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    Glycycoumarin
    Glycycoumarin
    Information
    CAS No. 94805-82-0 Price $268 / 10mg
    Catalog No.CFN89408Purity>=98%
    Molecular Weight368.37Type of CompoundCoumarins
    FormulaC21H20O6Physical DescriptionPowder
    Download     COA    MSDSSimilar structuralComparison (Web)
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    Glycycoumarin Description
    Source: The roots of Licorice.
    Biological Activity or Inhibitors: 1. Glycycoumarin shows moderate inhibitory effects against CYP1A2 and CYP2B6.
    2. Glycycoumarin can inhibit hepatocyte lipoapoptosis through activation of autophagy and inhibition of ER stress/GSK-3-mediated mitochondrial pathway.
    3. Glycycoumarin exerts anti-liver cancer activity by directly targeting T-LAK cell-originated protein kinase.
    4. Glycycoumarin is an estrogen agonist.
    5. Glycycoumarin has antioxidant and anti-inflammatory activities.
    6. Glycycoumarin has ameliorative effects on Aβ oligomer-induced neurotoxicity.
    7. Glycycoumarin has anti-hepatitis C virus (HCV) activity, with the IC(50) value of 8.8, ug/mL.
    8. Glycycoumarin has an inhibitory effect on smooth muscle contraction induced by various types of stimulants through the inhibition of PDEs, especially isozyme 3, followed by the accumulation of intracellular cAMP.
    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 2.7147 mL 13.5733 mL 27.1466 mL 54.2932 mL 67.8665 mL
    5 mM 0.5429 mL 2.7147 mL 5.4293 mL 10.8586 mL 13.5733 mL
    10 mM 0.2715 mL 1.3573 mL 2.7147 mL 5.4293 mL 6.7867 mL
    50 mM 0.0543 mL 0.2715 mL 0.5429 mL 1.0859 mL 1.3573 mL
    100 mM 0.0271 mL 0.1357 mL 0.2715 mL 0.5429 mL 0.6787 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.
    Glycycoumarin References Information
    Citation [1]

    Eur J Pharm Sci. 2017 Nov 15;109:182-190.

    Cytochrome P450 inhibition by three licorice species and fourteen licorice constituents.[Pubmed: 28774812]
    The licorice compounds isoliquiritigenin, licoricidin, licochalcone A, 18β-glycyrrhetinic acid, and Glycycoumarin inhibited one or more members of the CYP2C family of enzymes. Glycycoumarin and licochalcone A inhibited CYP1A2, but only Glycycoumarin inhibited CYP2B6. Isoliquiritigenin, glabridin and licoricidin competitively inhibited CYP3A4, while licochalcone A (specific to G. inflata roots) was a mechanism-based inhibitor. The three licorice species commonly used in botanical dietary supplements have varying potential for drug-botanical interactions as inhibitors of cytochrome P450 isoforms. Each species of licorice displays a unique profile of constituents with potential for drug interactions.
    Citation [2]

    Sci Rep. 2016 Nov 30;6:38138.

    Glycycoumarin inhibits hepatocyte lipoapoptosis through activation of autophagy and inhibition of ER stress/GSK-3-mediated mitochondrial pathway.[Pubmed: 27901086 ]
    Glycycoumarin (GCM) is a representative of courmarin compounds isolated from licorice. In the present study, the protective effect of GCM on hepatocyte lipoapoptosis has been evaluated using both cell culture model of palmitate-induced lipoapoptosis and animal model of non-alcoholic steatohepatitis (NASH). The results demonstrated for the first time that GCM was highly effective in suppressing hepatocyte lipoapoptosis in both in vitro and in vivo. Mechanistically, GCM was able to re-activate the impaired autophagy by lipid metabolic disorders. In line with the activation of autophagy, ER stress-mediated JNK and mitochondrial apoptotic pathway activation was inhibited by GCM both in vitro and in vivo. In addition, inactivation of GSK-3 might also contribute to the protective effect of GCM on hepatocyte lipoapoptosis. Our findings supported GCM as a novel active component of licorice against non-alcoholic fatty liver disease (NAFLD).
    Citation [3]

    Oncotarget. 2016 Oct 4;7(40):65732-65743.

