Studies on the flavones using liquid chromatography–electrospray ionization tandem mass spectrometry

Wu, Wei; Yan, Cunyu; Li, Li; Liu, Zhiqiang; Liu, Shuying

doi:10.1016/j.chroma.2004.06.128

Cited by 66 publications

(43 citation statements)

References 27 publications

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“…For example, the MS 2 spectra of flavonol for normalized collision energies of 40 % (a) and 45 % (b) are presented in Figure 3; obviously, the relative abundance of the fragments produced by the [M+H] + ion increased. The negative ionization mode does not produce characteristic fragments for each flavonoid subgroup as may be deduced from the previously published mass spectra for a series of flavonols, flavones and flavanones [9][10][11][12][13]. .…”

Section: Resultsmentioning

confidence: 99%

“…The structures of the four flavonols (quercetin, fisetin kaempferol, flavonol), three flavones (luteolin, apigenin, chrysin), two flavanones (eriodictyol, hesperetin), two flavanols [(+)-catechin, (-)-epicatechin], and the dihydroflavonol taxifolin that were used, are presented in Figure 2. (11) (-)-epicatechin (12) Each standard flavonoid was diluted either in acetonitrile-water (1:1) or in isopropanol at a concentration of 4·10 -5 M. The retention times in the HPLC-DAD analysis as well as the UV-Vis characteristics of the studied compounds are presented in Table 1. The MS/MS analysis in the present study revealed that each subgroup exhibits a characteristic fragmentation behavior, which includes, as far as the protonated molecule is concerned, dehydration, loss of CO and fission of the C-ring.…”

Section: Resultsmentioning

confidence: 99%

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Characterization of Flavonoid Subgroups and Hydroxy Substitution by HPLC-MS/MS

et al. 2007

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HPLC-DAD coupled with mass spectrometry in the positive ionization mode was applied to study the fragmentation of twelve selected flavonoids. Compounds belonging to all the major subgroups found in common plants, i.e. flavonols, flavones, dihydroflavonols, flavanones and flavanols were studied. Compound standards were injected into the spectrometer and produced characteristic mass spectra. The fragmentation of each compound was studied and it was shown that the dehydration and carbon monoxide losses from the [M+H] + ion by the members of each subgroup produced specific fragments, thus allowing the characterization of the flavonoid subgroups. Moreover, fragments resulting from fission of the C-rings are specific of each subgroup and revealed the substitution pattern of A-and B-rings. In order to verify the identifying efficiency of the positive ionization mode through these characteristic fragmentations, the unknown flavonoids of an Origanum vulgare diethyl ether extract were separated with the HPLC system and the major peaks were successfully identified with the mass spectrometer.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Characterization of Flavonoid Subgroups and Hydroxy Substitution by HPLC-MS/MS

et al. 2007

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“…The storage stability of immobilized lipase was significantly better than the free form at 20°C within 20 days, and it retained about 55 % of the initial activity after being used for six times [35]. [36][37][38], compounds 1, 2, and 3 are identified as baicalin, wogonin, and oroxylin A, respectively.…”

Section: Synthesis and Characterization Of Lmnpsmentioning

confidence: 99%

Screening of lipase inhibitors from Scutellaria baicalensis extract using lipase immobilized on magnetic nanoparticles and study on the inhibitory mechanism

et al. 2016

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Scutellaria baicalensis is a traditional Chinese medicinal plant possessing a wide variety of biological activities. In this work, lipase immobilized on magnetic nanoparticles (LMNPs) was used as solid phase extract absorbent for screening of lipase inhibitors from this plant. Three flavonoids were found to bind to LMNPs and were identified as baicalin, wogonin, and oroxylin A by liquid chromatography-mass spectrometry (HPLC-MS). Their IC 50 values were determined to be 229.22 ± 12.67, 153.71 ± 9.21, and 56.07 ± 4.90 μM, respectively. Fluorescence spectroscopy and molecular docking were used to probe the interactions between these flavonoids and lipase. All the flavonoids quenched the fluorescence of lipase statically by forming new complexes, implying their affinities with the enzyme. The thermodynamic analysis suggested that van der Waals force and hydrogen bond were the main forces between wogonin and lipase, while hydrophobic force was the main force for the other two flavonoids. The results from a molecular docking study further revealed that all of them could insert into the pocket of lipase binding to a couple of amino acid residues.

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“…March et al employed high-resolution and exact mass/ charge measurements of flavonoids by using Q-TOF mass spectrometry [15]. In 2004, Liu and coworkers employed FTICR MS to verify a proposed neutral losses from the precursor ion of wogonin extracted from the Chinese medicinal herb Scutellaria baicalensis Georgi [16]. All these studies employing high-resolution and high mass methods to analyze known or unknown compounds were successful in providing more detailed fragment assignment.…”

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confidence: 99%

A study of isomeric diglycosyl flavonoids by SORI CID of fourier transform ion cyclotron mass spectrometry in negative ion mode

Yan

Liu

Zhou

et al. 2007

J. Am. Soc. Mass Spectrom.

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High-resolution Sustained off resonance irradiation (SORI) CID was employed to distinguish four pairs of isomeric diglycosyl flavonoids in the negative mode using the electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry (ESI FTICR MS). All of these isomers can be distinguished via MS/MS data. For these diglycosyl flavones and flavanones, the deprotonated ␣1¡6 linkage diglycosyl flavonoids produce fewer fragments than the ␣1¡2 linkage type compounds and the Retro-Diels-Alder (RDA) reaction in MS/MS only takes place when the aglycone is a flavanone and glycosylated with an ␣1¡2 intersaccharide linkage disaccharide. The deprotonation sites after collisional activation are discussed according to the high mass accuracy and high-resolution data of tandem spectrometry. Some of these high-resolution SORI CID product ions from ␣1¡2 linkage diglycosyl flavonoids involve multibond cleavages; the possible mechanism is discussed based on the computer modeling using Gaussian 03 program package at the B3LYP/6-31G level of theory. Unambiguous elementary composition data provides fragmentation information that has not been reported

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Studies on the flavones using liquid chromatography–electrospray ionization tandem mass spectrometry

Cited by 66 publications

References 27 publications

Characterization of Flavonoid Subgroups and Hydroxy Substitution by HPLC-MS/MS

Characterization of Flavonoid Subgroups and Hydroxy Substitution by HPLC-MS/MS

Screening of lipase inhibitors from Scutellaria baicalensis extract using lipase immobilized on magnetic nanoparticles and study on the inhibitory mechanism

A study of isomeric diglycosyl flavonoids by SORI CID of fourier transform ion cyclotron mass spectrometry in negative ion mode

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