibitor IκBα.
CONCLUSIONS:
All the results suggest that CEP exerts potent anti-inflammatory effects on LPS-induced mouse mastitis. Accordingly, CEP might be a potential therapeutic agent for mastitis.

Cepharanthine Dilution Calculator

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Preparing Stock Solutions of Cepharanthine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.6482 mL 8.2412 mL 16.4823 mL 32.9647 mL 41.2058 mL
5 mM 0.3296 mL 1.6482 mL 3.2965 mL 6.5929 mL 8.2412 mL
10 mM 0.1648 mL 0.8241 mL 1.6482 mL 3.2965 mL 4.1206 mL
50 mM 0.033 mL 0.1648 mL 0.3296 mL 0.6593 mL 0.8241 mL
100 mM 0.0165 mL 0.0824 mL 0.1648 mL 0.3296 mL 0.4121 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 Cepharanthine

Cepharanthine induces apoptosis through reactive oxygen species and mitochondrial dysfunction in human non-small-cell lung cancer cells.[Pubmed:25747710]

Biochem Biophys Res Commun. 2015 May 1;460(2):136-42.

Cepharanthine is a medicinal plant-derived natural compound which possesses potent anti-cancer properties. However, there is little report about its effects on lung cancer cells. In this study, we investigated the effects of Cepharanthine on the cell viability and apoptosis in human non-small-cell lung cancer H1299 and A549 cells. It was found that Cepharanthine inhibited the growth of H1299 and A549 cells in a dose-dependent manner which was associated with the generation of reactive oxygen species(ROS) and the dissipation of mitochondrial membrane potential (Deltapsim). These effects were markedly abrogated when cells were pretreated with N-acetylcysteine (NAC), a specific ROS inhibitor, indicating that the apoptosis-inducing effect of Cepharanthine in lung cancer cells was mediated by ROS. In addition, Cepharanthine triggered apoptosis in non-small lung cancer cells via the upregulation of Bax, downregulation of Bcl-2 and significant activation of caspase-3 and PARP. These results provide the rationale for further research and preclinical investigation of Cepharanthine's anti-tumor effect against human non-small-cell lung cancer.

Potent inhibition of HIV type 1 replication by an antiinflammatory alkaloid, cepharanthine, in chronically infected monocytic cells.[Pubmed:9764907]

AIDS Res Hum Retroviruses. 1998 Sep 20;14(14):1239-45.

Cepharanthine is a biscoclaurine alkaloid isolated from Stephania cepharantha Hayata and has been shown to have antiinflammatory, antiallergic, and immunomodulatory activities in vivo. As several inflammatory cytokines and oxidative stresses are involved in the pathogenesis of HIV-1 infection, we investigated the inhibitory effects of Cepharanthine on tumor necrosis factor alpha (TNF-alpha)- and phorbol 12-myristate 13-acetate (PMA)-induced HIV-1 replication in chronically infected cell lines. Two chronically HIV-1-infected cell lines, U1 (monocytic) and ACH-2 (T lymphocytic), were stimulated with TNF-alpha or PMA and cultured in the presence of various concentrations of the compound. HIV-1 replication was determined by p24 antigen level. The inhibitory effects of Cepharanthine on HIV-1 long terminal repeat (LTR)-driven gene expression and nuclear factor kappaB (NF-kappaB) activation were also examined. Cepharanthine dose dependently inhibited HIV-1 replication in TNF-alpha- and PMA-stimulated U1 cells but not in ACH-2 cells. Its 50% effective and cytotoxic concentrations were 0.016 and 2.2 microg/ml in PMA-stimulated U1 cells, respectively. Cepharanthine was found to suppress HIV-1 LTR-driven gene expression through the inhibition of NF-kappaB activation. These results indicate that Cepharanthine is a highly potent inhibitor of HIV-1 replication in a chronically infected monocytic cell line. Since biscoclaurine alkaloids, containing Cepharanthine as a major component, are widely used for the treatment of patients with various inflammatory diseases in Japan, Cepharanthine should be further pursued for its chemotherapeutic potential in HIV-1-infected patients.

Cepharanthine inhibited HIV-1 cell-cell transmission and cell-free infection via modification of cell membrane fluidity.[Pubmed:24704028]

Bioorg Med Chem Lett. 2014 May 1;24(9):2115-7.

The anti-HIV-1 activity of Cepharanthine (CEP), a natural product derived from Stephania cepharantha Hayata, was evaluated. CEP stabilized plasma membrane fluidity and inhibited HIV-1 envelope-dependent cell-to-cell fusion of HIV-1-infected cells as well as cell-free infection. It is suggested that CEP inhibited the HIV-1 entry process by reducing plasma membrane fluidity, and the plasma membrane is therefore an identical target to prevent viral infection.

