Equol: history, chemistry, and formation

J Nutr. 2010 Jul;140(7):1355S-62S. doi: 10.3945/jn.109.119776. Epub 2010 Jun 2.

Abstract

Equol, first isolated from equine urine in 1932 and identified 50 years later in human urine as a metabolite of the soy isoflavones, daidzin and daidzein, is produced by intestinal bacteria in some, but not all, adults. This observation led to the term equol-producers to define those adults that could make equol in response to consuming soy isoflavones and the hypothesis that the health benefits of soy-based diets may be greater in equol-producers than in equol nonproducers. By virtue of a chiral center, equol occurs as a diastereoisomer and intestinal bacteria are enantiospecific in synthesizing exclusively the S-(-)equol enantiomer, an enantiomer that has selective affinity for the estrogen receptor-beta. Both enantiomers are of interest from a clinical and pharmacological perspective and are currently being developed as nutraceutical and pharmacological agents. The wide range of biological activities these enantiomers possess warrants their investigation for the treatment of a number of hormone-related conditions involving estrogen-dependent and androgen-related conditions. The following review describes the history, chemistry, and factors governing the intestinal bacterial formation of equol.

Publication types

  • Research Support, N.I.H., Extramural
  • Review

MeSH terms

  • Animals
  • Bacteria / metabolism
  • Biotransformation
  • Equol
  • Humans
  • Intestines / microbiology
  • Isoflavones / chemistry*
  • Isoflavones / pharmacokinetics
  • Stereoisomerism

Substances

  • 4',7-dihydroxy-3,4-dihydroisoflavone
  • Isoflavones
  • Equol