Characterization of flavone and flavonol aglycones by collision-induced dissociation tandem mass spectrometry

L., Y.; Li, Q. M.; Heuvel, H. van den; Claeys, Magda

doi:10.1002/(sici)1097-0231(199708)11:12<1357::aid-rcm983>3.0.co;2-9

Cited by 368 publications

(332 citation statements)

References 10 publications

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“…Upon evaluating the MRM transitions corresponding to the 287xxx the results indicates (see Figure S5) that most likely more than 10 cyanidin containing compounds are present in the red onion sample. Peak nr 3,5,6,8,10,14,15,17,20,21,27,29,34,35, and 39 (see Figure S5), all show MRM patterns that are similar to the cyanidin standards that were analyzed in this study. The peak in Figure S5 with a retention time of 24.3 min (compound 10) has a retention time close to one of the available standards, Cy-3-rut entry 9 in Table 3, however, method 2 indicates that m/z 611 is the parent ion and not m/z 595.…”

Section: Plant Extractsmentioning

confidence: 54%

“…The flavonoids in Table 1 are grouped based on nominal mass of the positive ion, starting with m/z 271 followed by 287, 291, 301, 303, 317 and 331. As can be seen in Table 1 many MRM transitions are not unique for a particular aglycone, for example the transition 271/121 could be generated from cleavage of the C-ring at bound 0 and 2 producing the same [26] which was further developed by Ma et al [27] At the end of Table 1 a list of identical MRM transition numbers could be found. Further, detailed data from the standards is shown in Table 1.…”

Section: Resultsmentioning

confidence: 99%

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Strategies for differentiation of isobaric flavonoids using liquid chromatography coupled to electrospray ionization mass spectrometry

Fridén

Sjöberg

2014

J. Mass Spectrom.

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Flavonoids are a class of secondary plant metabolites existing in great variety. Due to this variety identification can be difficult, especially as overlapping compounds in both chromatographic separations and mass spectrometric detection are common. Methods for distinguishing isobaric flavonoids using MS 2 Additional supporting information may be found in the online version of this article at the publisher's web site.3

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Section: Plant Extractsmentioning

confidence: 54%

Section: Resultsmentioning

confidence: 99%

Strategies for differentiation of isobaric flavonoids using liquid chromatography coupled to electrospray ionization mass spectrometry

Fridén

Sjöberg

2014

J. Mass Spectrom.

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“…loss for each first product ion is noted in D. For phenylcoumarans and resinols, the pathway II first product ions are specified by superscripts indicating the bonds that are cleaved. This numbering system has been suggested previously to annotate the first product ions upon CID of flavonoids (Ma et al, 1997;Fabre et al, 2001;Morreel et al, 2006) and upon CID of oligosaccharides (Domon and Costello, 1988). Most first product ions are due to charge-driven fragmentations in which the charge center initiates the dissociation, yet the pathway I-associated formaldehyde loss upon CID of b-aryl ethers as well as the pathway I-associated methyl radical loss upon CID of phenylcoumarans and resinols are examples of charge-remote fragmentations (i.e.…”

Section: Characteristic Fragmentations Of Lignin Interunit Linkage Typesmentioning

confidence: 99%

Mass Spectrometry-Based Sequencing of Lignin Oligomers

Morreel

Dima²,

Kim³

et al. 2010

Plant Physiol.

