Tandem mass spectrometric analysis of a complex triterpene saponin mixture of Chenopodium quinoa

  • Tobias Mad
  • Heinz Sterk
  • Martin Mittelbach
  • Gerald N. Rechberger
Articles

DOI: 10.1016/j.jasms.2006.02.013

Cite this article as:
Mad, T., Sterk, H., Mittelbach, M. et al. J Am Soc Mass Spectrom (2006) 17: 795. doi:10.1016/j.jasms.2006.02.013

Abstract

A nano-HPLC electrospray ionization multi-stage tandem mass spectrometry (nLC-ESI-MS/MS) approach was applied to a complex crude triterpene saponin extract of Chenopodium quinoa seed coats. In ESI-MS/MS spectra of triterpene saponins, characteristic fragmentation reactions are observed and allow the determination of aglycones, saccharide sequences, compositions, and branching. Fragmentation of aglycones provided further structural information. The chemical complexity of the mixture was resolved by a complete profiling. Eighty-seven triterpene saponins comprising 19 reported and 68 novel components were identified and studied by MS. In addition to four reported, five novel triterpene aglycones were detected and characterized according to their fragmentation reactions in ESI-MS/MS and electron ionization mass spectrometry (EI-MS). As a novelty fragmentation pathways were proposed and analyzed based upon quantum chemical calculations using a hybrid Hartree-Fock density functional method. Accuracy of the assignment procedure was proven by isolation and structure determination of a novel compound. As the relative distribution and composition of saponins varies between different cultivars and soils, the presented strategy allows a rapid and complete analysis of Chenopodium quinoa saponin distribution and composition, and is particularly suitable for quality control and screening of extracts designated for pharmaceutical, agricultural, and industrial applications.

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Copyright information

© American Society for Mass Spectrometry 2006

Authors and Affiliations

  • Tobias Mad
    • 1
  • Heinz Sterk
    • 1
  • Martin Mittelbach
    • 1
  • Gerald N. Rechberger
    • 2
  1. 1.Department of Organic and Bioorganic Chemistry, Institute of ChemistryKarl Franzens University GrazGrazAustria
  2. 2.Institute of Molecular BiosciencesKarl Franzens UniversityGrazAustria

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