Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H20O4 |
| Molecular Weight | 324.3704 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1(C)OC2=CC=C3C[C@@H](COC3=C2C=C1)C4=C(O)C=C(O)C=C4
InChI
InChIKey=LBQIJVLKGVZRIW-ZDUSSCGKSA-N
InChI=1S/C20H20O4/c1-20(2)8-7-16-18(24-20)6-3-12-9-13(11-23-19(12)16)15-5-4-14(21)10-17(15)22/h3-8,10,13,21-22H,9,11H2,1-2H3/t13-/m0/s1
| Molecular Formula | C20H20O4 |
| Molecular Weight | 324.3704 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Glabridin is an isoflavane found in the root extract of licorice (Glycyrrhiza glabra). Glabridin is considered to be a phytoestrogen and has been associated with numerous biological properties ranging from antioxidant, anti-inflammatory, neuroprotective, anti-atherogenic effects, to the regulation of energy metabolism, but also including anti-tumorigenic, anti-nephritic, antibacterial and skin-whitening activities. A glabridin-enriched extract is widely used in a cosmetic formulation as anti-inflammatory, antioxidant and skin whitening agent. Anti-inflammatory action of glabridin is linked to downregulation of NF-κB, AP-1 and MAPKS signaling. Glabridin-induced attenuation of atherosclerosis is related to a reduction in macrophages-associated oxidation of low-density lipoprotein.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P03372 Gene ID: 2099.0 Gene Symbol: ESR1 Target Organism: Homo sapiens (Human) |
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Target ID: map04064 |
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Target ID: GO:0034444 |
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Target ID: P31645 Gene ID: 6532.0 Gene Symbol: SLC6A4 Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Preventing | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Tissue and species differences in the glucuronidation of glabridin with UDP-glucuronosyltransferases. | 2015-04-25 |
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| Anti-hepatitis C virus compounds obtained from Glycyrrhiza uralensis and other Glycyrrhiza species. | 2014-03 |
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| Anti-obesity effects of glabridin-rich supercritical carbon dioxide extract of licorice in high-fat-fed obese mice. | 2013-01 |
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| Effect of licorice compounds licochalcone A, glabridin and glycyrrhizic acid on growth and virulence properties of Candida albicans. | 2011-11 |
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| Glabridin protects osteoblastic MC3T3-E1 cells against antimycin A induced cytotoxicity. | 2011-08-15 |
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| Factors influencing glabridin stability. | 2010-12 |
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| Inhibition of bone marrow-derived dendritic cell maturation by glabridin. | 2010-10 |
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| Overcoming multidrug resistance in human cancer cells by natural compounds. | 2010-06 |
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| Effect of vitamin E alone and in combination with lycopene on biochemical and histopathological alterations in isoproterenol-induced myocardial infarction in rats. | 2010-01 |
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| Licorice infusion: Chemical profile and effects on the activation and the cell cycle progression of human lymphocytes. | 2010-01 |
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| Glabridin inhibits lipopolysaccharide-induced activation of a microglial cell line, BV-2, by blocking NF-kappaB and AP-1. | 2010-01 |
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| Anti-inflammatory effects of licorice and roasted licorice extracts on TPA-induced acute inflammation and collagen-induced arthritis in mice. | 2010 |
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| Effect of Carnitine and herbal mixture extract on obesity induced by high fat diet in rats. | 2009-10-16 |
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| Glabridin from Chinese herb licorice inhibits fatigue in mice. | 2009-10-15 |
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| Antidyslipidaemic activity of Glycyrrhiza glabra in high fructose diet induced dsyslipidaemic Syrian golden hamsters. | 2009-10 |
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| Mechanisms regulating skin pigmentation: the rise and fall of complexion coloration. | 2009-09-15 |
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| Antioxidant effect of polyphenolic glabridin on LDL oxidation. | 2009-08-05 |
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| Antifungal activity of Glycyrrhiza glabra extracts and its active constituent glabridin. | 2009-08 |
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| Lipid abnormalities in streptozotocin-diabetes: Amelioration by Morus indica L. cv Suguna leaves. | 2009-07 |
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| A validated stability-indicating HPLC method for analysis of glabridin prodrugs in hydrolysis studies. | 2009-06 |
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| An updated review of tyrosinase inhibitors. | 2009-05-26 |
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| Synthesis of glabridin derivatives as tyrosinase inhibitors. | 2009-05 |
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| The response of creatine kinase specific activity in rat pituitary to estrogenic compounds and vitamin d less-calcemic analogs. | 2009 |
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| Topical treatment of melasma. | 2009 |
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| Liquorice health check, Oro-dental implications, and a case report. | 2009 |
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| Inhibition of P-glycoprotein and multidrug resistance protein 1 by dietary phytochemicals. | 2008-10 |
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| Cancer is a preventable disease that requires major lifestyle changes. | 2008-09 |
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| 90-Day repeated-dose toxicity study of licorice flavonoid oil (LFO) in rats. | 2008-07 |
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| Extraction of glycyrrhizic acid and glabridin from licorice. | 2008-04 |
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| Antimicrobial potential of Glycyrrhiza glabra roots. | 2008-03-05 |
