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The Gut Microbiota Ellagic Acid-Derived Metabolite Urolithin A and Its Sulfate Conjugate Are Substrates for the Drug Efflux Transporter Breast Cancer Resistance Protein (ABCG2/BCRP)

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    Article

    The Gut Microbiota Ellagic Acid-Derived Metabolite Urolithin A and Its Sulfate Conjugate Are Substrates for the Drug Efflux Transporter Breast Cancer Resistance Protein (ABCG2/BCRP)
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    † Research Group on Quality, Safety and Bioactivity of Plant Foods, Department of Food Science and Technology, CEBAS-CSIC, P.O. Box 164, 30100 Campus de Espinardo, Murcia, Spain
    ‡ Department of Biomedical Sciences-Physiology, Campus Vegazana, University of León, 24071 León, Spain
    # Department of Bioorganic Chemistry, Institute of Chemical Research, CSIC−University of Seville, 41092 Seville, Spain
    *Phone: +34 968 396344. Fax. +34 968 396213. E-mail: [email protected]
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    Journal of Agricultural and Food Chemistry

    Cite this: J. Agric. Food Chem. 2013, 61, 18, 4352–4359
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    https://doi.org/10.1021/jf4007505
    Published April 15, 2013
    Copyright © 2013 American Chemical Society
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    Abstract

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    The breast cancer resistance protein (BCRP/ABCG2) is a drug efflux transporter that can affect the pharmacological and toxicological properties of many molecules. Urolithins, metabolites produced by the gut microbiota from ellagic acid (EA) and ellagitannins, have been acknowledged with in vivo anti-inflammatory and cancer chemopreventive properties. This study evaluated whether urolithins (Uro-A, -B, -C, and -D) and their main phase II metabolites Uro-A sulfate, Uro-A glucuronide, and Uro-B glucuronide as well as their precursor EA were substrates for ABCG2/BCRP. Parental and Bcrp1-transduced MDCKII cells were used for active transport assays. Uro-A and, to a lesser extent, Uro-A sulfate showed a significant increase in apically directed translocation in Bcrp1-transduced cells. Bcrp1 did not show affinity for the rest of the tested compounds. Data were confirmed for murine, human, bovine, and ovine BCRP-transduced subclones as well as with the use of the selective BCRP inhibitor Ko143. The transport inhibition by Uro-A was analyzed by flow cytometry compared to Ko143 using the antineoplastic agent mitoxantrone as a model substrate. Results showed that Uro-A was able to inhibit mitoxantrone transport in a dose-dependent manner. This study reports for the first time that Uro-A and its sulfate conjugate are ABCG2/BCRP substrates. The results suggest that physiologically relevant concentrations of these gut microbiota-derived metabolites could modulate ABCG2/BCRP-mediated transport processes and mechanisms of cancer drug resistance. Further in vivo investigations are warranted.

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    Experimental procedure for the synthesis of Uro-A glucuronide and Uro-A sulfate. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cite this: J. Agric. Food Chem. 2013, 61, 18, 4352–4359
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    https://doi.org/10.1021/jf4007505
    Published April 15, 2013
    Copyright © 2013 American Chemical Society
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