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
CAS Number	578-86-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28777 ;
ChEMBL	ChEMBL252642;
ChemSpider	102790;
KEGG	C09762;
PubChem CID	114829;
UNII	T194LKP9W6 ;
CompTox Dashboard (EPA)	DTXSID90206493 ;
	InChI 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;
	SMILES O=C2c3c(O(c1ccc(O)cc1)C2)cc(O)cc3;
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 , 100 kPa). Infobox references

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⁺.

References

^ ^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.
^ 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.
^ 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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[Kim-1] 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.

[Green2015-3] 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

[1]

[2]

[3]

v t e Flavanones and their glycosides
Flavanones	Butin Eriodictyol Naringenin Pinocembrin
O-methylated flavanones	Alpinetin Hesperetin Homoeriodictyol Isosakuranetin Pinostrobin (Pinocembrin-7-methylether) Sakuranetin Sterubin
C-methylated flavanones	Poriol
Glycosides	Eriocitrin Neoeriocitrin Hesperidin Liquiritin Naringin (Narigenin 7-O-neohesperidoside) Narirutin (Naringenin 7-O-rutinoside) Poncirin Prunin (Naringenin-7-O-glucoside) Sakuranin
Acetylated	8-Prenylnaringenin Isoxanthohumol Sophoraflavanone G
Acetylated glycosides	Nirurin

See also

References