Theoretical Study of the Radical Scavenging Activity of Shikonin and Its Derivatives
Corresponding Author
Ruifa Jin
College of Chemistry and Chemical Engineering, Chifeng University, Chifeng, Inner Mongolia 024000, China
College of Chemistry and Chemical Engineering, Chifeng University, Chifeng, Inner Mongolia 024000, ChinaSearch for more papers by this authorJie Li
College of Chemistry and Chemical Engineering, Chifeng University, Chifeng, Inner Mongolia 024000, China
Search for more papers by this authorCorresponding Author
Ruifa Jin
College of Chemistry and Chemical Engineering, Chifeng University, Chifeng, Inner Mongolia 024000, China
College of Chemistry and Chemical Engineering, Chifeng University, Chifeng, Inner Mongolia 024000, ChinaSearch for more papers by this authorJie Li
College of Chemistry and Chemical Engineering, Chifeng University, Chifeng, Inner Mongolia 024000, China
Search for more papers by this authorAbstract
A series of shikonin derivatives have been designed and their radical scavenging activity has been characterized by the B3LYP/6-31+G(d) approach. The hydrogen bond properties of the studied structures were investigated using the atoms in molecules (AIM) theory. The calculated results reveal that the hydrogen bond is important for good scavenging activity. The introduction of electron-drawing (electron-donating) groups increases (decreases) the scavenging activities of radical and radical cations of shikonin derivatives. Shikonin derivatives appear to be good candidates for the single-electron-transfer mechanism, particularly for N(CH3)2 derivative. Taking this system as an example, we present an efficient method for the investigation of radical scavenging activity from theoretical point of view. With the current work, we hope to highlight the radical scavenging activity of hydroxynaphthoquinones derivatives and stimulate the interest for further studies and exploitation in pharmaceutical industry.
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