Isoliquiritigenin

Last updated
Isoliquiritigenin
Isoliquiritigenin.svg
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 InfoCard 100.202.617 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 237-316-5
KEGG
PubChem CID
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+ X mark.svgN
    Key: DXDRHHKMWQZJHT-FPYGCLRLSA-N X mark.svgN
  • 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 mass 256.257 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]

Contents

Occurrence

Liquorice roots Market Aix-en-Provence 20100828 Liquorice.jpg
Liquorice roots

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]

References

  1. ↑ PubChem. "Trihydroxychalcone". pubchem.ncbi.nlm.nih.gov. Retrieved 2025-06-12.
  2. 1 2 Fu 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.
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