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

Polyphenols are natural compounds showing a variety of health-promoting effects. Unfortunately, due to low lipid solubility, their applications in the pharmaceutical, food, and cosmetic industries are limited. With the aim of obtaining novel lipophilic derivatives, the present study reports the synt...

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Autores principales: Bernini, Roberta, Barontini, Maurizio, Cis, Valentina, Carastro, Isabella, Tofani, Daniela, Chiodo, Rosa Anna, Lupattelli, Paolo, Incerpi, Sandra
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6017616/
https://www.ncbi.nlm.nih.gov/pubmed/29351214
http://dx.doi.org/10.3390/molecules23010208
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author Bernini, Roberta
Barontini, Maurizio
Cis, Valentina
Carastro, Isabella
Tofani, Daniela
Chiodo, Rosa Anna
Lupattelli, Paolo
Incerpi, Sandra
author_facet Bernini, Roberta
Barontini, Maurizio
Cis, Valentina
Carastro, Isabella
Tofani, Daniela
Chiodo, Rosa Anna
Lupattelli, Paolo
Incerpi, Sandra
author_sort Bernini, Roberta
collection PubMed
description Polyphenols are natural compounds showing a variety of health-promoting effects. Unfortunately, due to low lipid solubility, their applications in the pharmaceutical, food, and cosmetic industries are limited. With the aim of obtaining novel lipophilic derivatives, the present study reports the synthesis of a series of phenethyl trifluoroacetate esters containing up to two hydroxyl groups in the aromatic ring. Experimental logP values confirmed a greater lipophilicity of the novel compounds compared to the parent compounds. The radical scavenging capacity of all phenethyl trifluoroacetate esters was evaluated by in vitro assays (ABTS, DPPH) and in cultured cells (L6 myoblasts and THP-1 leukemic monocytes) using 2′,7′-dichlorodihydrofluorescein diacetate. These data revealed that the esters showed a good antioxidant effect that was strictly dependent on the grade of hydroxylation of the phenyl ring. The lack of toxicity, evaluated by the MTT assay and proliferation curves, makes these trifluoroacetates attractive derivatives for pharmaceutical, food, and cosmetic applications.
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spelling pubmed-60176162018-11-13 Synthesis and Evaluation of the Antioxidant Activity of Lipophilic Phenethyl Trifluoroacetate Esters by In Vitro ABTS, DPPH and in Cell-Culture DCF Assays Bernini, Roberta Barontini, Maurizio Cis, Valentina Carastro, Isabella Tofani, Daniela Chiodo, Rosa Anna Lupattelli, Paolo Incerpi, Sandra Molecules Article Polyphenols are natural compounds showing a variety of health-promoting effects. Unfortunately, due to low lipid solubility, their applications in the pharmaceutical, food, and cosmetic industries are limited. With the aim of obtaining novel lipophilic derivatives, the present study reports the synthesis of a series of phenethyl trifluoroacetate esters containing up to two hydroxyl groups in the aromatic ring. Experimental logP values confirmed a greater lipophilicity of the novel compounds compared to the parent compounds. The radical scavenging capacity of all phenethyl trifluoroacetate esters was evaluated by in vitro assays (ABTS, DPPH) and in cultured cells (L6 myoblasts and THP-1 leukemic monocytes) using 2′,7′-dichlorodihydrofluorescein diacetate. These data revealed that the esters showed a good antioxidant effect that was strictly dependent on the grade of hydroxylation of the phenyl ring. The lack of toxicity, evaluated by the MTT assay and proliferation curves, makes these trifluoroacetates attractive derivatives for pharmaceutical, food, and cosmetic applications. MDPI 2018-01-19 /pmc/articles/PMC6017616/ /pubmed/29351214 http://dx.doi.org/10.3390/molecules23010208 Text en © 2018 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/).
spellingShingle Article
Bernini, Roberta
Barontini, Maurizio
Cis, Valentina
Carastro, Isabella
Tofani, Daniela
Chiodo, Rosa Anna
Lupattelli, Paolo
Incerpi, Sandra
Synthesis and Evaluation of the Antioxidant Activity of Lipophilic Phenethyl Trifluoroacetate Esters by In Vitro ABTS, DPPH and in Cell-Culture DCF Assays
title Synthesis and Evaluation of the Antioxidant Activity of Lipophilic Phenethyl Trifluoroacetate Esters by In Vitro ABTS, DPPH and in Cell-Culture DCF Assays
title_full Synthesis and Evaluation of the Antioxidant Activity of Lipophilic Phenethyl Trifluoroacetate Esters by In Vitro ABTS, DPPH and in Cell-Culture DCF Assays
title_fullStr Synthesis and Evaluation of the Antioxidant Activity of Lipophilic Phenethyl Trifluoroacetate Esters by In Vitro ABTS, DPPH and in Cell-Culture DCF Assays
title_full_unstemmed Synthesis and Evaluation of the Antioxidant Activity of Lipophilic Phenethyl Trifluoroacetate Esters by In Vitro ABTS, DPPH and in Cell-Culture DCF Assays
title_short Synthesis and Evaluation of the Antioxidant Activity of Lipophilic Phenethyl Trifluoroacetate Esters by In Vitro ABTS, DPPH and in Cell-Culture DCF Assays
title_sort synthesis and evaluation of the antioxidant activity of lipophilic phenethyl trifluoroacetate esters by in vitro abts, dpph and in cell-culture dcf assays
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6017616/
https://www.ncbi.nlm.nih.gov/pubmed/29351214
http://dx.doi.org/10.3390/molecules23010208
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