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=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
| 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) |
|||
Target ID: map04064 |
|||
Target ID: GO:0034444 |
|||
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 |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Preventing | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Cytotoxic activity of low molecular weight polyphenols against human oral tumor cell lines. | 2000 Jul-Aug |
|
| Oxidative stress increases the expression of the CD36 scavenger receptor and the cellular uptake of oxidized low-density lipoprotein in macrophages from atherosclerotic mice: protective role of antioxidants and of paraoxonase. | 2002 Apr |
|
| Anti-Helicobacter pylori flavonoids from licorice extract. | 2002 Aug 9 |
|
| The licorice root derived isoflavan glabridin inhibits the activities of human cytochrome P450S 3A4, 2B6, and 2C9. | 2002 Jun |
|
| Evaluation of the antioxidant activity of different flavonoids by the chemiluminescence method. | 2003 |
|
| Preliminary evaluation of antinephritis and radical scavenging activities of glabridin from Glycyrrhiza glabra. | 2003 Dec |
|
| Glabrene and isoliquiritigenin as tyrosinase inhibitors from licorice roots. | 2003 Feb 26 |
|
| Field survey of Glycyrrhiza plants in Central Asia (1). Characterization of G. uralensis, G. glabra and the putative intermediate collected in Kazakhstan. | 2003 Jun |
|
| Estrogen-like activity of licorice root constituents: glabridin and glabrene, in vascular tissues in vitro and in vivo. | 2004 Jul |
|
| Licorice flavonoids suppress abdominal fat accumulation and increase in blood glucose level in obese diabetic KK-A(y) mice. | 2004 Nov |
|
| 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 |
|
| Clinical outcomes and management of mechanism-based inhibition of cytochrome P450 3A4. | 2005 Mar |
|
| Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
|
| Absorption of dietary licorice isoflavan glabridin to blood circulation in rats. | 2007 Aug |
|
| Clinical safety of licorice flavonoid oil (LFO) and pharmacokinetics of glabridin in healthy humans. | 2007 Jun |
|
| Atorvastatin and cardiovascular risk in the elderly--patient considerations. | 2008 |
|
| 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 |
|
| 90-Day repeated-dose toxicity study of licorice flavonoid oil (LFO) in rats. | 2008 Jul |
|
| Effect of glabridin from Glycyrrhiza glabra on learning and memory in mice. | 2008 Mar |
|
| Antimicrobial potential of Glycyrrhiza glabra roots. | 2008 Mar 5 |
|
| Inhibition of P-glycoprotein and multidrug resistance protein 1 by dietary phytochemicals. | 2008 Oct |
|
| Cancer is a preventable disease that requires major lifestyle changes. | 2008 Sep |
|
| Antifungal activity of Glycyrrhiza glabra extracts and its active constituent glabridin. | 2009 Aug |
|
| Lipid abnormalities in streptozotocin-diabetes: Amelioration by Morus indica L. cv Suguna leaves. | 2009 Jul |
|
| Glabridin from Chinese herb licorice inhibits fatigue in mice. | 2009 Oct 15 |
|
| Anti-inflammatory effects of licorice and roasted licorice extracts on TPA-induced acute inflammation and collagen-induced arthritis in mice. | 2010 |
|
| Factors influencing glabridin stability. | 2010 Dec |
|
| Glabridin inhibits lipopolysaccharide-induced activation of a microglial cell line, BV-2, by blocking NF-kappaB and AP-1. | 2010 Jan |
|
| Effect of licorice compounds licochalcone A, glabridin and glycyrrhizic acid on growth and virulence properties of Candida albicans. | 2011 Nov |
|
| Anti-hepatitis C virus compounds obtained from Glycyrrhiza uralensis and other Glycyrrhiza species. | 2014 Mar |
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
Fri Dec 15 20:17:42 GMT 2023
by
admin
on
Fri Dec 15 20:17:42 GMT 2023
|
| Record UNII |
HOC5567T41
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Official Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
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 | ||
|---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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).
|
