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Molecules 2018, 23(1), 208; https://doi.org/10.3390/molecules23010208

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

1
Department of Agricultural and Forestry Sciences (DAFNE), University of Tuscia, Via S. Camillo de Lellis, 01100 Viterbo, Italy
2
Department of Sciences, University Roma Tre, Viale G. Marconi 446, 00146 Rome, Italy
3
Centro Interdipartimentale di Servizi per la Didattica della Chimica (CIDSiC), University Roma Tre, Via della Vasca Navale 79, 00146 Rome, Italy
4
Department of Sciences, University of Basilicata, Via dell’Ateneo Lucano 10, 85100 Potenza, Italy
*
Authors to whom correspondence should be addressed.
Received: 29 December 2017 / Revised: 14 January 2018 / Accepted: 16 January 2018 / Published: 19 January 2018
(This article belongs to the Section Medicinal Chemistry)
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Abstract

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. View Full-Text
Keywords: phenethyl trifluoroacetate esters; tyrosol trifluoroacetate; hydroxytyrosol trifluoroacetate; lipophilic antioxidants; ABTS assay; DPPH assay; cell culture DCF assay phenethyl trifluoroacetate esters; tyrosol trifluoroacetate; hydroxytyrosol trifluoroacetate; lipophilic antioxidants; ABTS assay; DPPH assay; cell culture DCF assay
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Bernini, R.; Barontini, M.; Cis, V.; Carastro, I.; Tofani, D.; Chiodo, R.A.; Lupattelli, P.; Incerpi, S. Synthesis and Evaluation of the Antioxidant Activity of Lipophilic Phenethyl Trifluoroacetate Esters by In Vitro ABTS, DPPH and in Cell-Culture DCF Assays. Molecules 2018, 23, 208.

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