Iron and copper chelation by flavonoids: an electrospray mass spectrometry study

Fernandez, M. Tereza; Mira, M. Lurdes; Florêncio, M. Helena; Jennings, Keith R.

doi:10.1016/s0162-0134(02)00511-1

Cited by 292 publications

(181 citation statements)

References 32 publications

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“…Some of these stoichiometries have been previously reported for copper and iron complexes of flavonoids [77]. Figure 2 shows the full scan mass spectrum of isovitexin and Ca(II), which form complexes with several different stoichiometries.…”

Section: Resultsmentioning

confidence: 55%

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: 55%

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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“…Le Nest et al [20,21] reported the structure of the possible metallic complexes formed between quercetin and catechin with Zn 2+ , as well as those of quercetin and rutin with Cu 2+ , claiming that the catechol moiety is the most probable binding point between this metal and the flavonoid molecule. On the contrary, other reports [22,23] suggest that the binding site Cu 2+ -flavonoid corresponds to the 4-oxo-5-OH group of the organic structure. Thermogravimetric and atomic absorption spectrophotometric studies tend to indicate that the 3-OH-4-oxo and 3'-OH-4'-OH moieties are the most likely binding sites of the flavonoids for metals [24].…”

Section: Introductionmentioning

confidence: 77%

Electrochemical and theoretical complexation studies for Zn and Cu with individual polyphenols

Esparza

Salinas

Santamaría

et al. 2005

Analytica Chimica Acta

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Zn and Cu interactions with three selected flavonoids (catechin, quercetin and rutin) have been electrochemically monitored. It has been shown that catechin takes 1 atom of metal per molecule; quercetin takes 2 atoms, and rutin is able to take up to 3 atoms. Not all ligands bind metals equally strong, and weakly bonded metals can be distinguished. Zn shows a sluggish kinetics and, at the same time, the highest conditional formation constants. The method could be applied to a real sample. Theoretical models are proposed for the most favourable compounds.

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“…Flavonoids are good chelating agents towards metal ions and, in the case of iron and copper, the favoured places of chelation are catechol groups, hydroxyl groups adjacent to oxo groups, and 1-oxo-3-hydroxyl-containing moieties (Fernandez et al, 2002;Ren et al, 2008). This ability to chelate metals has been used to enhance the capabilities of MS; it has been used to assist the elucidation of flavonoid glucuronides (Davis et al, 2006;Davis et al, 2007) and various diglycosides (Pikulski et al, 2007).…”

Section: Fig 1 Binding Sites For Trace Metals Where Men+ Indicates mentioning

confidence: 99%

Iron Chelating Activity of Gossypitrin Isolated from the Petals of Talipariti elatum Sw. (Fryxell) Malvaceae

González¹,

Cuéllar²,

Nossin³

et al. 2017

JAS

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A Fe(III)-gossypitrin complex was prepared with a metal to ligand molar ratio of 1:1; 2:1 and 3:2 by mixing stoichiometric amounts of gossypitrin and FeCl 3 . The isolated complex was characterized by visual observation, UV/Vis, IR and ESI-MS spectroscopy. In this study, we selected the major flavonoid glycoside present in the petals of the flowers of Talipariti elatum Sw. (Fryxell) Malvaceae that grows in Cuba, gossypitrin, to characterize the chelating activity of it chemical compound with FeCl 3 , to find alternative sources with lower side effects in asthmatic patients. A high chelating activity can be observed as a good source of new agents for asthmatic patients.

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Iron and copper chelation by flavonoids: an electrospray mass spectrometry study

Cited by 292 publications

References 32 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

Electrochemical and theoretical complexation studies for Zn and Cu with individual polyphenols

Iron Chelating Activity of Gossypitrin Isolated from the Petals of Talipariti elatum Sw. (Fryxell) Malvaceae

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