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
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: P03372 Gene ID: 2099.0 Gene Symbol: ESR1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21573846 |
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Target ID: map04064 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15537821 |
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Target ID: GO:0034444 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10318783 |
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Target ID: P31645 Gene ID: 6532.0 Gene Symbol: SLC6A4 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/12794307 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Preventing | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Cytotoxic activity of low molecular weight polyphenols against human oral tumor cell lines. | 2000 Jul-Aug |
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Increased macrophage glutathione content reduces cell-mediated oxidation of LDL and atherosclerosis in apolipoprotein E-deficient mice. | 2002 Jul |
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Antinephritis and radical scavenging activity of prenylflavonoids. | 2003 Dec |
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Preliminary evaluation of antinephritis and radical scavenging activities of glabridin from Glycyrrhiza glabra. | 2003 Dec |
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Estrogen-like activity of licorice root constituents: glabridin and glabrene, in vascular tissues in vitro and in vivo. | 2004 Jul |
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Therapeutic drugs that behave as mechanism-based inhibitors of cytochrome P450 3A4. | 2004 Oct |
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The licorice root derived isoflavan glabridin increases the function of osteoblastic MC3T3-E1 cells. | 2005 Aug 1 |
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Determination of glabridin in human plasma by solid-phase extraction and LC-MS/MS. | 2005 Dec 15 |
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Analysis and comparison of Radix Glycyrrhizae (licorice) from Europe and China by capillary-zone electrophoresis (CZE). | 2005 Jul 15 |
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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 |
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Suppression by licorice flavonoids of abdominal fat accumulation and body weight gain in high-fat diet-induced obese C57BL/6J mice. | 2007 Jan |
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Post TLC developing technique for tyrosinase inhibitor detection. | 2007 Jan |
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Constituent properties of licorices derived from Glycyrrhiza uralensis, G. glabra, or G. inflata identified by genetic information. | 2007 Jul |
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The effect of an endogenous antioxidant glabridin on oxidized LDL. | 2008 |
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Atorvastatin and cardiovascular risk in the elderly--patient considerations. | 2008 |
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Extraction of glycyrrhizic acid and glabridin from licorice. | 2008 Apr |
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Glabridin, a functional compound of liquorice, attenuates colonic inflammation in mice with dextran sulphate sodium-induced colitis. | 2008 Jan |
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In vitro and in vivo neuroprotective effect and mechanisms of glabridin, a major active isoflavan from Glycyrrhiza glabra (licorice). | 2008 Jan 2 |
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Effect of glabridin from Glycyrrhiza glabra on learning and memory in mice. | 2008 Mar |
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Inhibition of P-glycoprotein and multidrug resistance protein 1 by dietary phytochemicals. | 2008 Oct |
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The response of creatine kinase specific activity in rat pituitary to estrogenic compounds and vitamin d less-calcemic analogs. | 2009 |
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Antifungal activity of Glycyrrhiza glabra extracts and its active constituent glabridin. | 2009 Aug |
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A validated stability-indicating HPLC method for analysis of glabridin prodrugs in hydrolysis studies. | 2009 Jun |
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Antioxidant effect of polyphenolic glabridin on LDL oxidation. | 2009 May-Jun |
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Antidyslipidaemic activity of Glycyrrhiza glabra in high fructose diet induced dsyslipidaemic Syrian golden hamsters. | 2009 Oct |
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Effect of Carnitine and herbal mixture extract on obesity induced by high fat diet in rats. | 2009 Oct 16 |
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Mechanisms regulating skin pigmentation: the rise and fall of complexion coloration. | 2009 Sep 15 |
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Factors influencing glabridin stability. | 2010 Dec |
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Licorice infusion: Chemical profile and effects on the activation and the cell cycle progression of human lymphocytes. | 2010 Jan |
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Overcoming multidrug resistance in human cancer cells by natural compounds. | 2010 Jun |
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Effect of licorice compounds licochalcone A, glabridin and glycyrrhizic acid on growth and virulence properties of Candida albicans. | 2011 Nov |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7381508
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
Edited
Fri Dec 15 20:17:42 GMT 2023
by
admin
on
Fri Dec 15 20:17:42 GMT 2023
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Record UNII |
HOC5567T41
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C306
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C107601
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DTXSID00208589
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HOC5567T41
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GLABRIDIN
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HOC5567T41
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59870-68-7
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C64171
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124052
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1603522
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PRIMARY | RxNorm |
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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.
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DERIVATIVE -> PARENT |
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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).
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PARENT -> CONSTITUENT ALWAYS PRESENT |
0.11% of dry weight of contents.
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Anti-HCV activity IC50 was found to be be 6.2 ug/mL.
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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).
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