Nutr Res Pract.  2013 Oct;7(5):393-399. 10.4162/nrp.2013.7.5.393.

Plasma pharmacokinetics and urinary excretion of isoflavones after ingestion of soy products with different aglycone/glucoside ratios in South Korean women

• Chang Y
• Choue R

• KMID: 1841311
• DOI: http://doi.org/10.4162/nrp.2013.7.5.393

Abstract

Asian populations are thought to receive significant health benefits from traditional diets rich in soybeans due to high isoflavone contents. However, available epidemiologic data only weakly support this hypothesis. The present study was carried out to assess the pharmacokinetics of isoflavones in South Korean women after ingestion of soy-based foods. Twenty-six healthy female volunteers (20-30 y old) consumed three different soy products (i.e., isogen, soymilk, and fermented soybeans) with different aglycone/glucoside ratios. Plasma and urine isoflavone concentrations were measured by high-performance liquid chromatography (HPLC) after ingestion of one of the soy products. Pharmacokinetic parameters were determined using the WinNonlin program. The area under the curve (AUC) for plasma daidzein levels of the soymilk group (2,101 +/- 352 ng . h/mL) was significantly smaller than those of the isogen (2,628 +/- 573 ng . h/mL) and fermented soybean (2,593 +/- 465 ng . h/mL) groups. The maximum plasma concentration (Cmax) of daidzein for the soymilk group (231 +/- 44 ng/mL) was significantly higher than those of the isogen (160 +/- 32 ng/mL) and fermented soybean (195 +/- 35 ng/mL) groups. The half-lives of daidzein and genistein in the soymilk group (5.9 and 5.6 h, respectively) were significantly shorter than those in the individuals given isogen (9.6 and 8.5 h, respectively) or fermented soybean (9.5 and 8.2 h, respectively). The urinary recovery rates of daidzein and genistein were 42% and 17% for the isogen group, 46% and 23% for the fermented soybean group, and 33% and 22% for the soymilk group. In conclusion, our data indicated that soy products containing high levels of isoflavone aglycone are more effective for maintaining plasma isoflavone concentrations. Additional dose-response, durational, and interventional studies are required to evaluate the ability of soy-based foods to increase the bioavailability of isoflavones that positively affect human health.

Keyword

Soy-based foods; isoflavone; pharmacokinetics; plasma; urine

MeSH Terms

Asian Continental Ancestry Group
Biological Availability
Chromatography, Liquid
Diet
Eating
Female
Genistein
Humans
Insurance Benefits
Isoflavones
Plasma
Soybeans
Genistein
Isoflavones

Reference

1. Messina MJ. Legumes and soybeans: overview of their nutritional profiles and health effects. Am J Clin Nutr. 1999; 70:439S–450S.

2. Adlercreutz H. Phytoestrogens: epidemiology and a possible role in cancer protection. Environ Health Perspect. 1995; 103:Suppl 7. 103–112.

3. Cassidy A. Physiological effects of phyto-oestrogens in relation to cancer and other human health risks. Proc Nutr Soc. 1996; 55:399–417.

4. Setchell KD. Phytoestrogens: the biochemistry, physiology, and implications for human health of soy isoflavones. Am J Clin Nutr. 1998; 68:1333S–1346S.

5. Setchell KD, Adlercreutz H. Mammalian lignans and phytooestrogens. Recent studies on their formation, metabolism and biological role in health and disease. In : Rowland IR, editor. Role of the Gut Flora in Toxicity and Cancer. London: Academic Press;1988. p. 315–345.

6. Windholz M, Budavari S. The Merck Index: an Encyclopedia of Chemicals, Drugs, and Biologicals. Rahway (NJ): Merck and Co., Inc;1983.

7. Kurzer MS. Hormonal effects of soy isoflavones: studies in premenopausal and postmenopausal women. J Nutr. 2000; 130:660S–661S.

8. Setchell KD, Cassidy A. Dietary isoflavones: biological effects and relevance to human health. J Nutr. 1999; 129:758S–767S.

9. Setchell KD, Brown NM, Zimmer-Nechemias L, Brashear WT, Wolfe BE, Kirschner AS, Heubi JE. Evidence for lack of absorption of soy isoflavone glycosides in humans, supporting the crucial role of intestinal metabolism for bioavailability. Am J Clin Nutr. 2002; 76:447–453.

10. Coward L, Barnes NC, Setchell KD, Barnes S. Genistein, daidzein, and their β-glycoside conjugates: antitumor isoflavones in soybean foods from American and Asian diets. J Agric Food Chem. 1993; 41:1961–1967.

11. Murphy PA. Phytoestrogen content of processed soybean products. Food Technol. 1982; 36:60–64.

12. Wang H, Murphy PA. Isoflavone content in commercial soybean foods. J Agric Food Chem. 1994; 42:1666–1673.

13. Izumi T, Piskula MK, Osawa S, Obata A, Tobe K, Saito M, Kataoka S, Kubota Y, Kikuchi M. Soy isoflavone aglycones are absorbed faster and in higher amounts than their glucosides in humans. J Nutr. 2000; 130:1695–1699.

