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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
Structure of GLABRIDIN

SMILES

CC1(C)OC2=C(C=C1)C3=C(C[C@@H](CO3)C4=CC=C(O)C=C4O)C=C2

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

HIDE SMILES / InChI

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P03372
Gene ID: 2099.0
Gene Symbol: ESR1
Target Organism: Homo sapiens (Human)
Target ID: P31645
Gene ID: 6532.0
Gene Symbol: SLC6A4
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Cytotoxic activity of low molecular weight polyphenols against human oral tumor cell lines.
2000 Jul-Aug
Increased macrophage glutathione content reduces cell-mediated oxidation of LDL and atherosclerosis in apolipoprotein E-deficient mice.
2002 Jul
Antinephritis and radical scavenging activity of prenylflavonoids.
2003 Dec
Preliminary evaluation of antinephritis and radical scavenging activities of glabridin from Glycyrrhiza glabra.
2003 Dec
Estrogen-like activity of licorice root constituents: glabridin and glabrene, in vascular tissues in vitro and in vivo.
2004 Jul
Therapeutic drugs that behave as mechanism-based inhibitors of cytochrome P450 3A4.
2004 Oct
The licorice root derived isoflavan glabridin increases the function of osteoblastic MC3T3-E1 cells.
2005 Aug 1
Determination of glabridin in human plasma by solid-phase extraction and LC-MS/MS.
2005 Dec 15
Analysis and comparison of Radix Glycyrrhizae (licorice) from Europe and China by capillary-zone electrophoresis (CZE).
2005 Jul 15
Glabridin, an isoflavan from licorice root, inhibits inducible nitric-oxide synthase expression and improves survival of mice in experimental model of septic shock.
2005 Mar
Suppression by licorice flavonoids of abdominal fat accumulation and body weight gain in high-fat diet-induced obese C57BL/6J mice.
2007 Jan
Post TLC developing technique for tyrosinase inhibitor detection.
2007 Jan
Constituent properties of licorices derived from Glycyrrhiza uralensis, G. glabra, or G. inflata identified by genetic information.
2007 Jul
The effect of an endogenous antioxidant glabridin on oxidized LDL.
2008
Atorvastatin and cardiovascular risk in the elderly--patient considerations.
2008
Extraction of glycyrrhizic acid and glabridin from licorice.
2008 Apr
Glabridin, a functional compound of liquorice, attenuates colonic inflammation in mice with dextran sulphate sodium-induced colitis.
2008 Jan
In vitro and in vivo neuroprotective effect and mechanisms of glabridin, a major active isoflavan from Glycyrrhiza glabra (licorice).
2008 Jan 2
Effect of glabridin from Glycyrrhiza glabra on learning and memory in mice.
2008 Mar
Inhibition of P-glycoprotein and multidrug resistance protein 1 by dietary phytochemicals.
2008 Oct
The response of creatine kinase specific activity in rat pituitary to estrogenic compounds and vitamin d less-calcemic analogs.
2009
Antifungal activity of Glycyrrhiza glabra extracts and its active constituent glabridin.
2009 Aug
A validated stability-indicating HPLC method for analysis of glabridin prodrugs in hydrolysis studies.
2009 Jun
Antioxidant effect of polyphenolic glabridin on LDL oxidation.
2009 May-Jun
Antidyslipidaemic activity of Glycyrrhiza glabra in high fructose diet induced dsyslipidaemic Syrian golden hamsters.
2009 Oct
Effect of Carnitine and herbal mixture extract on obesity induced by high fat diet in rats.
2009 Oct 16
Mechanisms regulating skin pigmentation: the rise and fall of complexion coloration.
2009 Sep 15
Factors influencing glabridin stability.
2010 Dec
Licorice infusion: Chemical profile and effects on the activation and the cell cycle progression of human lymphocytes.
2010 Jan
Overcoming multidrug resistance in human cancer cells by natural compounds.
2010 Jun
Effect of licorice compounds licochalcone A, glabridin and glycyrrhizic acid on growth and virulence properties of Candida albicans.
2011 Nov
Patents

