New Dihydroxytyrosyl Esters from Dicarboxylic Acids: Synthesis and Evaluation of the Antioxidant Activity In Vitro (ABTS) and in Cell-Cultures (DCF Assay)
Elia Roma,
Elena Mattoni,
Paolo Lupattelli,
Seyed Sepehr Moeini,
Tecla Gasperi,
Roberta Bernini,
Sandra Incerpi,
Daniela Tofani
Affiliations
Elia Roma
Department of Science, Roma Tre University, Viale G. