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Ralfuranone Thioether Production by the Plant Pathogen Ralstonia solanacearum

Authors

  • Julia Pauly,

    1. Friedrich-Schiller-Universität, Department of Pharmaceutical Biology at the Hans-Knöll-Institut, Beutenbergstrasse 11a, 07745 Jena (Germany)
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  • Prof. Dr. Dieter Spiteller,

    1. University of Konstanz, Department of Chemical Ecology/Chemical Biology, Universitätsstrasse 10, 78457 Konstanz (Germany)
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  • Jeanine Linz,

    1. Max Planck Institute for Chemical Ecology, Department of Evolutionary Neuroethology, Hans-Knöll-Strasse 8, 07745 Jena (Germany)
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  • Dr. Jonathan Jacobs,

    1. University of Wisconsin–Madison, Department of Plant Pathology, 1630 Linden Drive, Madison, WI 53706 (USA)
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  • Prof. Dr. Caitilyn Allen,

    1. University of Wisconsin–Madison, Department of Plant Pathology, 1630 Linden Drive, Madison, WI 53706 (USA)
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  • Dr. Markus Nett,

    1. Leibniz Institute for Natural Product Research and Infection Biology e.V. Hans-Knöll-Institut, Beutenbergstrasse 11a, 07745 Jena (Germany)
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  • Prof. Dr. Dirk Hoffmeister

    Corresponding author
    1. Friedrich-Schiller-Universität, Department of Pharmaceutical Biology at the Hans-Knöll-Institut, Beutenbergstrasse 11a, 07745 Jena (Germany)
    • Friedrich-Schiller-Universität, Department of Pharmaceutical Biology at the Hans-Knöll-Institut, Beutenbergstrasse 11a, 07745 Jena (Germany)

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Abstract

Ralfuranones are aryl-substituted furanone secondary metabolites of the Gram-negative plant pathogen Ralstonia solanacearum. New sulfur-containing ralfuranone derivatives were identified, including the methyl thioether-containing ralfuranone D. Isotopic labeling in vivo, as well as headspace analyses of volatiles from R. solanacearum liquid cultures, established a mechanism for the transfer of an intact methylthio group from L-methionine or α-keto-γ-methylthiobutyric acid. The methylthio acceptor molecule ralfuranone I, a previously postulated biosynthetic intermediate in ralfuranone biosynthesis, was isolated and characterized by NMR. The highly reactive Michael acceptor system of this intermediate readily reacts with various thiols, including glutathione.

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