Quercetin (3,3',4',5,7-pentahydroxyflavone) Complexes with Calcium (II) and Magnesium(II), Its Potentiometrie and Spectrophotometric studies

Erdoğan, Gülbin; Karadağ, Recep

doi:10.1515/revac.2005.24.1.9

Cited by 15 publications

(11 citation statements)

References 9 publications

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“…5) [34]. Although generally the chelating properties of flavonoids have been attributed to the presence of the 3-and 5-hydroxychromone moieties, there were studies revealing the catechol moiety as well [18,26,35]. For example, in the paper of Conrad and Merlin describing the Al(III) complex of quercetin, in the alkaline medium one of the complex form was Al(III)/quercetin 1:1 where the complexing site was catechol group [18].…”

Section: Thermogravimetric and Elemental Analysesmentioning

confidence: 99%

“…The complexes of Fe(II), Ni(II), Co(II) and Zn(II) with quercetin possessed metal/ligand stoichiometries 2:1, and the 5-hydroxychromone moieties were involved in metal coordination [22]. Moreover, the composition of Cd(II) [23], Ni(II), Co(II), Pd(II) [24], Cu(II) [25], Ca(II) and Mg(II) [26] complexes with quercetin was established as 1:1 in different pH from 5 to 11. In the case of Ca(II) and Mg(II) complexes, the metals were coordinated through a bidentate ligand (through the catechol moiety on the B ring) [26].…”

Section: Introductionmentioning

confidence: 99%

“…Moreover, the composition of Cd(II) [23], Ni(II), Co(II), Pd(II) [24], Cu(II) [25], Ca(II) and Mg(II) [26] complexes with quercetin was established as 1:1 in different pH from 5 to 11. In the case of Ca(II) and Mg(II) complexes, the metals were coordinated through a bidentate ligand (through the catechol moiety on the B ring) [26]. Due to the discrepancy in chelation of metal ions by quercetin, it is important to carry out studies that may confirm the exact chelating sites in quercetin molecule.…”

Section: Introductionmentioning

confidence: 99%

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Spectroscopic, thermogravimetric and biological studies of Na(I), Ni(II) and Zn(II) complexes of quercetin

Kalinowska

Świderski

Matejczyk

et al. 2016

J Therm Anal Calorim

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The Na(I), Zn(II) and Ni(II) complexes with quercetin have been synthesized. The composition of these compounds was established by means of elemental and thermogravimetric analyses. To study the molecular structure of synthesized compounds, many miscellaneous analytical methods, which complement one another, were used: infrared (FT-IR), Raman (FT-Raman) and electronic absorption UV/VIS spectroscopy. For studying the cytotoxic and genotoxic activity of synthesized compounds, bioreporter strain of Escherichia coli K-12 recA::gfpmut2 has been used.

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Section: Thermogravimetric and Elemental Analysesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Spectroscopic, thermogravimetric and biological studies of Na(I), Ni(II) and Zn(II) complexes of quercetin

Kalinowska

Świderski

Matejczyk

et al. 2016

J Therm Anal Calorim

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“…Complexation of flavonoids with metal ion causes further bathochromic shift of characteristic absorption bands (19), and in the presence of Mg(II) and Ca(II) ions absorption maximum of the cinnamoyl band shifted to 406 nm and 395 nm, respectively, while there was almost no shift of the benzoyl band. As in the case of quercetin complexation with Mg(II) and Ca(II) ions (21), larger bathochromic shift was caused by the presence of Mg(II) ion which may be explained by its higher ionic potential (charge/ionic radius ratio) in comparison to Ca(II) ion.…”

Section: Resultsmentioning

confidence: 89%

The Influence of Mg(II) and Ca(II) Ions on Rutin Autoxidation in Weakly Alkaline Aqueous Solutions

