A DFT Study on the Radical-Scavenging Properties of Ferruginol-Type Diterpenes
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Ferruginol-type diterpenes have been identified in extracts from numerous plant species. These secondary metabolites are characterized by the multifaceted bioactivity and beneficial impact on the human health. Unfortunately, the antioxidant properties and function of these foods components is not well recognized so far. Therefore, in the current study the theoretical calculations based on the Density Functional Theory (DFT) method were undertaken to investigate in details the radical-scavenging mechanism of ferruginol (1) and its derivatives such as hinokiol (2) and sugiol (3) for the first time. According to these results the direct hydrogen atom transfer (HAT) and sequential proton loss electron transfer (SPLET) mechanism was exhibited by the ferruginol-type abietanes in the non-polar media and polar solvents, respectively. Ferruginol (1) and hinokiol (2) were found to be the most promising free radical scavengers with activity comparable to that of butylated hydroxytoluene (BHT), a synthetic antioxidant commonly used in the food industry.
KeywordsFerruginol Hinokiol Sugiol DFT method Radical-scavenging activity Structure–activity relationships
Wiesław Majzner (Faculty of Biotechnology and Food Sciences, Lodz University of Technology, Poland) is gratefully acknowledged for help in handling the crystallographic data base. I also thank Reviewers for valuable suggestions and comments on the manuscript.
This research did not receive any specific grant from funding agencies in the public, commercial, or not-for-profit sectors.
Compliance with Ethical Standards
Conflict of Interest
Author declares no conflicts of interest.
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