4H-1-benzopyran-4-one, 2,3-dihydro-7-hydroxy-2-(4-hydroxyphenyl)-, (S)-
None found
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(2S)-7-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one (Click)
CAS Number: 578-86-9Picture of molecule
Nikkaji Web: J22.604A
Beilstein Number: 359378
MDL: MFCD00287289
XlogP3-AA: 2.20 (est)
Molecular Weight: 256.25744000
Formula: C15 H12 O4
NMR Predictor: Predict (works with chrome or firefox)
Category: antioxidants, skin conditioning
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Soluble in:
 water, 873.5 mg/L @ 25 °C (est)
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Organoleptic Properties:
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: antioxidants
skin conditioning
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Sigma-Aldrich: Sigma
For experimental / research use only.
(-)-Liquiritigenin Radix glycyrrhizae ≥97.0% (HPLC)
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Safety Information:
Preferred SDS: View
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: antioxidants, skin conditioning
Recommendation for S-liquiritigenin usage levels up to:
 not for fragrance use.
Recommendation for S-liquiritigenin flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
ClinicalTrials.gov: search
Cancer Citations: Search
Toxicology Citations: Search
Env. Mutagen Info. Center: Search
NLM Developmental and Reproductive Toxicity: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 114829
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
Chemidplus: 0000578869
RTECS: DJ2981789 for cas# 578-86-9
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NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 114829
Pubchem (sid): 135072367
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
KEGG (GenomeNet): C09762
HMDB (The Human Metabolome Database): HMDB29519
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
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Potential Blenders and core components note
None Found
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 pterocarpus marsupium
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4H-1-benzopyran-4-one, 2,3-dihydro-7-hydroxy-2-(4-hydroxyphenyl)-, (S)-
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PubMed: Polymeric Nanoparticles of Brazilian Red Propolis Extract: Preparation, Characterization, Antioxidant and Leishmanicidal Activity.
PubMed: Spectroscopic and Docking Studies on the Binding of Liquiritigenin with Hyaluronidase for Antiallergic Mechanism.
PubMed: Development and Validation of an UHPLC-QqQ-MS Technique for Simultaneous Determination of Ten Bioactive Components in Fangji Huangqi Tang.
PubMed: [comparisons of pharmacokinetic profile of eleven bioactive components in Haizao Yuhu decoction modified with Haizao and Gancao anti-drug pair in normal rats].
PubMed: Liquiritigenin reverses depression-like behavior in unpredictable chronic mild stress-induced mice by regulating PI3K/Akt/mTOR mediated BDNF/TrkB pathway.
PubMed: Protective effect of liquiritigenin on depressive-like behavior in mice after lipopolysaccharide administration.
PubMed: [Chemical constituents from EtOAc fraction of Sophora dunnii].
PubMed: Biological activities of polyphenols-enriched propolis from Argentina arid regions.
PubMed: Tyrosinase inhibitory activity of flavonoids from Artocarpus heterophyllous.
PubMed: Hepatoprotective effect of licorice, the root of Glycyrrhiza uralensis Fischer, in alcohol-induced fatty liver disease.
PubMed: Simultaneous quantification of 5 main components of Psoralea corylifolia L. in rats' plasma by utilizing ultra high pressure liquid chromatography tandem mass spectrometry.
PubMed: Analysis of bioactive components and pharmacokinetic study of herb-herb interactions in the traditional Chinese patent medicine Tongmai Yangxin Pill.
PubMed: Flavone synthases from Lonicera japonica and L. macranthoides reveal differential flavone accumulation.
PubMed: Chemical characterisation of Nigerian red propolis and its biological activity against Trypanosoma Brucei.
PubMed: AMPK activation by liquiritigenin inhibited oxidative hepatic injury and mitochondrial dysfunction induced by nutrition deprivation as mediated with induction of farnesoid X receptor.
PubMed: Licorice root components in dietary supplements are selective estrogen receptor modulators with a spectrum of estrogenic and anti-estrogenic activities.
PubMed: Cancer therapy using natural ligands that target estrogen receptor beta.
PubMed: Simultaneous quantification of catechin, epicatechin, liquiritin, isoliquiritin, liquiritigenin, isoliquiritigenin, piperine, and glycyrrhetinic acid in rat plasma by HPLC-MS/MS: Application to a pharmacokinetic study of Longhu Rendan pills.
PubMed: The antiviral and antimicrobial activities of licorice, a widely-used Chinese herb.
PubMed: Suppression of Propionibacterium acnes-Induced Dermatitis by a Traditional Japanese Medicine, Jumihaidokuto, Modifying Macrophage Functions.
PubMed: 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.
PubMed: Combination of the advantages of chromatographic methods based on active components for the quality evaluation of licorice.
