The Use of Mass Spectrometric Techniques to Differentiate Isobaric and Isomeric Flavonoid Conjugates from Axyris amaranthoides
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...
| Main Authors: | , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2016-09-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | http://www.mdpi.com/1420-3049/21/9/1229 |
| _version_ | 1819094313027502080 |
|---|---|
| author | Łukasz Marczak Paulina Znajdek-Awiżeń Wiesława Bylka |
| author_facet | Łukasz Marczak Paulina Znajdek-Awiżeń Wiesława Bylka |
| author_sort | Łukasz Marczak |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-21T23:25:25Z |
| format | Article |
| id | doaj.art-51d3e63cc279458196cb7dd71958e765 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-21T23:25:25Z |
| publishDate | 2016-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-51d3e63cc279458196cb7dd71958e7652022-12-21T18:46:39ZengMDPI AGMolecules1420-30492016-09-01219122910.3390/molecules21091229molecules21091229The Use of Mass Spectrometric Techniques to Differentiate Isobaric and Isomeric Flavonoid Conjugates from Axyris amaranthoidesŁukasz Marczak0Paulina Znajdek-Awiżeń1Wiesława Bylka2European Centre for Bioinformatics and Genomics, Institute of Bioorganic Chemistry, Polish Academy of Sciences, Noskowskiego 12/14, 61-704 Poznan, PolandDepartment of Pharmacognosy, Poznan University of Medical Sciences, Świecickiego 4, 60-781 Poznan, PolandDepartment of Pharmacognosy, Poznan University of Medical Sciences, Świecickiego 4, 60-781 Poznan, PolandFlavonoids 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.http://www.mdpi.com/1420-3049/21/9/1229collision-induced dissociationelectrosprayflavonoid conjugatesAxyris amaranthoidestandem mass spectrometryfragmentation spectraisomeric compoundsisobaric compounds |
| spellingShingle | Łukasz Marczak Paulina Znajdek-Awiżeń Wiesława Bylka The Use of Mass Spectrometric Techniques to Differentiate Isobaric and Isomeric Flavonoid Conjugates from Axyris amaranthoides Molecules collision-induced dissociation electrospray flavonoid conjugates Axyris amaranthoides tandem mass spectrometry fragmentation spectra isomeric compounds isobaric compounds |
| title | The Use of Mass Spectrometric Techniques to Differentiate Isobaric and Isomeric Flavonoid Conjugates from Axyris amaranthoides |
| title_full | The Use of Mass Spectrometric Techniques to Differentiate Isobaric and Isomeric Flavonoid Conjugates from Axyris amaranthoides |
| title_fullStr | The Use of Mass Spectrometric Techniques to Differentiate Isobaric and Isomeric Flavonoid Conjugates from Axyris amaranthoides |
| title_full_unstemmed | The Use of Mass Spectrometric Techniques to Differentiate Isobaric and Isomeric Flavonoid Conjugates from Axyris amaranthoides |
| title_short | The Use of Mass Spectrometric Techniques to Differentiate Isobaric and Isomeric Flavonoid Conjugates from Axyris amaranthoides |
| title_sort | use of mass spectrometric techniques to differentiate isobaric and isomeric flavonoid conjugates from axyris amaranthoides |
| topic | collision-induced dissociation electrospray flavonoid conjugates Axyris amaranthoides tandem mass spectrometry fragmentation spectra isomeric compounds isobaric compounds |
| url | http://www.mdpi.com/1420-3049/21/9/1229 |
| work_keys_str_mv | AT łukaszmarczak theuseofmassspectrometrictechniquestodifferentiateisobaricandisomericflavonoidconjugatesfromaxyrisamaranthoides AT paulinaznajdekawizen theuseofmassspectrometrictechniquestodifferentiateisobaricandisomericflavonoidconjugatesfromaxyrisamaranthoides AT wiesławabylka theuseofmassspectrometrictechniquestodifferentiateisobaricandisomericflavonoidconjugatesfromaxyrisamaranthoides AT łukaszmarczak useofmassspectrometrictechniquestodifferentiateisobaricandisomericflavonoidconjugatesfromaxyrisamaranthoides AT paulinaznajdekawizen useofmassspectrometrictechniquestodifferentiateisobaricandisomericflavonoidconjugatesfromaxyrisamaranthoides AT wiesławabylka useofmassspectrometrictechniquestodifferentiateisobaricandisomericflavonoidconjugatesfromaxyrisamaranthoides |