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Research ArticleArticle

Metabolism and Disposition of Isoflavone Conjugated Metabolites in Humans after Ingestion of Kinako

Kaori Hosoda, Takashi Furuta and Kazuo Ishii
Drug Metabolism and Disposition September 2011, 39 (9) 1762-1767; DOI: https://doi.org/10.1124/dmd.111.038281
Kaori Hosoda
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Takashi Furuta
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Kazuo Ishii
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Abstract

Isoflavone aglycones daidzein (Dein) and genistein (Gein) are present primarily as glucuronides and sulfates in human plasma; however, very little is known about the plasma pharmacokinetics of isoflavone conjugates after soy ingestion. The aim of this study was to investigate metabolism and disposition of the isoflavone conjugated metabolites glucuronide or sulfate or both after ingestion of kinako (baked soybean flour) by 10 volunteers. The quantifications of 16 metabolites in plasma and urine were performed by our previously reported high-performance liquid chromatography-UV-diode-array detector method. Plasma concentrations of total Dein and Gein metabolites reached maximal values of 0.64 ± 0.18 μM at 4.7 ± 2.5 h and 1.58 ± 0.55 μM at 5.4 ± 2.1 h, respectively. The area under the curve from 0 to 48 h demonstrated that daidzein-7-glucuronide-4′-sulfate (D-7G-4′S) (53.3%) was a major metabolite of Dein and that genistein-7-glucuronide-4′-sulfate (G-7G-4′S) (54.0%) and genistein-4′,7-diglucuronide (G-4′,7-diG) (26.6%) were major metabolites of Gein in plasma. The compositions of isoflavone metabolites in urine and plasma were greatly different. Approximately half of the 48-h urinary excretion of total Dein metabolites consisted of daidzein-7-glucuronide. The total amounts of genistein-7-glucuronide and genistein-4′-glucuronide were half the total amount of the urinary Gein metabolites. Excretion into urine of D-7G-4′S and G-7G-4′S accounted for only 16% each of the total Dein and Gein metabolites, respectively. The plasma and urine profiles of 16 metabolites of Dein and Gein demonstrate the involvement of desulfation and deglucuronidation of the conjugated metabolites D-7G-4′S, G-7G-4′S, and G-4′,7-diG in the process of renal excretion.

Footnotes

  • This work was supported in part by the Ministry of Education, Culture, Sports, Science and Technology of Japan [Grants-in-Aid for Scientific Research 22780125]; and Kyorin University.

  • Article, publication date, and citation information can be found at http://dmd.aspetjournals.org.

    doi:10.1124/dmd.111.038281.

  • ABBREVIATIONS:

    Dein
    daidzein
    Gein
    genistein
    D-4′,7-diS
    daidzein-4′,7-disulfate
    D-7G-4′S
    daidzein-7-glucuronide-4′-sulfate
    HPLC
    high-performance liquid chromatography
    DAD
    diode-array detector
    G-7G-4′S
    genistein-7-glucuronide-4′-sulfate
    G-4′,7-diG
    genistein-4′,7-diglucuronide
    G-7-G
    genistein-7-glucuronide
    D-4′,7-diG
    daidzein-4′,7-diglucuronide
    D-4′-G
    daidzein-4′-glucuronide
    G-4′-G
    genistein-4′-glucuronide
    D-7-G
    daidzein-7-glucuronide
    D-7-S
    daidzein-7-sulfate
    D-4′-S
    daidzein-4′-sulfate
    G-7-S
    genistein-7-sulfate
    G-4′-S
    genistein-4′-sulfate
    G-4′,7-diS
    genistein-4′,7-disulfate
    Din
    daidzin
    Gin
    genistin
    SPE
    solid-phase extraction
    RSD
    relative standard deviation
    tmax
    time to maximum plasma concentration
    Cmax
    peak plasma concentration
    AUC
    area under the curve.

  • Received January 18, 2011.
  • Accepted May 26, 2011.
  • Copyright © 2011 by The American Society for Pharmacology and Experimental Therapeutics
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Drug Metabolism and Disposition: 39 (9)
Drug Metabolism and Disposition
Vol. 39, Issue 9
1 Sep 2011
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Research ArticleArticle

Metabolism and Disposition of Isoflavone Conjugated Metabolites in Humans after Ingestion of Kinako

Kaori Hosoda, Takashi Furuta and Kazuo Ishii
Drug Metabolism and Disposition September 1, 2011, 39 (9) 1762-1767; DOI: https://doi.org/10.1124/dmd.111.038281

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Research ArticleArticle

Metabolism and Disposition of Isoflavone Conjugated Metabolites in Humans after Ingestion of Kinako

Kaori Hosoda, Takashi Furuta and Kazuo Ishii
Drug Metabolism and Disposition September 1, 2011, 39 (9) 1762-1767; DOI: https://doi.org/10.1124/dmd.111.038281
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