Equol

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Equol
Equol structure.png
Identifiers
CAS number 531-95-3 YesY
PubChem 91469
ChemSpider 82594 YesY
KEGG C14131 YesY
ChEMBL CHEMBL198877 YesY
Jmol-3D images Image 1
Image 2
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 (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox 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] bone health [5][6] skin health and physiological changes during menopause,[7] including reducing severity and frequency of hot flashes and stiffness in the neck and shoulder.[8] Other benefits may be realized in treating male pattern baldness, acne, and other problems because it functions as a DHT blocker.[9] Equol can exist in two enantiomeric forms, (S)-equol and (R)-equol.[10] S-equol preferentially activates estrogen receptor type β.[2][11]

See also[edit]

References[edit]

  1. ^ 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).
  2. ^ a b Wang XL, Hur HG, Lee JH, Kim KT, Kim SI (January 2005). "Enantioselective synthesis of S-equol from dihydrodaidzein by a newly isolated anaerobic human intestinal bacterium". Appl. Environ. Microbiol. 71 (1): 214–9. doi:10.1128/AEM.71.1.214-219.2005. PMC 544246. PMID 15640190. 
  3. ^ Frankenfeld CL, Atkinson C, Thomas WK, et al. (December 2005). "High concordance of daidzein-metabolizing phenotypes in individuals measured 1 to 3 years apart". Br. J. Nutr. 94 (6): 873–6. doi:10.1079/bjn20051565. PMID 16351761. 
  4. ^ Akaza H, Miyanaga N, Takashima N, et al. (February 2004). "Comparisons of percent equol producers between prostate cancer patients and controls: case-controlled studies of isoflavones in Japanese, Korean and American residents". Jpn. J. Clin. Oncol. 34 (2): 86–9. doi:10.1093/jjco/hyh015. PMID 15067102. 
  5. ^ Wu, Jian; Oka, Jun; Ezaki, Junko; Ohtomo, Takuya; Ueno, Tomomi; Uchiyama, Shigeto; Toda, Toshiya; Uehara, Mariko; Ishimi, Yoshiko (September–October 2007). "Possible role of equol status in the effects of isoflavone on bone and fat mass in postmenopausal Japanese women: a double-blind, randomized, controlled trial". MENOPAUSE 14 (5): 866–874. doi:10.1097/gme.0b013e3180305299. PMID 17464237. Retrieved 13 December 2011. 
  6. ^ Tousen, Yuko; Ezaki, Junko; Fujii, Yasuhiro; Ueno, Tomomi; Nishimuta, Mamoru; Ishimi, Yoshiko (May 2011). "Natural S-equol decreases bone resorption in postmenopausal, non-equol-producing Japanese women: a pilot randomized, placebo-controlled trial". MENOPAUSE 18 (5): 563–574. doi:10.1097/gme.0b013e3181f85aa7. PMID 21252728. Retrieved 13 December 2011. 
  7. ^ Frankenfeld CL, McTiernan A, Aiello EJ, et al. (July 2004). "Mammographic density in relation to daidzein-metabolizing phenotypes in overweight, postmenopausal women". Cancer Epidemiol. Biomarkers Prev. 13 (7): 1156–62. PMID 15247126. 
  8. ^ Aso, Takeshi (May 19, 2010). "Equol Improves Menopausal Symptoms in Japanese Women". J Nutr 140 (7): 1386S–9S. doi:10.3945/jn.109.118307. PMID 20484552. Retrieved 13 December 2011. 
  9. ^ Lund TD, Munson DJ, Haldy ME, Setchell KD, Lephart ED, Handa RJ (April 2004). "Equol is a novel anti-androgen that inhibits prostate growth and hormone feedback". Biol. Reprod. 70 (4): 1188–95. doi:10.1095/biolreprod.103.023713. PMID 14681200. 
  10. ^ Setchell, Kenneth D. R.; Carlo Clerici (June 2, 2010). "Equol: history, chemistry, and formation". J Nutr 140 (7): 1355S–62S. doi:10.3945/jn.109.119776. PMC 2884333. PMID 20519412. Retrieved 13 December 2011. 
  11. ^ Mueller SO, Simon S, Chae K, Metzler M, Korach KS (July 2004). "Phytoestrogens and their human metabolites show distinct agonistic and antagonistic properties on estrogen receptor {α} (ER{α}) and ERβ in human cells". Toxicol. Sci. 80 (1): 14–25. doi:10.1093/toxsci/kfh147. PMID 15084758. 
 12.^Equol - Toxical Assessment