Next Article in Journal
Celastrol Induces Apoptosis in Gefitinib-Resistant Non-Small Cell Lung Cancer Cells via Caspases-Dependent Pathways and Hsp90 Client Protein Degradation
Previous Article in Journal
Inhibition of GlcNAc-Processing Glycosidases by C-6-Azido-NAG-Thiazoline and Its Derivatives
Molecules 2014, 19(3), 3489-3507; doi:10.3390/molecules19033489
Article

Antioxidant Activity of Hispidin Oligomers from Medicinal Fungi: A DFT Study

1,* , 1,2, 1,2, 3, 4, 1,2 and 1,2
Received: 30 January 2014 / Revised: 17 March 2014 / Accepted: 17 March 2014 / Published: 21 March 2014
View Full-Text   |   Download PDF [853 KB, 18 June 2014; original version 18 June 2014]   |   Browse Figures

Abstract

Hispidin oligomers are styrylpyrone pigments isolated from the medicinal fungi Inonotus xeranticus and Phellinus linteus. They exhibit diverse biological activities and strong free radical scavenging activity. To rationalize the antioxidant activity of a series of four hispidin oligomers and determine the favored mechanism involved in free radical scavenging, DFT calculations were carried out at the B3P86/6-31+G (d, p) level of theory in gas and solvent. The results showed that bond dissociation enthalpies of OH groups of hispidin oligomers (ArOH) and spin density delocalization of related radicals (ArO) are the appropriate parameters to clarify the differences between the observed antioxidant activities for the four oligomers. The effect of the number of hydroxyl groups and presence of a catechol moiety conjugated to a double bond on the antioxidant activity were determined. Thermodynamic and kinetic studies showed that the PC-ET mechanism is the main mechanism involved in free radical scavenging. The spin density distribution over phenoxyl radicals allows a better understanding of the hispidin oligomers formation.
Keywords: hispidin; antioxidant activity; DFT; BDE; PC-ET hispidin; antioxidant activity; DFT; BDE; PC-ET
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote
MDPI and ACS Style

Anouar, E.H.; Shah, S.A.A.; Hassan, N.B.; Moussaoui, N.E.; Ahmad, R.; Zulkefeli, M.; Weber, J.-F.F. Antioxidant Activity of Hispidin Oligomers from Medicinal Fungi: A DFT Study. Molecules 2014, 19, 3489-3507.

View more citation formats

Related Articles

Article Metrics

Comments

Citing Articles

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert