Pharmacokinetics of equol, a soy isoflavone metabolite, changes with the form of equol (Dietary versus Intestinal Production) in ovariectomized rats

Journal of Agricultural and Food Chemistry

Volumn 62, Issue 6, 2014, Pages 1294-1300

  Legette, Leecole L ^a   Prasain, Jeevan ^b,c   King, Jennifer ^b   Arabshahi, Ali ^b,c   Barnes, Stephen ^b,c   Weaver, Connie M ^a  

^a PURDUE UNIVERSITY   (United States)

^b University of Alabama at Birmingham   (United States)

^c UNIVERSITY OF ALABAMA AT BIRMINGHAM   (United States)

Author keywords

equol; equol conjugates; ovariectomized rats; pharmacokinetics; soy isoflavones

Indexed keywords

DAIDZEIN; EQUOL; ISOFLAVONE DERIVATIVE;

ANIMAL; ARTICLE; BACTERIUM; BIOSYNTHESIS; BLOOD; COMPARATIVE STUDY; DIET; FEMALE; INTESTINE; METABOLISM; MICROBIOLOGY; OVARIECTOMY; RAT; SPRAGUE DAWLEY RAT;

ANIMALS; BACTERIA; DIET; EQUOL; FEMALE; INTESTINES; ISOFLAVONES; OVARIECTOMY; RATS; RATS, SPRAGUE-DAWLEY;

BIOMOLECULES; METABOLITES; PHARMACOKINETICS; RATS;

EQUOL; EQUOL CONJUGATES; GLUCURONIDE CONJUGATES; INTESTINAL BACTERIA; ORAL ADMINISTRATION; OVARIECTOMIZED RATS; PLASMA CONCENTRATION; SOY ISOFLAVONES;

FLAVONOIDS;

RATTUS;

EID: 84894161954     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf400097m     Document Type: Article

References (38)

