Antioxidant properties and free radical-scavenging reactivity of a family of hydroxynaphthalenones and dihydroxyanthracenones. 2007

Jorge Rodríguez, and Claudio Olea-Azar, and Cristina Cavieres, and Ester Norambuena, and Tomás Delgado-Castro, and Jorge Soto-Delgado, and Ramiro Araya-Maturana
Departamento de Química Inorgánica y Analítica, Facultad de Ciencias Químicas y Farmacéuticas, Universidad de Chile, Chile.

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 (k(2)), were obtained under pseudo-first-order conditions. The free radical-scavenging activities and k(2) 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.

UI MeSH Term Description Entries
D007700 Kinetics The rate dynamics in chemical or physical systems.
D009281 Naphthalenes Two-ring crystalline hydrocarbons isolated from coal tar. They are used as intermediates in chemical synthesis, as insect repellents, fungicides, lubricants, preservatives, and, formerly, as topical antiseptics.
D010100 Oxygen An element with atomic symbol O, atomic number 8, and atomic weight [15.99903; 15.99977]. It is the most abundant element on earth and essential for respiration. Dioxygen,Oxygen-16,Oxygen 16
D004578 Electron Spin Resonance Spectroscopy A technique applicable to the wide variety of substances which exhibit paramagnetism because of the magnetic moments of unpaired electrons. The spectra are useful for detection and identification, for determination of electron structure, for study of interactions between molecules, and for measurement of nuclear spins and moments. (From McGraw-Hill Encyclopedia of Science and Technology, 7th edition) Electron nuclear double resonance (ENDOR) spectroscopy is a variant of the technique which can give enhanced resolution. Electron spin resonance analysis can now be used in vivo, including imaging applications such as MAGNETIC RESONANCE IMAGING. ENDOR,Electron Nuclear Double Resonance,Electron Paramagnetic Resonance,Paramagnetic Resonance,Electron Spin Resonance,Paramagnetic Resonance, Electron,Resonance, Electron Paramagnetic,Resonance, Electron Spin,Resonance, Paramagnetic
D006860 Hydrogen Bonding A low-energy attractive force between hydrogen and another element. It plays a major role in determining the properties of water, proteins, and other compounds. Hydrogen Bonds,Bond, Hydrogen,Hydrogen Bond
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D000873 Anthracenes A group of compounds with three aromatic rings joined in linear arrangement.
D000975 Antioxidants Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. Anti-Oxidant,Antioxidant,Antioxidant Activity,Endogenous Antioxidant,Endogenous Antioxidants,Anti-Oxidant Effect,Anti-Oxidant Effects,Anti-Oxidants,Antioxidant Effect,Antioxidant Effects,Activity, Antioxidant,Anti Oxidant,Anti Oxidant Effect,Anti Oxidant Effects,Anti Oxidants,Antioxidant, Endogenous,Antioxidants, Endogenous
D012680 Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed) Specificity,Sensitivity,Specificity and Sensitivity
D015203 Reproducibility of Results The statistical reproducibility of measurements (often in a clinical context), including the testing of instrumentation or techniques to obtain reproducible results. The concept includes reproducibility of physiological measurements, which may be used to develop rules to assess probability or prognosis, or response to a stimulus; reproducibility of occurrence of a condition; and reproducibility of experimental results. Reliability and Validity,Reliability of Result,Reproducibility Of Result,Reproducibility of Finding,Validity of Result,Validity of Results,Face Validity,Reliability (Epidemiology),Reliability of Results,Reproducibility of Findings,Test-Retest Reliability,Validity (Epidemiology),Finding Reproducibilities,Finding Reproducibility,Of Result, Reproducibility,Of Results, Reproducibility,Reliabilities, Test-Retest,Reliability, Test-Retest,Result Reliabilities,Result Reliability,Result Validities,Result Validity,Result, Reproducibility Of,Results, Reproducibility Of,Test Retest Reliability,Validity and Reliability,Validity, Face

Related Publications

Jorge Rodríguez, and Claudio Olea-Azar, and Cristina Cavieres, and Ester Norambuena, and Tomás Delgado-Castro, and Jorge Soto-Delgado, and Ramiro Araya-Maturana
January 2016, International journal of molecular sciences,
Jorge Rodríguez, and Claudio Olea-Azar, and Cristina Cavieres, and Ester Norambuena, and Tomás Delgado-Castro, and Jorge Soto-Delgado, and Ramiro Araya-Maturana
July 2008, Chemico-biological interactions,
Jorge Rodríguez, and Claudio Olea-Azar, and Cristina Cavieres, and Ester Norambuena, and Tomás Delgado-Castro, and Jorge Soto-Delgado, and Ramiro Araya-Maturana
September 2005, Organic & biomolecular chemistry,
Jorge Rodríguez, and Claudio Olea-Azar, and Cristina Cavieres, and Ester Norambuena, and Tomás Delgado-Castro, and Jorge Soto-Delgado, and Ramiro Araya-Maturana
December 2004, Phytotherapy research : PTR,
Jorge Rodríguez, and Claudio Olea-Azar, and Cristina Cavieres, and Ester Norambuena, and Tomás Delgado-Castro, and Jorge Soto-Delgado, and Ramiro Araya-Maturana
January 1998, Nutrition and cancer,
Jorge Rodríguez, and Claudio Olea-Azar, and Cristina Cavieres, and Ester Norambuena, and Tomás Delgado-Castro, and Jorge Soto-Delgado, and Ramiro Araya-Maturana
June 2002, Free radical research,
Jorge Rodríguez, and Claudio Olea-Azar, and Cristina Cavieres, and Ester Norambuena, and Tomás Delgado-Castro, and Jorge Soto-Delgado, and Ramiro Araya-Maturana
July 2009, Natural product communications,
Jorge Rodríguez, and Claudio Olea-Azar, and Cristina Cavieres, and Ester Norambuena, and Tomás Delgado-Castro, and Jorge Soto-Delgado, and Ramiro Araya-Maturana
December 2007, Biochemical and biophysical research communications,
Jorge Rodríguez, and Claudio Olea-Azar, and Cristina Cavieres, and Ester Norambuena, and Tomás Delgado-Castro, and Jorge Soto-Delgado, and Ramiro Araya-Maturana
January 1994, Advances in experimental medicine and biology,
Jorge Rodríguez, and Claudio Olea-Azar, and Cristina Cavieres, and Ester Norambuena, and Tomás Delgado-Castro, and Jorge Soto-Delgado, and Ramiro Araya-Maturana
January 2011, Journal of complementary & integrative medicine,
Copied contents to your clipboard!