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    Glabridin
    Information
    CAS No. 59870-68-7 Price $60 / 20mg
    Catalog No.CFN99731Purity>=98%
    Molecular Weight324.37Type of CompoundFlavonoids
    FormulaC20H20O4Physical DescriptionPowder
    Download Manual    COA    MSDSSimilar structuralComparison (Web)
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    Biological Activity
    Description: Glabridin is a GABAA receptor positive modulator promoting fatty acid oxidation and improving learning and memory, which has antioxidative,anti-inflammatory, antimalarial, estrogen receptor agonism, anti-metastasis, anti-melanogenesis and neuroprotective effects. Glabridin may possess a therapeutic effect on metabolic disorders( such as diabetes and hyperglycemia), by modulating glucose metabolism through AMPK in skeletal muscle cells.
    Targets: NOS | MMP(e.g.TIMP) | ERK | JNK | NF-kB | AMPK | Akt | GLUT | LDL | GABAA receptor
    In vitro:
    Br J Pharmacol. 2014 Jun;171(12):3037-50.
    Glabridin inhibits migration and invasion by transcriptional inhibition of matrix metalloproteinase 9 through modulation of NF-κB and AP-1 activity in human liver cancer cells.[Pubmed: 24641665]
    High mortality and morbidity rates for hepatocellular carcinoma in Taiwan primarily result from uncontrolled tumour metastasis. Glabridin, a prenylated isoflavonoid of licorice (Glycyrrhiza glabra) roots, is associated with a wide range of biological properties, such as regulation of energy metabolism, oestrogenic, neuroprotective, anti-osteoporotic and skin whitening. However, the effect of Glabridin on the metastasis of tumour cells has not been clarified.
    METHODS AND RESULTS:
    A wound healing model and Boyden chamber assays in vitro were used to determine the effects of Glabridin on the migration and invasion of human hepatocellular carcinoma (HHC) cells. Western blot analysis, gelatin zymography, real-time PCR and promoter assays were used to evaluate the inhibitory effects of Glabridin on matrix metalloproteinase 9 (MMP9) expression in these cells. Glabridin significantly inhibited migration/invasion capacities of HCC cells, Huh7 and Sk-Hep-1, cell lines that have low cytotoxicity in vitro, even at high concentrations. Western blot analysis and gelatin zymography showed that Glabridin inhibited the expression, activities and protein levels of MMP9 and the phosphorylation of ERK1/2 and JNK1/2. These inhibitory effects were associated with an up-regulation of tissue inhibitor of metalloproteinase-1 and a down-regulation of the transcription factors NF-κB and activator protein 1 signalling pathways. Finally, the administration of Glabridin effectively suppressed the tumour formation in the hepatoma xenograft model in vivo.
    CONCLUSIONS:
    Glabridin inhibited the invasion of human HCC cells and may have potential as a chemopreventive agent against liver cancer metastasis.
    Parasitol Int. 2014 Apr;63(2):349-58.
    Glabridin induces oxidative stress mediated apoptosis like cell death of malaria parasite Plasmodium falciparum.[Pubmed: 24361284]
    Plants are known as the source of novel agents for developing new antimalarial drugs. Glabridin is a polyphenolic flavonoid, a main constituent in the roots of Glycyrrhiza glabra possesses various biological activities. However, its anti-plasmodial activity is unexplored.
    METHODS AND RESULTS:
    In the present work, it is for the first time demonstrated that Glabridin inhibits Plasmodium falciparum growth in vitro with an IC50 23.9±0.43μM. Glabridin showed poor cytotoxicity in vitro with an IC50 246.6±0.88μM against Vero cell line and good selectivity index (9.6). In erythrocytic cycle, trophozoite stage was found to be most sensitive to Glabridin. In silico study showed that Glabridin inhibits Pf LDH enzyme activity by acting on NADH binding site. Glabridin induced oxidative stress by the generation of reactive oxygen and nitrogen species. Glabridin could induce apoptosis in parasite as evidenced by the depolarization of mitochondrial membrane potential (Δψm), activation of caspase like proteases and DNA fragmentation.
    CONCLUSIONS:
    These results indicate that Glabridin exhibits antiplasmodial activity and is suitable for developing antimalarial agent from a cheap and sustainable source.
    In vivo:
    Mol Nutr Food Res. 2015 Mar 3.
    Glabridin, an isoflavan from licorice root, downregulates iNOS expression and activity under high-glucose stress and inflammation.[Pubmed: 25737160]
    In females, hyperglycemia abolishes estrogen-vascular protection, leading to inflammation and oxidative stress that are related to diabetes-associated cardiovascular complications. Such knowledge led us to examine the potential of Glabridin, as a replacement of estrogen anti-inflammatory activity under high-glucose conditions.