PubMed: Plasma Pharmacokinetics of Polyphenols in a Traditional Japanese Medicine, Jumihaidokuto, Which Suppresses Propionibacterium acnes-Induced Dermatitis in Rats.
PubMed: [Anti-inflammatory mechanism research of flavonoid compounds in Dalbergiae Odoriferae Lignum by module-based network analysis].
PubMed: Inhibition of Melanogenesis by Yeast Extracts from Cultivations of Recombinant Pichia pastoris Catalyzing ortho-Hydroxylation of Flavonoids.
PubMed: Simultaneous determination of nine marker compounds in the traditional Korean medicine, Dangguisu-san by high-performance liquid chromatography.
PubMed: Laminaria japonica increases plasma exposure of glycyrrhetinic acid following oral administration of Liquorice extract in rats.
PubMed: Anti-Inflammatory activities of licorice extract and its active compounds, glycyrrhizic acid, liquiritin and liquiritigenin, in BV2 cells and mice liver.
PubMed: Liquiritigenin Protects Rats from Carbon Tetrachloride Induced Hepatic Injury through PGC-1α Pathway.
PubMed: Identification of Glycyrrhiza as the rikkunshito constituent with the highest antagonistic potential on heterologously expressed 5-HT3A receptors due to the action of flavonoids.
PubMed: Pharmacokinetic Profiles of Active Ingredients and Its Metabolites Derived from Rikkunshito, a Ghrelin Enhancer, in Healthy Japanese Volunteers: A Cross-Over, Randomized Study.
PubMed: Dual Effects of Liquiritigenin on the Proliferation of Bone Cells: Promotion of Osteoblast Differentiation and Inhibition of Osteoclast Differentiation.
PubMed: Differential Effects of Glycyrrhiza Species on Genotoxic Estrogen Metabolism: Licochalcone A Downregulates P450 1B1, whereas Isoliquiritigenin Stimulates It.
PubMed: Antibacterial evaluation of flavonoid compounds against E. coli by microcalorimetry and chemometrics.
PubMed: In vitro Study of the Antagonistic Effect of Low-dose Liquiritigenin on Gemcitabine-induced Capillary Leak Syndrome in Pancreatic Adenocarcinoma via Inhibiting ROS- Mediated Signalling Pathways.
PubMed: Combined Autodock and comparative molecular field analysis study on predicting 5-lipoxygenase inhibitory activity of flavonoids isolated from Spatholobus suberectus Dunn.
PubMed: [Changing rules study of effective components of Glycyrrhizae Radix et Rhizoma before and after compatibilities in Sini decoction].
PubMed: Liquiritigenin Potentiates the Inhibitory Effects of Cisplatin on Invasion and Metastasis Via Downregulation MMP-2/9 and PI3 K/AKT Signaling Pathway in B16F10 Melanoma Cells and Mice Model.
PubMed: Constituents of the leaves of Verbascum blattaria.
PubMed: A Review: The Pharmacology of Isoliquiritigenin.
PubMed: The influence of compatibility of processed radix Aconiti Kusnezoffii on the pharmacokinetic of four components in Glycyrrhiza uralensis Fisch.
PubMed: In vivo gastroprotective effect along with pharmacokinetics, tissue distribution and metabolism of isoliquiritigenin in mice.
PubMed: Flavonoids derived from liquorice suppress murine macrophage activation by up-regulating heme oxygenase-1 independent of Nrf2 activation.
PubMed: Species-specific Standardisation of Licorice by Metabolomic Profiling of Flavanones and Chalcones.
PubMed: Blood-brain barrier permeability of Gualou Guizhi granules and neuroprotective effects in ischemia/reperfusion injury.
PubMed: Establishment of hairy root cultures by Agrobacterium rhizogenes mediated transformation of Isatis tinctoria L. For the efficient production of flavonoids and evaluation of antioxidant activities.
PubMed: Extracts of Glycyrrhiza uralensis and isoliquiritigenin counteract amyloid-β toxicity in Caenorhabditis elegans.
PubMed: Tacrine, an oral acetylcholinesterase inhibitor, induced hepatic oxidative damage, which was blocked by liquiritigenin through GSK3-beta inhibition.
PubMed: Effect of genotype and environment on five bioactive components of cultivated licorice (Glycyrrhiza uralensis) populations in northern China.
PubMed: [Flavonoids from root of Machilus wangchiana].
PubMed: A protective mechanism of licorice (Glycyrrhiza uralensis): isoliquiritigenin stimulates detoxification system via Nrf2 activation.
PubMed: Determination of liquiritigenin by ultra high performance liquid chromatography coupled with triple quadrupole mass spectrometry: Application to a linear pharmacokinetic study of liquiritigenin in rat plasma.
