Electronic structure of some thymol derivatives correlated with the radical scavenging activity: Theoretical study

Jebelli Javan, Ashkan ; Sharif University of Technology

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  1. Type of Document: Article
  2. DOI: 10.1016/j.foodchem.2014.05.073
  3. Abstract:
  4. Molecules acting as antioxidants capable of scavenging reactive oxygen species (ROS) are of upmost importance in the living cell. Thymol derivatives exhibit various antioxidant activities and potential health benefits. Exploration of structure-radical scavenging activity (SAR) was approached with a wide range of thymol derivatives. To accomplish this task, the DPPH experimental assay along with quantum-chemical calculations were also employed for these compounds. By comparing the structural properties of the derivatives of interest, their antioxidant activity was explained by the formation of an intramolecular hydrogen bond and the presence of unsaturated double bond (–CHdouble bond; length as m-dashCH substituent) in their radical spices. Moreover, the delocalization of odd electrons in these radicals has been investigated by natural bond orbital analysis and interpretation of spin density maps. Reactivity order of the compound towards the ROS: HOradical dot, HOOradical dot, and O2radical dot- was found to be as HOradical dot > HOOradical dot >> O2.-
  5. Keywords:
  6. Bond dissociation energy ; DPPH assay ; Ionization potential ; Thymol radical scavenging activity ; Agents ; Bond strength (chemical) ; Chemical compounds ; Electronic structure ; Oxygen ; Quantum chemistry ; DFT study ; Radical scavenging activity ; Reactive oxygen species ; Phenols ; 1,1 diphenyl 2 picrylhydrazyl ; 8 methoxy 9 hydroxythymol ; 8,10 dihydroxy 9 isobutyryloxythymol ; 8,9 dehydro 10 hydroxythymol ; Antioxidant ; Reactive oxygen metabolite ; Scavenger ; Thymol ; Unclassified drug ; Antioxidant activity ; Article ; Conformational transition ; Correlation analysis ; Density functional theory ; DPPH radical scavenging assay ; Electron transport ; Enthalpy ; Geometry ; Hydrogen bond ; In vitro study ; nonhuman ; structure activity relation
  7. Source: Food Chemistry ; Vol. 165, issue , Dec , 2014 , p. 451-459
  8. URL: http://www.sciencedirect.com/science/article/pii/S0308814614007894