Analysis of caged xanthones from the resin of Garcinia hanburyi using ultra-performance liquid chromatography/electrospray ionization quadrupole time-of-flight tandem mass spectrometry

Yan Zhou, Xin Liu, Jing Yang, Quan Bin Han, Jing Zheng Song, Song Lin Li, Chun Feng Qiao, Li Sheng Ding*, Hong Xi Xu*

*Corresponding author for this work

Research output: Contribution to journalJournal articlepeer-review

48 Citations (Scopus)

Abstract

On-line ultra high-performance liquid chromatography (UHPLC) coupled with electrospray quadrupole time-of-flight tandem mass spectrometry (ESI-QTOF-MS/MS/MS) has been developed for the analysis of a series of caged xanthones in the resin of Garcinia hanburyi. The fragmentation of protonated molecular ions for 12 known cadged xanthones was carried out using low-energy collision-induced electrospray ionization tandem mass spectrometry. It was found that Retro-Diels-Alder rearrangement occurred in the CID processes and produced the characteristic fragment ions, which are especially valuable for the identification of this class of xanthones. The fragmentation differential between some cis-, trans-isomers was uncovered. Computation methods were utilized to rationalize the observed MS behaviors. On-line UHPLC-ESI-MS/MS/MS method has proved to be rapid and efficient in that within 6 min, 15 caged scaffold xanthones, including three pairs of epimers and four pairs of isomers in gamboges, were effectively separated and identified. Among them, two known, namely isogambogenin (13) and isomorellinol (14) and one likely new caged Garcinia xanthones from the Garcinia hanburyi were tentatively characterized based on the tandem mass spectra of known ones.

Original languageEnglish
Pages (from-to)104-118
Number of pages15
JournalAnalytica Chimica Acta
Volume629
Issue number1-2
DOIs
Publication statusPublished - 23 Nov 2008

Scopus Subject Areas

  • Analytical Chemistry
  • Biochemistry
  • Environmental Chemistry
  • Spectroscopy

User-Defined Keywords

  • Caged xanthones
  • Computation
  • Electrospray ionization quadrupole time-of-flight tandem mass spectrometry (ESI-QTOF-MS/MS/MS)
  • Fragmentation pathways
  • Garcinia hanburyi
  • Ultra high-performance liquid chromatography (UHPLC)

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