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    Isodiospyrin
    Isodiospyrin
    Information
    CAS No. 20175-84-2 Price
    Catalog No.CFN98019Purity>=98%
    Molecular Weight374.4 Type of CompoundQuinones
    FormulaC22H14O6Physical DescriptionRed powder
    Download Manual    COA    MSDSSimilar structuralComparison (Web)
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    Biological Activity
    Description: 1. Isodiospyrin is a novel human DNA topoisomerase I inhibitor, it exhibits cytotoxic activity to tumor cell lines.
    2. Isodiospyrin has antibacterial activity, the minimum inhibitory concentrations (MICs) against Gram-positive bacteria ranged from 0.78 to 50 microg/mL.
    3. Isodiospyrin shows high antifungal activity against P. obscurans at 30uM with 81.4% growth inhibition, and moderate activity against P. viticola (36.6%).
    Targets: Topoisomerase | Antifection
    Isodiospyrin Description
    Source: The herbs of Diospyros morrisiana
    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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    Recently, ChemFaces products have been cited in many studies from excellent and top scientific journals

    Cell. 2018 Jan 11;172(1-2):249-261.e12.
    doi: 10.1016/j.cell.2017.12.019.

    PMID: 29328914

    Mol Cell. 2017 Nov 16;68(4):673-685.e6.
    doi: 10.1016/j.molcel.2017.10.022.

    PMID: 29149595

    Scientific Reports 2017 Dec 11;7(1):17332.
    doi: 10.1038/s41598-017-17427-6.

    PMID: 29230013

    Molecules. 2017 Oct 27;22(11). pii: E1829.
    doi: 10.3390/molecules22111829.

    PMID: 29077044

    J Cell Biochem. 2018 Feb;119(2):2231-2239.
    doi: 10.1002/jcb.26385.

    PMID: 28857247

    Phytomedicine. 2018 Feb 1;40:37-47.
    doi: 10.1016/j.phymed.2017.12.030.

    PMID: 29496173
    Calculate Dilution Ratios(Only for Reference)
    1 mg 5 mg 10 mg 20 mg 25 mg
    1 mM 2.6709 mL 13.3547 mL 26.7094 mL 53.4188 mL 66.7735 mL
    5 mM 0.5342 mL 2.6709 mL 5.3419 mL 10.6838 mL 13.3547 mL
    10 mM 0.2671 mL 1.3355 mL 2.6709 mL 5.3419 mL 6.6774 mL
    50 mM 0.0534 mL 0.2671 mL 0.5342 mL 1.0684 mL 1.3355 mL
    100 mM 0.0267 mL 0.1335 mL 0.2671 mL 0.5342 mL 0.6677 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.
    Isodiospyrin References Information
    Citation [1]

    Biochem Pharmacol. 2003 Nov 15;66(10):1981-91.

    Isodiospyrin as a novel human DNA topoisomerase I inhibitor.[Pubmed: 14599556]
    Isodiospyrin is a natural product from the plant Diospyros morrisiana, which consists of an asymmetrical 1,2-binaphthoquinone chromophore. Isodiospyrin exhibits cytotoxic activity to tumor cell lines but very little is known about its cellular target and mechanism of action. Unlike the prototypic human topoisomerase I (htopo I) poison camptothecin, Isodiospyrin does not induce htopo I-DNA covalent complexes. However, Isodiospyrin antagonizes camptothecin-induced, htopo I-mediated DNA cleavage. Binding analysis indicated that Isodiospyrin binds htopo I but not DNA. These results suggest that Isodiospyrin inhibits htopo I by direct binding to htopo I, which limits htopo I access to the DNA substrate. Furthermore, Isodiospyrin exhibits strong inhibitory effect on the kinase activity of htopo I toward splicing factor 2/alternate splicing factor in the absence of DNA. Thus, these findings have important implications on naphthoquinone and its derivatives' cellular mode of actions, i.e. these novel DNA topoisomerase I inhibitors can prevent both DNA relaxation and kinase activities of htopo I.
    Citation [2]

    Phytother Res. 2000 Mar;14(2):112-7.

    Antibacterial activity of diospyrin, isodiospyrin and bisisodiospyrin from the root of Diospyros piscatoria (Gurke) (Ebenaceae).[Pubmed: 10685108 ]
    Two dimeric naphthoquinones, diospyrin and Isodiospyrin, isolated from the root of Diospyros piscatoria (Gurke), a common ingredient in several folk medicines, have been shown to have a broad spectrum of antibacterial activity. The minimum inhibitory concentrations (MICs) of diospyrin against Streptococcus pyogenes ATCC 12344 and Streptococcus pneumoniae ATCC 33400 ranged from 1.56 to 50 microg/mL. While those against Salmonella choleraesuis serotype typhi (S. typhi), ATCC 6539 and Mycobacterium chelonae ATCC 19977 were between 25 and 100 microg/mL. Isodiospyrin was more active than its racemic isomer diospyrin. The MICs against Gram-positive bacteria ranged from 0.78 to 50 microg/mL. While those against Pseudomonas aeruginosa ATCC 15443 and S. typhi ranged from 50 to 100 microg/mL. The MIC for M. chelonae was between 6.25 and 25 microg/mL. MICs were found to increase with the concentration of cells used for the inoculum. The MICs for Bacillus subtilis ATCC 6633 increased up to the highest concentration of cells tested. The same phenomenon was observed on M. chelonae, but with better effect in the latter. The kinetics of bacteria studies against both B. subtilis and M. chelonae increases with increasing concentration of Isodiospyrin tested. Two tetrameric forms of plumbagin were isolated. The naphthoquinone bisIsodiospyrin, gave MIC values between 300 and 400 micro g/mL. The second, as yet unidentified tetramer, was not active at 500 micro g/mL.
    Citation [3]

    Chem Biodivers. 2011 Dec;8(12):2331-40.

    Antifungal metabolites from the roots of Diospyros virginiana by overpressure layer chromatography.[Pubmed: 22162171 ]
    A preparative overpressure layer chromatography (OPLC) method was successfully used for the separation of two new natural compounds, 4-hydroxy-5,6-dimethoxynaphthalene-2-carbaldehyde (1) and 12,13-didehydro-20,29-dihydrobetulin (2) together with nine known compounds, including 7-methyljuglone (3), diospyrin (4), Isodiospyrin (5), shinanolone (6), lupeol (7), betulin (8), betulinic acid (9), betulinaldehyde (10), and ursolic acid (11) from the acetone extract of the roots of Diospyros virginiana. Their identification was accomplished by 1D- and 2D-NMR spectroscopy and HR-ESI-MS methods. All the isolated compounds were evaluated for their antifungal activities against Colletotrichum fragariae, C. gloeosporioides, C. acutatum, Botrytis cinerea, Fusarium oxysporum, Phomopsis obscurans, and P. viticola using in vitro micro-dilution broth assay. The results indicated that compounds 3 and 5 showed high antifungal activity against P. obscurans at 30 μM with 97.0 and 81.4% growth inhibition, and moderate activity against P. viticola (54.3 and 36.6%). It appears that an optimized OPLC system offers a rapid and efficient method of exploiting bioactive natural products.