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    Shikonin
    Information
    CAS No. 517-88-4 Price $80 / 20mg
    Catalog No.CFN99907Purity>=98%
    Molecular Weight288.31Type of CompoundQuinones
    FormulaC16H16O5Physical DescriptionPurple powder
    Download Manual    COA    MSDSSimilar structuralComparison (Web)
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    Biological Activity
    Description: Shikonin is a natural red naphthoquinone pigment, has antimicrobial, anti-tumor, and anti-inflammatory effects; a purified shikonin preparation is widely used for the production of medicinals, cosmetics, and some food products; shikonin also enters into the antiinflammatory ointment and cream compositions used for the treatment of burns. It can suppress the cell viability, adhesion, invasion and migratory ability of MGC-803 cells through TLR2- or NF-κB-mediated pathway.
    Targets: PI3K | Akt | TLR | NF-kB | MMP(e.g.TIMP) | ROS | Bcl-2/Bax | Caspase | PARP | p53 | Antifection
    In vitro:
    J Pharm Pharmacol. 2015 Apr 16.
    Shikonin inhibits the cell viability, adhesion, invasion and migration of the human gastric cancer cell line MGC-803 via the Toll-like receptor 2/nuclear factor-kappa B pathway.[Pubmed: 25880237]
    Shikonin is an active naphthoquinone pigment isolated from the root of Lithospermum erythrorhizon. This study was designed to explore the inhibition of Shikonin on cell viability, adhesion, migration and invasion ability of gastric cancer (GC) and its possible mechanism.
    METHODS AND RESULTS:
    3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay was performed for cell viability and adhesion ability of MGC-803 cells. Cell scratch repair experiments were conducted for the determination of migration ability while transwell assay for cell invasion ability. Western blot analysis and real-time polymerase chain reaction assay were used for the detection of protein and mRNA expressions. Fifty per cent inhibitory concentration of Shikonin on MGC-803 cells was 1.854 μm. Shikonin (1 μm) inhibited significantly the adhesion, invasion and migratory ability of MGC-803 cells. Interestingly, Shikonin in the presence or absence of anti-Toll-like receptor 2 (TLR2) antibody (2 μg) and nuclear factor-kappa B (NF-κB) inhibitor MG-132 (10 μm) could decrease these ability of MGC-803 cells markedly, as well as the expression levels of matrix metalloproteinases (MMP)-2, MMP-7, TLR2 and p65 NF-κB. In addition, the co-incubation of Shikonin and anti-TLR2/MG-132 has a significant stronger activity than anti-TLR2 or MG-132 alone.
    CONCLUSIONS:
    The results indicated that Shikonin could suppress the cell viability, adhesion, invasion and migratory ability of MGC-803 cells through TLR2- or NF-κB-mediated pathway. Our findings provide novel information for the treatment of Shikonin on GC.
    Pharm.Chem. J., 2001, 35(8):435-6.
    Antimicrobial Activity of Shikonin Preparations.[Reference: WebLink]
    Shikonin is a natural red naphthoquinone pigment synthesized in the roots of plants belonging to the Boraginaceae family.
    METHODS AND RESULTS:
    At present, a purified Shikonin preparation is widely used in Japan for the production of medicinals, cosmetics, and some food products [1]. In Russia, Shikonin enters into the antiinflammatory ointment and cream compositions used for the treatment of burns. Shikonin possesses a broad spectrum of antimicrobial activity.
    CONCLUSIONS:
    In this context, it was of interest to study the antimicrobial properties of commercial Shikonin and the related aqueous ethanol and oil extracts from the cell culture of Arnebia euchroma.
    Shikonin Description
    Source: The roots of Lithosperraum erythrorhizon Sieb. et Zucc.
    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.
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    Calculate Dilution Ratios(Only for Reference)
    1 mg 5 mg 10 mg 20 mg 25 mg
    1 mM 3.4685 mL 17.3424 mL 34.6849 mL 69.3698 mL 86.7122 mL
    5 mM 0.6937 mL 3.4685 mL 6.937 mL 13.874 mL 17.3424 mL
    10 mM 0.3468 mL 1.7342 mL 3.4685 mL 6.937 mL 8.6712 mL
    50 mM 0.0694 mL 0.3468 mL 0.6937 mL 1.3874 mL 1.7342 mL
    100 mM 0.0347 mL 0.1734 mL 0.3468 mL 0.6937 mL 0.8671 mL
    * Note: If you are in the process of experiment, it's need to make the dilution ratios of the samples. The dilution data of the sheet for your reference. Normally, it's can get a better solubility within lower of Concentrations.
    Protocol
    Kinase Assay:
    Inflamm Res. 2008 Oct;57(10):484-8.
