Relationship between structure, properties, and the radical scavenging activity of morin

Ana María Mendoza-Wilson, Hisila Santacruz-Ortega, René R. Balandrán-Quintana

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36 Scopus citations

Abstract

The relationship between structure, kinetic, thermochemical and electronic properties of the morin flavonoid was researched in order to establish the molecular characteristics related to its maximum radical scavenging activity. The reaction of morin with the 2,2-diphenyl-1-picrylhydrazyl radical (DPPH1) was carried out in ethanol, through the hydrogen-atom transfer (HAT) mechanism. Morin showed the highest radical scavenging activity under conditions of excess of free radical. It was found, by means of experimental and computational methods, that 3-OH, 2′-OH and 4′-OH are the main reactive sites, as well as that the 3-O-2′-O quinone is the first product of the reaction, tending to prevail in the enol form through a tautomerism effect, whose observed structural arrangement corresponds to the 3-O semiquinone. © 2011 Elsevier B.V. All rights reserved.
Original languageAmerican English
Pages (from-to)134-141
Number of pages8
JournalJournal of Molecular Structure
DOIs
StatePublished - 31 May 2011

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