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Isoliquiritigenin

From Wikipedia, the free encyclopedia
Isoliquiritigenin
Names
Preferred IUPAC name
2′,4,4′-Trihydroxychalcone
Other names
  • 6'-Deoxychalcone
  • 4,2',4'-Trihydroxychalcone
  • 2',4,4'-Trihydroxychalcone
Identifiers
3D model (JSmol)
AbbreviationsILTG
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.202.617Edit this at Wikidata
EC Number
  • 237-316-5
KEGG
UNII
  • InChI=1S/C15H12O4/c16-11-4-1-10(2-5-11)3-8-14(18)13-7-6-12(17)9-15(13)19/h1-9,16-17,19H/b8-3+ ☒N
    Key: DXDRHHKMWQZJHT-FPYGCLRLSA-N ☒N
  • InChI=1/C15H12O4/c16-11-4-1-10(2-5-11)3-8-14(18)13-7-6-12(17)9-15(13)19/h1-9,16-17,19H/b8-3+
    Key: DXDRHHKMWQZJHT-FPYGCLRLBB
  • C1=CC(=CC=C1C=CC(=O)C2=C(C=C(C=C2)O)O)O
Properties
C15H12O4
Molar mass256.257 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Isoliquiritigenin is achalcone found in the roots of severalGlycyrrhiza species, such asliquorice, studied for its activity as atyrosinase inhibitor,NMDA receptor antagonist,GABA modulator, and its potentialantineoplastic and geroprotective effects.[1]

Occurrence

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Liquorice roots

Isoliquiritigenin occurs in some species of the genusGlycyrrhiza, includingGlycyrrhiza glabra (licorice).[2]

Pharmacological properties

[edit]

Isoliquiritigenin has been studied for its potential pharmacological properties, and ongoing research is exploring its use infood 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 potentialanti-inflammatory effects through multiple molecular pathways.[3] It has been studied for its effects onmelanoma cells, where it was found to modulate microRNA-301b and its target geneLRIG1 in experimental models.[4] It is under preliminary research for potential therapeutic effects against age-relatedneurodegenerative diseases by targeting multiple pathological mechanisms such asoxidative stress, neurotransmitter imbalance, andmitochondrial dysfunction.[5]

Pharmakokinetics

[edit]

Isoliquiritigenin exhibits various biological activities but has low oralbioavailability (11.8%) in rats due to extensive metabolism in theliver andsmall intestine, resulting in high levels of its metabolites M1 and M2.[6]

Mechanism of action

[edit]

Isoliquiritigenin has been found to be a potent (65 times higheraffinity thandiazepam)GABA-A benzodiazepine receptorpositive allosteric modulator withhypnotic effects in mice.[7] It competitivelyinhibits human monoamine oxidase enzymes and interacts withdopamine andvasopressin receptors.[8]

References

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  1. ^PubChem."Trihydroxychalcone".pubchem.ncbi.nlm.nih.gov. Retrieved2025-06-12.
  2. ^abFu Peng, Qiaohui Du, Cheng Peng, Neng Wang, Hailin Tang, Xiaoming Xie, Jiangang Shen, Jianping Chen (July 2015), "A Review: The Pharmacology of Isoliquiritigenin",Phytotherapy Research, vol. 29, no. 7, pp. 969–977,doi:10.1002/ptr.5348,PMID 25907962{{citation}}: CS1 maint: multiple names: authors list (link)
  3. ^Ziyi Chen, Wenwen Ding, Xiaoxue Yang, Tiangong Lu, Ying Liu (January 2024), "Isoliquiritigenin, a potential therapeutic agent for treatment of inflammation-associated diseases",Journal of Ethnopharmacology, vol. 318, no. Pt B, p. 117059,doi:10.1016/j.jep.2023.117059,PMID 37604329{{citation}}: CS1 maint: multiple names: authors list (link)
  4. ^Xiang, Shijian; Chen, Huoji; Luo, Xiaojun; An, Baichao; Wu, Wenfeng; Cao, Siwei; Ruan, Shifa; Wang, Zhuxian; Weng, Lidong; Zhu, Hongxia; Liu, Qiang (2018)."Isoliquiritigenin suppresses human melanoma growth by targeting miR-301b/LRIG1 signaling".Journal of Experimental & Clinical Cancer Research.37 (1): 184.doi:10.1186/s13046-018-0844-x.PMC 6091185.PMID 30081934.
  5. ^Ramalingam, Mahesh; Kim, Hyojung; Lee, Yunjong; Lee, Yun-Il (2018-11-01)."Phytochemical and Pharmacological Role of Liquiritigenin and Isoliquiritigenin From Radix Glycyrrhizae in Human Health and Disease Models".Frontiers in Aging Neuroscience.10.doi:10.3389/fnagi.2018.00348.ISSN 1663-4365.PMC 6221911.
  6. ^Lee, Yu Kyung; Chin, Young-Won; Bae, Jin-Kyung; Seo, Jun Su; Choi, Young Hee (2013). "Pharmacokinetics of isoliquiritigenin and its metabolites in rats: low bioavailability is primarily due to the hepatic and intestinal metabolism".Planta Medica.79 (17):1656–1665.Bibcode:2013PlMed..79.1656L.doi:10.1055/s-0033-1350924.ISSN 1439-0221.PMID 24108436.
  7. ^Cho, S; Kim, S; Jin, Z; Yang, H; Han, D; Baek, N. I.; Jo, J; Cho, C. W.; Park, J. H.; Shimizu, M; Jin, Y. H. (2011). "Isoliquiritigenin, a chalcone compound, is a positive allosteric modulator of GABAA receptors and shows hypnotic effects".Biochemical and Biophysical Research Communications.413 (4):637–42.doi:10.1016/j.bbrc.2011.09.026.PMID 21945440.
  8. ^Prajapati, Ritu; Seong, Su Hui; Park, Se Eun; Paudel, Pradeep; Jung, Hyun Ah; Choi, Jae Sue (2021-12-07)."Isoliquiritigenin, a potent human monoamine oxidase inhibitor, modulates dopamine D1, D3, and vasopressin V1A receptors".Scientific Reports.11 (1): 23528.doi:10.1038/s41598-021-02843-6.ISSN 2045-2322.PMC 8651714.PMID 34876600.
Chalconoids and theirglycosides
Chalconoids
Chalconoidglycosides
Acylated chalconoids
O-methylated chalconoids
Flavokavains
Synthetic
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