1. Tezval, M.; Sehmisch, S.; Seidlova-Wuttke, D.; Rack, T.; Kolios, L.; Wuttke, W.; Stuermer, K. M.; Stuermer, E. K. Changes in the histomorphometric and biomechanical properties of the proximal femur of ovariectomized rat after treatment with the phytoestrogens genistein and equol Planta Med. 2010, 76 (3) 235-240
2. Rachon, D.; Seidlova-Wuttke, D.; Vortherms, T.; Wuttke, W. Effects of dietary equol administration on ovariectomy induced bone loss in Sprague-Dawley rats Maturitas 2007, 58 (3) 308-315
3. Kolios, L.; Sehmisch, S.; Daub, F.; Rack, T.; Tezval, M.; Stuermer, K. M.; Stuermer, E. K. Equol but not genistein improves early metaphyseal fracture healing in osteoporotic rats Planta Med. 2009, 75 (5) 459-465
4. Setchell, K. D.; Brown, N. M.; Lydeking-Olsen, E. The clinical importance of the metabolite equol-a clue to the effectiveness of soy and its isoflavones J. Nutr. 2002, 132 (12) 3577-3584
5. Setchell, K. D.; Lydeking-Olsen, E. Dietary phytoestrogens and their effect on bone: evidence from in vitro and in vivo, human observational, and dietary intervention studies Am. J. Clin. Nutr. 2003, 78 (3 Suppl.) 593S-609S
6. Xu, X.; Harris, K. S.; Wang, H. J.; Murphy, P. A.; Hendrich, S. Bioavailability of soybean isoflavones depends upon gut microflora in women J. Nutr. 1995, 125 (9) 2307-2315
7. Adlercreutz, H.; van der Wildt, J.; Kinzel, J.; Attalla, H.; Wahala, K.; Makela, T.; Hase, T.; Fotsis, T. Lignan and isoflavonoid conjugates in human urine J. Steroid Biochem. Mol. Biol. 1995, 52 (1) 97-103
8. Shelnutt, S. R.; Cimino, C. O.; Wiggins, P. A.; Badger, T. M. Urinary pharmacokinetics of the glucuronide and sulfate conjugates of genistein and daidzein Cancer Epidemiol. Biomarkers Prev. 2000, 9 (4) 413-419
9. Thomas, B. F.; Zeisel, S. H.; Busby, M. G.; Hill, J. M.; Mitchell, R. A.; Scheffler, N. M.; Brown, S. S.; Bloeden, L. T.; Dix, K. J.; Jeffcoat, A. R. Quantitative analysis of the principle soy isoflavones genistein, daidzein and glycitein, and their primary conjugated metabolites in human plasma and urine using reversed-phase high-performance liquid chromatography with ultraviolet detection J. Chromatogr., B: Biomed. Sci. Appl. 2001, 760 (2) 191-205
10. Wong, C. K.; Keung, W. M. Daidzein sulfoconjugates are potent inhibitors of sterol sulfatase (EC 3.1.6.2) Biochem. Biophys. Res. Commun. 1997, 233 (3) 579-583
11. Zhang, Y.; Song, T. T.; Cunnick, J. E.; Murphy, P. A.; Hendrich, S. Daidzein and genistein glucuronides in vitro are weakly estrogenic and activate human natural killer cells at nutritionally relevant concentrations J. Nutr. 1999, 129 (2) 399-405
12. Schwen, R. J.; Nguyen, L.; Jackson, R. L. Elucidation of the metabolic pathway of S-equol in rat, monkey and man Food Chem. Toxicol. 2012, 50 (6) 2074-2083
13. Fang, N.; Yu, S.; Badger, T. M. Characterization of isoflavones and their conjugates in female rat urine using LC/MS/MS J. Agric. Food Chem. 2002, 50 (9) 2700-2707
14. Holder, C. L.; Churchwell, M. I.; Doerge, D. R. Quantification of soy isoflavones, genistein and daidzein, and conjugates in rat blood using LC/ES-MS J. Agric. Food Chem. 1999, 47 (9) 3764-3770
15. King, R. A. Daidzein conjugates are more bioavailable than genistein conjugates in rats Am. J. Clin. Nutr. 1998, 68 (6 Suppl.) 1496S-1499S
16. King, R. A.; Broadbent, J. L.; Head, R. J. Absorption and excretion of the soy isoflavone genistein in rats J. Nutr. 1996, 126 (1) 176-182
17. Sepehr, E.; Cooke, G. M.; Robertson, P.; Gilani, G. S. Effect of glycosidation of isoflavones on their bioavailability and pharmacokinetics in aged male rats Mol. Nutr. Food Res. 2009, 53 (Suppl. 1) S16-S26
18. Sfakianos, J.; Coward, L.; Kirk, M.; Barnes, S. Intestinal uptake and biliary excretion of the isoflavone genistein in rats J. Nutr. 1997, 127 (7) 1260-1268
19. Soucy, N. V.; Parkinson, H. D.; Sochaski, M. A.; Borghoff, S. J. Kinetics of genistein and its conjugated metabolites in pregnant Sprague-Dawley rats following single and repeated genistein administration Toxicol. Sci. 2006, 90 (1) 230-240
20. Anupongsanugool, E.; Teekachunhatean, S.; Rojanasthien, N.; Pongsatha, S.; Sangdee, C. Pharmacokinetics of isoflavones, daidzein and genistein, after ingestion of soy beverage compared with soy extract capsules in postmenopausal Thai women BMC Clin. Pharmacol. 2005, 5, 2
21. Doerge, D. R.; Chang, H. C.; Churchwell, M. I.; Holder, C. L. Analysis of soy isoflavone conjugation in vitro and in human blood using liquid chromatography-mass spectrometry Drug Metab. Dispos. 2000, 28 (3) 298-307