    METHODS AND RESULTS:
    In macrophage-like cells, chronic glucose stress (28 and 44 mM) upregulated inducible nitric oxide synthase (iNOS) mRNA expression by 42 and 189%, respectively. Pretreatment with Glabridin, under chronic glucose stress, downregulated the LPS-induced nitric oxide secretion and nitrotyrosine formation, by 39 and 21%, respectively. Pretreatment with estradiol did not prevent the LPS-induced nitrotyrosine formation. Furthermore, Glabridin, brought about a decrease in the LPS-induced iNOS mRNA expression by 48%, as compared to cells pretreated with estradiol. Glabridin decreased protein levels of liver iNOS by 69% in adult mouse offspring which developed hyperglycemia after early fetal exposure to a saturated fatty acid-enriched maternal diet. Glabridin also decreased liver nitrotyrosine levels in offspring of regular diet-fed mothers after further receiving high-fat diet.
    CONCLUSIONS:
    Such results indicate that Glabridin retains anti-inflammatory abilities to regulate the synthesis and activity of iNOS under high-glucose levels, implying that a Glabridin supplement may serve as an anti-inflammatory agent in diabetes-related vascular dysfunction.
    Cancer Res. 2000 Oct 15;60(20):5704-9.
    Estrogenic and antiproliferative properties of glabridin from licorice in human breast cancer cells.[Pubmed: 11059763]

    METHODS AND RESULTS:
    There is an increasing demand for natural compounds that improve women's health by mimicking the critical benefits of estrogen to the bones and the cardiovascular system but avoiding its deleterious effects on the breast and uterus. The estrogenic properties of Glabridin, the major isoflavan in licorice root, were tested in view of the resemblance of its structure and lipophilicity to those of estradiol. The results indicate that Glabridin is a phytoestrogen, binding to the human estrogen receptor and stimulating creatine kinase activity in rat uterus, epiphyseal cartilage, diaphyseal bone, aorta, and left ventricle of the heart. The stimulatory effects of 2.5-25 microg/animal Glabridin were similar to those of 5 microg/animal estradiol. Chemical modification of Glabridin showed that the position of the hydroxyl groups has a significant role in binding to the human estrogen receptor and in proliferation-inducing activity. Glabridin was found to be three to four times more active than 2'-O-methylGlabridin and 4'-O-methylGlabridin, and both derivatives were more active than 2',4'-O-methylGlabridin. The effect of increasing concentrations of Glabridin on the growth of breast tumor cells was biphasic. Glabridin showed an estrogen receptor-dependent, growth-promoting effect at low concentrations (10 nM-10 microM) and estrogen receptor-independent antiproliferative activity at concentrations of > 15 microM.
    CONCLUSIONS:
    This is the first study to indicate that isoflavans have estrogen-like activities. Glabridin and its derivatives exhibited varying degrees of estrogen receptor agonism in different tests and demonstrated growth-inhibitory actions on breast cancer cells.
    Glabridin Description
    Source: The roots of Glycyrrhiza glabra L.
    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 3.0829 mL 15.4145 mL 30.829 mL 61.658 mL 77.0725 mL
    5 mM 0.6166 mL 3.0829 mL 6.1658 mL 12.3316 mL 15.4145 mL
    10 mM 0.3083 mL 1.5414 mL 3.0829 mL 6.1658 mL 7.7072 mL
    50 mM 0.0617 mL 0.3083 mL 0.6166 mL 1.2332 mL 1.5414 mL
    100 mM 0.0308 mL 0.1541 mL 0.3083 mL 0.6166 mL 0.7707 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
    Cell Research:
    Mol Cell Endocrinol. 2014 Aug 5;393(1-2):99-108.
    Glabridin induces glucose uptake via the AMP-activated protein kinase pathway in muscle cells.[Pubmed: 24953974]

    METHODS AND RESULTS:
    The present study demonstrates that Glabridin, a prenylated isoflavone in licorice, stimulates glucose uptake through the adenosine monophosphate-activated protein kinase (AMPK) pathway in L6 myotubes. Treatment with Glabridin for 4h induced glucose uptake in a dose-dependent manner accompanied by the translocation of glucose transporter type 4 (GLUT4) to the plasma membrane. Glabridin needed at least 4h to increase glucose uptake, while it significantly decreased glycogen and increased lactic acid within 15 min. Pharmacological inhibition of AMPK by Compound C suppressed the Glabridin-induced glucose uptake, whereas phosphoinositide 3-kinase and Akt inhibition by LY294002 and Akt1/2 inhibitor, respectively, did not. Furthermore, Glabridin induced AMPK phosphorylation, and siRNA for AMPK completely abolished Glabridin-induced glucose uptake. We confirmed that Glabridin-rich licorice extract prevent glucose intolerance accompanied by the AMPK-dependent GLUT4 translocation in the plasma membrane of mice skeletal muscle.
