Isoliquiritigenin
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| Names | |
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| Preferred IUPAC name
2′,4,4′-Trihydroxychalcone | |
Other names
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| Identifiers | |
3D model (JSmol)
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| Abbreviations | ILTG |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.202.617 |
| EC Number |
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| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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 phenolic chemical compound found in licorice.[1]
Occurrence
[edit]
Isoliquiritigenin occurs in some species of the genus Glycyrrhiza glabra (licorice).[2]
Pharmacological properties
[edit]Isoliquiritigenin has various pharmacological properties and is also responsible for the corresponding properties of the plants it contains. In various studies, its effects included anti-inflammatory, antimicrobial agent, and antioxidant activities, and it also demonstrated targeted cancer therapy effects.[2] In in vitro studies and some in vivo studies, isoliquiritigenin showed effects against breast cancer, colorectal carcinoma, ovarian carcinoma, bronchial carcinoma, and leukemia, among others.[3] It also interferes with several cellular signaling pathways and has an anti-inflammatory effect, which may have applications in the treatment of inflammatory diseases.[4]
Metabolism
[edit]The enzyme 6'-deoxychalcone synthase uses malonyl-CoA, 4-coumaroyl-CoA, NADPH, and H+ to produce CoA, isoliquiritigenin, CO2, NADP+, and H2O.
The enzyme isoliquiritigenin 2'-O-methyltransferase further transforms isoliquiritigenin into 2'-O-methylisoliquiritigenin.
Mechanism of action
[edit]Isoliquiritigenin has been found to be a potent (65 times higher affinity than diazepam) GABA-A benzodiapine receptor positive allosteric modulator.[5] It can target miR-301b/LRIG1 signaling pathways, resulting in the inhibition of melanoma growth in vitro.[6]
References
[edit]- ^ Nerya, Ohad; Vaya, Jacob; Musa, Ramadan; Izrael, Sarit; Ben-Arie, Ruth; Tamir, Snait (2003). "Glabrene and Isoliquiritigenin as Tyrosinase Inhibitors from Licorice Roots". Journal of Agricultural and Food Chemistry. 51 (5): 1201–1207. doi:10.1021/jf020935u. PMID 12590456.
- ^ a b 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
{{citation}}: CS1 maint: multiple names: authors list (link) - ^ Kai-Lee Wang, Ying-Chun Yu, Shih-Min Hsia (2021-01-01), "Perspectives on the Role of Isoliquiritigenin in Cancer", Cancers, vol. 13, no. 1, p. 115, doi:10.3390/cancers13010115, PMC 7795842, PMID 33401375
{{citation}}: CS1 maint: multiple names: authors list (link) - ^ 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) - ^ 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.
- ^ 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.