Antioxidant properties of selected 4-phenyl hydroxycoumarins: Integrated in vitro and computational studies
Samo za registrovane korisnike
2014
Autori
Veselinović, JovanaVeselinović, Aleksandar M.
Vitnik, Željko
Vitnik, Vesna
Nikolić, Goran M.
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
A study on the structure-activity relationship of three hydroxy 4-phenyl coumarins, carried out by employing a series of different chemical cell-free tests is presented. Different assays involving one redox reaction with the oxidant (DPPH, ABTS, FRAP and CUPRAC) were employed. Further, the measurement of inhibition of oxidative degradation, such as lipid peroxidation, was used to define compound antioxidant activity. Our results confirm the good antioxidant activity of the 7,8-dihydroxy-4-phenyl coumarin and moderate antioxidant activity of 5,7-dihydroxy-4-phenyl coumarin. In this work, quantum chemical calculations based on density functional theory have been employed at B3LYP/6-311++G(d,p) level of theory to study the influence of number and position of hydroxyl groups in coumarin molecules on antioxidant activity. Calculated values for HOMO and LUMO energies, energy gap, stabilization energies and spin density distribution confirmed experimental results and were used for SAR definit...ion. For determination of reaction mechanism in gas phase and selected solvents bond dissociation enthalpy, adiabatic ionization potential, proton dissociation enthalpy, proton affinity, electron transfer enthalpy and gas phase acidity have been calculated. Hydrogen Atom Transfer mechanism in vacuum and Single-Electron Transfer followed by the Proton Transfer mechanism in other studied systems are most probable free radical scavenging pathways. On the basis of these findings, these hydroxy 4-phenyl coumarins may be considered as potential therapeutic candidates for pathological conditions characterized by free radical overproduction.
Ključne reči:
4-Phenyl coumarins / Antioxidant / Basic structure / DFT / Free radical scavenging mechanismsIzvor:
Chemico-Biological Interactions, 2014, 214, 49-56Izdavač:
- Elsevier Ireland Ltd, Clare
Finansiranje / projekti:
- Proizvodnja novih dijetetskih mlečnih proizvoda za rizične populacije zasnovana na kvalitativnoj i kvantitativnoj analizi biohemijskih markera zdravstvenog rizika konzumiranja mleka (RS-MESTD-Technological Development (TD or TR)-31060)
- Racionalni dizajn i sinteza biološki aktivnih i koordinacionih jedinjenja i funkcionalnih materijala, relevantnih u (bio)nanotehnologiji (RS-MESTD-Basic Research (BR or ON)-172035)
DOI: 10.1016/j.cbi.2014.02.010
ISSN: 0009-2797
PubMed: 24602768
WoS: 000335705800007
Scopus: 2-s2.0-84896507553
Institucija/grupa
IHTMTY - JOUR AU - Veselinović, Jovana AU - Veselinović, Aleksandar M. AU - Vitnik, Željko AU - Vitnik, Vesna AU - Nikolić, Goran M. PY - 2014 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/1586 AB - A study on the structure-activity relationship of three hydroxy 4-phenyl coumarins, carried out by employing a series of different chemical cell-free tests is presented. Different assays involving one redox reaction with the oxidant (DPPH, ABTS, FRAP and CUPRAC) were employed. Further, the measurement of inhibition of oxidative degradation, such as lipid peroxidation, was used to define compound antioxidant activity. Our results confirm the good antioxidant activity of the 7,8-dihydroxy-4-phenyl coumarin and moderate antioxidant activity of 5,7-dihydroxy-4-phenyl coumarin. In this work, quantum chemical calculations based on density functional theory have been employed at B3LYP/6-311++G(d,p) level of theory to study the influence of number and position of hydroxyl groups in coumarin molecules on antioxidant activity. Calculated values for HOMO and LUMO energies, energy gap, stabilization energies and spin density distribution confirmed experimental