GLABRIDIN

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7381508 | https://www.ncbi.nlm.nih.gov/pubmed/23850540 | https://www.ncbi.nlm.nih.gov/pubmed/10318783

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Estrogen receptor 75 Target ID: P03372 Gene ID: 2099.0 Gene Symbol: ESR1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21573846	Antagonist 2778
NF-kappa B signaling pathway 84 Target ID: map04064 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15537821	Inhibitor 8297
regulation of plasma lipoprotein oxidation 1 Target ID: GO:0034444 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10318783	Inhibitor 8297
Sodium-dependent serotonin transporter 40 Target ID: P31645 Gene ID: 6532.0 Gene Symbol: SLC6A4 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/12794307	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Septic shock 21 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15537821	Primary	Preclinical	Unknown Approved Use Unknown
Inflammatory bowel disease 19 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18005263	Primary	Preclinical	Unknown Approved Use Unknown
Atherosclerosis 74 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9250104	Preventing	Preclinical	Unknown Approved Use Unknown
Bacterial infections 234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7381508	Primary	Basic research	Unknown Approved Use Unknown
Alzheimer’s disease 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18484526	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Cytotoxic activity of low molecular weight polyphenols against human oral tumor cell lines.	2000 Jul-Aug	10953322
Anti-Helicobacter pylori flavonoids from licorice extract.	2002 Aug 9	12127165
Evaluation of the antioxidant activity of different flavonoids by the chemiluminescence method.	2003	12866943
Inhibition of serotonin re-uptake by licorice constituents.	2003 Apr	12794307
Field survey of Glycyrrhiza plants in Central Asia (1). Characterization of G. uralensis, G. glabra and the putative intermediate collected in Kazakhstan.	2003 Jun	12808302
The licorice root derived isoflavan glabridin increases the function of osteoblastic MC3T3-E1 cells.	2005 Aug 1	15922308
Determination of glabridin in human plasma by solid-phase extraction and LC-MS/MS.	2005 Dec 15	16183339
Analysis and comparison of Radix Glycyrrhizae (licorice) from Europe and China by capillary-zone electrophoresis (CZE).	2005 Jul 15	15967286
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
Anti-oxidant constituents of the roots and stolons of licorice (Glycyrrhiza glabra).	2007 Jun 13	17516657
Role of P-glycoprotein in limiting the brain penetration of glabridin, an active isoflavan from the root of Glycyrrhiza glabra.	2007 Sep	17551811
The effect of an endogenous antioxidant glabridin on oxidized LDL.	2008	19024795
Atorvastatin and cardiovascular risk in the elderly--patient considerations.	2008	18686752
Inhibition of P-glycoprotein and multidrug resistance protein 1 by dietary phytochemicals.	2008 Oct	18204840
Cancer is a preventable disease that requires major lifestyle changes.	2008 Sep	18626751
Synthesis of glabridin derivatives as tyrosinase inhibitors.	2009 May	19471877
An updated review of tyrosinase inhibitors.	2009 May 26	19582213
Antidyslipidaemic activity of Glycyrrhiza glabra in high fructose diet induced dsyslipidaemic Syrian golden hamsters.	2009 Oct	23105868
Glabridin protects osteoblastic MC3T3-E1 cells against antimycin A induced cytotoxicity.	2011 Aug 15	21621525
Effect of licorice compounds licochalcone A, glabridin and glycyrrhizic acid on growth and virulence properties of Candida albicans.	2011 Nov	21615543
Anti-hepatitis C virus compounds obtained from Glycyrrhiza uralensis and other Glycyrrhiza species.	2014 Mar	24397541
Tissue and species differences in the glucuronidation of glabridin with UDP-glucuronosyltransferases.	2015 Apr 25	25765239

Patents

Sample Use Guides

In Vivo Use Guide

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).

Name

Type

Language

GLABRIDIN

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