Equol
From Wikipedia, the free encyclopedia
| Equol | |
|---|---|
 |
|
| IUPAC name | (3S)-3-(4-Hydroxyphenyl)-7-chromanol |
| Other names | 4',7-Isoflavandiol |
| Identifiers | |
| CAS number | [531-95-3] |
| PubChem | |
| SMILES | C1C(COC2=C1C=CC(=C2)O)C3=CC=C(C=C3)O |
| Properties | |
| Molecular formula | C15H14O3 |
| Molar mass | 242.27 g/mol |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
|
Equol (4',7-isoflavandiol) is an isoflavandiol[1] metabolized from daidzein, a type of isoflavone, by bacterial flora in the intestines.[2] While endogenous estrogenic hormones such as estradiol are steroids, equol is a nonsteroidal estrogen. However, only about 30-50% of people have intestinal bacteria that make equol.[3] Equol may have beneficial effects on the incidence of prostate cancer[4] and physiological changes after menopause.[5] Other benefits may be realized in treating male pattern baldness, acne, and other problems because it functions as a DHT blocker.[6] S-Equol preferentially activates estrogen receptor type β.[2][7]
[edit] See also
[edit] References
- ^ The structures of 7,4’-dihydroxy-isoflavan and its precursors is shown in Structural Elucidation of Hydroxylated Metabolites of the Isoflavan Equol by GC/MS and HPLC/MS by Corinna E. Rüfer, Hansruedi Glatt, and Sabine E. Kulling in Drug Metabolism and Disposition (2005, electronic publication).
- ^ a b Enantioselective Synthesis of S-Equol from Dihydrodaidzein by a Newly Isolated Anaerobic Human Intestinal Bacterium by Xiu-Ling Wang, Hor-Gil Hur, Je Hyeon Lee, Ki Tae Kim and Su-Il Kim in "Applied and Environmental Microbiology" (2005) Volume 71 pages 214-219.
- ^ "High concordance of daidzein-metabolizing phenotypes in individuals measured 1 to 3 years apart" by C. L. Frankenfeld, C. Atkinson, W. K. Thomas, A. Gonzalez, T. Jokela, K. Wahala, S. M. Schwartz, S. S. Li and J. W. Lampe (2005) The British journal of nutrition volume 94, pages 873-876. Entrez PubMed 16351761
- ^ Comparisons of percent equol producers between prostate cancer patients and controls: case-controlled studies of isoflavones in Japanese, Korean and American residents by H. Akaza, N. Miyanaga, N. Takashima, S. Naito, Y. Hirao, T. Tsukamoto, T. Fujioka, M. Mori, W. J. Kim, J. M. Song and A. J. Pantuck (2004) Japanese Journal of Clinical Oncology Volume 34, pages 86-39.
- ^ Mammographic density in relation to daidzein-metabolizing phenotypes in overweight, postmenopausal women by C. L. Frankenfeld, A. McTiernan, E. J. Aiello, W. k. Thomas, K. LaCroix, J. Schramm, S. M. Schwartz, V. L. Holt and J. W. Lampe in Cancer Epidemiology, Biomarkers and Prevention (2004) Volume 13 pages 1156-1162.
- ^ Equol is a novel anti-androgen that inhibits prostate growth and hormone feedback by T. D. Lund, D. J. Munson, M. E. Haldy, K. D. Setchell, E. D. Lephart and R. J. Handa (2004) Biology of Reproduction Volume 70 pages 1188-1195.
- ^ Phytoestrogens and Their Human Metabolites Show Distinct Agonistic and Antagonistic Properties on Estrogen Receptor {α} (ER{α}) and ERβ in Human Cells by Stefan O. Mueller, Stephanie Simon, Kun Chae, Manfred Metzler and Kenneth S. Korach in Toxicological Sciences (2004) Volume 80 pages 14-25.
 |
This biochemistry article is a stub. You can help Wikipedia by expanding it. |
