Characterization of prenylated xanthones and flavanones by liquid chromatography/atmospheric pressure chemical ionization mass spectrometry

Cristina T. Da Costa, Joseph J. Dalluge, Michael J. Welch, Bruce Coxon, Sam A. Margolis, Derek Horton

Research output: Contribution to journalArticle

27 Scopus citations

Abstract

Reversed-phase liquid chromatography with atmospheric pressure chemical ionization mass spectrometry (LC/APCI-MS) in the positive-ion mode was utilized to analyze crude ether extracts from the root bark of Maclura pomifera, a tree known to have a high content of prenylated xanthones and flavanones. Identification of three xanthones and two flavanones was based on their unique mass spectra. Under optimum conditions peaks corresponding to the [MH]+ ion and characteristic fragments for each compound were observed. 1H NMR data were used to confirm the identities of two xanthones that had the same molecular mass and similar fragmentation patterns. Fragmentation of the analytes was achieved by application of an electrostatic potential at the entrance of the single quadrupole mass spectrometer. The optimum voltage for fragmentation was found to be related to the class of compounds analyzed and, within each class, to be dependent on the structure of the prenyl moiety. Collision-induced pathways consistent with precedent literature describing the MS characterization of similar compounds and with the observed fragmentation patterns are tentatively proposed. Copyright (C) 2000 John Wiley and Sons, Ltd.

Original languageEnglish (US)
Pages (from-to)540-549
Number of pages10
JournalJournal of Mass Spectrometry
Volume35
Issue number4
DOIs
StatePublished - 2000

Keywords

  • Flavanones
  • Liquid chromatography/atmospheric pressure chemical ionization mass spectrometry
  • Maclura pomifera
  • Prenylated compounds
  • Xanthones

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