Literature DB >> 17078995

Hydroxytyrosol lipophilic analogues: enzymatic synthesis, radical scavenging activity and DNA oxidative damage protection.

Salvatore Grasso1, Laura Siracusa, Carmela Spatafora, Marcella Renis, Corrado Tringali.   

Abstract

The olive oil phenol hydroxytyrosol (3), as well its metabolite homovanillic alcohol (4), were subjected to chemoselective lipase-catalysed acylations, affording with good yield 10 derivatives (5-14) bearing C(2), C(3), C(4), C(10) and C(18) acyl chains at C-1. Hydroxytyrosol (3) and its lipophilic derivatives showed very good DPPH. radical scavenging activity. Compounds 3, 4 and their lipophilic analogues 5-14 were subjected to the atypical Comet test on whole blood cells: 3 and its analogues 5 and 6, with little hydrophobic character (logP<or=1.20), showed a good protective effect against H(2)O(2) induced oxidative DNA damage. The homovanillic alcohol 4 and its analogues 10-14 resulted scarcely effective both as radical scavengers and antioxidant agents.

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Year:  2006        PMID: 17078995     DOI: 10.1016/j.bioorg.2006.09.003

Source DB:  PubMed          Journal:  Bioorg Chem        ISSN: 0045-2068            Impact factor:   5.275


  14 in total

1.  Polyphenolic Fraction from Olive Mill Wastewater: Scale-Up and in Vitro Studies for Ophthalmic Nutraceutical Applications.

Authors:  Maria Domenica Di Mauro; Giovanni Fava; Marcella Spampinato; Danilo Aleo; Barbara Melilli; Maria Grazia Saita; Giovanni Centonze; Riccardo Maggiore; Nicola D'Antona
Journal:  Antioxidants (Basel)       Date:  2019-10-08

Review 2.  Biological activities of phenolic compounds present in virgin olive oil.

Authors:  Sara Cicerale; Lisa Lucas; Russell Keast
Journal:  Int J Mol Sci       Date:  2010-02-02       Impact factor: 5.923

3.  Variability of virgin olive oil phenolic compounds in a segregating progeny from a single cross in Olea europaea L. and sensory and nutritional quality implications.

Authors:  Ana G Pérez; Lorenzo León; Mar Pascual; Carmen Romero-Segura; Araceli Sánchez-Ortiz; Raúl de la Rosa; Carlos Sanz
Journal:  PLoS One       Date:  2014-03-20       Impact factor: 3.240

4.  A First Attempt into the Production of Acylglycerol Mixtures from Echium Oil.

Authors:  Luis Vázquez; Alejandro Jordán; Guillermo Reglero; Carlos F Torres
Journal:  Front Bioeng Biotechnol       Date:  2016-01-19

5.  Fruit Phenolic Profiling: A New Selection Criterion in Olive Breeding Programs.

Authors:  Ana G Pérez; Lorenzo León; Carlos Sanz; Raúl de la Rosa
Journal:  Front Plant Sci       Date:  2018-02-27       Impact factor: 5.753

6.  Synthesis and Evaluation of the Antioxidant Activity of Lipophilic Phenethyl Trifluoroacetate Esters by In Vitro ABTS, DPPH and in Cell-Culture DCF Assays.

Authors:  Roberta Bernini; Maurizio Barontini; Valentina Cis; Isabella Carastro; Daniela Tofani; Rosa Anna Chiodo; Paolo Lupattelli; Sandra Incerpi
Journal:  Molecules       Date:  2018-01-19       Impact factor: 4.411

7.  Antioxidant Effect of Hydroxytyrosol, Hydroxytyrosol Acetate and Nitrohydroxytyrosol in a Rat MPP+ Model of Parkinson's Disease.

Authors:  Gabriela Pérez-Barrón; Sergio Montes; Yoshajandith Aguirre-Vidal; Marti Santiago; Elena Gallardo; José Luis Espartero; Camilo Ríos; Antonio Monroy-Noyola
Journal:  Neurochem Res       Date:  2021-07-14       Impact factor: 3.996

8.  Hydroxytyrosol (HT) Analogs Act as Potent Antifungals by Direct Disruption of the Fungal Cell Membrane.

Authors:  George Diallinas; Nausica Rafailidou; Ioanna Kalpaktsi; Aikaterini Christina Komianou; Vivian Tsouvali; Iliana Zantza; Emmanuel Mikros; Alexios Leandros Skaltsounis; Ioannis K Kostakis
Journal:  Front Microbiol       Date:  2018-11-06       Impact factor: 5.640

9.  Synthesis of hydroxytyrosyl alkyl ethers from olive oil waste waters.

Authors:  Andrés Madrona; Gema Pereira-Caro; Raquel Mateos; Guillermo Rodríguez; Mariana Trujillo; Juan Fernández-Bolaños; José L Espartero
Journal:  Molecules       Date:  2009-05-11       Impact factor: 4.411

10.  A Three-Step, Gram-Scale Synthesis of Hydroxytyrosol, Hydroxytyrosol Acetate, and 3,4-Dihydroxyphenylglycol.

Authors:  Amalia D Kalampaliki; Vassiliki Giannouli; Alexios-Leandros Skaltsounis; Ioannis K Kostakis
Journal:  Molecules       Date:  2019-09-05       Impact factor: 4.411

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