Journal ArticleDOI
Reaction of benzoxanthene lignans with peroxyl radicals in polar and non-polar media: cooperative behaviour of OH groups
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TLDR
Benzo[kl]xanthene lignans, promising bioactive polyphenols obtained by biomimetic oxidative coupling of caffeic acid derivatives, react efficiently with peroxyl radicals in both polar and non-polar solvents, thanks to the simultaneous presence of guaiacol- like and catechol-like OH-groups.Abstract:
Benzo[kl]xanthene lignans, promising bioactive polyphenols obtained by biomimetic oxidative coupling of caffeic acid derivatives, react efficiently with peroxyl radicals in both polar and non-polar solvents, thanks to the simultaneous presence of guaiacol-like and catechol-like OH-groups.read more
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Dihydrobenzofuran Neolignanamides: Laccase-Mediated Biomimetic Synthesis and Antiproliferative Activity
Nunzio Cardullo,Luana Pulvirenti,Carmela Spatafora,Nicolò Musso,Vincenza Barresi,Daniele F. Condorelli,Corrado Tringali +6 more
TL;DR: The biomimetic synthesis of a small library of dihydrobenzofuran neolignanamides (the natural trans-grossamide and the related compounds 21-28) has been carried out through an eco-friendly oxidative coupling reaction mediated by Trametes versicolor laccase, and it was demonstrated that (±)-21 exerts its antiproliferative activity by inducing cell cycle arrest and apoptosis.
Journal ArticleDOI
Bio-inspired benzo[k,l]xanthene lignans: synthesis, DNA-interaction and antiproliferative properties
Carmela Spatafora,Vincenza Barresi,Vedamurthy M. Bhusainahalli,Simone Di Micco,Nicolò Musso,Raffaele Riccio,Giuseppe Bifulco,Daniele F. Condorelli,Corrado Tringali +8 more
TL;DR: Twelve benzo[k,l]xanthene lignans synthesized by biomimetic, Mn-mediated oxidative coupling of caffeic esters and amides interact with DNA in a dual mode, as confirmed by DF-STD NMR analysis and molecular docking.
Journal ArticleDOI
Synthesis, DNA-binding study, and antioxidant activity of 14-aryl-14H-dibenzo[a,j]xanthene derivatives
Andivelu Ilangovan,Karnambaram Anandhan,Kaushik Mahabir Prasad,Pakkiri Vijayakumar,Rajalingam Renganathan,Devanesan Arul Ananth,T. Sivasudha +6 more
TL;DR: In this paper, a simple and efficient one-pot method for the synthesis of 14-aryl-14H-dibenzo[a,j]xanthene derivatives using Ni(ClO4)2·6H2O as a catalyst is described.
Journal ArticleDOI
Oxidative Transformations of Lignans.
TL;DR: An overview on the current findings in the field of oxidative transformations of lignan structures is presented, and mechanisms based on hydrogen abstractions, epoxidations, hydroxylations, and radical reactions are discussed for the transformation and interconverted structures.
Journal ArticleDOI
Calibration of Squalene, p-Cymene, and Sunflower Oil as Standard Oxidizable Substrates for Quantitative Antioxidant Testing
TL;DR: The autoxidation kinetics of stripped sunflower oil, squalene, and p-cymene initiated by 2,2'-azobis(isobutyronitrile) at 303 K were investigated under controlled conditions by differential oximetry in order to build reference model systems that are representative of the natural variability of oxidizable materials, for quantitative antioxidant testing.
References
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Journal ArticleDOI
Thermochemistry of Proton-Coupled Electron Transfer Reagents and its Implications
TL;DR: This issue discusses proton-coupled electron transfer or PCET processes, which are central to a great many chemical and biochemical processes, from biological catalysis and energy transduction, to bulk industrial chemical processes, to new approaches to solar energy conversion.
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Autoxidation of biological molecules. 1. Antioxidant activity of vitamin E and related chain-breaking phenolic antioxidants in vitro
G. W. Burton,K. U. Ingold +1 more
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Autoxidation of biological molecules. 4. Maximizing the antioxidant activity of phenols
Graham W. Burton,Takahisa Doba,Eric J. Gabe,L. Hughes,Florence L. Lee,L. Prasad,Keith U. Ingold +6 more
TL;DR: On mesure les constantes de vitesse de l'elimination of l'hydrogene atomique par les radicaux peroxyles de lα-tocopherol and de 35 phenols structuralement apparentes.
Journal ArticleDOI
Solvent effects on the rates and mechanisms of reaction of phenols with free radicals.
TL;DR: The rates of formal abstraction of phenolic hydrogen atoms by free radicals, Y* + ArOH --> YH + ArO*, are profoundly influenced by the hydrogen-bond-accepting and anion-solvation abilities of solvents, by the electron affinities and reactivities of radicals, and by the phenol's ring substituents.
Journal ArticleDOI
Bond Dissociation Energies of O−H Bonds in Substituted Phenols from Equilibration Studies
Marco Lucarini,and Pamela Pedrielli,Gian Franco Pedulli,Salvatore Cabiddu and,Claudia Fattuoni +4 more
TL;DR: In this article, the equilibration of couples of phenols and of the corresponding phenoxyl radicals by means of EPR spectroscopy was studied by measuring the equilibrium concentrations of the two radicals in highly concentrated solutions submitted to continuous photolysis in the presence of di-tert-butyl peroxide.