Analysis of flavonoid constituents from leaves of <i>Acanthopanax senticosus</i> Harms by electrospray tandem mass spectrometry

Chen, Maolian; Song, Fengrui; Chen, Guofang; Liu, Zhiqiang; Liu, Shuying

doi:10.1002/rcm.574

Cited by 48 publications

(31 citation statements)

References 8 publications

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“…These ions should result from C 3-9 bond cleavage, followed by the neutral loss of CO, which were characteristic for Type I homoisoflavonoids. The above fragments were consistent with the known 5,7,4=-trihydroxy-3=,5=-dimethoxy-6,8-dimethyl homoisoflavanone (10), and allowed the identification of Peak 4.…”

Section: Identification Of Type I Homoisoflavonoidssupporting

confidence: 76%

“…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%

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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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Section: Identification Of Type I Homoisoflavonoidssupporting

confidence: 76%

Section: Identification Of Type I Homoisoflavonoidsmentioning

confidence: 99%

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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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“…With the development of mass spectrometry, many ionization methods have been used to characterize flavonoid compounds, such as EI, 17,18 CI, 19 and FAB. [20][21][22][23] Since the discovery of soft ionization, matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS) 24 and electrospray ionization (ESI) [25][26][27][28][29][30] have also been applied to the analysis of flavonoids. Because ESI-MS has a potential to generate ions directly from the liquid phase, which means that it is possible to provide molecule structure information in a solution environment, it has become a very popular analytical method to analyze the compound structure in solution.…”

Section: Introductionmentioning

confidence: 99%

Characterization of the Rutin-Metal Complex by Electrospray Ionization Tandem Mass Spectrometry

et al. 2004

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According to the strong application background of bioflavonoid and metal-flavonoid complexes, novel electrospray ionization tandem mass spectrometry (ESI-MS n ) was applied to investigate the structure and fragmentation mechanism of transition metal-rutin complexes. In the full-scan mass spectra, different stoichiometric ratios of rutin-metal complexes were found. In the reaction between rutin and Cu, four kinds of complexes with four different stoichiometric ratios were produced. In the reaction between rutin and Zn, Mn(II), and Fe(II), only two kind of complexes with stoichiometric ratios of 1:1 and 1:2 occured. In further tandem mass spectrometric experiments of different rutin-metal complexes, product fragments came from the neutral loss of the external rhamnose and the internal glucose unit, oligosaccharide chain, aglycone, and small organic molecules. According to the MS n data, we proposed a mechanism for all fragments of the rutin-Cu complex A and the structure of two rutin-Cu complexes, C and D.

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“…[16][17][18] Isofraxidin, chlorogenic acid and rutin are the main active compounds in this herb, 11,15,19 and their structures are illustrated in Fig. 1.…”

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confidence: 99%