Liquiritigenin
Liquiritigenin
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| Names |
| IUPAC name
(2S)-7-Hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one |
| Other names
4',7-Dihydroxyflavanone |
| Identifiers |
| |
578-86-9  Y |
| 3D model (Jmol) |
Interactive image |
| ChEBI |
CHEBI:28777 Y |
| ChEMBL |
ChEMBL252642 |
| ChemSpider |
102790 |
| PubChem |
114829 |
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
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O=C2c3c(O[C@H](c1ccc(O)cc1)C2)cc(O)cc3
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| Properties |
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C15H12O4 |
| Molar mass |
256.26 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
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| Infobox references |
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Liquiritigenin is a flavanone that was isolated from Glycyrrhiza uralensis, and is found in a variety of plants, 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 2 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
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| ER | Agonists |
- Steroidal: 3α-Androstanediol
- 3β-Androstanediol
- 3α-Hydroxytibolone
- 3β-Hydroxytibolone
- 4-Androstenediol
- 4-Androstenedione
- 4-Hydroxyestradiol
- 4-Hydroxyestrone
- 5-Androstenediol
- 7-Oxo-DHEA
- 7α-Hydroxy-DHEA
- 7β-Hydroxyepiandrosterone
- 8,9-Dehydroestradiol
- 8,9-Dehydroestrone
- 8β-VE2
- 16α-Hydroxy-DHEA
- 16α-Hydroxyestrone
- 16α-Iodo-E2
- 16α-LE2
- 16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)
- 17α-Dihydroequilenin
- 17α-Dihydroequilin
- 17α-Epiestriol (16α-hydroxy-17α-estradiol)
- 17β-Dihydroequilenin
- 17β-Dihydroequilin
- Abiraterone
- Abiraterone acetate
- 17α-Estradiol (alfatradiol)
- Alestramustine
- Almestrone
- Anabolic steroids (e.g., testosterone and esters, methyltestosterone, metandienone (methandrostenolone), nandrolone and esters, many others; via estrogenic metabolites)
- Atrimustine
- Bolandiol
- Bolandiol dipropionate
- Butolame
- Clomestrone
- Cloxestradiol
- DHEA
- DHEA-S
- Digitoxin (digitalis)
- Diosgenin
- Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)
- Epimestrol
- Equilenin
- Equilin
- Estetrol
- Estradiol
- Estramustine
- Estramustine phosphate
- Estrapronicate
- Estrazinol
- Estriol
- Estrofurate
- Estromustine
- Estrone
- Etamestrol (eptamestrol)
- Ethinyl estradiol
- Ethinyl estriol
- Etynodiol diacetate
- Guggulsterone
- Hexolame
- Hydroxyestrone diacetate
- Mestranol
- Methylestradiol
- Moxestrol
- Mytatrienediol
- Nilestriol
- Noretynodrel
- Orestrate
- Pentolame
- Phytosterols (e.g., β-sitosterol, campesterol, stigmasterol)
- Polyestradiol phosphate
- Prodiame
- Prolame
- Promestriene
- Quinestradol
- Quinestrol
- Non-steroidal: (R,R)-THC
- (S,S)-THC
- 1-Keto-1,2,3,4-tetrahydrophenanthrene
- 2,8-DHHHC
- Allenoic acid
- Alternariol
- Anethole
- Anol
- Benzestrol
- Bifluranol
- Biochanin A
- Bisdehydrodoisynolic acid
- Carbestrol
- Chalconoids (e.g., isoliquiritigenin, phloretin, phlorizin (phloridzin), wedelolactone)
- Coumestans (e.g., coumestrol, psoralidin)
- Deoxymiroestrol
- Dianethole
- Dianol
- Diarylpropionitrile
- Dieldrin
- Dienestrol
- Diethylstilbestrol
- Dimestrol (dianisylhexene)
- Dimethylallenolic acid
- Doisynoestrol (fenocycline)
- Doisynolic acid
- Efavirenz
- Endosulfan
- ERB-196 (WAY-202196)
- Estrobin (DBE)
- Fenarimol
- Fenestrel
- FERb 033
- Flavonoids (incl. 7,8-DHF, 8-prenylnaringenin, apigenin, baicalein, baicalin, calycosin, catechin, daidzein, daidzin, ECG, EGCG, epicatechin, equol, formononetin, glabrene, glabridin, genistein, genistin, glycitein, kaempferol, liquiritigenin, mirificin, myricetin, naringenin, pinocembrin, prunetin, puerarin, quercetin, tectoridin, tectorigenin)
- Fosfestrol (diethylstilbestrol diphosphate)
- Furostilbestrol (diethylstilbestrol difuroate)
- GTx-758
- Hexestrol
- ICI-85966 (Stilbostat)
- Lavender oil
- Lignans (e.g., enterodiol, enterolactone)
- Mestilbol
- Metalloestrogens (e.g., cadmium)
- Methallenestril
- Methestrol
- Methestrol dipropionate
- Methiocarb
- Methoxychlor
- Miroestrol
- Nyasol (cis-hinokiresinol)
- Paroxypropione
- Pentafluranol
- Phenestrol
- Photoanethole
- Prinaberel (ERB-041, WAY-202041)
- Propylpyrazoletriol
- Resorcylic acid lactones (e.g., zearalanone, zearalenol, zearalenone, zeranol (α-zearalanol), taleranol (teranol, β-zearalanol))
- Quadrosilan
- SC-4289
- SKF-82,958
- Stilbenoids (e.g., resveratrol)
- Synthetic xenoestrogens (e.g., alkylphenols, bisphenols (e.g., BPA, BPF, BPS), DDT, parabens, PBBs, PHBA, phthalates, PCBs)
- Terfluranol
- WAY-166818
- WAY-200070
- Triphenylchlorethylene
- Triphenylmethylethylene
- WAY-214156
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See also: Androgenics • Glucocorticoidics • Mineralocorticoidics • Progestogenics • Steroid hormone metabolism modulators |