Mass spectrometry of underivatized naturally occurring glycosides

Wolfender, Jean‐Luc; Maillard, Marc; Marston, Andrew; Hostettmann, Kurt

doi:10.1002/pca.2800030502

Cited by 61 publications

(43 citation statements)

References 126 publications

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“…For example, the product ion of the base peak in MS 2 The production-ion tag with " " represents the precursor ion of the next stage MS; the production-ion tag with " & " represents the product ions of the precursor ion. …”

Section: Structural Characterization Of Target Compound In F Aurantimentioning

confidence: 99%

“…Therefore, they have been extensively investigated in the past and during the recent years by MS coupled to a soft ionization-source such as APCI and ESI. The publications using MS to study flavonoids focused on the three following aspects: first, most publications deal with glycosides studied for determining (i) the types of carbohydrates present (mono-, di-, tri-, or tetrasaccharides and hexoses, deoxyhexoses, or pentoses) [2]; (ii) the stereochemistry of terminal monosaccharide units [3]; (iii) the sequence of the glycan part [4]; (iv) the interglycosidic linkages [5 -7]; and (v) the glycosylation position [8]. Secondly, some publications deal with flavonoid aglycones for structural elucidation [9 -11].…”

Section: Introductionmentioning

confidence: 99%

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Rapid qualitative and quantitative analyses of flavanone aglycones in Fructus aurantii by HPLC ion‐trap MS

Zhou

Xue

et al. 2007

J of Separation Science

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IT-MS operated in the positive mode was applied for the rapid characterization/quantification of the flavanones in extracts from Fructus aurantii. APCI-MS and CID MS/MS provide unequivocal molecular weight (MW) data of these compounds and useful information about their structures (diagnostic fragment ions). Main fragment pathways include neutral losses of H2O, C2H2O, and B-ring as well as a retro-Diels-Alder (RDA) fragment giving rise to [1,3A + H], [1,3B+H]+, and [1,4B-H2 + H]+ ions, which form the characteristic MS/MS "fingerprint" of flavanone aglycones. When screening extracts of F. aurantii for flavanone aglycones, eight target compounds were characterized using this fingerprint. Meanwhile, ESI-MS in full-scan mode was developed and validated for the quantification of the main flavanone aglycones in F. aurantii. This method is simple, accurate, fast and requires only 16 min per sample for direct detection and quantification of naringenin and hesperetin. All the results and these characteristic fragments showed that the IT-MS is a powerful tool for the structural characterization and quantitative determination offlavanone aglycones.

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Section: Structural Characterization Of Target Compound In F Aurantimentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Rapid qualitative and quantitative analyses of flavanone aglycones in Fructus aurantii by HPLC ion‐trap MS

Zhou

Xue

et al. 2007

J of Separation Science

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“…A careful study of the fragmentation patterns in CID MS/ MS can also be of particular value in the structural elucidation of O-and C-glycosides. 15 With regard to the structural characterization of flavonoid glycosides with MS methods, information can be obtained on several structural features including the aglycone part, [16][17][18] the nature of carbohydrates present, 19 the stereochemistry of terminal monosaccharide units, 20 the site of attachment and the sequence of the glycan part, 10,21,22 and the interglycosidic linkages. 23,24 Since the number of known flavonoid compounds is steadily increasing, and in order to further increase the applicability of LC/ESI-MS/MS in the analysis of plant phenolics, it appeared important to investigate the fragmentation pathways of new flavonoids in order to correlate the structures with their fragmentation patterns, thus facilitating the rapid identification and analysis of flavonoids.…”

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confidence: 99%

Application of positive and negative electrospray ionization, collision‐induced dissociation and tandem mass spectrometry to a study of the fragmentation of 6‐hydroxyluteolin 7‐O‐glucoside and 7‐O‐glucosyl‐(1 → 3)‐glucoside

Es‐Safi

Kerhoas

Ducrot

2005

Rapid Comm Mass Spectrometry

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Mass spectrometric methodology based on the combined use of positive and negative electrospray ionization, collision-induced dissociation (CID) and tandem mass spectrometry (MS/MS) has been applied to the structural characterization of 6-hydroxyluteolin 7-O-glucoside and 7-O-glucosyl-(1 --> 3)-glucoside. In-source fragmentation of both glycosides at an increased potential yielded the protonated and deprotonated aglycone, allowing CID spectra to be obtained. The differentiation between quercetin and 6-hydroxyluteolin aglycones was achieved by product ion analysis of the protonated and deprotonated aglycone (m/z 303 and 301), that showed the characteristic product ions (1,3)A at m/z 151 and 153 for quercetin, and m/z 167 and 169 for 6-hydroxyluteolin, consistent with the trihydroxylated A-ring skeleton. In the negative ion mode both glycosides were shown to undergo collision-induced homolytic and heterolytic cleavages of the O-glycosidic bond producing the aglycone radical-anion [Y0-H]-* and Y0(-) product ions. At lower collision energy, various fragmentations involving the glucose moieties were observed with a relatively higher abundance for the monoglucoside compared to the diglucoside. In the latter case both the inner and the terminal glucose residues were involved in the fragmentations, giving useful information on the 1 --> 3 interglycosidic linkage. CID MS/MS analysis of the sodiated molecules gave complementary information for the structural characterization of the studied compounds. Fragmentation mechanisms are proposed for the observed product ions.

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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%

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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Mass spectrometry of underivatized naturally occurring glycosides

Cited by 61 publications

References 126 publications

Rapid qualitative and quantitative analyses of flavanone aglycones in Fructus aurantii by HPLC ion‐trap MS

Rapid qualitative and quantitative analyses of flavanone aglycones in Fructus aurantii by HPLC ion‐trap MS

Application of positive and negative electrospray ionization, collision‐induced dissociation and tandem mass spectrometry to a study of the fragmentation of 6‐hydroxyluteolin 7‐O‐glucoside and 7‐O‐glucosyl‐(1 → 3)‐glucoside

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

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