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

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

Research output: Contribution to journalArticlepeer-review

38 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 (DPPH 1) 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.

Original languageEnglish
Pages (from-to)134-141
Number of pages8
JournalJournal of Molecular Structure
Volume995
Issue number1-3
DOIs
StatePublished - 31 May 2011

Bibliographical note

Funding Information:
The authors of this paper are very grateful with the Consejo Nacional de Ciencia y Tecnología (CONACYT) which financed the investigation under Grant No. 91541 . Also with Centro de Investigación en Alimentación y Desarrollo, A.C. (CIAD, A.C.), especially with the Ph.D. Rogerio R. Sotelo-Mundo, and Universidad de Sonora, for the support to carry out this work.

Keywords

  • Antioxidant activity
  • Density functional theory
  • Infrared spectroscopy
  • Morin
  • Radical scavenging
  • Stopped-flow

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