Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C15H12O4 |
| Molecular Weight | 256.2534 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC=C(C=C1)[C@@H]2CC(=O)C3=CC=C(O)C=C3O2
InChI
InChIKey=FURUXTVZLHCCNA-AWEZNQCLSA-N
InChI=1S/C15H12O4/c16-10-3-1-9(2-4-10)14-8-13(18)12-6-5-11(17)7-15(12)19-14/h1-7,14,16-17H,8H2/t14-/m0/s1
DescriptionCurator's Comment: Description was created using several sources including: https://www.ncbi.nlm.nih.gov/pubmed/18669586 | https://www.ncbi.nlm.nih.gov/pubmed/11501051 | https://www.ncbi.nlm.nih.gov/pubmed/24738081
Curator's Comment: Description was created using several sources including: https://www.ncbi.nlm.nih.gov/pubmed/18669586 | https://www.ncbi.nlm.nih.gov/pubmed/11501051 | https://www.ncbi.nlm.nih.gov/pubmed/24738081
Liquiritigenin is a plant-derived flavonoid isolated from the roots of plants belonging to licorice species (Glycyrrhiza uralensis, Glycyrrhiza glabra, Glycyrrhiza inflate etc) and is available in common foods and alternative medicine. Liquiritigenin is one of the major active compounds of MF101, selective ER-beta agonist herbal extract of 22 botanical ingredients originally tested for reducing the frequency and severity of menopausal hot flashes. At sufficient concentrations, liquiritigenin is also a partial agonist of ER-alpha but has a 20-fold higher affinity for ER-beta than for ER-alpha. Several studies showed that liquiritigenin exerts cytoprotective effects against heavy metal-induced toxicity in cultured hepatocytes, has protective effects against liver injuries induced by acetaminophen and buthione sulfoximine in rats and has an anti-inflammatory effect in macrophages suggesting its potential therapeutic use for liver diseases. Liquiritigenin inhibits the activity of MAO A and B in rat brain mitochondria and displayed favorable properties as a specific transient receptor potential melastatin 3 (TRPM3) blocker. Anti-hepatocellular carcinoma effects of liquiritigenin are related to its modulation of the activations of mitogen-activated protein kinase (MAPKs) and was discovered, that this compound is a potential therapeutic agent for hepatocellular carcinoma treatment.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27113683 | https://www.ncbi.nlm.nih.gov/pubmed/27107388
Curator's Comment: Known to be CNS penetrant in mouse; rats. Human data not available
https://www.ncbi.nlm.nih.gov/pubmed/25815607
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Studies on chemical constituents of Heterosmilax yunnanensis]. | 2007 Aug |
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| Saikokeishito Extract Exerts a Therapeutic Effect on alpha-Naphthylisothiocyanate-Induced Liver Injury in Rats through Attenuation of Enhanced Neutrophil Infiltration and Oxidative Stress in the Liver Tissue. | 2007 Jan |
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| Indian herbs and herbal drugs used for the treatment of diabetes. | 2007 May |
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| Biosynthesis of 5-deoxyflavanones in microorganisms. | 2007 Oct |
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| In vitro antimalarial activity of prenylated flavonoids from Erythrina fusca. | 2008 Apr |
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| Brazilian red propolis--chemical composition and botanical origin. | 2008 Dec |
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| Liquiritigenin is a plant-derived highly selective estrogen receptor beta agonist. | 2008 Feb 13 |
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| Cytoprotective Activity of Glycyrrhizae radix Extract Against Arsenite-induced Cytotoxicity. | 2008 Jun |
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| Isoliquiritigenin suppresses cocaine-induced extracellular dopamine release in rat brain through GABA(B) receptor. | 2008 Jun 10 |
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| Anti-cancer effects of xanthones from pericarps of mangosteen. | 2008 Mar |
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| Anti-inflammatory effects of liquiritigenin as a consequence of the inhibition of NF-kappaB-dependent iNOS and proinflammatory cytokines production. | 2008 May |
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| Oxidative in vitro metabolism of liquiritigenin, a bioactive compound isolated from the Chinese herbal selective estrogen beta-receptor agonist MF101. | 2008 Nov |
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| Biotransformation of the chemopreventive agent 2',4',4-trihydroxychalcone (isoliquiritigenin) by UDP-glucuronosyltransferases. | 2008 Oct |
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| Transport and metabolism of flavonoids from Chinese herbal remedy Xiaochaihu- tang across human intestinal Caco-2 cell monolayers. | 2008 Sep |
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| Screening of herbal constituents for aromatase inhibitory activity. | 2008 Sep 15 |
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| Survey of Glycyrrhizae Radix resources in Mongolia: chemical assessment of the underground part of Glycyrrhiza uralensis and comparison with Chinese Glycyrrhizea Radix. | 2009 Apr |
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| Liquiritigenin inhibits Abeta(25-35)-induced neurotoxicity and secretion of Abeta(1-40) in rat hippocampal neurons. | 2009 Jul |
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| Ethyl acetate extracts of alfalfa (Medicago sativa L.) sprouts inhibit lipopolysaccharide-induced inflammation in vitro and in vivo. | 2009 Jul 14 |
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| Drug and cell type-specific regulation of genes with different classes of estrogen receptor beta-selective agonists. | 2009 Jul 17 |
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| Pharmacokinetics and first-pass effects of liquiritigenin in rats: low bioavailability is primarily due to extensive gastrointestinal first-pass effect. | 2009 Jun |
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| Phytochemical analysis of young fustic (Cotinus coggygria heartwood) and identification of isolated colourants in historical textiles. | 2009 Jun |
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| Hepatoprotective Activity of Licorice Water Extract against Cadmium-induced Toxicity in Rats. | 2009 Jun |
