FAPA mass spectrometry of hydroxychalcones. Comparative studies with classical methods of ionization

Authors

  • Marek Smoluch AGH University of Science and Technology, Department of Biochemistry and Neurobiology, Faculty of Materials Science and Ceramics, Mickiewicza 30, 30-059 Cracow, Poland Author
  • Grazyna Bartkowiak Adam Mickiewicz University in Poznań, Faculty of Chemistry, Umultowska 89b, 61-614 Poznan, Poland Author
  • Edward Reszke ERTEC-Poland, Rogowska 146/5, 54-440 Wroclaw, Poland Author
  • Wojciech Lechowicz Institute of Forensic Research, Westerplatte 9, 31-033 Cracow, Poland Author
  • Jerzy Silberring AGH University of Science and Technology, Department of Biochemistry and Neurobiology, Faculty of Materials Science and Ceramics, Mickiewicza 30, 30-059 Cracow, Poland / Centre of Polymer and Carbon Materials, Polish Academy of Sciences, Curie-Sklodowskiej 34, 41-819 Zabrze, Poland Author
  • Grzegorz Schroeder Adam Mickiewicz University in Poznań, Faculty of Chemistry, Umultowska 89b, 61-614 Poznan, Poland Author

DOI:

https://doi.org/10.2478/cipms-2014-0008

Keywords:

mass spectrometry, hydroxychalcones, FAPA

Abstract

In this paper we are focused on analysis of hydroxychalcones, i.e. 2’ –hydroxychalcone, 3’ –hydroxychalcone and 4’ –hydroxychalcone, by the Flowing Atmospheric Pressure Afterglow mass spectrometry (FAPA-MS), and on comparison of the obtained data with other classical methods including ESI-MS, APCI, MALDI, and GC/EI-MS. The paper is presenting fragmentation pathways of both positive-, and negative hydroxychalcone ions. Tested compounds were characterized by comparison of the results (signals m/z and relative intensities) from the five mass spectrometry techniques, showing very good utility of FAPA method for fast and easy analysis of the low molecular weight compounds. Moreover, FAPA does not require a time-consuming derivatization, nor search for a suitable solvent or matrix, often incompatible with various ion sources. 

References

1. S. Alam, S. Mostahar. Studies of Antimicrobial Activity of two Synthetic 2’,4’,6’-trioxygenated Flavones. J. Applied Sci. 2005, 5, 327-333.

2. J. R. Dimmock, D. W. Elias, M. A. Beazely, N. M. Kandepu. Bioactivities of chalcones. Curr Med Chem. 1999, 6, 1125-49.

3. P. M. Sivakumar, T. Muthu Kumar, M. Doble. Antifungal activity, mechanism and QSAR studies on chalcones. Chem Biol Drug Des. 2009, 74, 68-79.

4. S. J. Won, C. T. Liu, L. T. Tsao, J. R. Weng, H. H. Ko, J. P. Wang, C. N. Lin. Synthetic chalcones as potential anti-inflammatory and cancer chemopreventive agents. Eur. J. Med. Chem. 2005, 40, 103-12.

5. E. C. Amor, I. M. Villaseñor, M. N. Ghayur, A. H. Gilani, M.I.Choudhary. Spasmolytic flavonoids from Syzygium samarangense (Blume) Merr. & L.M. Perry. Z Naturforsch C. 2005, 60, 67-71.

6. J. B. Daskiewicz, F. Depeint, L. Viornery, C. Bayet, G. Comte- Sarrazin, G. Comte, J. M. Gee, I. T. Johnson, K. Ndjoko, K.Hostettmann, D. Barron. Effects of Flavonoids on Cell Proliferation and Caspase Activation in a Human Colonic Cell Line HT29: An SAR Study. J. Med. Chem. 2005, 48, 2790-2804.

7. F. J. Andrade, J. T. Shelley, W. C. Wetzel, M. R. Webb, G. Gamez, S. J. Ray, G.M. Hieftje. Atmospheric Pressure Chemical Ionization Source. 2. Desorption-Ionization for the Direct Analysis of Solid Compounds. Anal. Chem. 2008, 80, 2654-2663.

8. M. Smoluch, K. Labuz, E. Reszke, A. Ramsza, K. Labuz, J. Silberring.Direct analysis of methcathinone from crude reaction mixture by flowing atmospheric-pressure afterglow mass spectrometry. Rapid Commun. Mass Spectrom. 2012, 26, 1577-1580.

9. M. Smoluch, E. Reszke, A. Ramsza, J. Silberring. Development of a novel ambient glow discharge plasma source for direct analysis of organic compounds. In: Biomacromolecular Mass Spectrometry: Tips from the Bench (S. König, ed.) Nova Science Publ. 2012, ISBN: 978-1-62081-933-3.

10. Y. Tai, S. Pei, J. Wan, X. Cao, Y. Pan. Fragmentation study of protonated chalcones by atmospheric pressure chemical ionization and tandem mass spectrometry. Rapid Commun. Mass Spectrom. 2006, 20, 994-1000.

11. J. Zhang, J. S. Brodbelt. Structural characterization and isomer differentiation of chalcones by electrospray ionization tandem mass spectrometry. J Mass Spectrom. 2003, 38, 555-72.

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Published

2014-05-30