PubMed: Simultaneous Determination of Nine Active Compounds of the Traditional Chinese Medicinal Prescription Shaoyao-Gancao-Tang and Analysis of the Relationship between Therapeutical Effect and Compatibility of Medicines.
PubMed: Preliminary identification of the absorbed bioactive components and metabolites in rat plasma after oral administration of Shaoyao-Gancao decoction by ultra-performance liquid chromatography with electrospray ionization tandem mass spectrometry.
PubMed: Estrogen receptor β selective agonists reduce invasiveness of triple-negative breast cancer cells.
PubMed: Transcriptomic analysis identifies gene networks regulated by estrogen receptor α (ERα) and ERβ that control distinct effects of different botanical estrogens.
PubMed: Effect of genotype and environment on five bioactive components of cultivated licorice (Glycyrrhiza uralensis FISCH.) populations in northern China.
PubMed: Estrogen receptor β agonist enhances temozolomide sensitivity of glioma cells by inhibiting PI3K/AKT/mTOR pathway.
PubMed: Amelioration of trinitrobenzene sulfonic acid-induced colitis in mice by liquiritigenin.
PubMed: LC-MS/MS analysis of Gegen Qinlian Decoction and its pharmacokinetics after oral administration to rats.
PubMed: Enhanced skin delivery of liquiritigenin and liquiritin-loaded liposome-in-hydrogel complex system.
PubMed: [Studies on effects of Achyranthes bidentata on tongsaimai pellets main active ingredients chlorogenic acid, isoliquiritin, harpagoside and glycyrrhizin in vivo pharmacokinetics].
PubMed: Liquiritigenin alleviates mechanical and cold hyperalgesia in a rat neuropathic pain model.
PubMed: Simultaneous Quantification of Ten Active Components in Traditional Chinese Formula Sijunzi Decoction Using a UPLC-PDA Method.
PubMed: Distribution patterns of the contents of five active components in taproot and stolon of Glycyrrhiza uralensis.
PubMed: Protective effect of liquiritigenin against methylglyoxal cytotoxicity in osteoblastic MC3T3-E1 cells.
PubMed: Liquiritigenin induces tumor cell death through mitogen-activated protein kinase- (MPAKs-) mediated pathway in hepatocellular carcinoma cells.
PubMed: Preparative isolation and analysis of alcohol dehydrogenase inhibitors from Glycyrrhiza uralensis root using ultrafiltration combined with high-performance liquid chromatography and high-speed countercurrent chromatography.
PubMed: Simultaneous determination of 12 index components and compatibility changes in Longchai decoction by liquid chromatography-mass spectrometry.
PubMed: The effects of Glycyrrhizae uralenis and its major bioactive components on pharmacokinetics of daphnetin in Cortex daphnes in rats.
PubMed: Simultaneous determination of puerarin, daidzin, daidzein, paeoniflorin, albiflorin, liquiritin and liquiritigenin in rat plasma and its application to a pharmacokinetic study of Ge-Gen Decoction by a liquid chromatography-electrospray ionization-tandem mass spectrometry.
PubMed: Liquiritigenin exhibits antitumour action in pituitary adenoma cells via Ras/ERKs and ROS-dependent mitochondrial signalling pathways.
PubMed: Anti-hepatitis C virus compounds obtained from Glycyrrhiza uralensis and other Glycyrrhiza species.
PubMed: Correlation analysis between the rate of respiration in the root and the active components in licorice (Glycyrrhiza uralensis).
PubMed: Computer-guided approach to access the anti-influenza activity of licorice constituents.
PubMed: In vivo anti-diabetic activity of derivatives of isoliquiritigenin and liquiritigenin.
PubMed: Identification of key licorice constituents which interact with cytochrome P450: evaluation by LC/MS/MS cocktail assay and metabolic profiling.
PubMed: Liquiritigenin restores osteoblast damage through regulating oxidative stress and mitochondrial dysfunction.
PubMed: Pharmacokinetics of isoliquiritigenin and its metabolites in rats: low bioavailability is primarily due to the hepatic and intestinal metabolism.
PubMed: Neuroprotective effects of liquiritigenin isolated from licorice roots on glutamate-induced apoptosis in hippocampal neuronal cells.
PubMed: [Chemical constituents from the twigs and leaves of Melodinus suaveolens].
PubMed: Flavanones that selectively inhibit TRPM3 attenuate thermal nociception in vivo.
PubMed: Quantification of three chiral flavonoids with reported bioactivity in selected licensed Canadian natural health products and US marketed dietary supplements.
PubMed: Mechanisms enforcing the estrogen receptor β selectivity of botanical estrogens.
