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Title

Synthesis and antioxidant activity of nitrohydroxytyrosol and its acyl derivatives

AuthorsTrujillo Pérez-Lanzac, Mariana; Gallardo, Elena; Madrona, Andrés; Bravo, Laura ; Sarriá, Beatriz ; González Correa, José A.; Mateos, Raquel ; Espartero, José L.
Keywordsantioxidant activity
Parkinson’s disease
hydroxytyrosol
nitroester derivatives
Nitrocatechol
Issue Date2014
CitationJournal of agricultural and food chemistry 62: 10297- 10303 (2014)
Abstract© 2014 American Chemical Society. A series of nitroderivatives has been synthesized from hydroxytyrosol, the natural olive oil phenol, to increase the assortment of compounds with putative effects against Parkinsons disease. Nitrohydroxytyrosyl esters were obtained from nitrohydroxytyrosol using a chemoselective one-step, high-yield, transesterification procedure. The antioxidant activity of these new series of nitrocatechols was evaluated using FRAP, ABTS, and ORAC assays and compared to that of free hydroxytyrosol. The nitro functional group induced a significant increase in the antioxidant activity of nitrohydroxytyrosol compared to hydroxytyrosol. Regarding nitroester derivatives, variable antioxidant activity was observed depending on the acyl side-chain length; shorter chains maintained or even enhanced the antioxidant activity compared to nitrohydroxytyrosol, decreasing the activity with longer side chains in keeping with their lipophilic nature. Therefore, it may be concluded that nitroester derivatives of hydroxytyrosol, which may be obtained by a simple, high-yield reaction, have elevated antioxidant activity and thus present potential bioactivity.
URIhttp://hdl.handle.net/10261/107648
DOI10.1021/jf503543x
Identifiersdoi: 10.1021/jf503543x
issn: 1520-5118
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