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Glabrene

Glabrene is an isoflavonoid that is found in Glycyrrhiza glabra (licorice).[1] It has estrogenic activity, showing estrogenic effects on breast, vascular, and bone tissue, and hence is a phytoestrogen (IC50 for estrogen receptor binding = 1 μM).[1][2][3] It has also been found to act as a tyrosinase inhibitor (IC50 = 3.5 μM) and to inhibit the formation of melanin in melanocytes, and for these reasons, has been suggested as a potential skin-lightening agent.[4]

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
  • 60008-03-9
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL462722
ChemSpider
  • 421858
  • 480774
UNII
  • C6Y321Q75O
  • DTXSID90208715
  • 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 mass 322.36 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

See also edit

References edit

  1. ^ a b Tamir 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.


glabrene, isoflavonoid, that, found, glycyrrhiza, glabra, licorice, estrogenic, activity, showing, estrogenic, effects, breast, vascular, bone, tissue, hence, phytoestrogen, ic50, estrogen, receptor, binding, also, been, found, tyrosinase, inhibitor, ic50, inh. Glabrene is an isoflavonoid that is found in Glycyrrhiza glabra licorice 1 It has estrogenic activity showing estrogenic effects on breast vascular and bone tissue and hence is a phytoestrogen IC50 for estrogen receptor binding 1 mM 1 2 3 It has also been found to act as a tyrosinase inhibitor IC50 3 5 mM and to inhibit the formation of melanin in melanocytes and for these reasons has been suggested as a potential skin lightening agent 4 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 CAS Number 60008 03 9 3D model JSmol Interactive image ChEMBL ChEMBL462722 ChemSpider 421858 PubChem CID 480774 UNII C6Y321Q75O CompTox Dashboard EPA DTXSID90208715 InChI 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 2H3Key NGGYSPUAKQMTNP UHFFFAOYSA N SMILES CC1 C CC2 C C CC C2O1 C3 CC4 C C C C C4 O OC3 O C Properties Chemical formula C 20H 18O 4 Molar mass 322 36 g mol Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox referencesSee also editGlabridin Isoliquiritigenin LiquiritigeninReferences edit a b Tamir 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 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 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 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 nbsp This article about an organic compound is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Glabrene amp oldid 1152827644, wikipedia, wiki, book, books, library,

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