(S)-Equol

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(S)-Equol
Equol structure.png
Identifiers
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
Formula C15H14O3
Molar mass 242.26986 g/mol
3D model (JSmol)

(S)-Equol, or (S)-(–)-4',7-isoflavandiol, is the (S)-enantiomer of the naturally occurring isoflavandiol estrogen, equol.[1] It is a nonsteroidal, selective agonist of ERβ (Ki = 16 nM), with 13-fold selectivity for ERβ over ERα.[1] Relative to (S)-equol, (R)-equol is less potent and, in contrast, binds to ERα (Ki = 50 nM) with 3.5-fold selectivity over ERβ.[1] Under the code name AUS-131, (S)-equol is under development for the treatment of menopausal symptoms such as hot flashes and benign prostatic hyperplasia.[2][3][1] Human intestinal bacteria metabolize the soy isoflavone daidzein into (S)-equol, and it has been determined that (S)-equol is exclusively produced.[4]

See also[edit]

References[edit]

  1. ^ a b c Muthyala, Rajeev S; Ju, Young H; Sheng, Shubin; Williams, Lee D; Doerge, Daniel R; Katzenellenbogen, Benita S; Helferich, William G; Katzenellenbogen, John A (2004). "Equol, a natural estrogenic metabolite from soy isoflavones". Bioorganic & Medicinal Chemistry. 12 (6): 1559–1567. doi:10.1016/j.bmc.2003.11.035. ISSN 0968-0896. 
  2. ^ Nilsson, Stefan; Koehler, Konrad F.; Gustafsson, Jan-Åke (2011). "Development of subtype-selective oestrogen receptor-based therapeutics". Nature Reviews Drug Discovery. 10 (10): 778–792. doi:10.1038/nrd3551. ISSN 1474-1776. PMID 21921919. 
  3. ^ Jackson, Richard L.; Greiwe, Jeffrey S.; Desai, Pankaj B.; Schwen, Richard J. (2010). "Single-dose and steady-state pharmacokinetic studies of S-equol, a potent nonhormonal, estrogen receptor β-agonist being developed for the treatment of menopausal symptoms". Menopause: 1. doi:10.1097/gme.0b013e3181e9779c. ISSN 1072-3714. 
  4. ^ Setchell KD, Clerici C, Lephart ED, Cole SJ, Heenan C, Castellani D, Wolfe BE, Nechemias-Zimmer L, Brown NM, Lund TD, Handa RJ, Heubi JE (2005). "S-equol, a potent ligand for estrogen receptor beta, is the exclusive enantiomeric form of the soy isoflavone metabolite produced by human intestinal bacterial flora". Am. J. Clin. Nutr. 81 (5): 1072–9. PMID 15883431.