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
Anti-Helicobacter pylori flavonoids from licorice extract.	2002 Aug 9	12127165
Antinephritis and radical scavenging activity of prenylflavonoids.	2003 Dec	14630182
Field survey of Glycyrrhiza plants in Central Asia (3). Chemical characterization of G. glabra collected in Uzbekistan.	2003 Nov	14600388
Estrogenic activity of glabridin and glabrene from licorice roots on human osteoblasts and prepubertal rat skeletal tissues.	2004 Aug	15336701
Herbal bioactivation: the good, the bad and the ugly.	2004 Jan 9	14672753
Estrogen-like activity of licorice root constituents: glabridin and glabrene, in vascular tissues in vitro and in vivo.	2004 Jul	15276622
The licorice root derived isoflavan glabridin increases the function of osteoblastic MC3T3-E1 cells.	2005 Aug 1	15922308
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
Metabolic activation of herbal and dietary constituents and its clinical and toxicological implications: an update.	2007 Aug	17691916
Suppression by licorice flavonoids of abdominal fat accumulation and body weight gain in high-fat diet-induced obese C57BL/6J mice.	2007 Jan	17213668
Constituent properties of licorices derived from Glycyrrhiza uralensis, G. glabra, or G. inflata identified by genetic information.	2007 Jul	17603166
Clinical safety of licorice flavonoid oil (LFO) and pharmacokinetics of glabridin in healthy humans.	2007 Jun	17634165
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
Extraction of glycyrrhizic acid and glabridin from licorice.	2008 Apr	19325770
Lipid abnormalities in streptozotocin-diabetes: Amelioration by Morus indica L. cv Suguna leaves.	2009 Jul	20165649
Antioxidant effect of polyphenolic glabridin on LDL oxidation.	2009 May-Jun	19651803
Anti-inflammatory effects of licorice and roasted licorice extracts on TPA-induced acute inflammation and collagen-induced arthritis in mice.	2010	20300198
Factors influencing glabridin stability.	2010 Dec	21299118
Licorice infusion: Chemical profile and effects on the activation and the cell cycle progression of human lymphocytes.	2010 Jan	20548933
Inhibition of bone marrow-derived dendritic cell maturation by glabridin.	2010 Oct	20633530
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