Desorption chemical ionization mass spectrometry of C‐glycosylflavones

Bakhtiar, Amri; Gleye, J.; Moulis, Claire; Fourasté, I.

doi:10.1002/pca.2800050208

Cited by 25 publications

(14 citation statements)

References 13 publications

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“…The short LC retention times, resistance to acid hydrolysis and absence of the aglycone ion in the firstorder MS, suggested that 6 and 9 were flavone Cglycosides. The characteristic losses of 90 and 120 amu from the pseudomolecular ions were also observed by Bakhtiar et al (1994) for flavone C-glycosides after positive desorption chemical ionisation MS and they explained them as fragments originating by cleaving specific parts of the C-sugars. According to their data, the fragments of 6 indicate it is a di-C-hexoside and those of 9 that it is a mono-C-hexoside.…”

Section: Apigenin C-glycosides (6 and 9)mentioning

confidence: 78%

The application of atmospheric pressure chemical ionisation liquid chromatography-mass spectrometry in the chemotaxonomic study of flavonoids: characterisation of flavonoids from Ocimum gratissimum var. gratissimum

et al. 2000

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Liquid chromatography coupled to mass spectrometry (LC‐MS), using atmospheric pressure chemical ionisation (APCI), was found to complement data obtained from diode array detection enabling common flavonoids in Ocimum gratissimum var. gratissimum to be characterised at the analytical level without complete purification, or even to be characterised in crudely purified ethanolic extracts. Xanthomicrol, cirsimaritin, rutin, kaempferol 3‐O‐rutinoside and vicenin‐2 were identified as the major flavonoids, whereas luteolin 5‐O‐glucoside, luteolin 7‐O‐glucoside, apigenin 7‐O‐glucoside, vitexin, isovitexin, quercetin 3‐O‐glucoside and isothymusin were detected as minor constituents. First‐order positive ion APCI‐MS provided not only the pseudomolecular ion of flavonoid O‐glycosides, but also an ion corresponding to the aglycone and an intermediate ion if more than one sugar was attached to the flavonoid. Information on the type and sequence of sugars was therefore obtained without the need to undertake MS2 product ion analyses. Product ion analysis was useful for confirming the glycoside fragmentation observed in first‐order MS, especially with co‐eluting compounds, and for obtaining fragmentation patterns of either free aglycones or the aglycone moiety of flavonoid O‐glycosides; the latter could be used to support the aglycone identification achieved from the UV spectra. Negative ion APCI‐MS was found useful for flavone C‐glycosides and gave very characteristic product ions due to fragmentation of the C‐sugars. For flavonoid O‐glycosides analysed in the negative ion mode, there was evidence that the position and nature of the attached sugars could influence the aglycone product ion formed by MS2 analysis and hence its product ion spectrum. APCI is considered to be a more useful ion source than electrospray in the chemotaxonomic study of flavonoids. Copyright © 2000 John Wiley & Sons, Ltd.

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Section: Apigenin C-glycosides (6 and 9)mentioning

confidence: 78%

The application of atmospheric pressure chemical ionisation liquid chromatography-mass spectrometry in the chemotaxonomic study of flavonoids: characterisation of flavonoids from Ocimum gratissimum var. gratissimum

et al. 2000

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“…The mass spectrum of this compound showed a molecular ion at m/z 433 nm, releasing a wide range of MS 2 fragments, one of them at m/z 271, related to apigenin, and others at m/z 283, 313 and 343, which correspond to the losses of 150, 120 and 90 mass units. These fragments are due to the cross-ring cleavages that occurred in the sugar unit and are characteristic of the flavone C-hexoses (Bakhtiar et al, 1994;Sanchez-Rabaneda et al, 2003). This assumption was corroborated by the losses of one, two and three water moieties (fragments at m/z 415, 397 and 379) that are more intense than the ions resulting from the sugar cleavage (Grayer et al, 2000).…”

Section: Phytochemical Characterizationmentioning

confidence: 79%

Polyphenolic profile characterization ofAgrimonia eupatoria L. by HPLC with different detection devices

Correia

González-Paramás

Amaral

et al. 2005

Biomed. Chromatogr.

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Liquid chromatography coupled to diode array and electrospray ionization mass spectrometry detection was used to establish the polyphenolic profile of an ethyl acetate fraction from Agrimonia eupatoria L. aqueous-alcoholic extract. Additionally, an HPLC technique with post-column derivatization by p-dimethylaminocinnamaldehyde was employed for the selective detection and quantification of flavan-3-ols. Important information was obtained by combining the data of these two HPLC techniques. Flavan-3-ols (catechin and procyanidins B1, B2, B3, B6, B7, C1, C2 and epicatechin-epicatechin-catechin), quercetin 3-O-glucoside, quercetin 3-O-galactoside, kaempferol 3-O-glucoside, kaempferol 3-O-(6''-O-p-coumaroyl)-glucoside, apigenin 6-C-glucoside and various phenolic acids were identified. Antioxidant activity of the Agrimonia eupatoria L. fraction containing these compounds was assessed through the 1,1-diphenyl-2-picrylhydrazyl, trolox equivalent antioxidant capacity and thiobarbituric acid reactive substances methods. Significant activity was observed for this fraction, where compounds with recognized antiinflammatory properties such as procyanidins, kaempferol 3-O-(6''-O-p-coumaroyl)-glucoside and quercetin glycosides were identified for the first time. These results are predictive of the beneficial effects of this fraction, or some of its compounds, in human health, as possible anti-inflammatory drug.

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“…In contrast, in the MS 2 spectra of mono‐ C ‐glycosides, product ions from cleavage of the sugar moiety were observed but the aglycone product ions not found, and losses of 90, 120 and 150 Da for hexose residues were taken as the main characteristics 22, 28, 29. In most cases, [M±H−90] ± , [M±H−120] ± , [M±H−134] ± and [M±H−150] ± were taken as 0,3 X ± , 0,2 X ± , 1,5 X ± , and 0,1 X ± or [ 0,2 XCH 2 O] ± ,19, 30–32 respectively. Pereira et al 19.…”

mentioning

confidence: 99%

Fragmentation study of a 8‐C‐glycosyl isoflavone, puerarin, using electrospray ion trap time‐of‐flight mass spectrometry at high resolution

Li¹,

Wan²,

Hashi³

et al. 2007

Rapid Comm Mass Spectrometry

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Desorption chemical ionization mass spectrometry of C‐glycosylflavones

Cited by 25 publications

References 13 publications

The application of atmospheric pressure chemical ionisation liquid chromatography-mass spectrometry in the chemotaxonomic study of flavonoids: characterisation of flavonoids from Ocimum gratissimum var. gratissimum

The application of atmospheric pressure chemical ionisation liquid chromatography-mass spectrometry in the chemotaxonomic study of flavonoids: characterisation of flavonoids from Ocimum gratissimum var. gratissimum

Polyphenolic profile characterization ofAgrimonia eupatoria L. by HPLC with different detection devices

Fragmentation study of a 8‐C‐glycosyl isoflavone, puerarin, using electrospray ion trap time‐of‐flight mass spectrometry at high resolution

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