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| Liquiritigenin, a licorice flavonoid, helps mice resist disseminated candidiasis due to Candida albicans by Th1 immune response, whereas liquiritin, its glycoside form, does not. | 2009 May |
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| Pharmacokinetics of liquiritigenin in mice, rats, rabbits, and dogs, and animal scale-up. | 2009 Nov |
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| Simultaneous determination of five flavonoids in licorice using pressurized liquid extraction and capillary electrochromatography coupled with peak suppression diode array detection. | 2009 Oct 23 |
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| Separation, characterization and dose-effect relationship of the PPARgamma-activating bio-active constituents in the Chinese herb formulation 'San-Ao decoction'. | 2009 Oct 9 |
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| Aldose reductase inhibitory compounds from Glycyrrhiza uralensis. | 2010 |
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| Flavone synthase II (CYP93B16) from soybean (Glycine max L.). | 2010 Apr |
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| [Studies on changes of in vitro and in vivo material base of Shaoyao Gancao decoction based on HPLC-DAD-ESI-MS]. | 2010 Aug |
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| Liquiritigenin derivatives and their hepatotoprotective activity. | 2010 Aug |
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| Soybean metabolites regulated in root hairs in response to the symbiotic bacterium Bradyrhizobium japonicum. | 2010 Aug |
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| Synthesis and antitumor activity of liquiritigenin thiosemicarbazone derivatives. | 2010 Aug |
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| Identification and characterisation of CYP75A31, a new flavonoid 3'5'-hydroxylase, isolated from Solanum lycopersicum. | 2010 Feb 3 |
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| Pharmacokinetic interaction between liquiritigenin (LQ) and DDB: increased glucuronidation of LQ in the liver possibly due to increased hepatic blood flow rate by DDB. | 2010 Jan 31 |
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| [Studies on the flavonoids from Lignum Dalbergiae Odoriferae (II)]. | 2010 Jun |
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| Pharmacokinetics of liquiritigenin and its two glucuronides, M1 and M2, in rats with acute hepatitis induced by d-galactosamine/lipopolysaccharide or CCl(4). | 2010 Jun |
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| Inhibition of hepatoma 22 tumor by Liquiritigenin. | 2010 Jun |
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| Intricate environment-modulated genetic networks control isoflavone accumulation in soybean seeds. | 2010 Jun 11 |
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| Effects of liquiritigenin treatment on the learning and memory deficits induced by amyloid beta-peptide (25-35) in rats. | 2010 Jun 26 |
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| Determination of flavonoids in licorice using acid hydrolysis and reversed-phase HPLC and evaluation of the chemical quality of cultivated licorice. | 2010 May |
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| Whole genome co-expression analysis of soybean cytochrome P450 genes identifies nodulation-specific P450 monooxygenases. | 2010 Nov 9 |
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| Liquiritigenin pharmacokinetics in a rat model of diabetes mellitus induced by streptozotocin: greater formation of glucuronides in the liver, especially M2, due to increased hepatic uridine 5'-diphosphoglucuronic acid level. | 2010 Oct |
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| [On-line sample stacking for the analysis of glycyrrhiza flavonoids by anion selective exhaustive injection-sweeping micellar electrokinetic chromatography]. | 2010 Sep |
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| Fuscacarpans A-C, new pterocarpans from the stems of Erythrina fusca. | 2010 Sep |
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| Promotion of rat brain-derived progenitor cell neurogenesis by liquiritigenin treatment: underlying mechanisms. | 2010 Sep 13 |
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| Estradiol antagonism of glucocorticoid-induced GILZ expression in human uterine epithelial cells and murine uterus. | 2013 Jan |
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| Antispasmodic effect of shakuyakukanzoto extract on experimental muscle cramps in vivo: role of the active constituents of Glycyrrhizae radix. | 2013 Jan 9 |
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| Anti-hepatitis C virus compounds obtained from Glycyrrhiza uralensis and other Glycyrrhiza species. | 2014 Mar |
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| Selectivity of natural, synthetic and environmental estrogens for zebrafish estrogen receptors. | 2014 Oct 1 |
|
| Induction of NAD(P)H:Quinone Oxidoreductase 1 (NQO1) by Glycyrrhiza Species Used for Women's Health: Differential Effects of the Michael Acceptors Isoliquiritigenin and Licochalcone A. | 2015 Nov 16 |
Patents
Sample Use Guides
4.5 g/day (dry weight of extract) of MF101 (Liquiritigeni is one of the major active compounds of MF101), 9.0 g/day (dry weight of extract) of MF101 for 12 weeks in healthy postmenopausal women experiencing at least 5 hot flashes per day or 35 hot flashes per week.
Route of Administration:
Oral
Liquiritigenin was added in final concentrations of 10*(−11) –10*(−5) M every 48–120 hours to human breast cancer cell lines HCC1806 and HCC1937. Proliferation was determined by a colorimetric assay. Changes in viability were used as marker for proliferation. Treatment with liquiritigenin reduced the ability to invade a reconstituted basement membrane and to migrate in response to the cellular stimulus also treatment with liquiritigenin resulted in a significant decrease of CXCR4 protein expression
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LIQUIRITIGENIN
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METABOLITE (PARENT)
SUBSTANCE RECORD
