Skip to main content

Advertisement

SpringerLink
Log in

Variations in metabolism of the soy isoflavonoid daidzein by human intestinal microfloras from different individuals

  • Original Paper
  • Published:
Archives of Microbiology Aims and scope Submit manuscript

Abstract

Isoflavonoids found in legumes, such as soybeans, are converted by intestinal bacteria to metabolites that might have increased or decreased estrogenic activity. Variation in the effects of dietary isoflavonoids among individuals has been attributed to differences in their metabolism by intestinal bacteria. To investigate this variation, the metabolism of the isoflavonoid daidzein by bacteria from ten fecal samples, provided at different times by six individuals on soy-containing diets, was compared. After anaerobic incubation of bacteria with daidzein for 2 weeks, four samples had metabolized daidzein and six samples had not. Three of the positive samples were from individuals whose microflora had not metabolized daidzein in previous samples. Dihydrodaidzein was observed in one sample, dihydrodaidzein and equol in another sample, and equol and O-desmethylangolensin in two other samples. These results corroborate the hypothesis that the microflora of the gastrointestinal tract of an individual influences the particular isoflavone metabolites produced following consumption.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1A–C.
Fig. 2A–C.
Fig. 3.

Similar content being viewed by others

References

  • Adlercreutz H (1995) Phytoestrogens: epidemiology and possible role in cancer protection. Environ Health Perspect 103:103–112

    CAS  Google Scholar 

  • Adlercreutz H, Bannwart C, Wähälä K, Makela T, Brunow G, Hase T, Arosemena PJ, Kellis JT, Vickery LE (1993) Inhibition of human aromatase by mammalian lignans and isoflavonoid phytoestrogens. J Steroid Biochem Mol Biol 44:147–153

    CAS  PubMed  Google Scholar 

  • Anderson JJB, Ambrose WW, Garner SC (1998) Biphasic effects of genistein on bone tissue in the ovariectomized, lactating rat model. Proc Soc Exp Biol Med 217:345–350

    CAS  PubMed  Google Scholar 

  • Chang Y-C, Nair MG (1995) Metabolism of daidzein and genistein by intestinal bacteria. J Nat Prod 58:1892–1896

    CAS  PubMed  Google Scholar 

  • Coward L, Barnes N, Setchell KDR, Barnes S (1993) Genistein and daidzein, and their β-glycoside conjugates: anti-tumor isoflavones in soybean foods from American and Asian diets. J Agric Food Chem 41:1961–1967

    CAS  Google Scholar 

  • Duncan AM, Merz-Demlow BE, Xu X, Phipps WR, Kurzer MS (2000) Premenopausal equol excretors show plasma hormone profiles associated with lowered risk of breast cancer. Cancer Epidemiol Biomarkers Prevent 9:581–586

    CAS  Google Scholar 

  • Hur H-G, Lay JO, Beger RD, Freeman JP, Rafii F (2000) Isolation of human intestinal bacteria metabolizing the natural isoflavone glycosides daidzin and genistin. Arch Microbiol 174:422–428

    PubMed  Google Scholar 

  • Hur H-G, Beger RD, Heinze TM, Lay JO, Freeman JP, Dore J, Rafii F (2002) Isolation of an anaerobic intestinal bacterium capable of cleaving the C-ring of the isoflavonoid daidzein. Arch Microbiol 178:8–12

    Article  CAS  PubMed  Google Scholar 

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

    PubMed  Google Scholar 

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

    CAS  PubMed  Google Scholar 

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

    CAS  PubMed  Google Scholar 

  • Lampe J, Messina M (1998) Are phytoestrogens nature's cure for what ails us? A look at the research. J Amer Diet Assoc 98:974–976

    CAS  Google Scholar 

  • Lampe JW, Skor HE, Li S, Wähälä K, Howald WN, Chen C (2001) Wheat bran and soy protein feeding do not alter urinary excretion of the isoflavan equol in premenopausal women. J Nutr. 131:740–744

    Google Scholar 

  • Lichtenstein AH (1998) Soy protein, isoflavones and cardiovascular disease risk. J Nutr 128:1589–1592

    CAS  PubMed  Google Scholar 

  • Messina M (2000) Soyfoods and soybean phyto-oestrogens (isoflavones) as possible alternatives to hormone replacement therapy (HRT). Eur J Cancer 36:71–72

