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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
  • 961-29-5 Y
3D model (JSmol)
  • Interactive image
Abbreviations ILTG
ChEBI
  • CHEBI:310312 N
ChEMBL
  • ChEMBL129795 N
ChemSpider
  • 553829 N
ECHA InfoCard 100.202.617
EC Number
  • 237-316-5
KEGG
  • C08650 N
  • 638278
UNII
  • B9CTI9GB8F Y
  • DTXSID2022466
  • 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 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 ?)

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.[2] It can target miR-301b/LRIG1 signaling pathways, resulting in the inhibition of melanoma growth in vitro.[3]

References edit

  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.

isoliquiritigenin, phenolic, chemical, compound, found, licorice, names, preferred, iupac, name, trihydroxychalcone, other, names, deoxychalcone4, trihydroxychalcone2, trihydroxychalcone, identifiers, number, model, jsmol, interactive, image, abbreviations, il. Isoliquiritigenin is a phenolic chemical compound found in licorice 1 Isoliquiritigenin Names Preferred IUPAC name 2 4 4 Trihydroxychalcone Other names 6 Deoxychalcone4 2 4 Trihydroxychalcone2 4 4 Trihydroxychalcone Identifiers CAS Number 961 29 5 Y 3D model JSmol Interactive image Abbreviations ILTG ChEBI CHEBI 310312 N ChEMBL ChEMBL129795 N ChemSpider 553829 N ECHA InfoCard 100 202 617 EC Number 237 316 5 KEGG C08650 N PubChem CID 638278 UNII B9CTI9GB8F Y CompTox Dashboard EPA DTXSID2022466 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 NKey DXDRHHKMWQZJHT FPYGCLRLSA N NInChI 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 C 15H 12O 4 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 Y N Infobox referencesMetabolism editThe 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 editIsoliquiritigenin 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 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 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 amp Clinical Cancer Research 37 1 184 doi 10 1186 s13046 018 0844 x PMC 6091185 PMID 30081934 Retrieved from https en wikipedia org w index php title Isoliquiritigenin amp oldid 1188142466, wikipedia, wiki, book, books, library,

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