Elementary reactions of the antioxidant action of trans-stilbene derivatives: resveratrol, pinosylvin and 4-hydroxystilbene

Literature Information

Publication Date 2002-01-29
DOI 10.1039/B109063C
Impact Factor 3.676
Authors

Sandra Stojanović, Ortwin Brede


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Abstract

Using pulse radiolysis, elementary reactions of oxidizing radicals such as OH˙, N3˙ and Tl2+ with three trans-stilbene derivatives (4-hydroxy-, 3,5-dihydroxy- and 3,5,4′-trihydroxystilbene) were studied in detail. Depending on the reaction conditions (pH, oxidizing radical), hydroxycyclohexadienyl and phenoxyl radicals of all three polyphenols could beidentified from the transient absorption spectra. The hydroxycyclohexadienyl radicals decay by water- or OH−-elimination forming phenoxyl radicals in a delayed manner. For trans-3,5-dihydroxystilbene it was found that its phenoxyl radicals were mesomeric with keto C-centered radical forms which could explain their sensitivity towards oxygen. From comparison of the spectral and kinetic properties of the transients derived from trans-resveratrol (trans-3,5,4′-trihydroxystilbene) and its analogues, it could be concluded that in the neutral and acidic solution the para-hydroxy group of trans-resveratrol is more reactive than its meta-hydroxy groups, whereas the reactivity of meta-hydroxy groups increases in alkaline solution. This occurrence enables trans-resveratrol to effectively scavenge free radicals in the pH range 2–12.

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Source Journal

Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics
CiteScore: 5.5
Self-citation Rate: 10.3%
Articles per Year: 3036

Physical Chemistry Chemical Physics (PCCP) is an international journal co-owned by 19 physical chemistry and physics societies from around the world. This journal publishes original, cutting-edge research in physical chemistry, chemical physics and biophysical chemistry. To be suitable for publication in PCCP, articles must include significant innovation and/or insight into physical chemistry; this is the most important criterion that reviewers and Editors will judge against when evaluating submissions. The journal has a broad scope and welcomes contributions spanning experiment, theory, computation and data science. Topical coverage includes spectroscopy, dynamics, kinetics, statistical mechanics, thermodynamics, electrochemistry, catalysis, surface science, quantum mechanics, quantum computing and machine learning. Interdisciplinary research areas such as polymers and soft matter, materials, nanoscience, energy, surfaces/interfaces, and biophysical chemistry are welcomed if they demonstrate significant innovation and/or insight into physical chemistry. Joined experimental/theoretical studies are particularly appreciated when complementary and based on up-to-date approaches.

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