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      Green Route for the Isolation and Purification of Hyrdoxytyrosol, Tyrosol, Oleacein and Oleocanthal from Extra Virgin Olive Oil

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          Abstract

          Extra virgin olive oil (EVOO) phenols represent a significant part of the intake of antioxidants and bioactive compounds in the Mediterranean diet. In particular, hydroxytyrosol (HTyr), tyrosol (Tyr), and the secoiridoids oleacein and oleocanthal play central roles as anti-inflammatory, neuro-protective and anti-cancer agents. These compounds cannot be easily obtained via chemical synthesis, and their isolation and purification from EVOO is cumbersome. Indeed, both processes involve the use of large volumes of organic solvents, hazardous reagents and several chromatographic steps. In this work we propose a novel optimized procedure for the green extraction, isolation and purification of HTyr, Tyr, oleacein and oleocanthal directly from EVOO, by using a Natural Deep Eutectic Solvent (NaDES) as an extracting phase, coupled with preparative high-performance liquid chromatography. This purification method allows the total recovery of the four components as single pure compounds directly from EVOO, in a rapid, economic and ecologically sustainable way, which utilizes biocompatible reagents and strongly limits the use or generation of hazardous substances.

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          Extraction of phenolic compounds from virgin olive oil by deep eutectic solvents (DESs)

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            Biological Activities of Phenolic Compounds of Extra Virgin Olive Oil

            Over the last few decades, multiple biological properties, providing antioxidant, anti-inflammatory, chemopreventive and anti-cancer benefits, as well as the characteristic pungent and bitter taste, have been attributed to Extra Virgin Olive Oil (EVOO) phenols. In particular, growing efforts have been devoted to the study of the antioxidants of EVOO, due to their importance from health, biological and sensory points of view. Hydrophilic and lipophilic phenols represent the main antioxidants of EVOO, and they include a large variety of compounds. Among them, the most concentrated phenols are lignans and secoiridoids, with the latter found exclusively in the Oleaceae family, of which the drupe is the only edible fruit. In recent years, therefore, we have tackled the study of the main properties of phenols, including the relationships between their biological activity and the related chemical structure. This review, in fact, focuses on the phenolic compounds of EVOO, and, in particular, on their biological properties, sensory aspects and antioxidant capacity, with a particular emphasis on the extension of the product shelf-life.
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              Inhibition of tau fibrillization by oleocanthal via reaction with the amino groups of tau.

              Tau is a microtubule-associated protein that promotes microtubule assembly and stability. In Alzheimer's disease and related tauopathies, tau fibrillizes and aggregates into neurofibrillary tangles. Recently, oleocanthal isolated from extra virgin olive oil was found to display non-steroidal anti-inflammatory activity similar to ibuprofen. As our unpublished data indicates an inhibitory effect of oleocanthal on amyloid beta peptide fibrillization, we reasoned that it might inhibit tau fibrillization as well. Herein, we demonstrate that oleocanthal abrogates fibrillization of tau by locking tau into the naturally unfolded state. Using PHF6 consisting of the amino acid residues VQIVYK, a hexapeptide within the third repeat of tau that is essential for fibrillization, we show that oleocanthal forms an adduct with the lysine via initial Schiff base formation. Structure and function studies demonstrate that the two aldehyde groups of oleocanthal are required for the inhibitory activity. These two aldehyde groups show certain specificity when titrated with free lysine and oleocanthal does not significantly affect the normal function of tau. These findings provide a potential scheme for the development of novel therapies for neurodegenerative tauopathies.
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                Author and article information

                Contributors
                Role: Academic Editor
                Role: Academic Editor
                Journal
                Molecules
                Molecules
                molecules
                Molecules
                MDPI
                1420-3049
                11 August 2020
                August 2020
                : 25
                : 16
                : 3654
                Affiliations
                [1 ]Department of Biochemical Sciences, “Sapienza” University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy; anna.maggiore@ 123456uniroma1.it (A.M.); mario.fontana@ 123456uniroma1.it (M.F.); alberto.boffi@ 123456uniroma1.it (A.B.); maria.derme@ 123456uniroma1.it (M.D.); luciana.mosca@ 123456uniroma1.it (L.M.)
                [2 ]MOLIROM s.r.l, via Carlo Bartolomeo Piazza 8, 00161 Rome, Italy; r.federico@ 123456molirom.com
                Author notes
                [* ]Correspondence: antonio.francioso@ 123456uniroma1.it ; Tel.: +39-06-4991-0987
                Author information
                https://orcid.org/0000-0001-9822-0260
                https://orcid.org/0000-0002-7524-3395
                https://orcid.org/0000-0003-2748-9021
                Article
                molecules-25-03654
                10.3390/molecules25163654
                7464626
                32796621
                fab1d27e-595d-49ec-830b-36e93fb02502
                © 2020 by the authors.

                Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license ( http://creativecommons.org/licenses/by/4.0/).

                History
                : 06 July 2020
                : 10 August 2020
                Categories
                Article

                extra virgin olive oil,oleocanthal,secoiridoids,green chemistry,hydoxytyrosol,tyrosol,oleacein,natural deep eutectic solvents,ultra-high-performance liquid chromatography,mass spectrometry

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