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Título: | Synthesis and antioxidant evaluation of isochroman-derivatives of hydroxytyrosol: Structure-activity relationship |
Autor: | Mateos, Raquel CSIC ORCID ; Madrona, Andrés CSIC ORCID; Pereira-Caro, Gema; Domínguez, Vanessa; Cert, María Rosa CSIC ORCID ; Parrado, Juan; Sarriá, Beatriz CSIC ORCID; Bravo, Laura CSIC ORCID | Palabras clave: | Antioxidant activity Olive oil isochromans Polar paradox Lipophilic phenolic antioxidants Hydroxytyrosol |
Fecha de publicación: | 2015 | Editor: | Elsevier | Citación: | Food Chemistry 173: 313- 320 (2015) | Resumen: | © 2014 Elsevier Ltd. All rights reserved. Isochroman-derivatives of the natural olive oil phenol hydroxytyrosol (HT) have been synthesised via Oxa-Pictet-Spengler reaction in high yields. Lipophilicity and antioxidant activity were determined to establish the structure-activity relationship of isochromans compared to HT, BHT and α-tocopherol. Antioxidant capacity was tested in two different media: bulk oils, using the Rancimat test, and brain homogenates, by measuring malondialdehyde (MDA) levels as a lipoperoxidation biomarker. In addition, other antioxidant assays (FRAP, ABTS and ORAC) were carried out. Rancimat and MDA results show that antioxidant activity was related with lipophilicity, directly in brain homogenates and inversely in the oils, in agreement with the polar paradox. Free o-diphenolic groups positively determined the activity in the oils, whereas reducing and radical-scavenging activities were related to the number of free hydroxyl moieties. BHT and α-tocopherol showed lower antioxidant activity than isochromans and HT. We conclude that HT-isochromans present significant potential as bioactive compounds. | URI: | http://hdl.handle.net/10261/108078 | DOI: | 10.1016/j.foodchem.2014.10.036 | Identificadores: | doi: 10.1016/j.foodchem.2014.10.036 issn: 1873-7072 |
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