Mass spectral characterization of phloroglucinol derivatives hyperforin and adhyperforin

Authors

  • Lekha Sleno,

    1. Institute for Marine Biosciences, 1411 Oxford Street, Halifax, Nova Scotia B3H 3Z1, Canada
    2. Department of Chemistry, Dalhousie University, Halifax, Nova Scotia B3H 4J3, Canada
    Current affiliation:
    1. Life Sciences Mass Spectrometry, School of Pharmaceutical Sciences, EPGL, University of Geneva, Switzerland.
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  • Rambod Daneshfar,

    1. Institute for Marine Biosciences, 1411 Oxford Street, Halifax, Nova Scotia B3H 3Z1, Canada
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  • Gunter P. Eckert,

    1. Institute of Pharmacology, Johann Wolfgang Goethe-University, Biocenter, Max-von-Laue-Strasse 9, D-60438 Frankfurt, Germany
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  • Walter E. Müller,

    1. Institute of Pharmacology, Johann Wolfgang Goethe-University, Biocenter, Max-von-Laue-Strasse 9, D-60438 Frankfurt, Germany
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  • Dietrich A. Volmer

    Corresponding author
    1. Institute for Marine Biosciences, 1411 Oxford Street, Halifax, Nova Scotia B3H 3Z1, Canada
    2. Department of Chemistry, Dalhousie University, Halifax, Nova Scotia B3H 4J3, Canada
    • Institute for Marine Biosciences, 1411 Oxford Street, Halifax, Nova Scotia B3H 3Z1, Canada.
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Abstract

Active phloroglucinol constituents of Hypericum perforatum (St. John's wort) extracts, hyperforin and adhyperforin, have been studied following ion activation using tandem mass spectrometry (MS/MS) and complemented by accurate mass measurements. These two compounds were readily analyzed as protonated and deprotonated molecules with electrospray ionization. MS/MS and MS3 data from a quadrupole-linear ion trap tandem mass spectrometer were employed to elucidate fragmentation pathways. Fourier transform ion cyclotron resonance measurements afforded excellent mass accuracies for the confirmation of elemental formulae of product ions formed via infrared multiphoton dissociation and sustained off-resonance irradiation collision-induced dissociation. Fragmentation schemes have been devised for the dissociation of hyperforin and adhyperforin in negative and positive ion modes. This information is expected to be especially valuable for the characterization of related compounds, such as degradation products, metabolites and novel synthetic analogs of hyperforin. Copyright © 2006 John Wiley & Sons, Ltd.

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