    Glycycoumarin exerts anti-liver cancer activity by directly targeting T-LAK cell-originated protein kinase.[Pubmed: 27582549 ]
    Glycycoumarin (GCM) is a major bioactive coumarin compound isolated from licorice and the anti-cancer activity of GCM has not been scientifically addressed. In the present study, we have tested the anti-liver cancer activity of GCM using both in vitro and in vivo models and found for the first time that GCM possesses a potent activity against liver cancer evidenced by cell growth inhibition and apoptosis induction in vitro and tumor reduction in vivo. Mechanistically, GCM was able to bind to and inactivate oncogenic kinase T-LAK cell-originated protein kinase (TOPK), which in turn led to activation of p53 pathway. Our findings supported GCM as a novel active compound that contributed to the anti-cancer activity of licorice and TOPK could be an effective target for hepatocellular carcinoma (HCC) treatment.
    Citation [4]

    Steroids. 2016 Jan;105:42-9.

    Licorice root components in dietary supplements are selective estrogen receptor modulators with a spectrum of estrogenic and anti-estrogenic activities.[Pubmed: 26631549 ]
    We have investigated the estrogenic activity of 7 of these components, obtained from an extract of Glycyrrhiza glabra powder, namely Glabridin (L1), Calycosin (L2), Methoxychalcone (L3), Vestitol (L4), Glyasperin C (L5), Glycycoumarin (L6), and Glicoricone (L7), and compared them with Liq, Iso-Liq, and estradiol (E2). All components, including Liq and Iso-Liq, have low binding affinity for estrogen receptors (ERs). Their potency and efficacy in stimulating the expression of estrogen-regulated genes reveal that Liq and Iso-Liq and L2, L3, L4, and L6 are estrogen agonists. Interestingly, L3 and L4 have an efficacy nearly equivalent to E2 but with a potency ca. 10,000-fold less. The other components, L1, L5 and L7, acted as partial estrogen antagonists. All agonist activities were reversed by the antiestrogen, ICI 182,780, or by knockdown of ERα with siRNA, indicating that they are ER dependent.
    Citation [5]

    Food Chem. 2013 Nov 15;141(2):1063-71.

    Antioxidant and anti-inflammatory activities of six flavonoids separated from licorice.[Pubmed: 23790887]
    Licorice, the roots and rhizomes of several Glycyrrhiza species (Leguminosae), is an important natural sweetening agent and a widely used herbal medicine. In this work, six flavonoids, 5-(1,1-dimethylallyl)-3,4,4'-trihydroxy-2-methoxychalcone (1), licochalcone B (2), licochalcone A (3), echinatin (4), Glycycoumarin (5) and glyurallin B (6), were isolated from the extracts of licorice (Glycyrrhiza inflata and Glycyrrhiza uralensis). Their structures were elucidated using various spectroscopic methods. To our knowledge, compound 1 was isolated from natural plants for the first time. All the isolates were tested by antioxidant and anti-inflammatory assays. Compounds 2, 4 and 5 showed strong scavenging activity toward the ABTS(+) radical, and compounds 1, 2, 3, 5 and 6 exhibited potent inhibition of lipid peroxidation in rat liver microsomes compared with the reference controls. Compounds 1-4 dose-dependently inhibited LPS induced reactive oxygen species (ROS) production in RAW 264.7 cells. Furthermore, compounds 1-5 were demonstrated to inhibit the production of nitric oxide (NO), interleukin-6 (IL-6) and prostaglandin E2 (PGE2) in LPS-induced macrophage cells. Moreover, the contents of the six compounds, in different Glycyrrhiza species, were quantified by HPLC-MS.
    Citation [6]

    J Ethnopharmacol. 2015 Jan 15;159:122-8.

