Spektrometria mas niskocząsteczkowych związków fenolowych pochodzenia naturalnego
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2017
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Mass spectrometry of low molecular weight phenolic compounds of natural origin
Abstract
Celem przedstawionej pracy doktorskiej było pogłębienie wiedzy na temat przebiegu procesu jonizacji metodą elekrorozpraszania dla szeregu produktów naturalnych. Bardziej precyzyjne poznanie mechanizmów jonizacji oraz udziału w niej innych związków chemicznych, obecnych w skomplikowanych mieszaninach pochodzenia naturalnego, może pomóc w określeniu możliwości wykorzystania spektrometrii mas do analizy jakościowej związków pochodzenia naturalnego. Obiektem badań przygotowanej rozprawy doktorskiej są wybrane niskocząsteczkowe związki fenolowe: kwasy i aldehydy fenolowe, kurkuminoidy oraz dehydrodimery i cyklodimery kwasu ferulowego, a także próbki ekstraktów roślinnych zawierających te związki.
W rozprawie zostały przedstawione wyniki prac nad przebiegiem procesu jonizacji metodą rozpraszania standardów aldehydów i kwasów fenolowych, omówiony został udział jonów metali alkalicznych w procesie jonizacji i tworzeniu klasterów oraz adduktów dla tych cząsteczek. Badano próbki ekstraktów roślinnych pod kątem identyfikacji kwasów w tym materiale.
Przeprowadzono również serię analiz stechiometrii jonów kompleksowych tworzonych przez kurkuminoidy z jonami żelaza.
W kolejnej części pracy analizowano próbki zawierające dehydrodimery oraz cyklodimery butanowe kwasu ferulowego. Zastosowano metodę LC/MS oraz LC/MS/MS, w celu poznania struktur izomerów powyższych związków. Dzięki wykorzystaniu spektrometrii mobilności jonów pokazano, że taka strategia badawcza pozwala wyeliminować obserwowany problem koelucji związków.
The aim of this PhD thesis was to improve knowledge about the electrospray ionization process for a number of natural products commonly found in nature. A more precise understanding of the mechanisms of ionization and participation in this process of other chemical compounds presented in complex mixtures of biological origin would help to determine the possibility of using mass spectrometry for the qualitative analysis of compounds of natural origin. The objects of the study of the presented dissertation are selected low molecular weight phenolic compounds: phenolic aldehydes and acids, curcuminoids, cyclo- and dehydrodimers of ferulic acid and also samples of the extracts of different plant species containing these compounds. In this thesis the results of research conducted on the electrospray ionization process of standards of phenolic aldehydes and acids were presented. Formation of alkali metals ions (adducts and clusters) for these molecules was also discussed. Analyses of samples of plant extracts for identification of phenolic acids were also done. Analyses of stoichiometry of complex ions formed by curcuminoids and iron ions were conducted. In the next part of the dissertation analyses of cyclo- and dehydrodimes of ferulic acid were carried out. To identify the structures of dimes LC/MS and LC/MS/MS methods were applied. By using ion mobility spectrometry, I was able to show that this experimental strategy can eliminate coelution problem observed in earlier analysis.
The aim of this PhD thesis was to improve knowledge about the electrospray ionization process for a number of natural products commonly found in nature. A more precise understanding of the mechanisms of ionization and participation in this process of other chemical compounds presented in complex mixtures of biological origin would help to determine the possibility of using mass spectrometry for the qualitative analysis of compounds of natural origin. The objects of the study of the presented dissertation are selected low molecular weight phenolic compounds: phenolic aldehydes and acids, curcuminoids, cyclo- and dehydrodimers of ferulic acid and also samples of the extracts of different plant species containing these compounds. In this thesis the results of research conducted on the electrospray ionization process of standards of phenolic aldehydes and acids were presented. Formation of alkali metals ions (adducts and clusters) for these molecules was also discussed. Analyses of samples of plant extracts for identification of phenolic acids were also done. Analyses of stoichiometry of complex ions formed by curcuminoids and iron ions were conducted. In the next part of the dissertation analyses of cyclo- and dehydrodimes of ferulic acid were carried out. To identify the structures of dimes LC/MS and LC/MS/MS methods were applied. By using ion mobility spectrometry, I was able to show that this experimental strategy can eliminate coelution problem observed in earlier analysis.
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Wydział Chemii
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Keywords
chemia, chemistry, spektrometria mas, mass spectrometry, związki fenolowe, phenolic compounds, produkty naturalne, natural products, chromatografia, chromatography