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dc.contributor.authorMateos, Raquel-
dc.contributor.authorMadrona, Andrés-
dc.contributor.authorPereira-Caro, Gema-
dc.contributor.authorDomínguez, Vanessa-
dc.contributor.authorCert, María Rosa-
dc.contributor.authorParrado, Juan-
dc.contributor.authorSarriá, Beatriz-
dc.contributor.authorBravo, Laura-
dc.identifierdoi: 10.1016/j.foodchem.2014.10.036-
dc.identifierissn: 1873-7072-
dc.identifier.citationFood Chemistry 173: 313- 320 (2015)-
dc.description.abstract© 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.-
dc.description.sponsorshipThis research was supported by Grant P09-AGR-5098 from Junta de Andalucía (Spain) and AGL2010-18269 and Consolider-Ingenio CSD2007-00063 from Spanish Ministry of Science and innovation.-
dc.subjectAntioxidant activity-
dc.subjectOlive oil isochromans-
dc.subjectPolar paradox-
dc.subjectLipophilic phenolic antioxidants-
dc.titleSynthesis and antioxidant evaluation of isochroman-derivatives of hydroxytyrosol: Structure-activity relationship-
dc.description.versionPeer Reviewed-
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