Chemistry:Isoliquiritigenin
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| IUPAC name
(E)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
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| Other names
6'-deoxychalcone
2',4,4'-Trihydroxychalcone 4,2',4'-Trihydroxychalcone 4'2'4'-trihydroxychalcone 2',4',4-Trihydroxychalcone | |
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3D model (JSmol)
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| Properties | |
| C15H12O4 | |
| Molar mass | 256.25 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is   ?)
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| Infobox references | |
Isoliquiritigenin is a phenolic chemical compound found in licorice.[1] It is under experimentation phase testing for use as a cancer treatment and as an aide for cocaine addiction.[citation needed] It is a sirtuin-activating compound.[citation needed]
Metabolism
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
Isoliquiritigenin has been found to be a potent (65 times higher affinity than diazepine) GABA-A benzodiapine receptor positive allosteric modulator.[2] It can target miR-301b/LRIG1 signaling pathways, resulting in the inhibition of melanoma growth.[3]
References
- ↑ 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.
- ↑ Cho, S; Kim, S; Jin, Z; Yang, H; Han, D; Baek, N. I.; Jo, J; Cho, C. W. et al. (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 et al. (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. PMID 30081934.
category:Phenols
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