results and were used for SAR definition. For determination of reaction mechanism in gas phase and selected solvents bond dissociation enthalpy, adiabatic ionization potential, proton dissociation enthalpy, proton affinity, electron transfer enthalpy and gas phase acidity have been calculated. Hydrogen Atom Transfer mechanism in vacuum and Single-Electron Transfer followed by the Proton Transfer mechanism in other studied systems are most probable free radical scavenging pathways. On the basis of these findings, these hydroxy 4-phenyl coumarins may be considered as potential therapeutic candidates for pathological conditions characterized by free radical overproduction. PB - Elsevier Ireland Ltd, Clare T2 - Chemico-Biological Interactions T1 - Antioxidant properties of selected 4-phenyl hydroxycoumarins: Integrated in vitro and computational studies VL - 214 SP - 49 EP - 56 DO - 10.1016/j.cbi.2014.02.010 ER -
@article{ author = "Veselinović, Jovana and Veselinović, Aleksandar M. and Vitnik, Željko and Vitnik, Vesna and Nikolić, Goran M.", year = "2014", abstract = "A study on the structure-activity relationship of three hydroxy 4-phenyl coumarins, carried out by employing a series of different chemical cell-free tests is presented. Different assays involving one redox reaction with the oxidant (DPPH, ABTS, FRAP and CUPRAC) were employed. Further, the measurement of inhibition of oxidative degradation, such as lipid peroxidation, was used to define compound antioxidant activity. Our results confirm the good antioxidant activity of the 7,8-dihydroxy-4-phenyl coumarin and moderate antioxidant activity of 5,7-dihydroxy-4-phenyl coumarin. In this work, quantum chemical calculations based on density functional theory have been employed at B3LYP/6-311++G(d,p) level of theory to study the influence of number and position of hydroxyl groups in coumarin molecules on antioxidant activity. Calculated values for HOMO and LUMO energies, energy gap, stabilization energies and spin density distribution confirmed experimental results and were used for SAR definition. For determination of reaction mechanism in gas phase and selected solvents bond dissociation enthalpy, adiabatic ionization potential, proton dissociation enthalpy, proton affinity, electron transfer enthalpy and gas phase acidity have been calculated. Hydrogen Atom Transfer mechanism in vacuum and Single-Electron Transfer followed by the Proton Transfer mechanism in other studied systems are most probable free radical scavenging pathways. On the basis of these findings, these hydroxy 4-phenyl coumarins may be considered as potential therapeutic candidates for pathological conditions characterized by free radical overproduction.", publisher = "Elsevier Ireland Ltd, Clare", journal = "Chemico-Biological Interactions", title = "Antioxidant properties of selected 4-phenyl hydroxycoumarins: Integrated in vitro and computational studies", volume = "214", pages = "49-56", doi = "10.1016/j.cbi.2014.02.010" }
Veselinović, J., Veselinović, A. M., Vitnik, Ž., Vitnik, V.,& Nikolić, G. M.. (2014). Antioxidant properties of selected 4-phenyl hydroxycoumarins: Integrated in vitro and computational studies. in Chemico-Biological Interactions Elsevier Ireland Ltd, Clare., 214, 49-56. https://doi.org/10.1016/j.cbi.2014.02.010
Veselinović J, Veselinović AM, Vitnik Ž, Vitnik V, Nikolić GM. Antioxidant properties of selected 4-phenyl hydroxycoumarins: Integrated in vitro and computational studies. in Chemico-Biological Interactions. 2014;214:49-56. doi:10.1016/j.cbi.2014.02.010 .
Veselinović, Jovana, Veselinović, Aleksandar M., Vitnik, Željko, Vitnik, Vesna, Nikolić, Goran M., "Antioxidant properties of selected 4-phenyl hydroxycoumarins: Integrated in vitro and computational studies" in Chemico-Biological Interactions, 214 (2014):49-56, https://doi.org/10.1016/j.cbi.2014.02.010 . .