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Research ArticleArticle

Effect of Resveratrol on 17β-Estradiol Sulfation by Human Hepatic and Jejunal S9 and Recombinant Sulfotransferase 1E1

Anna M. Furimsky, Carol E. Green, Lewanne E. Hunt Sharp, Paul Catz, Araba A. Adjei, Toufan Parman, Izet M. Kapetanovic, Richard M. Weinshilboum and Lalitha V. Iyer
Drug Metabolism and Disposition January 2008, 36 (1) 129-136; DOI: https://doi.org/10.1124/dmd.107.016725
Anna M. Furimsky
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Carol E. Green
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Lewanne E. Hunt Sharp
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Paul Catz
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Araba A. Adjei
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Toufan Parman
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Izet M. Kapetanovic
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Richard M. Weinshilboum
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Lalitha V. Iyer
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Abstract

The purpose of this study was to investigate the sulfation of resveratrol (3,5,4′-trihydroxystilbene) and its potential to exhibit drug-drug interactions via sulfation. The possible interaction of resveratrol with 17β-estradiol (E2), a major estrogen hormone and prototypic substrate for sulfate conjugation, was studied. Resveratrol and E2 are both known to undergo sulfate conjugation catalyzed by human sulfotransferases (SULTs). Resveratrol is a phytoestrogen with mixed estrogen agonist/antagonist properties that is being developed as a chemopreventive agent. The sulfate conjugation of E2 and resveratrol were studied individually using S9 fractions from human liver and jejunum as well as recombinant human SULT isoforms. The sulfation of E2 (3–20 nM) was then investigated in the presence of various concentrations (0, 0.5, 1, and 2 μM) of resveratrol using the two S9 preparations as well as recombinant SULT1E1, the major isoform responsible for E2 sulfation. Resveratrol inhibited E2 sulfation with estimated Ki values of 1.1 μM (liver), 0.6 μM (jejunum), and 2.3 μM (SULT1E1), concentrations that could be pharmacologically relevant. The results suggest that these phytoestrogens can potentially alter the homeostasis of estrogen levels. These findings also imply that resveratrol may inhibit the metabolism of other estrogen analogs or therapeutic agents such as ethinylestradiol or dietary components that are also substrates for SULT1E1.

Footnotes

  • This study was supported by funds from the National Cancer Institute ((N01-CN-43305; to C.E.G.), the National Institutes of General Medical Sciences (R01 GM35720 and U01 GM61388), The Pharmacogenetics Research Network (to A.A. and R.W.) and the PhRMA Foundation (A Center of Excellence in Clinical Pharmacology Award to R.W.).

  • Preliminary results from this study were presented in “Inhibition of human hepatic and jejunal estradiol sulfation by resveratrol and piceatannol” (Furimsky AM, Sharp LE, Bettridge A, Kapetanovic IM, Green CE, Iyer LV) at Experimental Biology 2006 in San Francisco, CA, April 1–5, 2006.

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

  • doi:10.1124/dmd.107.016725.

  • ABBREVIATIONS: ER, estrogen receptor; SULT, sulfotransferase; UGT, uridine diphosphate glucuronosyltransferase; E2, 17β-estradiol; EST, estrogen sulfotransferase, SULT1E1; DTT, dithiothreitol; PAPS, adenosine 3′-phosphate 5′-phosphosulfate; BSA, bovine serum albumin; HPLC, high-performance liquid chromatography; PDA, photodiode array detector; LC, liquid chromatography; MS, mass spectrometry, MS/MS, tandem mass spectrometry.

    • Received June 1, 2007.
    • Accepted October 17, 2007.
  • The American Society for Pharmacology and Experimental Therapeutics
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Drug Metabolism and Disposition: 36 (1)
Drug Metabolism and Disposition
Vol. 36, Issue 1
1 Jan 2008
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Research ArticleArticle

Effect of Resveratrol on 17β-Estradiol Sulfation by Human Hepatic and Jejunal S9 and Recombinant Sulfotransferase 1E1

Anna M. Furimsky, Carol E. Green, Lewanne E. Hunt Sharp, Paul Catz, Araba A. Adjei, Toufan Parman, Izet M. Kapetanovic, Richard M. Weinshilboum and Lalitha V. Iyer
Drug Metabolism and Disposition January 1, 2008, 36 (1) 129-136; DOI: https://doi.org/10.1124/dmd.107.016725

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Research ArticleArticle

Effect of Resveratrol on 17β-Estradiol Sulfation by Human Hepatic and Jejunal S9 and Recombinant Sulfotransferase 1E1

Anna M. Furimsky, Carol E. Green, Lewanne E. Hunt Sharp, Paul Catz, Araba A. Adjei, Toufan Parman, Izet M. Kapetanovic, Richard M. Weinshilboum and Lalitha V. Iyer
Drug Metabolism and Disposition January 1, 2008, 36 (1) 129-136; DOI: https://doi.org/10.1124/dmd.107.016725
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