Chromatographia

, Volume 78, Issue 19–20, pp 1233–1243 | Cite as

Study of Electrochemical Oxidation of Xanthohumol by Ultra-Performance Liquid Chromatography Coupled to High Resolution Tandem Mass Spectrometry and Ion Mobility Mass Spectrometry

  • Luís F. Guido
  • Daniel O. Carvalho
  • Jakub Taborsky
  • Jana Skopalova
  • Helena M. E. B. Saldanha
  • Petr Bednar
Original

Abstract

Electrochemically assisted oxidation off-line combined with UPLC/ESI–MS and ion mobility mass spectrometry enabled us to gain insight into the oxidation mechanisms of xanthohumol. Several types of monomeric oxidation products were identified, i.e., monohydroxylated and dehydrogenated derivatives and related quinones. Besides, high contents of dimers were observed. The structures of four main oxidative condensation products of two xanthohumol molecules were proposed based on combination of retention time, exact mass measurement, fragmentation pattern, data from on-line ion mobility mass spectrometric experiments and with the support of independent electrochemical experiments. To the best of our knowledge, this is the first evidence on formation of xanthohumol dimers. The effect of the pH on the generation of oxidation products was further investigated. The monomeric and dimeric oxidation products are favored at pH of 5.5 and 4.5, respectively.

Keywords

Ultra-performance liquid chromatography Mass spectrometry Ion mobility Xanthohumol Prenylchalcone Oxidation Dimer 

Notes

Acknowledgments

This work received financial support from the European Union (FEDER funds) under the framework of QREN through Project NORTE-07-0124-FEDER-000069). LFG wishes to thank Foundation for Science and Technology (FCT) for his Sabbatical Leave Grant (SFRH/BSAB/1272/2012). DOC wishes to acknowledge FCT for his Ph.D. studentship (SFRH/BD/79939/2011). Authors thank to the project of Ministry of Education, Youth and Sports (Project LO1305), European Social Fund OP—Education for Competitiveness (Project CZ.1.07/2.3.00/30.0041) and Grant Agency of Czech Republic (Project P206/12/1150).

Compliance with ethical standards

Conflict of interest

All authors declare no conflict of interest regarding the present work.

Supplementary material

10337_2015_2954_MOESM1_ESM.pdf (257 kb)
Supplementary material 1 (PDF 258 kb)

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Copyright information

© Springer-Verlag Berlin Heidelberg 2015

Authors and Affiliations

  • Luís F. Guido
    • 1
    • 2
  • Daniel O. Carvalho
    • 2
  • Jakub Taborsky
    • 1
  • Jana Skopalova
    • 1
  • Helena M. E. B. Saldanha
    • 1
  • Petr Bednar
    • 1
  1. 1.Regional Centre of Advanced Technologies and Materials, Department of Analytical Chemistry, Faculty of SciencePalacky UniversityOlomoucCzech Republic
  2. 2.REQUIMTE - Departamento de Química e Bioquímica, Faculdade de CiênciasUniversidade do PortoPortoPortugal

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