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Molecules 2016, 21(9), 1229; doi:10.3390/molecules21091229

The Use of Mass Spectrometric Techniques to Differentiate Isobaric and Isomeric Flavonoid Conjugates from Axyris amaranthoides

1
European Centre for Bioinformatics and Genomics, Institute of Bioorganic Chemistry, Polish Academy of Sciences, Noskowskiego 12/14, 61-704 Poznan, Poland
2
Department of Pharmacognosy, Poznan University of Medical Sciences, Świecickiego 4, 60-781 Poznan, Poland
*
Author to whom correspondence should be addressed.
Academic Editors: Arturo San Feliciano and Celestino Santos-Buelga
Received: 27 July 2016 / Revised: 1 September 2016 / Accepted: 8 September 2016 / Published: 19 September 2016
(This article belongs to the Special Issue Flavonoids: From Structure to Health Issues)
View Full-Text   |   Download PDF [2026 KB, uploaded 19 September 2016]   |  

Abstract

Flavonoids are a group of compounds that are commonly found in various plants, where they play important roles in many processes, including free radical scavenging and UV protection. These compounds can also act as chemical messengers, physiological regulators or protectants against pathogens in the defense reactions of plants. Flavonoid activity is regulated by the addition of various substituents, usually mono- or oligosaccharides of common sugars, such as glucose, rhamnose or galactose. In some plants, glucuronic acid is attached, and this sugar is often acylated by phenylpropanoic acids. Identification of these compounds and their derivatives is of great importance to understanding their role in plant metabolism and defense mechanisms; this research is important because flavonoids are frequently a significant constituent of the human diet. In this study, we identify the flavonoid conjugates present in Axyris amaranthoides L. extracts and demonstrate the usefulness of high-resolution mass spectrometry (HRMS) analyzers for the differentiation of isobaric compounds and the utility of fragmentation spectra for the differentiation of isomeric structures. According to our knowledge, some of the structures, especially dehydrodiferulated conjugates of tricin, whose structures are proposed here have been found for the first time in plant material. View Full-Text
Keywords: collision-induced dissociation; electrospray; flavonoid conjugates; Axyris amaranthoides; tandem mass spectrometry; fragmentation spectra; isomeric compounds; isobaric compounds collision-induced dissociation; electrospray; flavonoid conjugates; Axyris amaranthoides; tandem mass spectrometry; fragmentation spectra; isomeric compounds; isobaric compounds
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Marczak, Ł.; Znajdek-Awiżeń, P.; Bylka, W. The Use of Mass Spectrometric Techniques to Differentiate Isobaric and Isomeric Flavonoid Conjugates from Axyris amaranthoides. Molecules 2016, 21, 1229.

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