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Negative ion tandem mass spectrometry of prenylated fungal metabolites and their derivatives

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Abstract

Liquid chromatography negative ion electrospray ionisation tandem mass spectrometry has been used for characterisation of naturally occurring prenylated fungal metabolites and synthetic derivatives. The fragmentation studies allow an elucidation of the decomposition pathways for these compounds. It could be shown, that the prenyl side chain is degraded by successive radical losses of C5 units. Both the benzoquinones and the phenolic derivatives display significant key ions comprising the aromatic ring. In some cases, the formation of significant oxygen-free key ions could be evidenced by high-resolution MS/MS measurements. Furthermore, the different types of basic skeletons, benzoquinones and phenol type as well as cyclic prenylated compounds, can be differentiated by their MS/MS behaviour.

Fruiting bodies of Suillus bovinus, the structure of boviquinone-4 and its negative ion MS2 spectrum

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Acknowledgements

The authors are indebted to Prof. Dr. Dr. h.c. Wolfgang Steglich and co-workers (Ludwig-Maximilians-University, Munich) for kindly providing the compounds investigated. We thank Petra Majovsky for technical assistance. Ramona Heinke is gratefully acknowledged to the Studienstiftung des Deutschen Volkes for a grant.

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Authors and Affiliations

  1. Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, 06120, Halle, Germany

    Ramona Heinke, Norbert Arnold, Ludger Wessjohann & Jürgen Schmidt

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  1. Ramona Heinke
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  2. Norbert Arnold
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  3. Ludger Wessjohann
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  4. Jürgen Schmidt
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Correspondence to Jürgen Schmidt.

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Heinke, R., Arnold, N., Wessjohann, L. et al. Negative ion tandem mass spectrometry of prenylated fungal metabolites and their derivatives. Anal Bioanal Chem 405, 177–189 (2013). https://doi.org/10.1007/s00216-012-6498-1

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  • DOI: https://doi.org/10.1007/s00216-012-6498-1

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