Liquiritigenin

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 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).

Liquiritigenin is a flavanone that was isolated from Glycyrrhiza uralensis, and is found in a variety of plants of the Glycyrrhiza genus, including Glycyrrhiza glabra (licorice).[1] It is an estrogenic compound which acts as a selective agonist of the ERβ subtype of the estrogen receptor (ER),[2] though it is also reported to act as an ERα partial agonist at sufficient concentrations.[3] It also has a choleretic effect.[1]

Liquiritigenin,NADPH:oxygen oxidoreductase (hydroxylating, aryl migration) is an enzyme that uses liquiritigenin, O2, NADPH and H+ to produce 2,7,4'-trihydroxyisoflavanone, H2O, and NADP+.

See also

References

  1. ^ a b Kim, 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 from the original on 2016-02-22, retrieved 2016-01-01


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