Zivanovic¹,

Nikolić²,

Nikolić³

2016

Acta Facultatis Medicae Naissensis

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Rutin (quercetin-3-O-rutinoside) is one of the most abundant bioflavonoids with various biological and pharmacological activities. Considering the ubiquitous presence of Mg(II) and Ca(II)ions in biological systems we decided to investigate their influence on the autoxidation of rutin in weakly alkaline aqueous solutions. Changes in UV-Vis spectra recorded during the rutin autoxidation in aqueous solution at pH 8.4 revealed that this process was very slow in the absence of metal ions. The presence of Mg(II) and, especially Ca(II) ion, increased the transformation rate of rutin. UV-Vis spectra recorded after prolonged autoxidation indicated the formation of humic acidlike products in the presence of Mg(II) and Ca(II) ions. Four new compounds formed during the initial stage of rutin autoxidation in the presence of Mg(II) and Ca(II) ions were detected by HPLC-DAD. Based on the analysis of their DAD UV-Vis spectra and comparison of their retention times with the retention time value for rutin, we concluded that the initial rutin transformation products were formed by the water addition on double bond in ring C and hydroxylation of ring B. A very small decrease of the initial rutin concentration (4%) was observed by HPLC-DAD in the absence of metal ions for the period of 90 minutes. However, rutin concentration decrease was much larger in the presence of Mg(II) and Ca(II) ions (14% and 24%, respectively). The more pronounced effect of Ca(II) ion on the rutin autoxidation may be explained by the stronger binding of Mg(II) ion to rutin and thus greater stabilizing effect on reaction intermediates caused by its higher ionic potential (charge/ionic radius ratio) in comparison to Ca(II) ion. The results of this study may contribute to the better understanding of interactions of Mg(II) and Ca(II) ions with natural phenolic antioxidants which are important for their various biological activities.Key words: rutin, autoxidation, magnesium, calcium O r i g i n a l a r t i c l e I NT ROD U CT I ONPhenolic compounds are ubiquitous in plants and their dietary intake has many beneficial effects on human health (1, 2). Rutin (quercetin-3-O-rutinoside), the glycoside between the flavonol quercetin and disaccharide rutinose (α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranose) (Figure 1) is one of the most abundant bioflavonoids with various biological and pharmacological activities (2, 3). Oxidation or/and autoxidation of natural phenolic compounds may have profound influence on their biological activity and stability of certain types of foods (4). Compounds having two or three vicinal hydroxyl groups on the same benzene ring are especially susceptible to autoxidation, and it was found that this process is mainly influenced by the pH value (4) and the presence of transition metal ions like Mn(II), Fe(II), and Cu(II) (5, 6) which are redox active and strongly enhance the autoxidation process. However, the influence of Mg(II) and Ca(II) ions on the autoxidation of natural phenolic compounds was studied less frequently (5, 7), although these t...

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“…Sentetik boyarmaddelerin birçoğunun toksik, kanserojen olması ve atıklarının çevre kirliliğine neden olması doğal boyarmaddeleri yeniden gündeme taşımış ve kullanımları; gıda, ilaç, kozmetik ve tekstil boyama endüstrisi alanında ivme kazanmıştır (9,10). Bazı flavonoid grubu boyarmaddelerin çeşitli metallerle yaptıkları kompleksler potansiyometrik ve spektrofotometrik olarak incelenmiştir (11)(12)(13)(14). Ancak kırmızı boyarmadde kaynağı olan kabuklu böceklerden elde edilen antrokinon türevi boyarmaddelerin potansiyometrik olarak asit sabitlerinin ve metallerle yaptıkları komplekslerin kararlılık sabitlerine ilişkin bir kaynak bulunamamıştır.…”

Section: öZetunclassified

Flavokermesik Asitin Asit Sabitlerinin ve Kalay(II), Alüminyum(III) İyonları İle Oluşturduğu Komplekslerin Kararlılık Sabitlerinin Potansiyometrik Yöntemle Tayini

Seyhan¹,

Dölen²

2015

Marmara Pharm J

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Quercetin (3,3',4',5,7-pentahydroxyflavone) Complexes with Calcium (II) and Magnesium(II), Its Potentiometrie and Spectrophotometric studies

Cited by 15 publications

References 9 publications

Spectroscopic, thermogravimetric and biological studies of Na(I), Ni(II) and Zn(II) complexes of quercetin

Spectroscopic, thermogravimetric and biological studies of Na(I), Ni(II) and Zn(II) complexes of quercetin

The Influence of Mg(II) and Ca(II) Ions on Rutin Autoxidation in Weakly Alkaline Aqueous Solutions

Flavokermesik Asitin Asit Sabitlerinin ve Kalay(II), Alüminyum(III) İyonları İle Oluşturduğu Komplekslerin Kararlılık Sabitlerinin Potansiyometrik Yöntemle Tayini

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