PubMed: Synaptodendritic recovery following HIV Tat exposure: neurorestoration by phytoestrogens.
PubMed: Evaluation of estrogenic activity of licorice species in comparison with hops used in botanicals for menopausal symptoms.
PubMed: Employing bifunctional enzymes for enhanced extraction of bioactives from plants: flavonoids as an example.
PubMed: [Anti-inflammation of flavonoid compounds from Dalbergia odorifera T. Chen in lipopolysaccharide stimulated RAW264.7 macrophages].
PubMed: Pharmacokinetic comparisons of different combinations of Shaoyao-Gancao-Decoction in rats: simultaneous determination of ten active constituents by HPLC-MS/MS.
PubMed: Screening and determination for potential α-glucosidase inhibitory constituents from Dalbergia odorifera T. Chen using ultrafiltration-LC/ESI-MS(n).
PubMed: Preparation and enantioseparation of a new click derived β-cyclodextrin chiral stationary phase.
PubMed: Flavonoids from Astragalus membranaceus and their inhibitory effects on LPS-stimulated pro-inflammatory cytokine production in bone marrow-derived dendritic cells.
PubMed: Expression of flavonoid 6-hydroxylase candidate genes in normal and mutant soybean genotypes for glycitein content.
PubMed: Pharmacokinetic study of four flavones of Glycyrrhiza in rat plasma using HPLC-MS.
PubMed: Simultaneous quantification of paeoniflorin, nobiletin, tangeretin, liquiritigenin, isoliquiritigenin, liquiritin and formononetin from Si-Ni-San extract in rat plasma and tissues by liquid chromatography-tandem mass spectrometry.
PubMed: Isolation of liquiritigenin-4'-apiosyl-glucoside and liquiritin from the root of Glycyrrhiza uralensis by high-performance centrifugal partition chromatography.
PubMed: [Chemical constituents and activities of total flavonoids from Yushen Tang].
PubMed: Liquiritigenin prevents Staphylococcus aureus-mediated lung cell injury via inhibiting the production of α-hemolysin.
PubMed: Dynamic residual complexity of the isoliquiritigenin-liquiritigenin interconversion during bioassay.
PubMed: Simultaneous determination of five bioactive components in radix glycyrrhizae by pressurised liquid extraction combined with UPLC-PDA and UPLC/ESI-QTOF-MS confirmation.
PubMed: Facile optimization for chromatographic separation of liquiritin and liquiritigenin.
PubMed: Content determination of the major constituents of Yinchenzhufu decoction via ultra high-performance liquid chromatography coupled with electrospray ionisation tandem mass spectrometry.
PubMed: Simultaneous quantitative determination of nine active chemical compositions in traditional Chinese medicine Glycyrrhiza by RP-HPLC with full-time five-wavelength fusion method.
PubMed: Chemical constituents of Spatholobus suberectus.
PubMed: Anti-inflammatory effect of Sosihotang via inhibition of nuclear factor-κB and mitogen-activated protein kinases signaling pathways in lipopolysaccharide-stimulated RAW 264.7 macrophage cells.
PubMed: Comparative study of bioactive constituents in crude and processed Glycyrrhizae radix and their respective metabolic profiles in gastrointestinal tract in vitro by HPLC-DAD and HPLC-ESI/MS analyses.
PubMed: Estradiol antagonism of glucocorticoid-induced GILZ expression in human uterine epithelial cells and murine uterus.
PubMed: Glycyrrhiza uralensis flavonoids present in anti-asthma formula, ASHMI™, inhibit memory Th2 responses in vitro and in vivo.
PubMed: Antispasmodic effect of shakuyakukanzoto extract on experimental muscle cramps in vivo: role of the active constituents of Glycyrrhizae radix.
PubMed: Estrogen receptor β agonists affect growth and gene expression of human breast cancer cell lines.
PubMed: Deglycosylation of liquiritin strongly enhances its inhibitory potential towards UDP-glucuronosyltransferase (UGT) isoforms.
PubMed: Analytical strategy to reveal the in vivo process of multi-component herbal medicine: a pharmacokinetic study of licorice using liquid chromatography coupled with triple quadrupole mass spectrometry.
PubMed: [Chemical constituents from the fruits of Areca catechu].
PubMed: Chiral analytical method development of liquiritigenin with application to a pharmacokinetic study.
PubMed: [C-ring cleavage of liquiritigenin extracted from licorice roots by an oxygen-tolerant bovine rumen bacterium strain Aeroto-Niu-O16].
PubMed: Fermentation improves anti-inflammatory effect of sipjeondaebotang on LPS-stimulated RAW 264.7 cells.
PubMed: Decrease of microRNA-122 causes hepatic insulin resistance by inducing protein tyrosine phosphatase 1B, which is reversed by licorice flavonoid.
