Antioxidative Potency and UV–Vis spectra features of the compounds resulting from the chelation of Fe2+ by Caffeic Acid Phenethyl Ester and two of its derivatives

Holtomo, Olivier; Nsangou, Mama; Fifen, Jean Jules; Motapon, Ousmanou

doi:10.1016/j.comptc.2015.06.006

Cited by 22 publications

(19 citation statements)

References 52 publications

(76 reference statements)

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“…It is evident from Figure 4 that, in gas phase, the presence of the metal ions leads to a great increment in the IP value of juglone. This result agrees with those obtained by other authors in similar studies [9,26]. In gas phase, the Cu(I) chelate has the lowest IP value (12.74 eV).…”

Section: Electron Transfer-proton Transfer Mechanismsupporting

confidence: 83%

“…This signifies that metal chelation increases the acidity of the OH group. This result is in good agreement with those obtained by Holtomo and coworkers [9]. In gas phase, the PA values of the chelates increase in the order: Ni(II) < Co(II) < Cu(II) < Fe(II) < Zn(II) < Mg(II) < Ca(II) < Cu(I).…”

Section: Sequential Proton Loss Electron Transfer Mechanismsupporting

confidence: 82%

“…It is clear from this figure that the BDE and BDFE values of the chelates are lower than that of juglone in the two media investigated. This is a clear indication of the fact that the presence of these metal ions increases the AOA of juglone, which is in good agreement with the findings in the literature [9,26]. In gas phase, the Co(II) chelate has been found to possess the lowest BDE value (262 kJ/mol), which corroborates with its highest O-H bond length observed in the said phase (Section 3.3).…”

Section: Radical Scavenging Activitysupporting

confidence: 80%

“…With the aim of determining the nature of all the stationary points, frequency calculations were performed on all the optimized geometries at the same level of theory. The DFT/B3LYP method was used because it is frequently employed for the studies on metalation of natural antioxidant [9][10][11]26]. The calculations on closed shell systems were performed by the means of the Restricted Kohn-Sham formalism whereas the Unrestricted Kohn-Sham approach was used for open shell systems [23,27].…”

Section: Theoretical Background and Computational Detailsmentioning

confidence: 99%

“…This binding process occurs through an acid-base reaction in which the metal ion acts as the Lewis acid and the polyphenol functions as the Lewis base. The above-mentioned solutions toward mitigating the excesses of transition metal ions in living organisms have been subject to many studies [9][10][11][12].…”

Section: Introductionmentioning

confidence: 99%

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Quantum Chemical Investigation on the Antioxidant Activity of Neutral and Anionic Forms of Juglone: Metal Chelation and Its Effect on Radical Scavenging Activity

Tamafo

Ghogomu

Nkungli

et al. 2017

Journal of Chemistry

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The chelation ability of divalent Mg, Ca, Fe, Co, Ni, Cu, Zn, and monovalent Cu ions by neutral and anionic forms of juglone has been investigated at DFT/B3LYP/6-31+G(d,p) level of theory in gas and aqueous phases. It is noteworthy that only the 1 : 1 stoichiometry was considered herein. The effects of these metals on the radical scavenging activity of neutral juglone were evaluated via the usual descriptors of hydrogen atom transfer. According to our results, metal chelation by the two forms of juglone was spontaneous and exothermic in both media. Based on the binding energies, Cu(II) ion showed the highest affinity for the ligands. QTAIM analyses identified the metal-ligand bonds as intermediate type interactions in all the chelates, except those of Ca and Mg. It was also found that the chelates were better radical scavengers than the ligands. In the gas phase, the scavenging activity of the compounds was found to be governed by direct hydrogen atom transfer, the Co(II) chelate being the most reactive. In the aqueous phase also, the sequential proton loss electron transfer was preferred by all the molecules, while the Cu(II) chelates were the most reactive.

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Section: Electron Transfer-proton Transfer Mechanismsupporting

confidence: 83%

Section: Sequential Proton Loss Electron Transfer Mechanismsupporting

confidence: 82%

Section: Radical Scavenging Activitysupporting

confidence: 80%

Section: Theoretical Background and Computational Detailsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Quantum Chemical Investigation on the Antioxidant Activity of Neutral and Anionic Forms of Juglone: Metal Chelation and Its Effect on Radical Scavenging Activity

Tamafo

Ghogomu

Nkungli

et al. 2017

Journal of Chemistry

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DFT insights into the structure, reactivity and radical scavenging activity of cycloartocarpesin

Fouégué

Tedongmo

Ntieche

et al. 2021

J of Physical Organic Chem

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Daily increase in the number of patients suffering from illnesses due to reactive species has induced the permanent discovery and study of antioxidant compounds. The structure, reactivity, and antioxidant activity (AOA) of a phenolic compound named cycloartocarpesin (CAP), evaluated at DFT/B3LYP/6‐31 + G(d,p) level, is reported herein in the gas, pentyl ethanoate, and water phases. Bader topological analysis revealed that two of the three O‐H groups of CAP are involved in hydrogen bonds while the average local ionization energy (ALIE) and appropriate Fukui functions showed that electrons in the near vicinity of C7, C10, and C12 are the least tightly held and can easily be attacked by radicals. Analysis of the transition state of the reaction between CAP and HOO• radical shows that the proton coupled electron transfer process is not favored. Moreover, analyses of electronic spectra calculated at TD‐DFT/B3LYP/6‐31 + G(d,p) has interestingly demonstrate the ability of CAP to filtrate UVA, UVB, and UVC, thus exhibiting a photo‐protective activity.

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Infrared spectra of PEHA molecule and its resistance to oxidation in water and methanol media at 298.15 K: solvent cluster size dependency

et al. 2020

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Antioxidative Potency and UV–Vis spectra features of the compounds resulting from the chelation of Fe2+ by Caffeic Acid Phenethyl Ester and two of its derivatives

Cited by 22 publications

References 52 publications

Quantum Chemical Investigation on the Antioxidant Activity of Neutral and Anionic Forms of Juglone: Metal Chelation and Its Effect on Radical Scavenging Activity

Quantum Chemical Investigation on the Antioxidant Activity of Neutral and Anionic Forms of Juglone: Metal Chelation and Its Effect on Radical Scavenging Activity

DFT insights into the structure, reactivity and radical scavenging activity of cycloartocarpesin

Infrared spectra of PEHA molecule and its resistance to oxidation in water and methanol media at 298.15 K: solvent cluster size dependency

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