Characterization of polyprenylated xanthones in Garcinia xipshuanbannaensis using liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry

Yan Zhou, Quan Bin Han, Jing Zheng Song, Chun Feng Qiao, Hong Xi Xu*

*Corresponding author for this work

Research output: Contribution to journalJournal articlepeer-review

48 Citations (Scopus)

Abstract

A reliable and sensitive on-line high-performance liquid chromatography (HPLC) coupled with electrospray quadrupole time-of-flight tandem mass spectrometry (ESI-QTOF-MS/MS/MS) method has been optimized and established for the analysis of polyprenylated xanthones in the plant Garcinia xipshuanbannaensis. Collision induced MS/MS techniques were used to fragment the precursor molecular ions and MS/MS/MS techniques based on cone voltage fragmentation were used to further break down the resulting product ions sequentially. It was found that Retro-Diels-Alder rearrangement occurred from the xanthone skeleton in the MS/MS/MS process and produced characteristic fragment ions, which are useful for differentiating some positional isomers containing the prenyl unit on the A ring or B ring. Complementary fragmentation information, for instance the successive loss of prenyl residues, is also valuable for the identification of this class of xanthones. Under optimized HPLC-MS/MS/MS method, a total of 15 prenylated xanthones could be separated within 10 min. This method also provided information about the molecular formula of a precursor molecule and its fragments, which could be used for dereplication of known or likely new prenylated xanthones in Garcinia plants before the purification and structural elucidation process.

Original languageEnglish
Pages (from-to)131-139
Number of pages9
JournalJournal of Chromatography A
Volume1206
Issue number2
DOIs
Publication statusPublished - 10 Oct 2008

Scopus Subject Areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

User-Defined Keywords

  • Garcinia xipshuanbannaensis
  • HPLC-QTOF-MS/MS/MS
  • Polyprenylated xanthones

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