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| Effect of glabridin from Glycyrrhiza glabra on learning and memory in mice. | 2008-03 |
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| In vitro and in vivo neuroprotective effect and mechanisms of glabridin, a major active isoflavan from Glycyrrhiza glabra (licorice). | 2008-01-02 |
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| Glabridin, a functional compound of liquorice, attenuates colonic inflammation in mice with dextran sulphate sodium-induced colitis. | 2008-01 |
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| The effect of an endogenous antioxidant glabridin on oxidized LDL. | 2008 |
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| Atorvastatin and cardiovascular risk in the elderly--patient considerations. | 2008 |
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| Role of P-glycoprotein in limiting the brain penetration of glabridin, an active isoflavan from the root of Glycyrrhiza glabra. | 2007-09 |
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| Absorption of dietary licorice isoflavan glabridin to blood circulation in rats. | 2007-08 |
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| Metabolic activation of herbal and dietary constituents and its clinical and toxicological implications: an update. | 2007-08 |
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| Constituent properties of licorices derived from Glycyrrhiza uralensis, G. glabra, or G. inflata identified by genetic information. | 2007-07 |
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| Anti-oxidant constituents of the roots and stolons of licorice (Glycyrrhiza glabra). | 2007-06-13 |
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| Clinical safety of licorice flavonoid oil (LFO) and pharmacokinetics of glabridin in healthy humans. | 2007-06 |
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| Role of P-glycoprotein in the intestinal absorption of glabridin, an active flavonoid from the root of Glycyrrhiza glabra. | 2007-04 |
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| Suppression by licorice flavonoids of abdominal fat accumulation and body weight gain in high-fat diet-induced obese C57BL/6J mice. | 2007-01 |
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| Post TLC developing technique for tyrosinase inhibitor detection. | 2007-01 |
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| Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006-11 |
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| Glabridin suppresses intercellular adhesion molecule-1 expression in tumor necrosis factor-alpha-stimulated human umbilical vein endothelial cells by blocking sphingosine kinase pathway: implications of Akt, extracellular signal-regulated kinase, and nuclear factor-kappaB/Rel signaling pathways. | 2006-03 |
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| Determination of glabridin in human plasma by solid-phase extraction and LC-MS/MS. | 2005-12-15 |
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| The licorice root derived isoflavan glabridin increases the function of osteoblastic MC3T3-E1 cells. | 2005-08-01 |
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| Analysis and comparison of Radix Glycyrrhizae (licorice) from Europe and China by capillary-zone electrophoresis (CZE). | 2005-07-15 |
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| Clinical outcomes and management of mechanism-based inhibition of cytochrome P450 3A4. | 2005-03 |
Sample Use Guides
In vivo, Glabridin (1 to 10 mg/kg i.p.) was demonstrated to protect BDF1 mice against LPS-induced sepsis by reducing the production of various inflammatory mediators, such as TNF-α and NO. Oral administration of Glab (10 or 50 mg/kg for 7 days) to female BALB/C mice resulted in an attenuation of colonic inflammation induced by dextran sulfate sodium (DSS).
Route of Administration:
Other
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 20:06:42 GMT 2025
by
admin
on
Mon Mar 31 20:06:42 GMT 2025
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| Record UNII |
HOC5567T41
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| Record Status |
Validated (UNII)
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| Record Version |
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Official Name | English | ||
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Preferred Name | English | ||
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Common Name | English |
| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C306
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C107601
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DTXSID00208589
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HOC5567T41
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300000048634
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GLABRIDIN
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HOC5567T41
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59870-68-7
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C64171
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124052
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1603522
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PRIMARY | RxNorm |
| Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Minimum Inhibitory Concentration(MIC) for Staphylococcus aureus (ATCC 13709) = 6.25 mcg ml and Mycobacterium smegmatis (ATCC 6371) = 6.25 mcg ml.
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DERIVATIVE -> PARENT |
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PARENT -> CONSTITUENT ALWAYS PRESENT |
GLABRIDIN exhibited antimicrobial activity (MICs 3.13?12.5 ug/ml) against MSSAs (strains FDA 209P and Smith) and MRSAs(strains K3 and ST 28).
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PARENT -> CONSTITUENT ALWAYS PRESENT |
0.11% of dry weight of contents.
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Anti-HCV activity IC50 was found to be be 6.2 ug/mL.
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Among the chemical constituents of the plant, glabridin and glabrene exhibit inhibitory activity against the growth of Helicobacter pylori in vitro. These flavonoids also showed anti-H. pylori activity against a clarithromycin and amoxicillin resistant strain (Fukai et al. 2002).
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