Characterization ofC-glycosylflavones fromDissotis rotundifolia by liquid chromatography — UV diode array detection — tandem mass spectrometry

Rath, Guido; Touré, Almamy Amara; Nianga, M.; Wolfender, Jean‐Luc; Hostettmann, Kurt

doi:10.1007/bf02688048

Cited by 41 publications

(28 citation statements)

References 12 publications

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“…The negative ion APCI spectra of all the flavonoids (Table 3) show intense deprotonated molecules and some intense fragment ions. The characteristic fragment ions were [M − H − CH 3 ] −· for isorhamnetin, as reported to be typical for methoxylated flavonoids,44 and [M − H − 90] − and [M − H − 120] − for vitexin, typical for flavonoid‐C‐glycosides 25, 45. In general, the [M − H] − ions were base peaks for the analytes, except for luteolin‐3′,7‐diglucoside, the base peak of which was [M − H − Glu] − ( m / z 447).…”

Section: Resultsmentioning

confidence: 91%

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

2001

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The effect of nine different eluent compositions on the ionization efficiency of five flavonoids was studied using ion spray (IS), atmospheric pressure chemical ionization (APCI), and the novel atmospheric pressure photoionization (APPI), in positive and negative ion modes. The eluent composition had a great effect on the ionization efficiency, and the optimal ionization conditions were achieved in positive ion IS and APCI using 0.4% formic acid (pH 2.3) as a buffer, and in negative ion IS and APCI using ammonium acetate buffer adjusted to pH 4.0. For APPI work, the eluent of choice appeared to be a mixture of organic solvent and 5 mM aqueous ammonium acetate. The limits of detection (LODs) were determined in scan mode for the analytes by liquid chromatography/mass spectrometry using IS, APCI and APPI interfaces. The results show that negative ion IS with an eluent system consisting of acidic ammonium acetate buffer provides the best conditions for detection of flavonoids in mass spectrometry mode, their LODs being between 0.8 and 13 microM for an injection volume of 20 microl.

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Section: Resultsmentioning

confidence: 91%

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

2001

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“…As no sample preparation and preconcentration step is required before these initial analyses, the formation of compound 1 as an artifact can be excluded. The product ion spectrum of compound 1 as obtained by low-energy collision-induced dissociation (CID) of the protonated molecule (ESI positive mode) shows a fragmentation pattern dominated by the loss of 120 atomic mass units, corresponding to the cleavage of a C % H ) O % moiety characteristic of C-glycosyl compounds [2,15,16]. In addition, sequential retro-aldol cleavage occurs, combined with a loss of water.…”

Section: Resultsmentioning

confidence: 99%

Tryptophan glycoconjugates in food and human urine

Gutsche

Grun

Scheutzow

et al. 1999

Biochemical Journal

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Evaluating the formation of tryptophan glycoconjugates other than well-established Amadori rearrangement products, HPLCtandem MS (MS\MS) analysis of human urine collected from several healthy individuals proved the presence of one distinct tryptophan C-glycosyl compound [Horiuchi, Yonekawa, Iwahara, Kanno, Kurihara and Fujise (1994) J. Biochem. (Tokyo) 115, 362-366]. After isolation, unambiguous identification of this novel tryptophan metabolite as 2-(α-mannopyranosyl)--tryptophan was achieved by tandem MS combined with NMR spectroscopy including homonuclear COSY, heteronuclear multiple-bond connectivity and "H-detected heteronuclear multiple-quantum coherence experiments. Remarkably, a thorough evaluation of vicinal proton-proton coupling constants in different solvents and nuclear Overhauser effect experiments demonstrate the predominant axial orientation of the hydroxymethyl group of the hexopyranosyl residue. Likewise this spatial arrangement indicates that the respective α-anomeric C-mannosylhexopyranose is preferentially adopting a "C % con-

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“…Characteristic fragmentation patterns of O-glycosyl, C-glycosyl, and O-C-glycosyl flavonoids were used to differentiate between isomeric molecules [35,36]. The LC-ESI-MS/MS data and flavonoid structures are shown in Table 1 was also observed.…”

Section: Separation and Characterizationmentioning

confidence: 99%

Dietary-flavonoid-rich flowers ofRumex nervosusVahl: Liquid chromatography with electrospray ionization tandem mass spectrometry profiling and in vitro anti-inflammatory effects

et al. 2015

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Rumex nervosus is a plant species found widely in Eastern Africa and the Arabian Peninsula. In addition to its uses in traditional medicinal, the plant shows various biological activities, such as antiviral, antibacterial, and antioxidant activity. In this study, nine flavonols, six flavones, three flavanones, and one flavanol were characterized from the flowers of R. nervosus using liquid chromatography with electrospray ionization tandem mass spectrometry and literature data. Validation data indicated that the determination coefficients (R(2) ) were ≥ 0.9914. The limits of detection and quantification were in the ranges of 0.15-1.24 and 0.50-4.13 mg/L, respectively. Recoveries at 10 and 50 mg/L were 71.1-110.2 and 65.4-115.1%, with relative standard deviations of 7.4-40.1 and 2.1-13.0%, respectively. Quercetin 3-O-rhamnoside (10) was the dominant component, contributing 30.8% of total flavonoids (1003.0 ± 26.2 mg/kg fresh flower sample), whereas luteolin 6-C-glucoside (3) was the lowest yielding compound (0.1%). The 19 flavonoids identified were characterized for the first time. In vitro anti-inflammatory studies showed that this mixture can suppress the production of inflammatory mediators, including inducible nitric oxide synthase, cyclooxygenase-2, kappa B inhibitor, and interleukin-1β, by down-regulating the nuclear factor-kappa B and mitogen-activated protein kinases pathways. The results of this study may provide information for processing R. nervosus as a potential source of functional food.

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Characterization ofC-glycosylflavones fromDissotis rotundifolia by liquid chromatography — UV diode array detection — tandem mass spectrometry

Cited by 41 publications

References 12 publications

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

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

Tryptophan glycoconjugates in food and human urine

Dietary-flavonoid-rich flowers ofRumex nervosusVahl: Liquid chromatography with electrospray ionization tandem mass spectrometry profiling and in vitro anti-inflammatory effects

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