Equol

Publication Title: 
Biology of Reproduction

Soy isoflavonoids have well-established estrogenic properties in cell culture and rodent models, raising concerns that high isoflavonoid intake may promote development of uterine and breast cancers. To address this concern we evaluated the effects of high-dose isoflavonoid supplements on reproductive tissues in a postmenopausal primate model.

Author(s): 
Wood, Charles E.
Appt, Susan E.
Clarkson, Thomas B.
Franke, Adrian A.
Lees, Cynthia J.
Doerge, Daniel R.
Cline, J. Mark
Publication Title: 
The Journal of Nutrition

7-Hydroxy-3-(4'-hydroxyphenyl)-chroman (S-equol) is a specific end-metabolite formed in the biotransformation of the dietary soy isoflavones daidzin and daidzein by intestinal bacteria. The frequency of equol production varies among individuals and populations, and it is suggested that the efficacy of soy foods differs depending on the ability of an individual to produce equol.

Author(s): 
Setchell, Kenneth D. R.
Cole, Sidney J.
Publication Title: 
The Journal of Steroid Biochemistry and Molecular Biology

Estrogen exposure and metabolism may play an important role in the development of estrogen-sensitive cancers in postmenopausal women. In this study we investigated whether past oral contraceptive (OC) administration or current dietary isoflavonoids (IF) affected expression and/or activity of steroid hormone-metabolizing cytochrome P450 (CYP) enzymes using complementary primate and cell culture models.

Author(s): 
Scott, L. M.
Durant, P.
Leone-Kabler, S.
Wood, C. E.
Register, T. C.
Townsend, A.
Cline, J. M.
Publication Title: 
The Prostate

BACKGROUND: The effects of soy isoflavones on prostate cancer may be concentration-dependent. The impact of soy supplementation on isoflavone concentrations in prostate tissues and serum remain unclear. OBJECTIVE: To assess and compare concentrations of soy isoflavones in prostate tissue and serum among 19 men with prostate cancer who had elected to undergo radical prostatectomy. METHODS: Participants were randomized to receive either daily soy supplements (82 mg/day aglycone equivalents) or placebos for 2 weeks (14 days) prior to surgery.

Author(s): 
Gardner, Christopher D.
Oelrich, Beibei
Liu, Jenny P.
Feldman, David
Franke, Adrian A.
Brooks, James D.
Publication Title: 
The Journal of Nutrition

Pregnane X receptor (PXR) is an important component of the body's adaptive defense system responsible for the elimination of various toxic xenobiotics. PXR activation by endogenous and exogenous chemicals, including steroids, antibiotics, bile acids, and herbal compounds, results in induction of drug metabolism. We investigated the ability of the isoflavones genistein, daidzein, and the daidzein metabolite equol to activate human and mouse PXR in vitro using cell-based transient transfection studies and primary hepatocytes and in vivo in a mouse model.

Author(s): 
Li, Yilan
Ross-Viola, Jennifer S.
Shay, Neil F.
Moore, David D.
Ricketts, Marie-Louise
Publication Title: 
The Journal of Nutrition

Soy isoflavones and their metabolites, with estrogenic activity, have been considered candidates for reducing postmenopausal bone loss. In this study, we examined the effect of dietary equol, a bioactive metabolite of the soy isoflavone daidzein, on equol tissue distribution, bone parameters, and reproductive tissue activity using an adult ovariectomized (OVX) rat model. An 8-wk feeding study was conducted to compare 4 dietary treatments of equol (0, 50, 100, 200 mg/kg diet) in 6-mo-old OVX female Sprague-Dawley rats.

Author(s): 
Legette, LeeCole L.
Martin, Berdine R.
Shahnazari, Mohammad
Lee, Wang-Hee
Helferich, William G.
Qian, Junqi
Waters, David J.
Arabshahi, Alireza
Barnes, Stephen
Welch, Jo
Bostwick, David G.
Weaver, Connie M.
Publication Title: 
The American Journal of Clinical Nutrition

BACKGROUND: The nonsteroidal estrogen equol occurs as diastereoisomers, S-(-)equol and R-(+)equol, both of which have significant biological actions. S-(-)equol, the naturally occurring enantiomer produced by 20-30% of adults consuming soy foods, has selective affinity for estrogen receptor-beta, whereas both enantiomers modulate androgen action. Little is known about the pharmacokinetics of the diastereoisomers, despite current interest in developing equol as a nutraceutical or pharmaceutical agent.

Author(s): 
Setchell, Kenneth Dr
Zhao, Xueheng
Jha, Pinky
Heubi, James E.
Brown, Nadine M.
Publication Title: 
Carcinogenesis

We describe for the first time the chemopreventive effects of S-(-)equol and R-(+)equol, diastereoisomers with contrasting affinities for estrogen receptors (ERs). S-(-)equol, a ligand for ERbeta, is an intestinally derived metabolite formed by many humans and by rodents consuming diets containing soy isoflavones. Whether the well-documented chemopreventive effect of a soy diet could be explained by equol's action was unclear because neither diastereoisomers had been tested in animal models of chemoprevention.

Author(s): 
Brown, Nadine M.
Belles, Carrie A.
Lindley, Stephanie L.
Zimmer-Nechemias, Linda D.
Zhao, Xueheng
Witte, David P.
Kim, Mi-Ok
Setchell, Kenneth D. R.
Publication Title: 
The Journal of Nutrition

This summary addresses the progress and limitations of existing research on the physiologic properties of the isoflavone daidzein metabolite equol. Previous research demonstrating that physiological equol is its S-enantiomer has led to the preparation of S-(-)equol-enriched products formed by the bacterial fermentation of soy germ.

Author(s): 
Barnes, Stephen
Kim, Helen
Publication Title: 
The Journal of Nutrition

Equol, a product of intestinal metabolism of daidzein, is chemically similar to estrogen (without the lipophilic moiety) and has higher estrogen receptor-beta binding affinity than its parent precursor. In 2004, a long-term, randomized controlled trial that characterized postmenopausal women by their equol-producing status showed stronger advantages to lumbar spine bone mineral density (BMD) in equol- compared with nonequol-producers. Subsequent studies have related equol status of participants to change in bone turnover markers or BMD in response to soy isoflavone interventions.

Author(s): 
Weaver, Connie M.
Legette, LeeCole L.

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