Collision‐induced fragmentation of deprotonated methoxylated flavonoids, obtained by electrospray ionization mass spectrometry

Justesen, Ulla

doi:10.1002/jms.118

Cited by 170 publications

(149 citation statements)

References 17 publications

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“…Thus, the results suggested that the ion at m/z 299 is a methylated derivative of kaempferol. Most commonly, these substituents are linked to C-5 or C-7 of A-ring [29], but its exact position cannot be discriminated by MS analysis. Still, in accordance with Gardana et al [23], the fivederivative flavonoids tend to elute before the aglycones in HPLC reversed-phase conditions, and that was the reason why this position is considered in the present study (Fig.…”

Section: Derivatives Of Common Flavonoids the Phenolic Compounds Relamentioning

confidence: 99%

Phenolic characterization of Northeast Portuguese propolis: usual and unusual compounds

et al. 2009

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In this study, an ethanolic extract from Portuguese propolis was prepared, fractionated by highperformance liquid chromatography, and the identification of the phenolic compounds was done by electrospray mass spectrometry in the negative mode. This technical approach allowed the identification of 37 phenolic compounds, which included not only the typical phenolic acids and flavonoids found in propolis from temperate zones but also several compounds in which its occurrence have never been referred to in the literature. Four of the novel phenolic compounds were methylated and/or esterified or hydroxylated derivatives of common poplar flavonoids, although six peculiar derivatives of pinocembrin/pinobanksin, containing a phenylpropanoic acid derivative moiety in their structure, were also identified. Furthermore, the Portuguese propolis sample was shown to contain a p-coumaric ester derivative dimer.

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Section: Derivatives Of Common Flavonoids the Phenolic Compounds Relamentioning

confidence: 99%

Phenolic characterization of Northeast Portuguese propolis: usual and unusual compounds

et al. 2009

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“…Another abundant ion at m/z 169 in the MS/MS spectrum could not be explained by previously known fragmentation pathways. We assumed it should result from the simultaneous cleavage of C 2 OO and C [4][5][6][7][8][9][10][11] bonds. This ion could further fragment into m/z 154 by CID.…”

Section: Identification Of Type I Homoisoflavonoidsmentioning

confidence: 99%

“…Flavonoids, especially flavonols, flavones, and their glycosides, are the most frequently reported [5][6][7][8][9][10][11][12]. Electrospray ionization (ESI) and atmospheric pressure chemical ionization (APCI) sources are usually used as the interface between HPLC and a mass spectrometer.…”

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confidence: 99%

Analysis of homoisoflavonoids in Ophiopogon japonicus by HPLC-DAD-ESI-MS

Guo

Guan

et al. 2005

J. Am. Soc. Mass Spectrom.

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The homoisoflavonoids in Ophiopogon japonicus (Thunb.) Ker-Gawler were analyzed by high-performance liquid chromatography-diode array detection-electrospray ion trap tandem mass spectrometry (HPLC-DAD-ESI-MS n ). Homoisoflavonoids gave prominent [M Ϫ H] Ϫ ions by electrospray ionization monitored in the negative ion mode. They could be classified into two types depending on the fragmentation behavior of their [M Ϫ H] Ϫ ions in the ion trap mass analyzer. The [M Ϫ H] Ϫ ions of homoisoflavonoids with a saturated C 2-3 bond underwent C 3-9 bond cleavage to lose the B-ring, which was followed by the loss of a molecule of CO. The [M Ϫ H] Ϫ ions of homoisoflavonoids with a C 2-3 double bond usually eliminated a CO molecule first, and then underwent the cleavage of C 3-9 or C 9-1= bonds. For homoisoflavonoids with a C-6 formyl group, however, the neutral loss of CO was the first fragmentation step; the presence of a methoxyl group at C-8 could lead to the cleavage of C-ring. No retro Diels-Alder (RDA) fragmentation characteristic for normal flavonoids was observed. The above fragmentation rules were reported for the first time, and were implemented for the analysis of homoisoflavonoids in O. japonicus. The CHCl 3 -MeOH extract was separated on a Zorbax Extend-C 18 column, eluting with a acetonitrile-0.3% acetic acid gradient. A total of 18 homoisoflavonoids, including seven new minor constituents, were identified or tentatively characterized based on the UV spectra and tandem mass spectra of the HPLC peaks. (J Am Soc Mass Spectrom 2005, 16, 234 -243)

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“…Therefore, the combination of HPLC and MS facilitates rapid and accurate identification of chemical compounds in medicinal herbs, especially when a pure standard is unavailable. Recently, LC/MS has been extensively used for the analysis of phenolic compounds [17][18][19][20][21][22].°Electrospray°ionization°(ESI)°is°a°preferred°source°due to its high ionization efficiency for phenolic compounds. However, few efforts are devoted to anthraquinones, which are ubiquitously present in plants and show important bioactivities.…”

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confidence: 99%

Analysis of phenolic compounds in rhubarbs using liquid chromatography coupled with electrospray ionization mass spectrometry

Han

Chen

et al. 2007

J. Am. Soc. Mass Spectrom.

227

157

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Rhubarb is an important herbal medicine for the treatment of constipation, inflammation, and cancer. In this study, a facile method based on liquid chromatography coupled with electrospray ionization tandem mass spectrometry has been established for the analysis of bioactive phenolic compounds in rhubarbs. From six rhubarb species, official (Rheum officinale, R. palmatum, and R. tanguticum) and unofficial (R. franzenbachii, R. hotaoense, and R. emodi), a total of 107 phenolic compounds were identified or tentatively characterized based on their mass spectra. These compounds include sennosides, anthraquinones, stilbenes, glucose gallates, naphthalenes, and catechins. Ion chromatograms for the identified compounds of different rhubarbs were then compared. Consistent with previous reports, sennosides and rhein were only detected in official rhubarbs. Unexpectedly, we found that R. officinale contained very different phenolic compounds from the other two official species. Sennoside A, which has been considered as the major purgative component of rhubarb, was only detected in R. officinale, while its close isomers were observed in R. palmatum and R. tanguticum. In addition, the predominant anthraquinone glycosides in R. officinale were found to be rhein 8-O-glucoside and emodin 1-O-glucoside, whereas those in R. palmatum and R. tanguticum were rhein 1-O-glucoside and emodin 8-O-glucoside. Stilbenes, which are the major constituents of unofficial rhubarbs, were also different among the species. Our results clarify the chemical composition of rhubarbs comprehensively for the first time. Due to the significant differences in chemical components of rhubarbs, we suggest that different Rheum species be used separately in clinical practice. (J Am Soc Mass Spectrom 2007, 18, 82-91)

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Collision‐induced fragmentation of deprotonated methoxylated flavonoids, obtained by electrospray ionization mass spectrometry

Cited by 170 publications

References 17 publications

Phenolic characterization of Northeast Portuguese propolis: usual and unusual compounds

Phenolic characterization of Northeast Portuguese propolis: usual and unusual compounds

Analysis of homoisoflavonoids in Ophiopogon japonicus by HPLC-DAD-ESI-MS

Analysis of phenolic compounds in rhubarbs using liquid chromatography coupled with electrospray ionization mass spectrometry

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