    Protective effects of glycycoumarin and procyanidin B1, active components of traditional Japanese medicine yokukansan, on amyloid β oligomer-induced neuronal death.[Pubmed: 25446602 ]
    Two of the 16 components tested, Glycycoumarin derived from Glycyrrhiza and procyanidin B1 derived from Uncaria Hook, significantly inhibited Aβ oligomer-induced neuronal death in a dose-dependent manner. Glycyrrhiza, Uncaria Hook, and yokukansan significantly suppressed the Aβ oligomer-induced activation of caspase-3 as well as caspase-8 and -9. Glycycoumarin also suppressed the activation of caspase-3, but not caspase-8 and -9. Procyanidin B1 suppressed the activation of caspase-3, -8, and -9. CONCLUSIONS: Our results demonstrated that Glycycoumarin and procyanidin B1 had ameliorative effects on Aβ oligomer-induced neurotoxicity. The neuroprotective effects of Glycycoumarin are thought to be due to the attenuated activation of caspase-3, but not caspase-8 or -9. Procyanidin B1, as well as yokukansan, Glycyrrhiza, and Uncaria Hook, may attenuate the activation of caspase-3 by inhibiting that of caspase-8 and -9.
    Citation [7]

    Microbiol Immunol. 2014 Mar;58(3):180-7

    Anti-hepatitis C virus compounds obtained from Glycyrrhiza uralensis and other Glycyrrhiza species.[Pubmed: 24397541 ]
    In this study, extracts of G. uralensis roots and their components were examined for anti-HCV activity using an HCV cell culture system. It was found that a methanol extract of G. uralensis roots and its chloroform fraction possess anti-HCV activity with 50%-inhibitory concentrations (IC(50)) of 20.0 and 8.0 μg/mL, respectively. Through bioactivity-guided purification and structural analysis, Glycycoumarin, glycyrin, glycyrol and liquiritigenin were isolated and identified as anti-HCV compounds, their IC(50) being 8.8, 7.2, 4.6 and 16.4 μg/mL, respectively. However, glycyrrhizin, the major constituent of G. uralensis, and its monoammonium salt, showed only marginal anti-HCV activity.
    Citation [8]

    J Ethnopharmacol. 2006 May 24;105(3):409-14.

    Glycycoumarin from Glycyrrhizae Radix acts as a potent antispasmodic through inhibition of phosphodiesterase 3.[Pubmed: 16387459 ]
    In this paper we investigated the effects and the action mechanism of Glycycoumarin on the contraction of mouse jejunum. Glycycoumarin inhibited the contraction induced by various types of stimulants, such as CCh, KCl, BaCl(2), and A23187 (calcium ionophore III) with IC(50) values of 2.93+/-0.94 micromol/l (1.08+/-0.35 microg/ml), 2.59+/-0.58 micromol/l (0.95+/-0.29 microg/ml), 4.09+/-1.82 micromol/l (1.51+/-0.67 microg/ml) and 7.39+/-5.19 micromol/l (2.72+/-1.91 microg/ml), respectively, with a potency similar to that of papaverine (a representative antispasmodic for smooth muscle). Furthermore, pretreatment with Glycycoumarin enhanced the relaxation induced by forskolin on CCh-evoked contraction, similar to that by pretreatment with IBMX, a non-specific inhibitor of phosphodiesterases (PDEs). Pretreatment with Glycycoumarin also enhanced the relaxation effect of rolipram, a specific inhibitor of PDE isozyme 4, as pretreatment with milrinone, a specific inhibitor of isozyme 3, did. Moreover, the effect of Glycycoumarin was associated with dose-dependent accumulation of cAMP, but not cGMP, in mouse jejunum. These results indicate that Glycycoumarin has an inhibitory effect on smooth muscle contraction induced by various types of stimulants through the inhibition of PDEs, especially isozyme 3, followed by the accumulation of intracellular cAMP.