(S)-Equol
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| CAS Number | 531-95-3 |
| PubChem (CID) | 91469 |
| ChemSpider | 82594 |
| Chemical and physical data | |
| Formula | C15H14O3 |
| Molar mass | 242.26986 g/mol |
| 3D model (Jmol) | Interactive image |
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(S)-Equol, or (S)-(–)-4',7-isoflavandiol, is the (S)-enantiomer of the naturally-occurring isoflavandiol estrogen, equol.[1] It is a non-steroidal, 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] 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
References
- 1 2 3 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.
- ↑ 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.
- ↑ 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.
- ↑ 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.
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