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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H12O4
Molecular Weight 256.2539
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LIQUIRITIGENIN

SMILES

c1cc(ccc1[C@]2([H])CC(=O)c3ccc(cc3O2)O)O

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

HIDE SMILES / InChI

Molecular Formula C15H12O4
Molecular Weight 256.2539
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

Curator's Comment:: https://www.ncbi.nlm.nih.gov/pubmed/25815607

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

PubMed

PubMed

TitleDatePubMed
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
Indian herbs and herbal drugs used for the treatment of diabetes.
2007 May
In vitro antimalarial activity of prenylated flavonoids from Erythrina fusca.
2008 Apr
Brazilian red propolis--chemical composition and botanical origin.
2008 Dec
Liquiritigenin is a plant-derived highly selective estrogen receptor beta agonist.
2008 Feb 13
Cytoprotective Activity of Glycyrrhizae radix Extract Against Arsenite-induced Cytotoxicity.
2008 Jun
Isoliquiritigenin suppresses cocaine-induced extracellular dopamine release in rat brain through GABA(B) receptor.
2008 Jun 10
Anti-cancer effects of xanthones from pericarps of mangosteen.
2008 Mar
Anti-inflammatory effects of liquiritigenin as a consequence of the inhibition of NF-kappaB-dependent iNOS and proinflammatory cytokines production.
2008 May
Oxidative in vitro metabolism of liquiritigenin, a bioactive compound isolated from the Chinese herbal selective estrogen beta-receptor agonist MF101.
2008 Nov
Biotransformation of the chemopreventive agent 2',4',4-trihydroxychalcone (isoliquiritigenin) by UDP-glucuronosyltransferases.
2008 Oct
Transport and metabolism of flavonoids from Chinese herbal remedy Xiaochaihu- tang across human intestinal Caco-2 cell monolayers.
2008 Sep
Screening of herbal constituents for aromatase inhibitory activity.
2008 Sep 15
Effect of liquiritigenin, a flavanone existed from Radix glycyrrhizae on pro-apoptotic in SMMC-7721 cells.
2009 Apr
Survey of Glycyrrhizae Radix resources in Mongolia: chemical assessment of the underground part of Glycyrrhiza uralensis and comparison with Chinese Glycyrrhizea Radix.
2009 Apr
Liquiritigenin, a flavonoid aglycone from licorice, has a choleretic effect and the ability to induce hepatic transporters and phase-II enzymes.
2009 Feb
Licorice flavonoids inhibit eotaxin-1 secretion by human fetal lung fibroblasts in vitro.
2009 Feb 11
Liquiritigenin inhibits Abeta(25-35)-induced neurotoxicity and secretion of Abeta(1-40) in rat hippocampal neurons.
2009 Jul
Ethyl acetate extracts of alfalfa (Medicago sativa L.) sprouts inhibit lipopolysaccharide-induced inflammation in vitro and in vivo.
2009 Jul 14
Drug and cell type-specific regulation of genes with different classes of estrogen receptor beta-selective agonists.
2009 Jul 17
Pharmacokinetics and first-pass effects of liquiritigenin in rats: low bioavailability is primarily due to extensive gastrointestinal first-pass effect.
2009 Jun
Phytochemical analysis of young fustic (Cotinus coggygria heartwood) and identification of isolated colourants in historical textiles.
2009 Jun
Oral Administration of Ren-Shen-Yang-Rong-Tang 'Ninjin'yoeito' Protects Against Hematotoxicity and Induces Immature Erythroid Progenitor Cells in 5-Fluorouracil-induced Anemia.
2009 Jun
Hepatoprotective Activity of Licorice Water Extract against Cadmium-induced Toxicity in Rats.
2009 Jun
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
Pharmacokinetics of liquiritigenin in mice, rats, rabbits, and dogs, and animal scale-up.
2009 Nov
Simultaneous determination of five flavonoids in licorice using pressurized liquid extraction and capillary electrochromatography coupled with peak suppression diode array detection.
2009 Oct 23
Separation, characterization and dose-effect relationship of the PPARgamma-activating bio-active constituents in the Chinese herb formulation 'San-Ao decoction'.
2009 Oct 9
Aldose reductase inhibitory compounds from Glycyrrhiza uralensis.
2010
Flavone synthase II (CYP93B16) from soybean (Glycine max L.).
2010 Apr
[Studies on changes of in vitro and in vivo material base of Shaoyao Gancao decoction based on HPLC-DAD-ESI-MS].
2010 Aug
Liquiritigenin derivatives and their hepatotoprotective activity.
2010 Aug
Soybean metabolites regulated in root hairs in response to the symbiotic bacterium Bradyrhizobium japonicum.
2010 Aug
Synthesis and antitumor activity of liquiritigenin thiosemicarbazone derivatives.
2010 Aug
Identification and characterisation of CYP75A31, a new flavonoid 3'5'-hydroxylase, isolated from Solanum lycopersicum.
2010 Feb 3
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
[Studies on the flavonoids from Lignum Dalbergiae Odoriferae (II)].
2010 Jun
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
Inhibition of hepatoma 22 tumor by Liquiritigenin.
2010 Jun
Intricate environment-modulated genetic networks control isoflavone accumulation in soybean seeds.
2010 Jun 11
Determination of flavonoids in licorice using acid hydrolysis and reversed-phase HPLC and evaluation of the chemical quality of cultivated licorice.
2010 May
Whole genome co-expression analysis of soybean cytochrome P450 genes identifies nodulation-specific P450 monooxygenases.
2010 Nov 9
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
[On-line sample stacking for the analysis of glycyrrhiza flavonoids by anion selective exhaustive injection-sweeping micellar electrokinetic chromatography].
2010 Sep
Promotion of rat brain-derived progenitor cell neurogenesis by liquiritigenin treatment: underlying mechanisms.
2010 Sep 13
Estradiol antagonism of glucocorticoid-induced GILZ expression in human uterine epithelial cells and murine uterus.
2013 Jan
Antispasmodic effect of shakuyakukanzoto extract on experimental muscle cramps in vivo: role of the active constituents of Glycyrrhizae radix.
2013 Jan 9
Anti-hepatitis C virus compounds obtained from Glycyrrhiza uralensis and other Glycyrrhiza species.
2014 Mar
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

