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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Preventing
Unknown
Primary
Unknown
Primary
Unknown

PubMed

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).
Substance Class Chemical
Record UNII
HOC5567T41
Record Status Validated (UNII)
Record Version