Isoliquiritigenin
Chemical compound
From Wikipedia, the free encyclopedia
Isoliquiritigenin is a chalcone found in the roots of several Glycyrrhiza species, such as liquorice, studied for its activity as a tyrosinase inhibitor, NMDA receptor antagonist, GABA modulator, and its potential antineoplastic and geroprotective effects.[1]
| |
| Names | |
|---|---|
| Preferred IUPAC name
2â²,4,4â²-Trihydroxychalcone | |
Other names
| |
| Identifiers | |
3D model (JSmol) |
|
| Abbreviations | ILTG |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.202.617 |
| EC Number |
|
| KEGG | |
PubChem CID |
|
| UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
| Properties | |
| C15H12O4 | |
| Molar mass | 256.257 g·molâ1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Occurrence
Isoliquiritigenin occurs in some species of the genus Glycyrrhiza, including Glycyrrhiza glabra (licorice).[2]
Pharmacological properties
Isoliquiritigenin has been studied for its potential pharmacological properties, and ongoing research is exploring its use in food additives and therapeutic applications, although further studies are needed to evaluate its safety and potential target-organ toxicity.[2] It is also under preliminary research for potential anti-inflammatory effects through multiple molecular pathways.[3] It has been studied for its effects on melanoma cells, where it was found to modulate microRNA-301b and its target gene LRIG1 in experimental models.[4] It is under preliminary research for potential therapeutic effects against age-related neurodegenerative diseases by targeting multiple pathological mechanisms such as oxidative stress, neurotransmitter imbalance, and mitochondrial dysfunction.[5]
Pharmakokinetics
Isoliquiritigenin exhibits various biological activities but has low oral bioavailability (11.8%) in rats due to extensive metabolism in the liver and small intestine, resulting in high levels of its metabolites M1 and M2.[6]
Mechanism of action
Isoliquiritigenin has been found to be a potent (65 times higher affinity than diazepam) GABA-A benzodiazepine receptor positive allosteric modulator with hypnotic effects in mice.[7] It competitively inhibits human monoamine oxidase enzymes and interacts with dopamine and vasopressin receptors.[8]