    Article  Google Scholar 

  • Messina M, Messina V (2000) Soyfoods, soybean isoflavones, and bone health: a brief overview. J Renal Nutr 10:63–68

    CAS  Google Scholar 

  • Messina M, Persky V, Setchell KDR, Barnes S (1994) Soy intake and cancer risk: a review of the in vitro and in vivo data. Nutr Cancer 21:113–131

    CAS  PubMed  Google Scholar 

  • Nagel SCV, Van Saal FS, Welshone WV (1998) The effective free fraction of estradiol and xenoestrogens in human serum measured by the whole cell uptake assays: physiology of delivery modifies estrogenic activity. Proc Soc Exp Biol Med 217:300–309

    PubMed  Google Scholar 

  • Peters NK, Frost JN, Long SR (1986) A plant flavone, luteolin, induces expression of Rhizobium meliloti nodulation genes. Science 233:977–980

    CAS  PubMed  Google Scholar 

  • Phillips, DA (1992) Flavonoids: plant signals to soil microbes. Annu Rev Phytochem 26:201–231

    CAS  Google Scholar 

  • Rowland IR Wiseman H, Sanders TA, Adlercreutz H, Bowey EA (2000) Interindividual variation in metabolism of soy isoflavones and lignans: influence of habitual diet on equol production by the gut microflora. Nutr Cancer 36:27–32

    CAS  PubMed  Google Scholar 

  • Sathyamoorthy N, Wang TT (1997) Differential effects of dietary phyto-oestrogens daidzein and equol on human breast cancer MCF-7 cells. Eur J Cancer 33:2384–2389

    Article  CAS  PubMed  Google Scholar 

  • Schoefer L, Mohan R, Braune A, Birringer M, Blaut M (2002) Anaerobic C-ring cleavage of genistein and daidzein by Eubacterium ramulus. FEMS Microbiol Lett 208:197–202

    Article  CAS  PubMed  Google Scholar 

  • Setchell KDR, Brown NM, Lydeking-Olsen E (2002) The clinical importance of the metabolite equol-A clue to the effectiveness of soy and its isoflavones. J Nutr 132:3577–3584

    CAS  PubMed  Google Scholar 

  • Wähälä K, Salakka A, Adlercreutz H (1998) Synthesis of novel mammalian metabolites of the isoflavonoid phytoestrogens daidzein and genistein. Proc Soc Exp Biol Med 217:293–299

    PubMed  Google Scholar 

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

    CAS  PubMed  Google Scholar 

  • Wilcox G, Wahlqvist ML, Burger HG, Medley G (1990) Oestrogenic effects of plant foods in postmenopausal women. Brit Med J 301:905–906

    CAS  Google Scholar 

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

    CAS  PubMed  Google Scholar 

Download references

Acknowledgements

Special thanks to K. Barry Delclos for reviewing this manuscript, Dr. John B. Sutherland for discussion and suggestions during manuscript preparation, and Dr. Carl E. Cerniglia for his research support. This work was supported in part by an appointment of (MP and CD) at the National Center for Toxicological Research administered by the Oak Ridge Institute for Science and Education through an interagency agreement between the U.S. Department of Energy and the U.S. Food and Drug Administration and University of Arkansas at Little Rock, Arkansas (CD).

Author information

Authors and Affiliations

  1. Division of Microbiology, National Center for Toxicological Research, U.S. FDA, Jefferson, AR 72079, USA

    Fatemeh Rafii & Miseon Park

  2. Dollarway High School, Pine Bluff, AR 71602, USA

    Christy Davis

  3. Division of Chemistry, National Center for Toxicological Research, U.S. FDA, Jefferson, AR 72079, USA

    Thomas M. Heinze & Richard D. Beger

Authors
  1. Fatemeh Rafii
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Christy Davis
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Miseon Park
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Thomas M. Heinze
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Richard D. Beger
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Fatemeh Rafii.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Rafii, F., Davis, C., Park, M. et al. Variations in metabolism of the soy isoflavonoid daidzein by human intestinal microfloras from different individuals. Arch Microbiol 180, 11–16 (2003). https://doi.org/10.1007/s00203-003-0551-6

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00203-003-0551-6

Keywords

Search

Navigation