Cepharanthine attenuates lipopolysaccharide-induced mice mastitis by suppressing the NF-kappaB signaling pathway.[Pubmed:24062060]

Inflammation. 2014 Apr;37(2):331-7.

Cepharanthine (CEP), a biscoclaurine alkaloid isolated from Stephania cepharantha Hayata, has been reported to have potent anti-inflammatory properties. However, the anti-inflammatory effects of CEP on a mouse model of lipopolysaccharide (LPS)-induced mastitis and its underlying molecular mechanisms remain to be elucidated. The purpose of the present study was to investigate the effects of CEP on LPS-induced mouse mastitis. The mouse model of mastitis was induced by inoculation of LPS through the canals of the mammary gland. CEP was administered intraperitoneally at 1 h before and 12 h after induction of LPS. The results show that CEP significantly attenuates the infiltration of neutrophils, suppresses myeloperoxidase activity, and reduces the levels of TNF-alpha, IL-1beta, and IL-6 in LPS-induced mouse mastitis. Furthermore, CEP inhibited the phosphorylation of NF-kappaB p65 subunit and the degradation of its inhibitor IkappaBalpha. All the results suggest that CEP exerts potent anti-inflammatory effects on LPS-induced mouse mastitis. Accordingly, CEP might be a potential therapeutic agent for mastitis.

Antioxidant activity of bisbenzylisoquinoline alkaloids from Stephania rotunda: cepharanthine and fangchinoline.[Pubmed:20030508]

J Enzyme Inhib Med Chem. 2010 Feb;25(1):44-53.

In the present study, we determined the antioxidant activity of Cepharanthine and fangchinoline from Stephania rotunda by performing different in vitro antioxidant assays, including 1,1-diphenyl-2-picryl-hydrazyl (DPPH) free radical scavenging, 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) radical scavenging, N,N- dimethyl-p-phenylenediamine dihydrochloride (DMPD) radical scavenging, superoxide anion (O2*-) radical scavenging, hydrogen peroxide scavenging, total antioxidant activity, reducing power, and ferrous ion (Fe2+) chelating activities. Cepharanthine and fangchinoline showed 94.6 and 93.3% inhibition on lipid peroxidation of linoleic acid emulsion at 30 microg/mL concentration, respectively. On the other hand, butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), alpha-tocopherol, and trolox indicated inhibitions of 83.3, 92.2, 72.4, and 81.3% on peroxidation of linoleic acid emulsion at the same concentration (30 microg/mL), respectively. According to the results, Cepharanthine and fangchinoline have effective antioxidant and radical scavenging activity.

In vitro antiplasmodial activity of cepharanthine.[Pubmed:25145413]

Malar J. 2014 Aug 22;13:327.

BACKGROUND: New classes of anti-malarial drugs are needed to control the alarming Plasmodium falciparum resistance toward current anti-malarial therapy. The ethnopharmacological approach allows the discovery of original chemical structures from the vegetable biodiversity. Previous studies led to the selection of a bisbenzylisoquinoline, called Cepharanthine and isolated from a Cambodian plant: Stephania rotunda. Cepharanthine could exert a mechanism of action different from commonly used drugs. Potential plasmodial targets are reported here. METHODS: To study the mechanism of action of Cepharanthine, a combined approach using phenotypic and transcriptomic techniques was undertaken. RESULTS: Cepharanthine blocked P. falciparum development in ring stage. On a culture of synchronized ring stage, the comparisons of expression profiles showed that the samples treated with 5 muM of Cepharanthine (IC90) were significantly closer to the initial controls than to the final ones. After a two-way ANOVA (p-value < 0.05) on the microarray results, 1,141 probes among 9,722 presented a significant differential expression.A gene ontology analysis showed that the Maurer's clefts seem particularly down-regulated by Cepharanthine. The analysis of metabolic pathways showed an impact on cell-cell interactions (cytoadherence and rosetting), glycolysis and isoprenoid pathways. Organellar functions, more particularly constituted by apicoplast and mitochondrion, are targeted too. CONCLUSION: The blockage at the ring stage by Cepharanthine is described for the first time. Transcriptomic approach confirmed that Cepharanthine might have a potential innovative antiplasmodial mechanism of action. Thus, Cepharanthine might play an ongoing role in the progress on anti-malarial drug discovery efforts.

Description

Cepharanthine, an alkaloid derived from Stephania cepharantha Hayata, with possesses anti-inflammatory and antioxidative activities. Cepharanthine attenuates muscle and kidney injuries induced by limb ischemia/reperfusion (I/R). Cepharanthine induces autophagy, apoptosis and cell cycle arrest in breast cancer cells. Cepharanthine inhibits the HIV-1 entry process by reducing plasma membrane fluidity.

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