22. Hosoda, K.; Furuta, T.; Yokokawa, A.; Ogura, K.; Hiratsuka, A.; Ishii, K. Plasma profiling of intact isoflavone metabolites by high-performance liquid chromatography and mass spectrometric identification of flavone glycosides daidzin and genistin in human plasma after administration of kinako Drug Metab. Dispos. 2008, 36 (8) 1485-1495
23. Rufer, C. E.; Bub, A.; Moseneder, J.; Winterhalter, P.; Sturtz, M.; Kulling, S. E. Pharmacokinetics of the soybean isoflavone daidzein in its aglycone and glucoside form: a randomized, double-blind, crossover study Am. J. Clin. Nutr. 2008, 87 (5) 1314-1323
24. Setchell, K. D.; Brown, N. M.; Desai, P.; Zimmer-Nechemias, L.; Wolfe, B. E.; Brashear, W. T.; Kirschner, A. S.; Cassidy, A.; Heubi, J. E. Bioavailability of pure isoflavones in healthy humans and analysis of commercial soy isoflavone supplements J. Nutr. 2001, 131 (4 Suppl.) 1362S-1375S
25. Shelnutt, S. R.; Cimino, C. O.; Wiggins, P. A.; Ronis, M. J.; Badger, T. M. Pharmacokinetics of the glucuronide and sulfate conjugates of genistein and daidzein in men and women after consumption of a soy beverage Am. J. Clin. Nutr. 2002, 76 (3) 588-594
26. Zhang, Y.; Wang, G. J.; Song, T. T.; Murphy, P. A.; Hendrich, S. Urinary disposition of the soybean isoflavones daidzein, genistein and glycitein differs among humans with moderate fecal isoflavone degradation activity J. Nutr. 1999, 129 (5) 957-962
27. Walsh, K. R.; Failla, M. L. Transport and metabolism of equol by Caco-2 human intestinal cells J. Agric. Food Chem. 2009, 57 (18) 8297-8302
28. Setchell, K. D.; Clerici, C.; Lephart, E. D.; Cole, S. J.; Heenan, C.; Castellani, D.; Wolfe, B. E.; Nechemias-Zimmer, L.; Brown, N. M.; Lund, T. D.; Handa, R. J.; Heubi, J. E. S-equol, a potent ligand for estrogen receptor beta, is the exclusive enantiomeric form of the soy isoflavone metabolite produced by human intestinal bacterial flora Am. J. Clin. Nutr. 2005, 81 (5) 1072-1079
29. Setchell, K. D.; Zhao, X.; Jha, P.; Heubi, J. E.; Brown, N. M. The pharmacokinetic behavior of the soy isoflavone metabolite S-(-)equol and its diastereoisomer R-(+)equol in healthy adults determined by using stable-isotope-labeled tracers Am. J. Clin. Nutr. 2009, 90 (4) 1029-1037
30. Setchell, K. D.; Zhao, X.; Shoaf, S. E.; Ragland, K. The pharmacokinetics of S-(-)equol administered as SE5-OH tablets to healthy postmenopausal women J. Nutr. 2009, 139 (11) 2037-2043
31. Jackson, R. L.; Greiwe, J. S.; Desai, P. B.; Schwen, R. J. Single-dose and steady-state pharmacokinetic studies of S-equol, a potent nonhormonal, estrogen receptor beta-agonist being developed for the treatment of menopausal symptoms Menopause 2011, 18 (2) 185-193
32. Reeves, P. G.; Nielsen, F. H.; Fahey, G. C., Jr. AIN-93 purified diets for laboratory rodents: final report of the American Institute of Nutrition ad hoc writing committee on the reformulation of the AIN-76A rodent diet J. Nutr. 1993, 123 (11) 1939-1951
33. Muthyala, R. S.; Ju, Y. H.; Sheng, S.; Williams, L. D.; Doerge, D. R.; Katzenellenbogen, B. S.; Helferich, W. G.; Katzenellenbogen, J. A. Equol, a natural estrogenic metabolite from soy isoflavones: convenient preparation and resolution of R- and S-equols and their differing binding and biological activity through estrogen receptors alpha and beta Bioorg. Med. Chem. 2004, 12 (6) 1559-1567
34. 13C(3)]isoflavone internal standards Anal. Biochem. 2002, 309 (1) 158-172
35. Legette, L. L.; Martin, B. R.; Shahnazari, M.; Lee, W. H.; Helferich, W. G.; Qian, J.; Waters, D. J.; Arabshahi, A.; Barnes, S.; Welch, J.; Bostwick, D. G.; Weaver, C. M. Supplemental dietary racemic equol has modest benefits to bone but has mild uterotropic activity in ovariectomized rats J. Nutr. 2009, 139 (10) 1908-1913
36. Hedlund, T. E.; Maroni, P. D.; Ferucci, P. G.; Dayton, R.; Barnes, S.; Jones, K.; Moore, R.; Ogden, L. G.; Wahala, K.; Sackett, H. M.; Gray, K. J. Long-term dietary habits affect soy isoflavone metabolism and accumulation in prostatic fluid in Caucasian men J. Nutr. 2005, 135 (6) 1400-1406
37. Sites, C. K.; Cooper, B. C.; Toth, M. J.; Gastaldelli, A.; Arabshahi, A.; Barnes, S. Effect of a daily supplement of soy protein on body composition and insulin secretion in postmenopausal women Fertil. Steril. 2007, 88 (6) 1609-1617
38. Allred, C. D.; Twaddle, N. C.; Allred, K. F.; Goeppinger, T. S.; Churchwell, M. I.; Ju, Y. H.; Helferich, W. G.; Doerge, D. R. Soy processing affects metabolism and disposition of dietary isoflavones in ovariectomized BALB/c mice J. Agric. Food Chem. 2005, 53 (22) 8542-8550