Iron complexes of dietary flavonoids: Combined spectroscopic and mechanistic study of their free radical scavenging activity
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2011
Authors
Dimitrić Marković, Jasmina M.Markovic, Zoran S.
Brdaric, Tanja P.
Pavelkić, Vesna
Jadranin, Milka
Article (Published version)
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Combined spectroscopic (UV/visible, Raman, MS) and theoretical approaches were used to assess interaction of iron(III) with quercetin and baicalein in aqueous buffered solutions. Obtained results implicated formation of two iron quercetin complexes, with pH-dependent stoichiometries of 1:2 and 1:1, and one iron baicalein complex with stoichiometry of 1:1. Results of vibrational analysis and theoretical calculations implicated 3-hydroxy-4-carbonyl and the 3'-hydroxy-4'-hydroxy group of catechol as chelating sites for quercetin. For baicalein 5-hydroxy-6-hydroxy group is energetically the most favourable, although 5-hydroxy-4-carbonyl and 6-hydroxy-7-hydroxy chelating sites are energetically similar. Antiradical activity. reaction stoichiometry and number of inactivated DPPH molecules per mole of antioxidant indicated quercetin as a better antioxidant than its iron complex, baicalein and iron baicalein complex. The same structural features appeared to be important both in complexation an...d antioxidant activity. The equilibrium geometries, optimised using the B3LYP/6-31G (d, p) level of theory, predicted structural modifications between the ligand molecules in free state and in the complex structures. Correlation between experimental and theoretical results was very good.
Keywords:
Baicalein / Quercetin / Iron(III) complex formation / Electronic, mass and Raman spectra / DPPH test / B3LYP/6-31G (d, p) level of theorySource:
Food Chemistry, 2011, 129, 4, 1567-1577Publisher:
- Elsevier Sci Ltd, Oxford
Funding / projects:
- Dynamics of nonlinear physicochemical and biochemical systems with modeling and predicting of their behavior under nonequilibrium conditions (RS-MESTD-Basic Research (BR or ON)-172015)
DOI: 10.1016/j.foodchem.2011.06.008
ISSN: 0308-8146
WoS: 000294979600033
Scopus: 2-s2.0-80051795142
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IHTMTY - JOUR AU - Dimitrić Marković, Jasmina M. AU - Markovic, Zoran S. AU - Brdaric, Tanja P. AU - Pavelkić, Vesna AU - Jadranin, Milka PY - 2011 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/857 AB - Combined spectroscopic (UV/visible, Raman, MS) and theoretical approaches were used to assess interaction of iron(III) with quercetin and baicalein in aqueous buffered solutions. Obtained results implicated formation of two iron quercetin complexes, with pH-dependent stoichiometries of 1:2 and 1:1, and one iron baicalein complex with stoichiometry of 1:1. Results of vibrational analysis and theoretical calculations implicated 3-hydroxy-4-carbonyl and the 3'-hydroxy-4'-hydroxy group of catechol as chelating sites for quercetin. For baicalein 5-hydroxy-6-hydroxy group is energetically the most favourable, although 5-hydroxy-4-carbonyl and 6-hydroxy-7-hydroxy chelating sites are energetically similar. Antiradical activity. reaction stoichiometry and number of inactivated DPPH molecules per mole of antioxidant indicated quercetin as a better antioxidant than its iron complex, baicalein and iron baicalein complex. The same structural features appeared to be important both in complexation and antioxidant activity. The equilibrium geometries, optimised using the B3LYP/6-31G (d, p) level of theory, predicted structural modifications between the ligand molecules in free state and in the complex structures. Correlation between experimental and theoretical results was very good. PB - Elsevier Sci Ltd, Oxford T2 - Food Chemistry T1 - Iron complexes of dietary flavonoids: Combined spectroscopic and mechanistic study of their free radical scavenging activity VL - 129 IS - 4 SP - 1567 EP - 1577 DO - 10.1016/j.foodchem.2011.06.008 ER -
@article{ author = "Dimitrić Marković, Jasmina M. and Markovic, Zoran S. and Brdaric, Tanja P. and Pavelkić, Vesna and Jadranin, Milka", year = "2011", abstract = "Combined spectroscopic (UV/visible, Raman, MS) and theoretical approaches were used to assess interaction of iron(III) with quercetin and baicalein in aqueous buffered solutions. Obtained results implicated formation of two iron quercetin complexes, with pH-dependent stoichiometries of 1:2 and 1:1, and one iron baicalein complex with stoichiometry of 1:1. Results of vibrational analysis and theoretical calculations implicated 3-hydroxy-4-carbonyl and the 3'-hydroxy-4'-hydroxy group of catechol as chelating sites for quercetin. For baicalein 5-hydroxy-6-hydroxy group is energetically the most favourable, although 5-hydroxy-4-carbonyl and 6-hydroxy-7-hydroxy chelating sites are energetically similar. Antiradical activity. reaction stoichiometry and number of inactivated DPPH molecules per mole of antioxidant indicated quercetin as a better antioxidant than its iron complex, baicalein and iron baicalein complex. The same structural features appeared to be important both in complexation and antioxidant activity. The equilibrium geometries, optimised using the B3LYP/6-31G (d, p) level of theory, predicted structural modifications between the ligand molecules in free state and in the complex structures. Correlation between experimental and theoretical results was very good.", publisher = "Elsevier Sci Ltd, Oxford", journal = "Food Chemistry", title = "Iron complexes of dietary flavonoids: Combined spectroscopic and mechanistic study of their free radical scavenging activity", volume = "129", number = "4", pages = "1567-1577", doi = "10.1016/j.foodchem.2011.06.008" }
Dimitrić Marković, J. M., Markovic, Z. S., Brdaric, T. P., Pavelkić, V.,& Jadranin, M.. (2011). Iron complexes of dietary flavonoids: Combined spectroscopic and mechanistic study of their free radical scavenging activity. in Food Chemistry Elsevier Sci Ltd, Oxford., 129(4), 1567-1577. https://doi.org/10.1016/j.foodchem.2011.06.008
Dimitrić Marković JM, Markovic ZS, Brdaric TP, Pavelkić V, Jadranin M. Iron complexes of dietary flavonoids: Combined spectroscopic and mechanistic study of their free radical scavenging activity. in Food Chemistry. 2011;129(4):1567-1577. doi:10.1016/j.foodchem.2011.06.008 .
Dimitrić Marković, Jasmina M., Markovic, Zoran S., Brdaric, Tanja P., Pavelkić, Vesna, Jadranin, Milka, "Iron complexes of dietary flavonoids: Combined spectroscopic and mechanistic study of their free radical scavenging activity" in Food Chemistry, 129, no. 4 (2011):1567-1577, https://doi.org/10.1016/j.foodchem.2011.06.008 . .