The application of liquid chromatography-electrospray ionization mass spectrometry and collision-induced dissociation in the structural characterization of acylated flavonol O-glycosides from the seeds of Carrichtera annua
| Autor: | Filip Cuyckens, Hilde Van den Heuvel, Magda Claeys, Medhat M. Seif-El Nasr, Luc Pieters, Moustafa M. El-Messiry, Arnold J. Vlietinck, Khaled A. Abdel-Shafeek, Abdelaaty A. Shahat |
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| Rok vydání: | 2003 |
| Předmět: |
Spectrometry
Mass Electrospray Ionization Magnetic Resonance Spectroscopy Protein mass spectrometry Collision-induced dissociation Electrospray ionization Acylation Atmospheric-pressure chemical ionization 010402 general chemistry Tandem mass spectrometry Mass spectrometry 01 natural sciences Sample preparation in mass spectrometry Glycosides Spectroscopy Flavonoids Chromatography Molecular Structure Chemistry 010401 analytical chemistry Extractive electrospray ionization General Medicine Atomic and Molecular Physics and Optics 0104 chemical sciences Brassicaceae Seeds Chromatography Liquid |
| Zdroj: | European journal of mass spectrometry |
| ISSN: | 1469-0667 |
| Popis: | The flavonoid fraction from the seeds of Carrichtera annua was studied using high-performance liquid chromatography simultaneously coupled to a photodiode array detector (LC/UV-DAD) and a mass spectrometer equipped with an electrospray source (LC/ESI-MS). Collision-induced dissociation (CID) mass spectral data obtained off-line by nanospray (nano-ESI) analysis provided a wealth of complementary structural information, which was consistent with structures established by NMR or led to the proposal of base structures of the flavonol O-glycosides present in the Carrichtera annua seed extract. The flavonoid fraction was found to contain 12 structurally related flavonol O-glycosides. Eleven flavonoids, of which several were new compounds, were acylated with one or more benzoyl, feruloyl or sinapoyl groups. These acyl groups gave rise to characteristic product ions in the [M + H]+ and [M + Na]+ CID spectra as well as to radicalar acid-related product ions at high-energy collisional activation. In addition to the characterization of the acyl substituents, the mass spectral data allowed the identification of the aglycone, the determination of the base structure and the differentiation of several positional isomers. |
| Databáze: | OpenAIRE |
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