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
In Vitro Use Guide
The antimicrobial potency of glabridin was measured using an in vitro agar dilution-streak test. Glabridin displays inhibitory activity against Staphylococcus aureus (MIC 6.25 ug/ml), Mycobacterium smegmatis (MIC 6.25 ug/ml) and Candida albicans (MIC 25 ug/ml).
Substance Class Chemical
Created
by admin
on Fri Dec 15 20:17:42 GMT 2023
Edited
by admin
on Fri Dec 15 20:17:42 GMT 2023
Record UNII
HOC5567T41
Record Status Validated (UNII)
Record Version
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Name Type Language
GLABRIDIN
INCI  
INCI  
Official Name English
1,3-BENZENEDIOL, 4-((3R)-3,4-DIHYDRO-8,8-DIMETHYL-2H,8H-BENZO(1,2-B:3,4-B')DIPYRAN-3-YL)-
Systematic Name English
4-(3,4-DIHYDRO-8,8-DIMETHYL-2H,8H-BENZO(1,2-B:3,4-B')DIPYRAN-3-YL)-1,3-BENZENEDIOL
Systematic Name English
Glabridin [WHO-DD]
Common Name English
1,3-BENZENEDIOL, 4-(3,4-DIHYDRO-8,8-DIMETHYL-2H,8H-BENZO(1,2-B:3,4-B')DIPYRAN-3-YL)-, (R)-
Common Name English
GLABRIDIN [INCI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C306
Created by admin on Fri Dec 15 20:17:42 GMT 2023 , Edited by admin on Fri Dec 15 20:17:42 GMT 2023
Code System Code Type Description
MESH
C107601
Created by admin on Fri Dec 15 20:17:42 GMT 2023 , Edited by admin on Fri Dec 15 20:17:42 GMT 2023
PRIMARY
EPA CompTox
DTXSID00208589
Created by admin on Fri Dec 15 20:17:42 GMT 2023 , Edited by admin on Fri Dec 15 20:17:42 GMT 2023
PRIMARY
FDA UNII
HOC5567T41
Created by admin on Fri Dec 15 20:17:42 GMT 2023 , Edited by admin on Fri Dec 15 20:17:42 GMT 2023
PRIMARY
WIKIPEDIA
GLABRIDIN
Created by admin on Fri Dec 15 20:17:42 GMT 2023 , Edited by admin on Fri Dec 15 20:17:42 GMT 2023
PRIMARY
DAILYMED
HOC5567T41
Created by admin on Fri Dec 15 20:17:42 GMT 2023 , Edited by admin on Fri Dec 15 20:17:42 GMT 2023
PRIMARY
CAS
59870-68-7
Created by admin on Fri Dec 15 20:17:42 GMT 2023 , Edited by admin on Fri Dec 15 20:17:42 GMT 2023
PRIMARY
NCI_THESAURUS
C64171
Created by admin on Fri Dec 15 20:17:42 GMT 2023 , Edited by admin on Fri Dec 15 20:17:42 GMT 2023
PRIMARY
PUBCHEM
124052
Created by admin on Fri Dec 15 20:17:42 GMT 2023 , Edited by admin on Fri Dec 15 20:17:42 GMT 2023
PRIMARY
RXCUI
1603522
Created by admin on Fri Dec 15 20:17:42 GMT 2023 , Edited by admin on Fri Dec 15 20:17:42 GMT 2023
PRIMARY RxNorm
Related Record Type Details
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.
DERIVATIVE -> PARENT
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).
PARENT -> CONSTITUENT ALWAYS PRESENT
0.11% of dry weight of contents.
PARENT -> CONSTITUENT ALWAYS PRESENT
Anti-HCV activity IC50 was found to be be 6.2 ug/mL.
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).