PubMed: The isolation of bioactive flavonoids from Jacaranda obtusifolia H. B. K. ssp. rhombifolia (G. F. W. Meijer) Gentry.
PubMed: Liquiritigenin inhibits tumor growth and vascularization in a mouse model of HeLa cells.
PubMed: Hypnotic effects and GABAergic mechanism of licorice (Glycyrrhiza glabra) ethanol extract and its major flavonoid constituent glabrol.
PubMed: Inhibitory effect of liquiritigenin on migration via downregulation proMMP-2 and PI3K/Akt signaling pathway in human lung adenocarcinoma A549 cells.
PubMed: Therapeutic significance of estrogen receptor β agonists in gliomas.
PubMed: Comparative metabolite profiling and fingerprinting of medicinal licorice roots using a multiplex approach of GC-MS, LC-MS and 1D NMR techniques.
PubMed: [Identification of the metabolites of Sinisan extract in rat plasma, urine, feces and bile after intragastric administration].
PubMed: [Study on HPLC chromatographic fingerprint of anti-tumor active site SSCE of Caulis spatholobi].
PubMed: Liquiritigenin inhibits serum-induced HIF-1α and VEGF expression via the AKT/mTOR-p70S6K signalling pathway in HeLa cells.
PubMed: [Chemical constituents from the roots of Hedysarum polybotrys].
PubMed: Antibacterial activity of the flavonoids from Dalbergia odorifera on Ralstonia solanacearum.
PubMed: Liquiritigenin isolated from Glycyrrhiza uralensis stimulates osteoblast function in osteoblastic MC3T3-E1 cells.
PubMed: RETRACTED: Inhibition of LXRα-dependent steatosis and oxidative injury by liquiritigenin, a licorice flavonoid, as mediated with Nrf2 activation.
PubMed: Generation of stable reporter breast cancer cell lines for the identification of ER subtype selective ligands.
PubMed: Liquiritigenin decreases selective molecular and behavioral effects of cocaine in rodents.
PubMed: Liquiritigenin attenuates the learning and memory deficits in an amyloid protein precursor transgenic mouse model and the underlying mechanisms.
PubMed: Comparative evaluation of two structurally related flavonoids, isoliquiritigenin and liquiritigenin, for their oral infection therapeutic potential.
PubMed: Photosynthetic Bradyrhizobium Sp. strain ORS285 synthesizes 2-O-methylfucosylated lipochitooligosaccharides for nod gene-dependent interaction with Aeschynomene plants.
PubMed: LC-ESI-MS characterisation of phytoalexins induced in chickpea and pea tissues in response to a biotic elicitor of Hypnea musciformis (red algae).
PubMed: Augmented cocaine seeking in response to stress or CRF delivered into the ventral tegmental area following long-access self-administration is mediated by CRF receptor type 1 but not CRF receptor type 2.
PubMed: Traditional chinese medicine for senile dementia.
PubMed: Cuban and Brazilian red propolis: botanical origin and comparative analysis by high-performance liquid chromatography-photodiode array detection/electrospray ionization tandem mass spectrometry.
PubMed: C5-hydroxylation of liquiritigenin is catalyzed selectively by CYP1A2.
PubMed: [On-line sample stacking for the analysis of glycyrrhiza flavonoids by anion selective exhaustive injection-sweeping micellar electrokinetic chromatography].
PubMed: Phytoestrogenic compounds in alfalfa sprout (Medicago sativa) beyond coumestrol.
PubMed: Effects of acute renal failure induced by uranyl nitrate on the pharmacokinetics of liquiritigenin and its two glucuronides, M1 and M2, in rats.
PubMed: 20S proteasome inhibitory activity of flavonoids isolated from Spatholobus suberectus.
PubMed: [Studies on the flavonoids from Lignum Dalbergiae Odoriferae (II)].
PubMed: [Studies on changes of in vitro and in vivo material base of Shaoyao Gancao decoction based on HPLC-DAD-ESI-MS].
PubMed: Liquiritigenin derivatives and their hepatotoprotective activity.
PubMed: Inhibition of LXRα-dependent steatosis and oxidative injury by liquiritigenin, a licorice flavonoid, as mediated with Nrf2 activation.
PubMed: Liquiritigenin induces mitochondria-mediated apoptosis via cytochrome c release and caspases activation in HeLa Cells.
PubMed: Promotion of rat brain-derived progenitor cell neurogenesis by liquiritigenin treatment: underlying mechanisms.
PubMed: Synthesis and antitumor activity of liquiritigenin thiosemicarbazone derivatives.
PubMed: Aldose reductase inhibitory compounds from Glycyrrhiza uralensis.