    Shikonin inhibits IgE-mediated histamine release by human basophils and Syk kinase activity.[Pubmed: 18830561 ]
    Shikonin, a component of the herbal medicine "Shikon", is known to suppress inflammatory reactions, but its molecular targets are not identified. This study examines the effect of Shikonin on human basophil degranulation response and aims to identify its targets. Human basophils in isolated leukocytes from healthy volunteers' peripheral blood; recombinant human Syk and Lyn tyrosine kinases.
    METHODS AND RESULTS:
    Histamine release from basophils stimulated with anti-IgE antibody was analyzed fluorimetrically. Syk and Lyn kinase activities were tested in Vitro with recombinant proteins and analyzed by off-chip mobility shift assay. Shikonin dose-dependently inhibited the histamine release from basophils induced by anti-IgE antibody (IC50 = 2.6 +/- 1.0 microM; mean +/- SEM). A search for the target(s) of Shikonin in the signal cascade of IgE-mediated activation showed that it strongly inhibits Syk (IC50 = 7.8 microM, in the recombinant kinase assay), which plays a pivotal role in the degranulation response. A less significant inhibition was found for Lyn, which phosphorylates FcepsilonRI-betagamma subunits and also Syk.
    CONCLUSIONS:
    These results indicate that the inhibition of Syk-dependent phosphorylation events might underlie the blocked histamine release from human basophils, thus contributing to the anti-inflammatory effects of Shikonin.
    Cell Research:
    J Biomed Sci. 2015 Apr 1;22(1):26.
    Shikonin selectively induces apoptosis in human prostate cancer cells through the endoplasmic reticulum stress and mitochondrial apoptotic pathway.[Pubmed: 25879420]
    Despite the recent progress in screening and therapy, a majority of prostate cancer cases eventually attain hormone refractory and chemo-resistant attributes. Conventional chemotherapeutic strategies are effective at very high doses for only palliative management of these prostate cancers. Therefore chemo-sensitization of prostate cancer cells could be a promising strategy for increasing efficacy of the conventional chemotherapeutic agents in prostate cancer patients. Recent studies have indicated that the chemo-preventive natural agents restore the pro-apoptotic protein expression and induce endoplasmic reticulum stress (ER stress) leading to the inhibition of cellular proliferation and activation of the mitochondrial apoptosis in prostate cancer cells. Therefore reprogramming ER stress-mitochondrial dependent apoptosis could be a potential approach for management of hormone refractory chemoresistant prostate cancers.
    METHODS AND RESULTS:
    We aimed to study the effects of the natural naphthoquinone Shikonin in human prostate cancer cells. RESULTS: The results indicated that Shikonin induces apoptosis in prostate cancer cells through the dual induction of the endoplasmic reticulum stress and mitochondrial dysfunction. Shikonin induced ROS generation and activated ER stress and calpain activity. Moreover, addition of antioxidants attenuated these effects. Shikonin also induced the mitochondrial apoptotic pathway mediated through the enhanced expression of the pro-apoptotic Bax and inhibition of Bcl-2, disruption of the mitochondrial membrane potential (MMP) followed by the activation of caspase-9, caspase-3, and PARP cleavage.
    CONCLUSIONS:
    The results suggest that Shikonin could be useful in the therapeutic management of hormone refractory prostate cancers due to its modulation of the pro-apoptotic ER stress and mitochondrial apoptotic pathways.
    Mol Med Rep. 2015 Jul;12(1):1305-13.
    Cbl participates in shikonin-induced apoptosis by negatively regulating phosphoinositide 3-kinase/protein kinase B signaling.[Pubmed: 25815461]
    Shikonin, a naturally occurring naphthoquinone, exhibits anti-tumorigenic activity. However, its precise mechanisms of action have remained elusive.
    METHODS AND RESULTS:
    In the present study, the involvement in the action of Shikonin of the ubiquitin ligases Cbl‑b and c‑Cbl, which are negative regulators of phosphoinositide 3‑kinase (PI3K) activation, was investigated. Shikonin was observed to reduce cell viability and induce apoptosis and G2/M phase arrest in lung cancer cells. In addition, Shikonin increased the protein levels of B‑cell lymphoma 2 (Bcl‑2)‑associated X and p53 and reduced those of Bcl‑2. Additionally, Shikonin inhibited PI3k/Akt activity and upregulated Cbl protein expression. In addition, a specific inhibitor of PI3K, LY294002, was observed to have a synergistic effect on the proliferation inhibition and apoptotic induction of A549 cells with Shikonin.
    CONCLUSIONS:
    In conclusion, the results of the present study suggested that Cbl proteins promote Shikonin‑induced apoptosis by negatively regulating PI3K/Akt signaling in lung cancer cells.