14. Xu X, Harris KS, Wang HJ, Murphy PA, Hendrich S. Bioavailability of soybean isoflavones depends upon gut microflora in women. J Nutr. 1995; 125:2307–2315.

15. Xu X, Wang HJ, Murphy PA, Cook L, Hendrich S. Daidzein is a more bioavailable soymilk isoflavone than is genistein in adult women. J Nutr. 1994; 124:825–832.

16. Joannou GE, Kelly GE, Reeder AY, Waring M, Nelson C. A urinary profile study of dietary phytoestrogens. The identification and mode of metabolism of new isoflavonoids. J Steroid Biochem Mol Biol. 1995; 54:167–184.

17. Kelly GE, Joannou GE, Reeder AY, Nelson C, Waring MA. The variable metabolic response to dietary isoflavones in humans. Proc Soc Exp Biol Med. 1995; 208:40–43.

18. Shutt DA, Cox RI. Steroid and phyto-oestrogen binding to sheep uterine receptors in vitro. J Endocrinol. 1972; 52:299–310.

19. Cassidy A. Plant oestrogens and their relation to hormonal status in women [doctoral thesis]. Cambridge: University of Cambridge;1991.

20. Watanabe S, Yamaguchi M, Sobue T, Takahashi T, Miura T, Arai Y, Mazur W, Wähälä K, Adlercreutz H. Pharmacokinetics of soybean isoflavones in plasma, urine and feces of men after ingestion of 60 g baked soybean powder (kinako). J Nutr. 1998; 128:1710–1715.

21. Lu LJ, Grady JJ, Marshall MV, Ramanujam VM, Anderson KE. Altered time course of urinary daidzein and genistein excretion during chronic soya diet in healthy male subjects. Nutr Cancer. 1995; 24:311–323.

22. Franke AA, Custer LJ. High-performance liquid chromatographic assay of isoflavonoids and coumestrol from human urine. J Chromatogr B Biomed Appl. 1994; 662:47–60.

23. Franke AA, Custer LJ, Wang W, Shi CY. HPLC analysis of isoflavonoids and other phenolic agents from foods and from human fluids. Proc Soc Exp Biol Med. 1998; 217:263–273.

24. Wang G, Kuan SS, Francis OJ, Ware GM, Carman AS. A simplified HPLC method for the determination of phytoestrogens in soybean and its processed products. J Agric Food Chem. 1990; 38:185–190.

25. Brown JP. Hydrolysis of glycosides and esters. In : Rowland IR, editor. Role of the Gut Flora in Toxicity and Cancer. London: Academic Press;1988. p. 109–144.

26. Friend DR, Chang GW. A colon-specific drug-delivery system based on drug glycosides and the glycosidases of colonic bacteria. J Med Chem. 1984; 27:261–266.

27. Griffiths LA, Smith GE. Metabolism of apigenin and related compounds in the rat. Metabolite formation in vivo and by the intestinal microflora in vitro. Biochem J. 1972; 128:901–911.

28. King RA, Bursill DB. Plasma and urinary kinetics of the isoflavones daidzein and genistein after a single soy meal in humans. Am J Clin Nutr. 1998; 67:867–872.

29. Zhang Y, Wang GJ, Song TT, Murphy PA, Hendrich S. Urinary disposition of the soybean isoflavones daidzein, genistein and glycitein differs among humans with moderate fecal isoflavone degradation activity. J Nutr. 1999; 129:957–962.

30. Hutchins AM, Slavin JL, Lampe JW. Urinary isoflavonoid phytoestrogen and lignan excretion after consumption of fermented and unfermented soy products. J Am Diet Assoc. 1995; 95:545–551.

31. Xu X, Wang HJ, Murphy PA, Hendrich S. Neither background diet nor type of soy food affects short-term isoflavone bioavailability in women. J Nutr. 2000; 130:798–801.

32. Kelly GE, Nelson C, Waring MA, Joannou GE, Reeder AY. Metabolites of dietary (soya) isoflavones in human urine. Clin Chim Acta. 1993; 223:9–22.

33. Kapiotis S, Hermann M, Held I, Seelos C, Ehringer H, Gmeiner BM. Genistein, the dietary-derived angiogenesis inhibitor, prevents LDL oxidation and protects endothelial cells from damage by atherogenic LDL. Arterioscler Thromb Vasc Biol. 1997; 17:2868–2874.

34. Naim M, Gestetner B, Bondi A, Birk Y. Antioxidative and antihemolytic activities of soybean isoflavones. J Agric Food Chem. 1976; 24:1174–1177.

35. Anderson JJ, Garner SC. The effects of phytoestrogens on bone. Nutr Res. 1997; 17:1617–1632.

36. Ishida H, Uesugi T, Hirai K, Toda T, Nukaya H, Yokotsuka K, Tsuji K. Preventive effects of the plant isoflavones, daidzin and genistin, on bone loss in ovariectomized rats fed a calcium-deficient diet. Biol Pharm Bull. 1998; 21:62–66.

37. Adlercreutz CH, Goldin BR, Gorbach SL, Höckerstedt KA, Watanabe S, Hämäläinen EK, Markkanen MH, Mäkelä TH, Wähälä KT, Adlercreutz T. Soybean phytoestrogen intake and cancer risk. J Nutr. 1995; 125:757S–770S.