Antioxidant properties and free radical-scavenging reactivity of a family of hydroxynaphthalenones and dihydroxyanthracenones

Jorge Rodríguez, Claudio Olea-Azar, Cristina Cavieres, Ester Norambuena, Tomás Delgado-Castro, Jorge Soto-Delgado, Ramiro Araya-Maturana

Resultado de la investigación: Article

36 Citas (Scopus)

Resumen

This study was undertaken to investigate the free radical-scavenging and antioxidant activities of various structurally related hydroquinones including hydroxynaphthalenones and dihydroxyanthracenones. Electron spin resonance spectroscopy and spin trapping techniques were used to evaluate the ability of hydroquinones to scavenge hydroxyl, diphenylpicrylhydrazyl, and galvinoxyl radicals. In addition, the oxygen radical absorbing capacity assay using fluorescein (ORAC-FL) was used to obtain the relative antioxidant capacity of these radicals. The rate constants of the first H atom abstraction by 2,2-diphenyl-2-picrylhydrazyl (k2), were obtained under pseudo-first-order conditions. The free radical-scavenging activities and k2 values discriminate well between hydroxynaphthalenones and dihydroxyanthracenones, showing that the latter have better antioxidant properties. The aforementioned experimental data agree with quantum-chemical results demonstrating the relevance of intramolecular H bonding to radical-scavenging activities.

Idioma originalEnglish
Páginas (desde-hasta)7058-7065
Número de páginas8
PublicaciónBioorganic and Medicinal Chemistry
Volumen15
N.º22
DOI
EstadoPublished - 15 nov 2007

Huella dactilar

Scavenging
Hydroquinones
Free Radicals
Antioxidants
Electron spin resonance spectroscopy
Spin Trapping
Electron Spin Resonance Spectroscopy
Fluorescein
Hydroxyl Radical
Rate constants
Assays
Reactive Oxygen Species
Atoms

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

Citar esto

Rodríguez, Jorge ; Olea-Azar, Claudio ; Cavieres, Cristina ; Norambuena, Ester ; Delgado-Castro, Tomás ; Soto-Delgado, Jorge ; Araya-Maturana, Ramiro. / Antioxidant properties and free radical-scavenging reactivity of a family of hydroxynaphthalenones and dihydroxyanthracenones. En: Bioorganic and Medicinal Chemistry. 2007 ; Vol. 15, N.º 22. pp. 7058-7065.
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abstract = "This study was undertaken to investigate the free radical-scavenging and antioxidant activities of various structurally related hydroquinones including hydroxynaphthalenones and dihydroxyanthracenones. Electron spin resonance spectroscopy and spin trapping techniques were used to evaluate the ability of hydroquinones to scavenge hydroxyl, diphenylpicrylhydrazyl, and galvinoxyl radicals. In addition, the oxygen radical absorbing capacity assay using fluorescein (ORAC-FL) was used to obtain the relative antioxidant capacity of these radicals. The rate constants of the first H atom abstraction by 2,2-diphenyl-2-picrylhydrazyl (k2), were obtained under pseudo-first-order conditions. The free radical-scavenging activities and k2 values discriminate well between hydroxynaphthalenones and dihydroxyanthracenones, showing that the latter have better antioxidant properties. The aforementioned experimental data agree with quantum-chemical results demonstrating the relevance of intramolecular H bonding to radical-scavenging activities.",
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Antioxidant properties and free radical-scavenging reactivity of a family of hydroxynaphthalenones and dihydroxyanthracenones. / Rodríguez, Jorge; Olea-Azar, Claudio; Cavieres, Cristina; Norambuena, Ester; Delgado-Castro, Tomás; Soto-Delgado, Jorge; Araya-Maturana, Ramiro.

En: Bioorganic and Medicinal Chemistry, Vol. 15, N.º 22, 15.11.2007, p. 7058-7065.

Resultado de la investigación: Article

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AU - Rodríguez, Jorge

AU - Olea-Azar, Claudio

AU - Cavieres, Cristina

AU - Norambuena, Ester

AU - Delgado-Castro, Tomás

AU - Soto-Delgado, Jorge

AU - Araya-Maturana, Ramiro

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N2 - This study was undertaken to investigate the free radical-scavenging and antioxidant activities of various structurally related hydroquinones including hydroxynaphthalenones and dihydroxyanthracenones. Electron spin resonance spectroscopy and spin trapping techniques were used to evaluate the ability of hydroquinones to scavenge hydroxyl, diphenylpicrylhydrazyl, and galvinoxyl radicals. In addition, the oxygen radical absorbing capacity assay using fluorescein (ORAC-FL) was used to obtain the relative antioxidant capacity of these radicals. The rate constants of the first H atom abstraction by 2,2-diphenyl-2-picrylhydrazyl (k2), were obtained under pseudo-first-order conditions. The free radical-scavenging activities and k2 values discriminate well between hydroxynaphthalenones and dihydroxyanthracenones, showing that the latter have better antioxidant properties. The aforementioned experimental data agree with quantum-chemical results demonstrating the relevance of intramolecular H bonding to radical-scavenging activities.

AB - This study was undertaken to investigate the free radical-scavenging and antioxidant activities of various structurally related hydroquinones including hydroxynaphthalenones and dihydroxyanthracenones. Electron spin resonance spectroscopy and spin trapping techniques were used to evaluate the ability of hydroquinones to scavenge hydroxyl, diphenylpicrylhydrazyl, and galvinoxyl radicals. In addition, the oxygen radical absorbing capacity assay using fluorescein (ORAC-FL) was used to obtain the relative antioxidant capacity of these radicals. The rate constants of the first H atom abstraction by 2,2-diphenyl-2-picrylhydrazyl (k2), were obtained under pseudo-first-order conditions. The free radical-scavenging activities and k2 values discriminate well between hydroxynaphthalenones and dihydroxyanthracenones, showing that the latter have better antioxidant properties. The aforementioned experimental data agree with quantum-chemical results demonstrating the relevance of intramolecular H bonding to radical-scavenging activities.

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