Glabridin

Names

[ Name ]:
Glabridin

[Synonym ]:
1,3-Benzenediol,4-(3,4-dihydro-8,8-dimethyl-2H,8H-benzo(1,2-b:3,4-b')dipyran-3-yl)-,(R)
4-(3,4-Dihydro-8,8-dimethyl-2H,8H-benzo(1,2-b:3,4-b')dipyran-3-yl)-1,3-benzenediol
Glabridin
Bio-0904
4-[(3R)-8,8-dimethyl-3,4-dihydro-2H-pyrano[2,3-f]chromen-3-yl]benzene-1,3-diol
4-[(3R)-8,8-Dimethyl-3,4-dihydro-2H,8H-pyrano[2,3-f]chromen-3-yl]benzene-1,3-diol
BIDD:ER0172
4-[(3R)-8,8-Dimethyl-3,4-dihydro-2H,8H-pyrano[2,3-f]chromen-3-yl]-1,3-benzenediol
1,3-Benzenediol, 4-[(3R)-3,4-dihydro-8,8-dimethyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-3-yl]-
MFCD03427694

Biological Activity

[Description]:

Glabridin is a natural isoflavan from Glycyrrhiza glabra, binds to and activates PPARγ, with an EC50 of 6115 nM. Glabridin exhibits antioxidant, anti-bacterial, anti-nephritic, anti-diabetic, anti-fungal, antitumor, anti-inflammatory, antiosteoporotic, cardiovascular protective, neuroprotective and radical scavenging activities[1][2].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Cell Cycle/DNA Damage >> PPAR

Research Areas >> Inflammation/Immunology

[Target]

PPARγ:6.1 μM (EC50)

[In Vitro]

Glabridin binds to and activates PPARγ, with an EC50 of 6115 nM[1]. Glabridin (40, 80 μM) inhibits the proliferation of SCC-9 and SAS cell lines in a dose- and time-dependent manner after treatment for 24 and 48 h[2]. Glabridin (0-80 μM) also induces apoptosis, causes Sub-G1 cell cycle arrest in SCC-9 and SAS cell lines[2]. Glabridin (0, 20, 40, and 80 μM) dose-dependently activates caspase-3, −8, and −9 and increases PARP cleavage, significantly phosphorylates ERK1/2, JNK1/2, and p-38 MAPK in SCC-9 cells[2].

[In Vivo]

Glabridin (50 mg/kg, p.o. once daily) shows potent anti-inflammatory activity, ameliorates the inflammatory alterations induced by Dextran sodium sulphate (DSS) in rats[3].

[References]

[1]. Rebhun JF, et al. Identification of glabridin as a bioactive compound in licorice (Glycyrrhiza glabra L.) extract that activates human peroxisome proliferator-activated receptor gamma (PPARγ). Fitoterapia. 2015 Oct;106:55-61.

[2]. Chen CT, et al. Glabridin induces apoptosis and cell cycle arrest in oral cancer cells through the JNK1/2 signaling pathway. Environ Toxicol. 2018 Jun;33(6):679-685.

[3]. El-Ashmawy NE, et al. Downregulation of iNOS and elevation of cAMP mediate the anti-inflammatory effect of glabridin in rats with ulcerative colitis. Inflammopharmacology. 2018 Apr;26(2):551-559.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
518.6±50.0 °C at 760 mmHg

[ Melting Point ]:
154-155ºC

[ Molecular Formula ]:
C₂₀H₂₀O₄

[ Molecular Weight ]:
324.37

[ Flash Point ]:
267.4±30.1 °C

[ Exact Mass ]:
324.136169

[ PSA ]:
58.92000

[ LogP ]:
4.26

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.623

[ Storage condition ]:
room temp

MSDS

Click to get detail MSDS

Safety Information

[ Hazard Statements ]:
H413

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2942000000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2942000000

Articles

Glabridin inhibits migration and invasion by transcriptional inhibition of matrix metalloproteinase 9 through modulation of NF-κB and AP-1 activity in human liver cancer cells.

Br. J. Pharmacol. 171(12) , 3037-50, (2014)

High mortality and morbidity rates for hepatocellular carcinoma in Taiwan primarily result from uncontrolled tumour metastasis. Glabridin, a prenylated isoflavonoid of licorice (Glycyrrhiza glabra) ro...

Novel phytonutrient contributors to antioxidant protection against cardiovascular disease

Nutrition 28(6) , 605-10, (2012)

The associations linking endothelial inflammation, endothelial oxidative stress, and atherogenesis and the potential for dietary phytonutrients to decrease the impact of these associations were assess...

Glabridin inhibits migration, invasion, and angiogenesis of human non-small cell lung cancer A549 cells by inhibiting the FAK/rho signaling pathway.

Integr. Cancer Ther. 10(4) , 341-9, (2011)

This study reports the antimigration, anti-invasive effect of glabridin, a flavonoid obtained from licorice, in human non-small cell lung cancer A549 cells. Glabridin exhibited effective inhibition of...