Evaluation of quadrupole time-of-flight tandem mass spectrometry and ion-trap multiple-stage mass spectrometry for the differentiation of C-glycosidic flavonoid isomers

Waridel, Patrice; Wolfender, Jean‐Luc; Ndjoko, Karine; Hobby, Kirsten; Major, Hilary; Hostettmann, Kurt

doi:10.1016/s0021-9673(01)00806-8

Cited by 293 publications

(252 citation statements)

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“…Figure 3 more clearly shows which bonds are broken as the result of various crossring cleavages. These types of losses are well-known for C-glycosyl flavonoids, and were discussed in detail by Waridel et al [29]. The loss of one or more water molecules observed with some C-glycosyl flavonoid complexes has also been reported in mass spectral analysis of deprotonated C-glycosyl flavonoids [17,29,38] and alternate structures for these ions have been proposed [17].…”

Section: Resultsmentioning

confidence: 78%

“…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). Despite these inroads, mass spectrometric analysis has not yet reached the point where de novo identification of flavonoids is possible.…”

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confidence: 99%

“…The general fragmentation differences between flavonoid glycosides bonded through carbon versus oxygen atoms have been established [16], along with differentiation of 6-C-glycosyl and 8-C-glycosyl flavonoids [16,17,29,38,54]. However, to our knowledge no one has proposed a robust universal mass spectrometric method for determining five of the most common glycosylation positions encountered for the monoglucosyl flavonoids: attachment through oxygen at position 3, 4Ј, or 7; or through carbon at position 6 or 8.…”

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confidence: 99%

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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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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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“…4,14 This proposition is confirmed by the [M+H] + ion at m/z 447 and by the peak at m/z 327, which indicates a loss of 120 u ( 0,2 X ion, 16 Figure 2) from the [M+H] + ion, a characteristic feature of a C-glucoside flavonoid. 16 The CID-MS/MS data also indicated a fragmentation pathway of a C-linked glucose moiety (Figure 2; m/z 429, 411, 393, 381, 351, 327 and 297), and analysis of 0,2 X ion indicated an 6-C-glucoside. 16 The UV analysis with postcolumn addition of sodium acetate showed the absence of a bathochromic shift of band I, confirming the presence of a blocked 7-OH group and showed also a shoulder in band II indicating a free OH group in position 4'.…”

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confidence: 70%

On-line identification of minor flavones from sugarcane juice by LC/UV/MS and post-column derivatization

Colombo¹,

Yariwake²,

Queiroz³

et al. 2009

J. Braz. Chem. Soc.

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Este trabalho apresenta a identificação "on line" de flavonas minoritárias do suco da cana-deaçúcar (Saccharum officinarum), por cromatografia líquida de alta eficiência com detector UV acoplada à espectrometria de massas (CL/UV/EM) com ionização química à pressão atmosférica, dissociação induzida por colisão (IQPA-DIC-EM/EM) e derivatização pós-coluna utilizando reagentes de deslocamento de UV. As análises CLAE-UV com reagentes de deslocamento forneceram informações sobre a posição da substituição no esqueleto dos flavonóides e, em combinação com dados de EM, estas técnicas permitiram a identificação "on-line" de cinco flavonas da garapa: luteolina-8-C-glucosil-7-O-glucuronídeo; tricina-7-O-neoesperosideo-4'-O-ramnosídeo; tricina-7-O-metilglucuronato-4'-O-ramnosídeo; tricina-7-O-metilglucuronídeo; swertisina; e outras quatro substâncias foram parcialmente identificadas como flavonas glicosiladas. Somente a swertisina (7-O-metilapigenina-6-C-glicosídeo) foi anteriormente descrita no bagaço da cana-de-açúcar.This work describes the on-line characterization of minor flavones from sugarcane (Saccharum officinarum) juice by high-performance liquid chromatography coupled to diode array UV detection and mass spectrometry (LC/UV/MS) using atmospheric pressure chemical ionizationcollision-induced dissociation (APCI-CID-MS/MS) and post-column derivatization using UV shift reagents. HPLC-UV analysis with shift reagents provided information about the substitution pattern in the flavonoid skeleton and, combined with MS data, these techniques allowed for the on-line identification of five "garapa" flavones: luteolin-8-C-glucosyl-7-O-glucuronide; tricin-7-O-neohesperoside-4'-O-rhamnoside; tricin-7-O-methylglucuronate-4'-O-rhamnoside; tricin-7-O-methylglucuronide; swertisin, while four other compounds were partially identified as glycosylflavones. Only swertisin (7-O-methylapigenin-6-C-glucoside) was reported previously in sugarcane molasses.Keywords: sugarcane juice, Saccharum officinarum L. (Poaceae), flavones, LC/UV/MS, UV shift reagents IntroductionHyphenated techniques such as liquid chromatography with UV photodiode array detection (HPLC-UV) and on-line liquid chromatography-ultraviolet detection-mass spectrometry (HPLC-UV-MS) are powerful techniques for the structural identification of compounds found in extracts prepared from very small amounts of plant material. In the case of plant polyphenolic compounds such as flavonoids and xanthones, the possibility of obtaining on-line UV data by a combination with the post-column addition of UV shift reagents is a very important step to validate the structure assignments proposed for the position of oxygenated groups on the polyphenolic skeleton.1 Recently, HPLC-UV-MS and post-column UV-derivatization were employed in the study of Trifolium extracts containing clovamides, flavonoids and isoflavonoids and their UV data were discussed in detail.2 Hyphenated techniques may be the technique of choice in studies requiring analyses of several plant samples, as in metabolomic studies....

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“…Here, we demonstrate that high mass resolving power and ion-trapping capabilities of FT-ICR mass spectrometry can be utilized to differentiate GC eluted ␣-pinene and camphene isomers in real time. Other researchers reported isomer differentiation based on multiphoton ionization and dissociation (MPI/MPD) [33], GC/MPI-FTMS [34], FTMS proton affinity bracketing [35], collision-induced dissociation (CID) [36 -38], CID combined with chromatography [39], ion-molecule reactions combined with chromatographic techniques [40], oxygen negative chemical ionization (ONCI) [41], NCI GC [42], charge inversion MS [43], and by metal oxide sensors [44]. Modifying chromatographic parameters such as GC temperature programming or column type that can alter elution time and/or order will not change mass spectral appearances.…”

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confidence: 99%

A preconcentrator coupled to a GC/FTMS: Advantages of self-chemical ionization, mass measurement accuracy, and high mass resolving power for GC applications

Solouki

Szulejko

Bennett

et al. 2004

J. Am. Soc. Mass Spectrom.

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Evaluation of quadrupole time-of-flight tandem mass spectrometry and ion-trap multiple-stage mass spectrometry for the differentiation of C-glycosidic flavonoid isomers

Cited by 293 publications

References 26 publications

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

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

On-line identification of minor flavones from sugarcane juice by LC/UV/MS and post-column derivatization

A preconcentrator coupled to a GC/FTMS: Advantages of self-chemical ionization, mass measurement accuracy, and high mass resolving power for GC applications

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