Isoliquiritigenin

Isoliquiritigenin is a phenolic chemical compound found in licorice.[1]

Isoliquiritigenin
Names
Preferred IUPAC name
2′,4,4′-Trihydroxychalcone
Other names
  • 6'-Deoxychalcone
  • 4,2',4'-Trihydroxychalcone
  • 2',4',4-Trihydroxychalcone
Identifiers
CAS Number
3D model (JSmol)
Abbreviations ILTG
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.202.617
EC Number
  • 237-316-5
KEGG
PubChem CID
UNII
InChI
  • 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
SMILES
  • C1=CC(=CC=C1C=CC(=O)C2=C(C=C(C=C2)O)O)O
Properties
Chemical formula
 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).
N verify (what is YN ?)
Infobox references

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 diazepam) GABA-A benzodiapine receptor positive allosteric modulator.[2] It can target miR-301b/LRIG1 signaling pathways, resulting in the inhibition of melanoma growth in vitro.[3]

References
  1. 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.
  2. 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.
  3. 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.
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