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Liquiritigenin

From Wikipedia, the free encyclopedia
Liquiritigenin
Names
IUPAC name
(2S)-4′,7-Dihydroxyflavan-4-one
Systematic IUPAC name
(2S)-7-Hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
  • InChI=1S/C15H12O4/c16-10-3-1-9(2-4-10)14-8-13(18)12-6-5-11(17)7-15(12)19-14/h1-7,14,16-17H,8H2/t14-/m0/s1
    Key: FURUXTVZLHCCNA-AWEZNQCLSA-N
  • InChI=1/C15H12O4/c16-10-3-1-9(2-4-10)14-8-13(18)12-6-5-11(17)7-15(12)19-14/h1-7,14,16-17H,8H2/t14-/m0/s1
    Key: FURUXTVZLHCCNA-AWEZNQCLBC
  • O=C2c3c(O[C@H](c1ccc(O)cc1)C2)cc(O)cc3
Properties
C15H12O4
Molar mass256.257 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Liquiritigenin is aflavanone that was isolated fromGlycyrrhiza uralensis, and is found in a variety of plants of theGlycyrrhiza genus, includingGlycyrrhiza glabra (licorice).[1] It is anestrogenic compound which acts as a selectiveagonist of theERβ subtype of theestrogen receptor (ER),[2] though it is also reported to act as anERαpartial agonist at sufficient concentrations.[3] It also has acholeretic effect.[1]

Liquiritigenin,NADPH:oxygen oxidoreductase (hydroxylating, aryl migration) is anenzyme that uses liquiritigenin, O2, NADPH and H+ to produce2,7,4'-trihydroxyisoflavanone, H2O, and NADP+.

See also

[edit]

References

[edit]
  1. ^abKim, YW; Kang, HE; Lee, MG; Hwang, SJ; Kim, SC; Lee, CH; Kim, SG (2009)."Liquiritigenin, a flavonoid aglycone from licorice, has a choleretic effect and the ability to induce hepatic transporters and phase-II enzymes".American Journal of Physiology. Gastrointestinal and Liver Physiology.296 (2): G372–81.doi:10.1152/ajpgi.90524.2008.PMID 19074639.
  2. ^Mersereau, Jennifer E.; Levy, Nitzan; Staub, Richard E.; Baggett, Scott; Zogric, Tetjana; Chow, Sylvia; Ricke, William A.; Tagliaferri, Mary; et al. (2008)."Liquiritigenin is a plant-derived highly selective estrogen receptor β agonist".Molecular and Cellular Endocrinology.283 (1–2):49–57.doi:10.1016/j.mce.2007.11.020.PMC 2277338.PMID 18177995.
  3. ^Green, Sarah E (2015),In Vitro Comparison of Estrogenic Activities of Popular Women's Health Botanicals, archived fromthe original on 2016-02-22, retrieved2016-01-01
Flavanones and theirglycosides
Flavanones
O-methylated flavanones
C-methylated flavanones
Glycosides
Acetylated
Acetylated glycosides
Phytoestrogens
Flavanones
Flavones
Prenylflavonoids
Isoflavones
Isoflavanes
Dihydrochalcones
Isoflavenes
Coumestans
Lignans
Flavonolignans
Flavonols
Others
Mycoestrogens
Derivatives
Synthetic
Metalloestrogens
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown


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