PubMed: Pharmacokinetics of liquiritigenin and its two glucuronides, M1 and M2, in rats with acute hepatitis induced by d-galactosamine/lipopolysaccharide or CCl(4).
PubMed: 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.
PubMed: Flavone synthase II (CYP93B16) from soybean (Glycine max L.).
PubMed: Effects of liquiritigenin treatment on the learning and memory deficits induced by amyloid beta-peptide (25-35) in rats.
PubMed: Fuscacarpans A-C, new pterocarpans from the stems of Erythrina fusca.
PubMed: Determination of flavonoids in licorice using acid hydrolysis and reversed-phase HPLC and evaluation of the chemical quality of cultivated licorice.
PubMed: Pharmacokinetic interaction between liquiritigenin (LQ) and DDB: increased glucuronidation of LQ in the liver possibly due to increased hepatic blood flow rate by DDB.
PubMed: Inhibition of hepatoma 22 tumor by Liquiritigenin.
PubMed: Interactions between thrombin and natural products of Millettia nitita var. hirsutissima using capillary zone electrophoresis.
PubMed: Separation, characterization and dose-effect relationship of the PPARgamma-activating bio-active constituents in the Chinese herb formulation 'San-Ao decoction'.
PubMed: Simultaneous determination of five flavonoids in licorice using pressurized liquid extraction and capillary electrochromatography coupled with peak suppression diode array detection.
PubMed: Drug and cell type-specific regulation of genes with different classes of estrogen receptor beta-selective agonists.
PubMed: Liquiritigenin inhibits Abeta(25-35)-induced neurotoxicity and secretion of Abeta(1-40) in rat hippocampal neurons.
PubMed: Pharmacokinetics and first-pass effects of liquiritigenin in rats: low bioavailability is primarily due to extensive gastrointestinal first-pass effect.
PubMed: Phytochemical analysis of young fustic (Cotinus coggygria heartwood) and identification of isolated colourants in historical textiles.
PubMed: Bioactive flavonoids of the flowers of Butea monosperma.
PubMed: Liquiritigenin, a licorice flavonoid, helps mice resist disseminated candidiasis due to Candida albicans by Th1 immune response, whereas liquiritin, its glycoside form, does not.
PubMed: Pharmacokinetics of liquiritigenin in mice, rats, rabbits, and dogs, and animal scale-up.
PubMed: Effect of liquiritigenin, a flavanone existed from Radix glycyrrhizae on pro-apoptotic in SMMC-7721 cells.
PubMed: Licorice flavonoids inhibit eotaxin-1 secretion by human fetal lung fibroblasts in vitro.
PubMed: Liquiritigenin, a flavonoid aglycone from licorice, has a choleretic effect and the ability to induce hepatic transporters and phase-II enzymes.
PubMed: Survey of Glycyrrhizae Radix resources in Mongolia: chemical assessment of the underground part of Glycyrrhiza uralensis and comparison with Chinese Glycyrrhizea Radix.
PubMed: Intermolecular interactions identify ligand-selective activity of estrogen receptor alpha/beta dimers.
PubMed: Screening of herbal constituents for aromatase inhibitory activity.
PubMed: Transport and metabolism of flavonoids from Chinese herbal remedy Xiaochaihu- tang across human intestinal Caco-2 cell monolayers.
PubMed: Oxidative in vitro metabolism of liquiritigenin, a bioactive compound isolated from the Chinese herbal selective estrogen beta-receptor agonist MF101.
PubMed: Biotransformation of the chemopreventive agent 2',4',4-trihydroxychalcone (isoliquiritigenin) by UDP-glucuronosyltransferases.
PubMed: Isoliquiritigenin suppresses cocaine-induced extracellular dopamine release in rat brain through GABA(B) receptor.
PubMed: Rikkunshito, an herbal medicine, suppresses cisplatin-induced anorexia in rats via 5-HT2 receptor antagonism.
PubMed: In vitro antimalarial activity of prenylated flavonoids from Erythrina fusca.
PubMed: Anti-inflammatory effects of liquiritigenin as a consequence of the inhibition of NF-kappaB-dependent iNOS and proinflammatory cytokines production.
PubMed: Liquiritigenin is a plant-derived highly selective estrogen receptor beta agonist.
PubMed: [Studies on chemical constituents of Heterosmilax yunnanensis].
PubMed: 2-Hydroxyisoflavanone dehydratase is a critical determinant of isoflavone productivity in hairy root cultures of Lotus japonicus.
PubMed: Biosynthesis of 5-deoxyflavanones in microorganisms.
PubMed: Inactivation of pea genes by RNAi supports the involvement of two similar O-methyltransferases in the biosynthesis of (+)-pisatin and of chiral intermediates with a configuration opposite that found in (+)-pisatin.
