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    Acetylshikonin
    Information
    CAS No. 24502-78-1 Price $168 / 20mg
    Catalog No.CFN90523Purity>=98%
    Molecular Weight330.33Type of CompoundQuinones
    FormulaC18H18O6Physical DescriptionPowder
    Download Manual    COA    MSDSSimilar structuralComparison
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    Biological Activity
    Description: Acetylshikonin has anti-cancer and anti-inflammatory activity, it is a novel general P450 inhibitor with IC50 values of 1.4-4.0 μM for all tested P450s. Acetylshikonin exhibits weak cytotoxicity against human umbilical vein endothelial cells (HUVECs) with IC50 of over 20 microM, exhibits the antiangiogenic and antitumorigenic effects by suppressing proliferation and angiogenic factors. Certain shikonin derivatives(such as Acetylshikonin) act as modulators of the Nur77-mediated apoptotic pathway.
    Targets: NADPH-oxidase | HBV | P450 | VEGF | Nur77 | Bcl-2/Bax
    In vitro:
    Yakugaku Zasshi. 2008 Nov;128(11):1681-8.
    Shikonin, acetylshikonin, and isobutyroylshikonin inhibit VEGF-induced angiogenesis and suppress tumor growth in lewis lung carcinoma-bearing mice.[Pubmed: 18981704]
    Lithospermum erythrorhizon has been used for treatment of inflammatory diseases and cancer as a folk remedy. Based on the evidences that anti-inflammatory agents frequently exert antiangiogenic activity, thus we examined comparatively the antiangiogenic activities of three naphthoquinone derivatives (shikonin, Acetylshikonin, and isobutyroylshikonin) isolated from the plant.
    METHODS AND RESULTS:
    Three derivatives exhibited weak cytotoxicity against human umbilical vein endothelial cells (HUVECs) with IC50 of over 20 microM. Shikonin had more specific inhibitory effects on proliferation and vascular endothelial growth factor (VEGF) production by VEGF compared with different derivatives. All of derivatives significantly suppressed the migration of VEGF treated HUVECs at different optimal concentrations. Also, shikonin and Acetylshikonin significantly disrupted VEGF-induced tube formation. Furthermore, three derivatives effectively downregulated the expression of urokinase-type plasminogen activator (uPA), but not its receptor uPAR. Additionally, shikonin significantly inhibited tumor growth in LLC-bearing mice, whereas its derivatives had relatively mild effects.
    CONCLUSIONS:
    Taken together, our findings suggest that shikonin and its derivatives exhibit the antiangiogenic and antitumorigenic effects by suppressing proliferation and angiogenic factors.
    In vivo:
    Phytomedicine. 2003;10(5):375-80.
    Anti-inflammatory activity of shikonin derivatives from Arnebia hispidissima.[Pubmed: 12834001]
    Arnebia hispidissima ethanolic extract, after chromatography, yielded a number of shikonin derivatives, which were identified as arnebin-5, arnebin-6, teracryl shikonin, arnebinone and Acetylshikonin.
    METHODS AND RESULTS:
    All these compounds were firstly reported from this plant species and evaluated to the anti-inflammatory activity of ethanolic extract and isolated shikonin derivatives, models with carrageenan-induced paw edema and complete Freund's adjuvant (CFA)-induced chronic arthritis in rats were conducted.
    CONCLUSIONS:
    The observed results indicated that pre-treatment with arnebinone significantly inhibited the carrageenan-induced paw edema and also suppressed the development of chronic arthritis induced by CFA.
    Acetylshikonin 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 3.0273 mL 15.1364 mL 30.2728 mL 60.5455 mL 75.6819 mL
    5 mM 0.6055 mL 3.0273 mL 6.0546 mL 12.1091 mL 15.1364 mL
    10 mM 0.3027 mL 1.5136 mL 3.0273 mL 6.0546 mL 7.5682 mL
    50 mM 0.0605 mL 0.3027 mL 0.6055 mL 1.2109 mL 1.5136 mL
    100 mM 0.0303 mL 0.1514 mL 0.3027 mL 0.6055 mL 0.7568 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:
    Cancer Res. 2008 Nov 1;68(21):8871-80.
    Modulation of orphan nuclear receptor Nur77-mediated apoptotic pathway by acetylshikonin and analogues.[Pubmed: 18974131]
    Shikonin derivatives, which are the active components of the medicinal plant Lithospermum erythrorhizon, exhibit many biological effects including apoptosis induction through undefined mechanisms. We recently discovered that orphan nuclear receptor Nur77 migrates from the nucleus to the mitochondria, where it binds to Bcl-2 to induce apoptosis.
    METHODS AND RESULTS:
    Here, we report that certain shikonin derivatives could modulate the Nur77/Bcl-2 apoptotic pathway by increasing levels of Nur77 protein and promoting its mitochondrial targeting in cancer cells. Structural modification of Acetylshikonin resulted in the identification of a derivative 5,8-diacetoxyl-6-(1'-acetoxyl-4'-methyl-3'-pentenyl)-1,4-naphthaquinones (SK07) that exhibited improved efficacy and specificity in activating the pathway. Unlike other Nur77 modulators, shikonins increased the levels of Nur77 protein through their posttranscriptional regulation. The apoptotic effect of SK07 was impaired in Nur77 knockout cells and suppressed by cotreatment with leptomycin B that inhibited Nur77 cytoplasmic localization. Furthermore, SK07 induced apoptosis in cells expressing the COOH-terminal half of Nur77 protein but not its NH(2)-terminal region. Our data also showed that SK07-induced apoptosis was associated with a Bcl-2 conformational change and Bax activation.
    CONCLUSIONS:
    Together, our results show that certain shikonin derivatives act as modulators of the Nur77-mediated apoptotic pathway and identify a new shikonin-based lead that targets Nur77 for apoptosis induction.
    Structure Identification:
    Biol. Pharmaceut. Bull., 1994, 17(8):1075-7.
    Accelerative effect of shikonin, alkannin and acetylshikonin on the proliferation of granulation tissue in rats.[Pubmed: 7820111]

    METHODS AND RESULTS:
    The present study was carried out to compare the accelerative effect of shikonin (R-type), alkannin (S-type), and Acetylshikonin on the proliferation of granulation tissue in rats, and to elucidate the correlation between the potency of the effect and their optical activity. Koushikon mainly contained the R-type of Acetylshikonin, and Nanshikon mainly contained the S-type of Acetylshikonin. Each compound produced a dose-dependent acceleration of the cotton pellet-induced granuloma formation. In comparing identical doses of shikonin, alkannin and Acetylshikonin, the potency of their accelerative effects on the proliferation of granulation tissue was about the same.
    CONCLUSIONS:
    This result suggests that their absolute configurations (R-type or S-type) and their acetylation on the hydroxy group of the sidechain of shikonin or alkannin may not be important in producing the effect.