Mass Spectrometrical Analysis of Flavonoids and Glucose Esters of Hydroxycinnamic Acids in Dietary Plants

  • The present work describes the development and use of various mass spectrometry-based analytical tools for the investigation of particular members of the two most prominent classes of polyphenols, namely flavonoids and hydroxycinnamic acids in dietary plant of great economical importance. The first part is dedicated to the investigation of the polyphenolic fraction of cocoa. Both top down and a bottom up approaches were used in the investigation. In the top down approach, methanolic extracts of raw fermented cocoa beans from different origins were analyzed for the first time in literature by Fourier transform ion cyclotron resonance mass spectrometry (FTICR-MS. With approximately 11 000 peaks, cocoa was shown to be one of the most complex organic mixtures ever analyzed. In the bottom up approach, the methanolic extracts were analyzed by HPLC-MSn. The optimized method revealed a greater extract complexity than previously reported and allowed the identification of novel compounds. The second part is dedicated to the investigation of glycosylated derivatives of hydroxycinnamic acids, with particular emphasis on hydroxycinnamoylglucose esters. Authentic reference standards of hydroxycinnamoyl glucoses were selectively synthesized and subsequently used to develop a hierarchical HPLC-MSn scheme for the identification of all ten regioisomeric esters. Different edible plant sources of great economical relevance, including berries and Solanaceae vegetables, were analyzed qualitatively and quantitatively for their hydroxycinnamoyl glucose contents. Furthermore, a quantitative HPLC-MS method was developed and validated using authentic reference standards and applied to over fourty different samples, thus providing the first set of quantitative data ever reported for this class of compounds. The third part of the present work was dedicated to the in-depth study of the fragmentation mechanism of D-glucose, employing all 13C and all 2H labeled isotopomers.

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Publishing Institution:IRC-Library, Information Resource Center der Jacobs University Bremen
Granting Institution:Jacobs Univ.
Author:Maria Alexandra Patras
Referee:Matthias Ullrich, Ulrich Engelhardt
Advisor:Nikolai Kuhnert
Persistent Identifier (URN):urn:nbn:de:gbv:579-opus-1008158
Document Type:PhD Thesis
Date of Successful Oral Defense:2018/04/12
Date of First Publication:2018/08/23
Academic Department:Life Sciences & Chemistry
PhD Degree:Chemistry
Focus Area:Health
Call No:2018/16

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