Effect of eluent on the ionization efficiency of flavonoids by ion spray, atmospheric pressure chemical ionization, and atmospheric pressure photoionization mass spectrometry

Rauha, Jussi-Pekka; Vuorela, Heikki; Kostiainen, Risto

doi:10.1002/jms.231

Cited by 163 publications

(118 citation statements)

References 40 publications

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“…Greater sensitivity has been reported in the negative ion mode than in the positive ion mode [21,30,31,38], a factor attributed to the substantial acidities of flavonoids and the ease of deprotonation due to their multiple hydroxyl groups. However, the CAD spectra of deprotonated flavonoid glycosides generally show few fragments, and are therefore not particularly useful for isomer differentiation.…”

Section: Resultsmentioning

confidence: 99%

“…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%

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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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Section: Resultsmentioning

confidence: 99%

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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“…Acetic acid was added in the mobile phase to improve the ionization of homoisoflavonoids, though they did not alter their chromatographic retention significantly° [22].…”

Section: Hplc-dad-esi-ms N Analysis Of the Plant Extractmentioning

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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“…Tanaka et al [21] reported LODs in the range of 25-50 mg/mL for basic drugs analyzed by CE-APCI/MS. APPI was introduced by Robb et al in 2000 [25] as a complement to ESI and APCI to broaden the range of ionizable analytes in API techniques [26,27] and has been adapted for the analysis of nonpolar compounds [25,[28][29][30][31][32]. Technically, the APPI source is similar to APCI, i.e., the sample is vaporized in a heated nebulizer before ionization and nonvolatile salts can be easily removed during this step.…”

Section: Introductionmentioning

confidence: 99%

Coupling CE with atmospheric pressure photoionization MS for pharmaceutical basic compounds: Optimization of operating parameters

Schappler¹,

Guillarme²,

Prat³

et al. 2007

Electrophoresis

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The use of CE coupled with MS (CE-MS) has evolved as a useful tool to analyze charged species in small sample volumes. Because of its sensitivity, versatility and ease of implementation, the ESI interface is currently the method of choice to hyphenate CE to MS. An alternative can be the atmospheric pressure photoionization (APPI) source, however, numerous parameters must be optimized for its coupling to CE. After evaluation of the sheath liquid composition and the CE capillary outlet position, an experimental design methodology was assessed for optimizing other ionization source parameters, such as sheath liquid flow rate, drying gas flow rate and temperature, nebulizing gas pressure, vaporizer temperature, and capillary voltage. For this purpose, a fractional factorial design (FFD) was selected as a screening procedure to identify factors which significantly influence sensitivity and efficiency. A face-centered central composite design (CCD) was then used to predict and optimize sensitivity, taking into account the most relevant variables. Sensitivity was finally evaluated with the optimized conditions and height-to-noise ratios (H/N) around 10 were achieved for an injection of 200 ng/mL of each analyte.

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Effect of eluent on the ionization efficiency of flavonoids by ion spray, atmospheric pressure chemical ionization, and atmospheric pressure photoionization mass spectrometry

Cited by 163 publications

References 40 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

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

Coupling CE with atmospheric pressure photoionization MS for pharmaceutical basic compounds: Optimization of operating parameters

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