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    Natural Products
    Irigenin
    Information
    CAS No. 548-76-5 Price $188 / 20mg
    Catalog No.CFN93276Purity>=98%
    Molecular Weight360.31Type of CompoundFlavonoids
    FormulaC18H16O8Physical DescriptionPowder
    Download     COA    MSDS    SDFSimilar structuralComparison (Web)  (SDF)
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    According to end customer requirements, ChemFaces provide solvent format. This solvent format of product intended use: Signaling Inhibitors, Biological activities or Pharmacological activities.
    Size /Price /Stock 10 mM * 1 mL in DMSO / $67.5 / In-stock
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    Irigenin

    Irigenin
    Product Name Irigenin
    CAS No.: 548-76-5
    Catalog No.: CFN93276
    Molecular Formula: C18H16O8
    Molecular Weight: 360.31 g/mol
    Purity: >=98%
    Type of Compound: Flavonoids
    Physical Desc.: Powder
    Targets: COX | NOS | NAD(P)H:quinone reductase | 伪-glucosidase | NO | PGE | p65 | NF-魏B
    Source: The rhizomes of Belamcanda chinensis (L.) DC.
    Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
    Price: $188 / 20mg
    Inquire / Order: manager@chemfaces.com
    Technical Inquiries: service@chemfaces.com
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  • Biomedicine & Pharmacotherapy2020, 125:109950
  • Phytomedicine.2019, 57:95-104
  • Analytical sci. & Tech2020, 33(5):224-231
  • Int J Mol Sci.2020, 21(9):3144.
  • Oncol Rep.2016, 35(3):1356-64
  • Biosci. Rep.2020, 10.1024
  • Ann Transl Med.2019, 7(23):731
  • iScience.2020, 23(2):100849.
  • J of Health Science and Alternative Medicine2019, 1(1)
  • Neurochem Int.2018, 121:114-124
  • Related Screening Libraries
    Size /Price /Stock 10 mM * 100 uL in DMSO / Inquiry / In-stock
    10 mM * 1 mL in DMSO / Inquiry / In-stock
    Related Libraries
  • Anti-inflammatory Compound Library
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  • Biological Activity
    Description: Irigenin, an α-glucosidase inhibitor, which has anti-inflammatory, anti-cancer, and anti-metastatic effects. Irigenin can inhibit the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase (COX)-2 proteins and mRNAs without an appreciable cytotoxic effect. Irigenin displays moderate activity as inducers of NAD(P)H:quinone reductase (QR) in cultured mouse Hepa 1c1c7 cells.
    Targets: COX | NOS | NAD(P)H:quinone reductase | α-glucosidase | NO | PGE | p65 | NF-κB
    In vivo:
    Sci Rep. 2016 Nov 16;6:37151.
    Irigenin, a novel lead from Western Himalayan chemiome inhibits Fibronectin-Extra Domain A induced metastasis in Lung cancer cells.[Pubmed: 27849000 ]
    Several lines of evidence indicate that Fibronectin Extra Domain A (EDA) promotes metastatic capacity of tumor cells by engaging cell surface α9β1 integrins. This interaction mediated by the C-C loop of EDA activates pro-oncogenic signaling pathways leading to epithelial to mesenchymal transition (EMT) of tumor cells, thus signifying its importance in control of metastatic progression.
    METHODS AND RESULTS:
    In this context the present study was designed to explore the active compounds from selected ethno-medicinal plants of western Himalayan region for targeting EDA of Fibronectin in lung carcinoma cells. Structure based informatics for drug designing and screening was employed to generate a lead compound(s) feed that were conformationally and energetically viable. Out of 120 compounds selected, Irigenin showed best binding-affinity with C-C loop of EDA. Irigenin specifically targeted α9β1 and α4β1 integrin binding sites on EDA comprising LEU46, PHE47, PRO48, GLU58, LEU59 and GLN60 in its C-C loop as evaluated by energy decomposition per residue of Irigenin-EDA complex. In-vitro cell motility assays complemented with EDA knock-in and knockdown assays distinctively demonstrated that Irigenin prevents metastatic capacity of lung cancer cells by selectively blocking EDA.
    CONCLUSIONS:
    The results presented thus project Irigenin as a lead compound to overcome Fibronectin EDA induced metastatic progression in lung carcinoma cells.
    Irigenin Description
    Source: The rhizomes of Belamcanda chinensis (L.) DC.
    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.
    IF=36.216(2019)

    PMID: 29328914

    Cell Metab. 2020 Mar 3;31(3):534-548.e5.
    doi: 10.1016/j.cmet.2020.01.002.
    IF=22.415(2019)

    PMID: 32004475

    Mol Cell. 2017 Nov 16;68(4):673-685.e6.
    doi: 10.1016/j.molcel.2017.10.022.
    IF=14.548(2019)

    PMID: 29149595

    ACS Nano. 2018 Apr 24;12(4): 3385-3396.
    doi: 10.1021/acsnano.7b08969.
    IF=13.903(2019)

    PMID: 29553709

    Nature Plants. 2016 Dec 22;3: 16206.
    doi: 10.1038/nplants.2016.205.
    IF=13.297(2019)

    PMID: 28005066

    Sci Adv. 2018 Oct 24;4(10): eaat6994.
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    IF=12.804(2019)

