An exploratory study on the peroxyl-radical-scavenging activity of 2,6-dimethyl-5-hepten-2-ol and its heterocyclic analogues
| Autor: | Józef Kula, Agnieszka Stobiecka, Radosław Bonikowski, Magdalena Sikora |
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| Rok vydání: | 2016 |
| Předmět: |
ABTS
010304 chemical physics Oxygen radical absorbance capacity 010405 organic chemistry Chemistry Monoterpene Radical Organic Chemistry 01 natural sciences 0104 chemical sciences Analytical Chemistry Inorganic Chemistry chemistry.chemical_compound Radical ion Computational chemistry 0103 physical sciences Organic chemistry Molecule Density functional theory Molecular orbital Spectroscopy |
| Zdroj: | Journal of Molecular Structure. 1107:82-90 |
| ISSN: | 0022-2860 |
| DOI: | 10.1016/j.molstruc.2015.11.043 |
| Popis: | The structural properties and radical scavenging activity of 2,6-dimethyl-5-hepten-2-ol ( 1 ) and its new heterocyclic analogues, i.e. 2-methyl-4-(5-methylfuran-2-yl)-butan-2-ol ( 2 ) and 2-methyl-4-(5-methylthiophen-2-yl)-butan-2-ol ( 3 ) and have been studied by using the experimental and theoretical methods for the first time. Activity of title compounds against the peroxyl radical was determined by using standard fluorimetric test, i.e. the Oxygen Radical Absorbance Capacity assay (ORAC FL ). Furthermore, the electron-donating ability of odorants has been evaluated by using colorimetric ABTS assay. According to the experimental results obtained from the ORAC FL test 2,6-dimethyl-5-hepten-2-ol was characterized by the highest activity in comparison with the novel counterparts. Nevertheless, all investigated compounds exhibited pronounced anti-peroxyl radical activity comparable to that exerted by the one of the most prominent antioxidant among the monoterpene alcohols, i.e. by linalool. On the other hand, the title compounds exerted relatively low capacity to quench the radical cation of ABTS. Theoretical calculations based on the Density Functional Theory (DFT) method with the hybrid functional B3LYP were carried out in order to investigate selected structural and electronic properties including the geometrical parameters as well as the energy of frontier molecular orbitals of parent molecules and the resulting radicals. Furthermore, the possible mechanism of peroxyl-radical-scavenging has been determined by using the thermodynamic descriptors such as the bond dissociation enthalpies (BDEs) and ionization potentials (IPs). These theoretical data pointed out the relevance of HAT mechanism in the peroxyl-radical-scavenging exhibited by 2,6-dimethyl-5-hepten-2-ol and its new heterocyclic analogues in polar and non-polar medium. |
| Databáze: | OpenAIRE |
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