The formation and fragmentation of flavonoid radical anions

Feketeová, Linda; Barlow, Christopher K.; Benton, Timothy M.; Rochfort, Simone; O’Hair, Richard A. J.

doi:10.1016/j.ijms.2010.08.017

Cited by 15 publications

(13 citation statements)

References 61 publications

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“…Therefore, it would be important to have a rapid and effective method for determining and distinguishing them from other type of flavonoids. Electrospray ionisation multistage mass spectrometry (ESI/MS n ) in either negative or positive mode has been proven to be a powerful means used to rapidly identify and analyse flavones (Cuyckens and Claeys, 2004), flavonols (Justino et al, 2009), chalcones (Zhang and Brodbelt, 2003), isoflavonoids (Kang et al, 2007;Ablajan, 2011), bioflavones , homoisoflavonoids (Ye and Guo, 2005), methoxylated flavonoids (Ma et al, 1999;Justesen, 2001), prenylated flavonoids (Zhang et al, 2008;Simons et al, 2009), and their glycosides (Cuyckens et al, 2001;Hvattum and Ekeberg, 2003;Ferreres et al, 2004;Cuyckens and Claeys, 2005;Marcha et al, 2006;Feketeová et al, 2011). However, up to now, no report can be found on the HPLC with diode-array detection (DAD) and ESI/MS n analysis of homoflavonoids and their prenylated derivatives.…”

Section: Introductionmentioning

confidence: 99%

Characterisation of Homoflavonoids from Three Ophioglossum Species Using Liquid Chromatography with Diode Array Detection and Electrospray Ionisation Tandem Mass Spectrometry

Wan

Luo

et al. 2013

Phytochemical Analysis

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Section: Introductionmentioning

confidence: 99%

Characterisation of Homoflavonoids from Three Ophioglossum Species Using Liquid Chromatography with Diode Array Detection and Electrospray Ionisation Tandem Mass Spectrometry

Wan

Luo

et al. 2013

Phytochemical Analysis

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“…They also proposed that increased hydroxylation degree of ring B could enhance the homolytic fragmentation . Since then, this characteristic radical cleavage has been extensively applied to structural characterization of flavonoid O ‐glycosides . Recently, Ablajan proposed that [Y 0 –2H] – and [Y 3 0 –H] –• were diagnostic for the characterization of flavonols with 3‐ and 7‐ O ‐glycosyl substitutions .…”

mentioning

confidence: 99%

Low energy induced homolytic fragmentation of flavonol 3‐O‐glycosides by negative electrospray ionization tandem mass spectrometry

Yang

Qiao

Bo³

et al. 2014

Rapid Comm Mass Spectrometry

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“…Отметим, что аналогичный вывод может быть сделан для других поли-фенольных соединений -флавоноидов и спинохромов [11,12], что независимо подтверждается результатами исследований методом электрораспыления [37]. На этой основе предлагается новый механизм биологической активности (благотворного действия на организм в условиях окислительного стресса) полифенольных со-единений, связанный с характерной особенностью об-разования и распада их ОМИ.…”

Section: Discussionunclassified

Resonance electron attachment to natural polyphenolic compounds and their biological activity

Pshenichnyuk¹,

Asfandiarov²,

Воробьев³

et al. 2015

LoM

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Resonance low-energy (0-14 eV) electron attachment to natural polyphenolic stilbenes possessing antioxidant properties, namely resveratrol and piceatannol, was investigated by means of dissociative electron attachment spectroscopy. Experimental findings were assigned on base of density functional theory (DFT) calculations of energies and symmetry of vacant molecular orbitals. It was found that characteristic decay of the molecular negative ions of compounds under investigation under gasphase conditions can be associated with elimination of neutral H 2 molecule and formation of quinone-like structure bearing excess electron. These fragment species can be responsible for ability of polyphenolic compounds to scavenge free radicals in the living cells. The gas-phase data were extrapolated to reactions in cellular environment by means of DFT calculations using polarizable continuum model approach. A molecular mechanism for antioxidant activity of polyphenolic compounds in proximity to the mitochondrial respiratory chain under conditions of excess negative charge was suggested. Namely, it is thought that molecular hydrogen, known for its selective antioxidant properties, can be efficiently generated via attachment of electrons ("leaked" from the respiratory chain into mitochondrial intermembrane space) to polyphenolic compound and may be responsible for its antioxidant activity. The corresponding negative fragment, i.e., quinone bearing an excess negative charge, can serve as electron carrier and can return the captured electron back to the respiration cycle. The number of hydroxyl substituents and their relative positions on aromatic rings of polyphenolic molecule are crucial for the present molecular mechanism, because these properties determine dissociative electron attachment cross-section.

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The formation and fragmentation of flavonoid radical anions

Cited by 15 publications

References 61 publications

Characterisation of Homoflavonoids from Three Ophioglossum Species Using Liquid Chromatography with Diode Array Detection and Electrospray Ionisation Tandem Mass Spectrometry

Characterisation of Homoflavonoids from Three Ophioglossum Species Using Liquid Chromatography with Diode Array Detection and Electrospray Ionisation Tandem Mass Spectrometry

Low energy induced homolytic fragmentation of flavonol 3‐O‐glycosides by negative electrospray ionization tandem mass spectrometry

Resonance electron attachment to natural polyphenolic compounds and their biological activity

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