Liquiritigenin
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| IUPAC name
(2S)-4′,7-Dihydroxyflavan-4-one
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| Systematic IUPAC name
(2S)-7-Hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one | |
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| 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).
Infobox references
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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+.
Liquiritigenin is known for its estrogenic, anti-inflammatory, and anti-cancer properties. It acts as a selective estrogen receptor β (ERβ) agonist and has shown potential in treating menopausal symptoms and certain cancers.[4][5][6]
See also
- Menerba
- Prinaberel (ERB-041)
- Diarylpropionitrile (DPN)
- WAY-200070
- PHTPP
- (R,R)-Tetrahydrochrysene ((R,R)-THC)
- Propylpyrazoletriol (PPT)
- Methylpiperidinopyrazole (MPP)
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
- ^ Mersereau, Jennifer E.; Levy, Nitzan; Staub, Richard E.; Baggett, Scott; Zogovic, Tatjana; Chow, Sylvia; Ricke, William A.; Tagliaferri, Mary; Cohen, Isaac; Bjeldanes, Leonard F.; Leitman, Dale C. (2008-02-13). "Liquiritigenin is a plant-derived highly selective estrogen receptor beta agonist". Molecular and Cellular Endocrinology. 283 (1–2): 49–57. doi:10.1016/j.mce.2007.11.020. ISSN 0303-7207. PMC 2277338. PMID 18177995.
- ^ Babu, Vineet; Kapkoti, Deepak Singh; Binwal, Monika; Bhakuni, Rajendra S.; Shanker, Karuna; Singh, Manju; Tandon, Sudeep; Mugale, Madhav N.; Kumar, Narendra; Bawankule, Dnyaneshwar U. (2023-04-01). "Liquiritigenin, isoliquiritigenin rich extract of glycyrrhiza glabra roots attenuates inflammation in macrophages and collagen-induced arthritis in rats". Inflammopharmacology. 31 (2): 983–996. doi:10.1007/s10787-023-01152-w. ISSN 1568-5608. PMID 36947299.
- ^ Wang, Hao; Shan, Hu; Lü, Haitao (2020). "Preparative separation of liquiritigenin and glycyrrhetic acid from Glycyrrhiza uralensis Fisch using hydrolytic extraction combined with high-speed countercurrent chromatography". Biomedical Chromatography. 34 (4): e4788. doi:10.1002/bmc.4788. ISSN 1099-0801. PMID 31899545.