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Free Radical Research Volume 43, 2009 - Issue 1
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Original

Free radical generation in rosmarinic acid investigated by electron paramagnetic resonance spectroscopy

Katharina F. Pirker Department of Environmental Research, Austrian Research Centers GmbH-ARC, Seibersdorf, AustriaCorrespondence[email protected]
,
Christopher W. M. Kay Institute of Structural & Molecular Biology and London Centre for Nanotechnology, University College London, London, UK
,
Klaus Stolze Molecular Pharmacology and Toxicology Unit, Department for Biomedical Sciences, University of Veterinary Medicine Vienna, Vienna, Austria
,
Daniel Tunega Institute for Theoretical Chemistry, University of Vienna, Vienna, Austria; Institute of Soil Research, University of Natural Resources and Applied Life Sciences, Vienna, Austria
,
Thomas G. Reichenauer Department of Environmental Research, Austrian Research Centers GmbH-ARC, Seibersdorf, Austria
&
Bernard A. Goodman Department of Environmental Research, Austrian Research Centers GmbH-ARC, Seibersdorf, Austria; Department of Chemistry & Chemical Engineering, Guangxi University, Nanning, Guangxi, PR China
Pages 47-57 | Received 22 Aug 2008, Published online: 06 Aug 2009
 
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Abstract

Free radical generation as a result of oxidation reactions of rosmarinic acid (RA), a caffeic acid ester with 3,4-dihydroxyphenyllactate, was investigated by electron paramagnetic resonance (EPR) spectroscopy using a variety of oxidation conditions. Limitations and possibilities of using the various methodologies to obtain information about the reaction chemistry of polyphenols are discussed. Three different spectra were detected dependent on the pH and oxidizing agent. Feasible structures for the observed radicals were tested by density functional theory (DFT) calculations and the results indicate that oxidation reactions can occur at both of the catechol groups.

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