Equol

Equol
IUPAC name

(3S)-3-(4-Hydroxyphenyl)-7-chromanol
Other names

4',7-Isoflavandiol
Identifiers
CAS number 531-95-3 Y
PubChem 91469
ChemSpider 82594 Y
KEGG C14131 Y
ChEMBL CHEMBL198877 Y
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C15H14O3
Molar mass 242.27 g/mol
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 is a compound that can exist in two forms, known as the diastereoisomers S-equol and R-equol,[10] which means the compounds mirror each other, just as a person's left hand mirrors the right. S-equol preferentially activates estrogen receptor type β.[2][11]

See also

References

  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. http://aem.asm.org/cgi/pmidlookup?view=long&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. PMID 16351761. http://journals.cambridge.org/abstract_S0007114505002618. 
  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. PMID 15067102. http://jjco.oxfordjournals.org/cgi/content/full/34/2/86. 
  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. http://journals.lww.com/menopausejournal/Abstract/2007/14050/Possible_role_of_equol_status_in_the_effects_of.14.aspx. 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. http://journals.lww.com/menopausejournal/Abstract/2011/05000/Natural_S_equol_decreases_bone_resorption_in.19.aspx. 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. http://cebp.aacrjournals.org/cgi/content/full/13/7/1156. 
  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. http://jn.nutrition.org/content/140/7/1386S.long. 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. http://www.biolreprod.org/cgi/content/full/70/4/1188. 
  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. PMID 20519412. http://jn.nutrition.org/content/140/7/1355S.long. 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. http://toxsci.oxfordjournals.org/cgi/content/full/80/1/14. 
Isoflavanes
Isoflavanes:
Equol | Laxiflorane | Lonchocarpane