171

213

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Although the primary structure of proteins, nucleic acids, and carbohydrates can be readily determined, no sequencing method has been described yet for the second most abundant biopolymer on earth (i.e. lignin). Within secondary-thickened plant cell walls, lignin forms an aromatic mesh arising from the combinatorial radical-radical coupling of monolignols and many other less abundant monomers. This polymerization process leads to a plethora of units and linkage types that affect the physicochemical characteristics of the cell wall. Current methods to analyze the lignin structure focus only on the frequency of the major monomeric units and interunit linkage types but do not provide information on the presence of less abundant unknown units and linkage types, nor on how linkages affect the formation of neighboring linkages. Such information can only be obtained using a sequencing approach. Here, we describe, to our knowledge for the first time, a sequencing strategy for lignin oligomers using mass spectrometry. This strategy was then evaluated on the oligomers extracted from wild-type poplar (Populus tremula 3 Populus tremuloides) xylem. In total, 134 lignin trimers to hexamers were observed, of which 36 could be completely sequenced. Interestingly, based on molecular mass data of the unknown monomeric and dimeric substructures, at least 10 unknown monomeric units or interunit linkage types were observed, one of which was identified as an arylglycerol end unit.Lignin is an aromatic heteropolymer that is mainly present in secondary-thickened plant cell walls, allowing the transport of water and nutrients and providing the necessary strength for the plant to grow upwardly Vanholme et al., 2008Vanholme et al., , 2010. In angiosperms, lignin is predominantly composed of guaiacyl (G) and syringyl (S) units that are derived from combinatorial radical-radical coupling of the monolignols coniferyl and sinapyl alcohol, respectively Fig. 1A). Following oxidation of the monolignols by peroxidase and/or laccase, the resulting electron-delocalized radical has unpaired electron density at its 1-, 3-, O-4-, 5-, and 8-positions (Fig. 1B); note that much of the lignin literature uses Greek letters for the side chain, a, b, and g for the 7-, 8-, and 9-positions. As radical coupling at the 8-position is favored, coupling with another monolignol radical affords, after rearomatization, a mixture of dehydrodimers with 8-8-, 8-5-, and 8-O-4-linkages (Fig. 1C). Following dimerization, polymerization will continue by the coupling of the 8-position of an incoming monolignol radical to the O-4-position of the dimer's phenolic end. In the case of a G dimer, coupling can also occur, albeit at a lower frequency, to the 5-position. Thus, chain elongation creates 8-5-and 8-O-4-linkages (Adler, 1977). Besides the monolignols and other monomers that are present in minor amounts , the plasticity of lignin polymerization permits the incorporation of any phenolic that enters the lignification site, subject to its chemical cross-coupling propensit...

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“…Several groups have reported characterization of flavonoids by electron ionization (EI) [6 -10] or fast atom bombardment (FAB) mass spectrometry [7,[11][12][13][14][15][16][17][18][19]. More recently, electrospray ionization (ESI) [19 -29], atmospheric pressure chemical ionization (APCI) [27][28][29][30][31], and matrix-assisted laser desorption ionization (MALDI) [32,33] have been used to analyze flavonoids, typically in conjunction with tandem mass spectrometry (MS/MS) or high-performance liquid chromatography (HPLC).…”

mentioning

confidence: 99%

“…The fragmentation pathways of flavonoid aglycons obtained by tandem mass spectrometry have been well-documented [13,22,23,27,50]. In addition, commonly encountered diglycosyl flavonoids can often be distinguished by their fragmentation path-ways [14,18,20,51,52].…”

mentioning

confidence: 99%

Determination of the glycosylation site of flavonoid monoglucosides by metal complexation and tandem mass spectrometry

Davis

Brodbelt

2004

J. Am. Soc. Mass Spectrom.

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Metal complexation and tandem mass spectrometry were used to differentiate C-and O-bonded flavonoid monoglucoside isomers. Electrospray ionization of solutions containing a flavonoid glycoside and a metal salt led to the generation of the key [M(II) (L) (L-H)] ϩ complexes, where M is the metal ion and L is the flavonoid glycoside. Thirteen flavonoid monoglucosides were examined in combination with Ca(II), Mg(II), Co(II), Ni(II), and Cu(II). Collisional activated dissociation (CAD) of the [M(II) (L) (L-H)] ϩ complexes resulted in diagnostic mass spectra, in contrast to the CAD mass spectra of the protonated, deprotonated, and sodium-cationized flavonoid glucosides. Five common sites of glycosylation could be predicted based on the fragmentation patterns of the flavonoid glucoside/magnesium complexes, while flavonoid glucoside/calcium complexes also were effective for location of the glycosylation site when MS 3 was employed. Cobalt, nickel and copper complexation had only limited success in this application. The metal complexation methods were also applied for characterization of a flavonoid rhamnoside, and the dissociation pathways of the metal complexes indicate that flavonoid rhamnosides have distinctive dissociation features from flavonoid glucosides. (J Am Soc Mass Spectrom 2004, 15, 1287-1299

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Characterization of flavone and flavonol aglycones by collision-induced dissociation tandem mass spectrometry

Cited by 368 publications

References 10 publications

Strategies for differentiation of isobaric flavonoids using liquid chromatography coupled to electrospray ionization mass spectrometry

Strategies for differentiation of isobaric flavonoids using liquid chromatography coupled to electrospray ionization mass spectrometry

Mass Spectrometry-Based Sequencing of Lignin Oligomers

Determination of the glycosylation site of flavonoid monoglucosides by metal complexation and tandem mass spectrometry

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