Equol: history, chemistry, and formation.
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.
Pathology and Laboratory Medicine, Department of Pediatrics, Cincinnati Children's Hospital Medical Center, Cincinnati, OH 45229, USA. kenneth.setchell@cchmc.org
Kenneth D R
KD
Setchell
Carlo
C
Clerici
D000818:Animals; D001419:Bacteria / Q000378:metabolism; D001711:Biotransformation; D060754:Equol; D006801:Humans; D007422:Intestines / Q000382:microbiology; D007529:Isoflavones / Q000737:chemistry* / Q000493:pharmacokinetics; D013237:Stereoisomerism
C007610:4',7-dihydroxy-3,4-dihydroisoflavone; D007529:Isoflavones; D060754:Equol