PubMed: Orthogonal array design for optimizing extraction efficiency of active constituents from Jakyak-Gamcho Decoction, the complex formula of herbal medicines, Paeoniae Radix and Glycyrrhizae Radix.
PubMed: Aromatase inhibition by bioavailable methylated flavones.
PubMed: Constituent properties of licorices derived from Glycyrrhiza uralensis, G. glabra, or G. inflata identified by genetic information.
PubMed: [Relative adscriptions of components in the effective fractions of Yinqiao decoction and its composing individual herbs].
PubMed: Allergy-preventive flavonoids from Xanthorrhoea hastilis.
PubMed: In vitro and in vivo antiallergic effects of Glycyrrhiza glabra and its components.
PubMed: Simultaneous quantification of multiple licorice flavonoids in rat plasma.
PubMed: Simultaneous quantification of flavonoids and triterpenoids in licorice using HPLC.
PubMed: Prenylation enhances cytotoxicity of apigenin and liquiritigenin in rat H4IIE hepatoma and C6 glioma cells.
PubMed: Bioactive constituents of Spatholobus suberectus in regulating tyrosinase-related proteins and mRNA in HEMn cells.
PubMed: Silencing the flavonoid pathway in Medicago truncatula inhibits root nodule formation and prevents auxin transport regulation by rhizobia.
PubMed: Liquiritigenin, an aglycone of liquiritin in Glycyrrhizae radix, prevents acute liver injuries in rats induced by acetaminophen with or without buthionine sulfoximine.
PubMed: [Chromatographic fingerprint of Dalbergia odorifera and its application in the identification of the crude drugs of different origins].
PubMed: Application of LC/MS and ICP/MS for establishing the fingerprint spectrum of the traditional Chinese medicinal preparation Gan-Lu-Yin.
PubMed: Norditerpenoid alkaloids and other components from the processed tubers of Aconitum carmichaeli.
PubMed: Isoflavonoids isolated from Cuban propolis.
PubMed: [Effect of rare-earth element Eu3+ on callus growth and flavonoids content in Glycyrrhiza uralensis].
PubMed: CYP3A4 inhibitors isolated from Licorice.
PubMed: Binding of phytoestrogens to rat uterine estrogen receptors and human sex hormone-binding globulins.
PubMed: Isolation and identification of flavonoids in licorice and a study of their inhibitory effects on tyrosinase.
PubMed: Attractive properties of an isoflavonoid found in white clover root nodules on the clover root weevil.
PubMed: One step isolation and purification of liquiritigenin and isoliquiritigenin from Glycyrrhiza uralensis Risch. using high-speed counter-current chromatography.
PubMed: Simultaneous determination of 10 major flavonoids in Dalbergia odorifera by high performance liquid chromatography.
PubMed: Cytotoxic flavonoids from Platymiscium floribundum.
PubMed: [Studies on chemical constituents of sini tang].
PubMed: Pharmacokinetic and pharmacodynamic profiles of the antitussive principles of Glycyrrhizae radix (licorice), a main component of the Kampo preparation Bakumondo-to (Mai-men-dong-tang).
PubMed: Determination of liquiritigenin and isoliquiritigenin in Glycyrrhiza uralensis and its medicinal preparations by capillary electrophoresis with electrochemical detection.
PubMed: New metabolic pathways for flavanones catalyzed by rat liver microsomes.
PubMed: Cytoprotective effects of Glycyrrhizae radix extract and its active component liquiritigenin against cadmium-induced toxicity (effects on bad translocation and cytochrome c-mediated PARP cleavage).
PubMed: [Studies on chemical constituents from the root of Polygonatum kingianum].
PubMed: [Isolation and elucidation of chemical constituents with antiviral action from yinqiaosan on influenza virus].
PubMed: [Studies on flavonoid constituents of Caragana intermediia].
PubMed: Permeability of the flavonoids liquiritigenin and its glycosides in licorice roots and davidigenin, a hydrogenated metabolite of liquiritigenin, using human intestinal cell line Caco-2.
PubMed: Pharmacokinetic study on the multi-constituents of Huangqin-Tang decoction in rats.
PubMed: An overexpression of chalcone reductase of Pueraria montana var. lobata alters biosynthesis of anthocyanin and 5'-deoxyflavonoids in transgenic tobacco.
PubMed: [Studies on the chemical constituents of Lycianthes biflora].
PubMed: Key amino acid residues required for aryl migration catalysed by the cytochrome P450 2-hydroxyisoflavanone synthase.
PubMed: Metabolism of constituents in Huangqin-Tang, a prescription in traditional Chinese medicine, by human intestinal flora.
