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Research ArticleArticle

Absorption and Metabolization of Cytoprotective Epicatechin Thio Conjugates in Rats

Ariadna Selga, María Pilar Vinardell, Raquel Martín-Venegas, Olga Jáuregui, Josefina Casas and Josep Lluís Torres
Drug Metabolism and Disposition December 2010, 38 (12) 2188-2194; DOI: https://doi.org/10.1124/dmd.110.035279
Ariadna Selga
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María Pilar Vinardell
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Raquel Martín-Venegas
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Olga Jáuregui
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Josefina Casas
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Josep Lluís Torres
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Abstract

The epicatechin (EC) thio derivatives 4β-(S-cysteinyl)-epicatechin (Cys-EC) and 4β-(S-cysteaminyl)-epicatechin (Cya-EC) are compounds that may provide protection from oxidation via mechanisms involving either the flavonoid moiety or the nonphenolic cysteine or cysteamine part of the molecule. Because the metabolically modified molecules may be the actual active species, we estimated the absorption/metabolization of the thio derivatives through the small intestine in vitro and studied the body distribution of the compounds and their metabolites in rats. The analysis of the samples generated was done using a high-performance liquid chromatograph coupled to a UV detector and a tandem mass spectrometer. We show that Cya-EC follows the same phase II metabolization pattern as EC, whereas Cys-EC is transported with the intact catechol moiety through the small intestine and effectively metabolized systemically. We also found that Cya-EC generates Cys-EC in vivo, which provides evidence for a Cya-EC-mediated cytoprotective effect through cysteamine/cystine exchange with subsequent cysteine transport, ubiquitously throughout the organism.

Footnotes

  • This work was supported by the Spanish Ministry of Science and Technology [Awards PPQ2000-0688-C05-03, PTR1995-0611-OP].

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

    doi:10.1124/dmd.110.035279.

  • ↵Embedded Image The online version of this article (available at http://dmd.aspetjournals.org) contains supplemental material.

  • ABBREVIATIONS:

    Cys-EC
    4β-(S-cysteinyl)-epicatechin
    EC
    (−)-epicatechin
    Cya-EC
    4β-(2-aminoethylthio)-epicatechin or 4β-(S-cysteaminyl)-epicatechin
    HPLC
    high-performance liquid chromatography
    MS
    mass spectrometry
    TFA
    trifluoroacetic acid
    COMT
    catechol O-methyl transferase
    SAM
    S-adenosyl-l-methionine
    MS/MS
    tandem mass spectrometry
    AU
    arbitrary units
    FS
    full-scan
    MRM
    multiple reaction monitoring
    MES
    4-morpholineethanesulfonic acid
    DTT
    dithiothreitol
    Me
    methyl
    Gluc
    glucuronidyl
    UDPGA
    uridine diphosphate glucuronic acid.

  • Received July 6, 2010.
  • Accepted September 3, 2010.
  • Copyright © 2010 by The American Society for Pharmacology and Experimental Therapeutics
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Drug Metabolism and Disposition: 38 (12)
Drug Metabolism and Disposition
Vol. 38, Issue 12
1 Dec 2010
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Research ArticleArticle

Absorption and Metabolization of Cytoprotective Epicatechin Thio Conjugates in Rats

Ariadna Selga, María Pilar Vinardell, Raquel Martín-Venegas, Olga Jáuregui, Josefina Casas and Josep Lluís Torres
Drug Metabolism and Disposition December 1, 2010, 38 (12) 2188-2194; DOI: https://doi.org/10.1124/dmd.110.035279

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Research ArticleArticle

Absorption and Metabolization of Cytoprotective Epicatechin Thio Conjugates in Rats

Ariadna Selga, María Pilar Vinardell, Raquel Martín-Venegas, Olga Jáuregui, Josefina Casas and Josep Lluís Torres
Drug Metabolism and Disposition December 1, 2010, 38 (12) 2188-2194; DOI: https://doi.org/10.1124/dmd.110.035279
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