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

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 Jan 19;23(1):208. doi: 10.3390/molecules23010208.
Roberta Bernini 1,  Maurizio Barontini 2,  Valentina Cis 3,  Isabella Carastro 4,  Daniela Tofani 5 6,  Rosa Anna Chiodo 7,  Paolo Lupattelli 8,  Sandra Incerpi 9
Affiliations

Affiliations

  • 1 Department of Agricultural and Forestry Sciences (DAFNE), University of Tuscia, Via S. Camillo de Lellis, 01100 Viterbo, Italy. [email protected].
  • 2 Department of Agricultural and Forestry Sciences (DAFNE), University of Tuscia, Via S. Camillo de Lellis, 01100 Viterbo, Italy. [email protected].
  • 3 Department of Agricultural and Forestry Sciences (DAFNE), University of Tuscia, Via S. Camillo de Lellis, 01100 Viterbo, Italy. [email protected].
  • 4 Department of Agricultural and Forestry Sciences (DAFNE), University of Tuscia, Via S. Camillo de Lellis, 01100 Viterbo, Italy. [email protected].
  • 5 Department of Sciences, University Roma Tre, Viale G. Marconi 446, 00146 Rome, Italy. [email protected].
  • 6 Centro Interdipartimentale di Servizi per la Didattica della Chimica (CIDSiC), University Roma Tre, Via della Vasca Navale 79, 00146 Rome, Italy. [email protected].
  • 7 Department of Sciences, University Roma Tre, Viale G. Marconi 446, 00146 Rome, Italy. [email protected].
  • 8 Department of Sciences, University of Basilicata, Via dell'Ateneo Lucano 10, 85100 Potenza, Italy. [email protected].
  • 9 Department of Sciences, University Roma Tre, Viale G. Marconi 446, 00146 Rome, Italy. [email protected].
PMID: 29351214 DOI: 10.3390/molecules23010208
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.

Keywords

ABTS assay; DPPH assay; cell culture DCF assay; hydroxytyrosol trifluoroacetate; lipophilic antioxidants; phenethyl trifluoroacetate esters; tyrosol trifluoroacetate.

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