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Glabrene

From Wikipedia, the free encyclopedia
Glabrene
Names
IUPAC name
6′′,6′′-Dimethyl-6′′H-pyrano[2′′,3′′:2′,3′]isoflav-3-ene-4′,7-diol
Systematic IUPAC name
2′,2′-Dimethyl-2H,2′H-[3,8′-bi-1-benzopyran]-5′,7-diol
Other names
2',2'-dimethyl-2H,2'H-3,8'-bichromene-5',7-diol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C20H18O4/c1-20(2)8-7-16-17(22)6-5-15(19(16)24-20)13-9-12-3-4-14(21)10-18(12)23-11-13/h3-10,21-22H,11H2,1-2H3
    Key: NGGYSPUAKQMTNP-UHFFFAOYSA-N
  • CC1(C=CC2=C(C=CC(=C2O1)C3=CC4=C(C=C(C=C4)O)OC3)O)C
Properties
C20H18O4
Molar mass322.36 g/mol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Glabrene is anisoflavonoid that is found inGlycyrrhiza glabra (licorice).[1] It hasestrogenic activity, showing estrogenic effects onbreast,vascular, andbonetissue, and hence is aphytoestrogen (IC50 forestrogen receptor binding = 1 μM).[1][2][3] It has also been found to act as atyrosinaseinhibitor (IC50 = 3.5 μM) and to inhibit the formation ofmelanin inmelanocytes, and for these reasons, has been suggested as a potential skin-lightening agent.[4]

See also

[edit]

References

[edit]
  1. ^abTamir S, Eizenberg M, Somjen D, Izrael S, Vaya J (2001). "Estrogen-like activity of glabrene and other constituents isolated from licorice root".J. Steroid Biochem. Mol. Biol.78 (3):291–8.doi:10.1016/s0960-0760(01)00093-0.PMID 11595510.S2CID 40171833.
  2. ^Somjen D, Knoll E, Vaya J, Stern N, Tamir S (2004). "Estrogen-like activity of licorice root constituents: glabridin and glabrene, in vascular tissues in vitro and in vivo".J. Steroid Biochem. Mol. Biol.91 (3):147–55.doi:10.1016/j.jsbmb.2004.04.003.PMID 15276622.S2CID 41966251.
  3. ^Somjen D, Katzburg S, Vaya J, Kaye AM, Hendel D, Posner GH, Tamir S (2004). "Estrogenic activity of glabridin and glabrene from licorice roots on human osteoblasts and prepubertal rat skeletal tissues".J. Steroid Biochem. Mol. Biol.91 (4–5):241–6.doi:10.1016/j.jsbmb.2004.04.008.PMID 15336701.S2CID 16238533.
  4. ^Nerya O, Vaya J, Musa R, Izrael S, Ben-Arie R, Tamir S (2003). "Glabrene and isoliquiritigenin as tyrosinase inhibitors from licorice roots".J. Agric. Food Chem.51 (5):1201–7.doi:10.1021/jf020935u.PMID 12590456.
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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