PubMed: Induction of apoptosis in human lung fibroblasts and peripheral lymphocytes in vitro by Shosaiko-to derived phenolic metabolites.
PubMed: The herbal medicine Shosaiko-to exerts different modulating effects on lung local immune responses among mouse strains.
PubMed: Elicitor-induced association of isoflavone O-methyltransferase with endomembranes prevents the formation and 7-O-methylation of daidzein during isoflavonoid phytoalexin biosynthesis.
PubMed: In vitro inhibition of rat monoamine oxidase by liquiritigenin and isoliquiritigenin isolated from Sinofranchetia chinensis.
PubMed: Determination of 14 chemical constituents in the traditional Chinese medicinal preparation Huangqin-Tang by high performance liquid chromatography.
PubMed: Azorhizobium caulinodans ORS571 colonizes the xylem of Arabidopsis thaliana.
PubMed: New scheme of the biosynthesis of formononetin involving 2,7,4'-trihydroxyisoflavanone but not daidzein as the methyl acceptor.
PubMed: Pharmacological effects of urinary products obtained after treatment with saiboku-to, a herbal medicine for bronchial asthma, on type IV allergic reaction.
PubMed: Minor phenolics from Crinum bulbispermum bulbs.
PubMed: Prolyl endopeptidase inhibitory activity of fourteen Kampo formulas and inhibitory constituents of Tokaku-joki-to.
PubMed: Inhibition of xanthine oxidase by liquiritigenin and isoliquiritigenin isolated from Sinofranchetia chinensis.
PubMed: Modulation of lung local immune responses by oral administration of a herbal medicine Sho-saiko-to.
PubMed: An isoflavone from Pterocarpus santalinus.
PubMed: Cloning and functional expression of a cytochrome P450 cDNA encoding 2-hydroxyisoflavanone synthase involved in biosynthesis of the isoflavonoid skeleton in licorice.
PubMed: Molecular characterization of the enzyme catalyzing the aryl migration reaction of isoflavonoid biosynthesis in soybean.
PubMed: Characteristics of delayed excretion of flavonoids in human urine after administration of Shosaiko-to, a herbal medicine.
PubMed: Identification of a cytochrome P450 cDNA encoding (2S)-flavanone 2-hydroxylase of licorice (Glycyrrhiza echinata L.; Fabaceae) which represents licodione synthase and flavone synthase II.
PubMed: Chiral resolution of four major flavanones in post-administrative urine of Chinese herbal medicines by HPLC on macroporous silica gel coated with cellulose tris(3,5-dimethylphenylcarbamate).
PubMed: Three new flavonoids and antiallergic, anti-inflammatory constituents from the heartwood of Dalbergia odorifera.
PubMed: Systematic analysis of post-administrative saiboku-to urine by liquid chromatography to determine pharmacokinetics of traditional Chinese medicine.
PubMed: [Two new flavanone glycosides from Glycyrrhizia inflata].
PubMed: Biliary excretion of glycyrrhizin in rats: kinetic basis for multiplicity in bile canalicular transport of organic anions.
PubMed: Inhibitory effect of isoliquiritin, a compound in licorice root, on angiogenesis in vivo and tube formation in vitro.
PubMed: [Chemical components of decoction of radix Paeoniae and radix Glycyrrhizae].
PubMed: Multiple systems for the biliary excretion of organic anions in rats: liquiritigenin conjugates as model compounds.
PubMed: Licodione Synthase, a Cytochrome P450 Monooxygenase Catalyzing 2-Hydroxylation of 5-Deoxyflavanone, in Cultured Glycyrrhiza echinata L. Cells.
PubMed: Identification of tissues responsible for the conjugative metabolism of liquiritigenin in rats: an analysis based on metabolite kinetics.
PubMed: Antihyperlipidemic effect of flavonoids from Pterocarpus marsupium.
PubMed: Inhibitory effects of some natural products on the activation of hyaluronidase and their anti-allergic actions.
PubMed: A strategy for discovering biologically active compounds with high probability in traditional Chinese herb remedies: an application of saiboku-to in bronchial asthma.
PubMed: [Chemical studies of coumarins from Glycyrrhiza uralensis Fisch].
PubMed: [Quality evaluation of Chinese licorice].
PubMed: Reaction mechanism of oxidative rearrangement of flavanone in isoflavone biosynthesis.
PubMed: NAD(P)H-dependent 6'-deoxychalcone synthase activity in Glycyrrhiza echinata cells induced by yeast extract.
PubMed: Stimulation of chalcone synthase activity by yeast extract in cultured Glycyrrhiza echinata cells and 5-deoxyflavanone formation by isolated protoplasts.
PubMed: Purification and kinetic properties of chalcone-flavanone isomerase from soya bean.
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