In Vivo Use Guide
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
Substance Class Chemical
Created
by admin
on Sat Jun 26 13:11:27 UTC 2021
Edited
by admin
on Sat Jun 26 13:11:27 UTC 2021
Record UNII
T194LKP9W6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LIQUIRITIGENIN
INCI  
INCI  
Official Name English
4H-1-BENZOPYRAN-4-ONE, 2,3-DIHYDRO-7-HYDROXY-2-(4-HYDROXYPHENYL)-, (S)-
Systematic Name English
FLAVANONE, 4',7-DIHYDROXY-
Systematic Name English
LIQUIRITIGENIN [INCI]
Common Name English
4',7-DIHYDROXYFLAVANONE
Systematic Name English
(-)-LIQUIRITIGENIN
Common Name English
(2S)-LIQUIRITIGENIN
Common Name English
(-)-(2S)-7,4'-DIHYDROXYFLAVANONE
Systematic Name English
7,4'-DIHYDROXYFLAVANONE
Systematic Name English
4H-1-BENZOPYRAN-4-ONE, 2,3-DIHYDRO-7-HYDROXY-2-(4-HYDROXYPHENYL)-, (2S)-
Systematic Name English
Code System Code Type Description
CAS
578-86-9
Created by admin on Sat Jun 26 13:11:27 UTC 2021 , Edited by admin on Sat Jun 26 13:11:27 UTC 2021
PRIMARY
EPA CompTox
578-86-9
Created by admin on Sat Jun 26 13:11:27 UTC 2021 , Edited by admin on Sat Jun 26 13:11:27 UTC 2021
PRIMARY
FDA UNII
T194LKP9W6
Created by admin on Sat Jun 26 13:11:27 UTC 2021 , Edited by admin on Sat Jun 26 13:11:27 UTC 2021
PRIMARY
PUBCHEM
114829
Created by admin on Sat Jun 26 13:11:27 UTC 2021 , Edited by admin on Sat Jun 26 13:11:27 UTC 2021
PRIMARY
WIKIPEDIA
LIQUIRITIGENIN
Created by admin on Sat Jun 26 13:11:27 UTC 2021 , Edited by admin on Sat Jun 26 13:11:27 UTC 2021
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
MAJOR
PARENT -> CONSTITUENT ALWAYS PRESENT
LIQUIRITIGENIN was tested for antithrombotic activity.
PARENT -> CONSTITUENT ALWAYS PRESENT
LIQUIRITIGENIN was tested for antimicrobial activity against methicillin sensitive Staphylococcus aureus, methicillin resistant S. aureus, Micrococcus luteus, Bacillus subtilis, Escherichia coli, Klebsiella pneumoniae and Pseudomonas aeruginosa and found to be inactive.
METABOLIC ENZYME -> SUBSTRATE
MAJOR
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
Anti-HCV activity was found to be 16.4 ug/mL.
Related Record Type Details
METABOLITE -> PARENT