    PMID: 30417089
    Calculate Dilution Ratios(Only for Reference)
    1 mg 5 mg 10 mg 20 mg 25 mg
    1 mM 2.7754 mL 13.8769 mL 27.7539 mL 55.5078 mL 69.3847 mL
    5 mM 0.5551 mL 2.7754 mL 5.5508 mL 11.1016 mL 13.8769 mL
    10 mM 0.2775 mL 1.3877 mL 2.7754 mL 5.5508 mL 6.9385 mL
    50 mM 0.0555 mL 0.2775 mL 0.5551 mL 1.1102 mL 1.3877 mL
    100 mM 0.0278 mL 0.1388 mL 0.2775 mL 0.5551 mL 0.6938 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:
    Life Sci. 2006 Apr 11;78(20):2336-42.
    Inhibitory effects of Irigenin from the rhizomes of Belamcanda chinensis on nitric oxide and prostaglandin E(2) production in murine macrophage RAW 264.7 cells.[Pubmed: 16307761 ]

    METHODS AND RESULTS:
    In the present study, we investigated antiinflammatory effects of six flavonoids isolated from the rhizomes of Belamcanda chinensis (Iridaceae) in RAW 264.7 macrophages. The results indicated that Irigenin concentration dependently inhibited lipopolysaccharide (LPS)-induced nitric oxide (NO) and prostaglandin (PG) E(2) production. Furthermore, this compound inhibited the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase (COX)-2 proteins and mRNAs without an appreciable cytotoxic effect. Treatment of the transfectant RAW 264.7 cells with Irigenin reduced the level of nuclear factor-kappaB (NF-kappaB) activity, also effectively lowered NF-kappaB binding measured by electrophoretic mobility shift assay (EMSA), which was associated with decreased p65 protein levels in the nucleus. On the basis of the above data, we suggest that the effect of Irigenin in decreasing LPS-induced NO and PGE(2) synthesis is due to diminish the mRNA and protein expression of iNOS and COX-2, respectively, also may be due to under the suppression of NF-kappaB activation.
    CONCLUSIONS:
    Therefore, Irigenin isolated from the rhizomes of Belamcanda chinensis could be offered as a leading compound for anti-inflammation.
    Cell Research:
    Planta Med. 2003 Jan;69(1):15-20.
    Cancer chemopreventive in vitro activities of isoflavones isolated from Iris germanica.[Pubmed: 12567273 ]

    METHODS AND RESULTS:
    Six known isoflavones were isolated from the rhizomes of Iris germanica, and were established by UV, MS and NMR techniques as irisolidone (1), irisolidone 7-O-alpha-D-glucoside (1a), Irigenin (2), irilone (3), iriflogenin (4), and iriskashmirianin (5). These compounds were examined for their cancer chemopreventive potential. They were shown to be potent inhibitors of cytochrome P450 1A activity with IC 50 values in the range 0.25-4.9 microM. The isoflavones 2, 3 and 5 displayed moderate activity as inducers of NAD(P)H:quinone reductase (QR) in cultured mouse Hepa 1c1c7 cells, with CD values (concentration required to double the specific activity of QR) of 3.5-16.7 microM, whereas weak activity was observed with compounds 4 and 5 in the radical (DPPH) scavenging bioassay (IC 50 values 89.6 and 120.3 microM, respectively).
    CONCLUSIONS:
    With respect to anti-tumor promoting potential based on anti-inflammatory mechanisms, none of the compounds demonstrated significant activity in the concentration range tested.
    Structure Identification:
    J Sep Sci. 2017 Jun;40(12):2565-2574.
    Ionic-liquid-based ultrasound-assisted extraction of isoflavones from Belamcanda chinensis and subsequent screening and isolation of potential α-glucosidase inhibitors by ultrafiltration and semipreparative high-performance liquid chromatography.[Pubmed: 28444982 ]
    The separation of a compound of interest from its structurally similar homologues to produce high-purity natural products is a challenging problem.
    METHODS AND RESULTS:
    This work proposes a novel method for the separation of iristectorigenin A from its structurally similar homologues by ionic-liquid-based ultrasound-assisted extraction and the subsequent screening and isolation of potential α-glucosidase inhibitors via ultrafiltration and semipreparative high-performance liquid chromatography. Ionic-liquid-based ultrasound-assisted extraction was successfully applied to the extraction of tectorigenin, iristectorigenin A, Irigenin, and irisflorentin from Belamcanda chinensis. The optimum conditions for the efficient extraction of isoflavones were determined as 1.0 M 1-ethyl-3-methylimidazolium tetrafluoroborate with extraction time of 30 min and a solvent to solid ratio of 30 mL/g. Ultrafiltration with liquid chromatography and mass spectrometry was applied to screen and identify α-glucosidase inhibitors from B. chinensis, followed by the application of semipreparative high-performance liquid chromatography to separate and isolate the active constituents. Four major compounds including tectorigenin, iristectorigenin A, Irigenin, and irisflorentin were screened and identified as α-glucosidase inhibitors, and then the four active compounds abovementioned were subsequently isolated by semipreparative high-performance liquid chromatography (99.89, 88.97, 99.79, and 99.97% purity, respectively).
    CONCLUSIONS:
    The results demonstrate that ionic liquid extraction can be successfully applied to the extraction of isoflavones from B. chinensis.
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