    CONCLUSIONS:
    These results indicate that Glabridin may possess a therapeutic effect on metabolic disorders, such as diabetes and hyperglycemia, by modulating glucose metabolism through AMPK in skeletal muscle cells.
    Animal Research:
    Life Sci. 2008 Jan 2;82(1-2):68-78.
    In vitro and in vivo neuroprotective effect and mechanisms of glabridin, a major active isoflavan from Glycyrrhiza glabra (licorice).[Pubmed: 18048062]
    Stroke is a life-threatening disease characterized by rapidly developing clinical signs of focal or global disturbance of cerebral function due to cerebral ischemia. A number of flavonoids have been shown to attenuate the cerebral injuries in stroked animal models. Glabridin, a major flavonoid of Glycyrrhiza glabra (licorice), possesses multiple pharmacological activities. This study aimed to investigate whether Glabridin modulated the cerebral injuries induced by middle cerebral artery occlusion (MCAO) in rats and staurosporine-induced damage in cultured rat cortical neurons and the possible mechanisms involved.
    METHODS AND RESULTS:
    Our study showed that Glabridin at 25mg/kg by intraperitoneal injection, but not at 5mg/kg, significantly decreased the focal infarct volume, cerebral histological damage and apoptosis in MCAO rats compared to sham-operated rats. Glabridin significantly attenuated the level of brain malonyldialdehyde (MDA) in MCAO rats, while it elevated the level of two endogenous antioxidants in the brain, i.e. superoxide dismutase (SOD) and reduced glutathione (GSH). Co-treatment with Glabridin significantly inhibited the staurosporine-induced cytotoxicity and apoptosis of cultured rat cortical neurons in a concentration-dependent manner. Consistently, Glabridin significantly reduced the DNA laddering caused by staurosporine in a concentration-dependent manner. Glabridin also suppressed the elevated Bax protein and caspase-3 proenzyme and decreased bcl-2 induced by staurosporine in cultured rat cortical neurons, facilitating cell survival. Glabridin also inhibited superoxide production in cultured cortical neurons exposed to staurosporine.
    CONCLUSIONS:
    These findings indicated that Glabridin had a neuroprotective effect via modulation of multiple pathways associated with apoptosis. Further studies are warranted to further investigate the biochemical mechanisms for the protective effect of Glabridin on neurons and the evidence for clinical use of licorice in the management of cerebral ischemia.
    Structure Identification:
    Pigment Cell Res. 1998 Dec;11(6):355-61.
    The inhibitory effect of glabridin from licorice extracts on melanogenesis and inflammation.[Pubmed: 9870547]
    Glabridin is the main ingredient in hydrophobic fraction of licorice extract affecting on skins.
    METHODS AND RESULTS:
    In this study, we investigated inhibitory effects of Glabridin on melanogenesis and inflammation using cultured B16 murine melanoma cells and guinea pig skins. The results indicated that Glabridin inhibits tyrosinase activity of these cells at concentrations of 0.1 to 1.0 microg/ml and had no detectable effect on their DNA synthesis. Combined analysis of SDS-polyacrylamide gel electrophoresis and DOPA staining on the large granule fraction of these cells disclosed that Glabridin decreased specifically the activities of T1 and T3 tyrosinase isozymes. It was also shown that UVB-induced pigmentation and erythema in the skins of guinea pigs were inhibited by topical applications of 0.5% Glabridin. Anti-inflammatory effects of Glabridin in vitro were also shown by its inhibition of superoxide anion productions and cyclooxygenase activities. These data indicated that Glabridin is a unique compound possessing more than one function; not only the inhibition of melanogenesis but also the inhibition of inflammation in the skins. By replacing each of hydroxyl groups of Glabridin with others, it was revealed that the inhibitory effect of 2'-O-ethyl Glabridin was significantly stronger than that of 4'-O-ethyl-Glabridin on melanin synthesis in cultured B16 cells at the concentration of 1.0 mg/ml. With replacement of both of two hydroxyl groups, the inhibitory effect was totally lost.
    CONCLUSIONS:
    Based on these data, we concluded that two hydroxyl groups of Glabridin are important for the inhibition of melanin synthesis and that the hydroxyl group at the 4' position of this compound is more closely related to melanin synthesis.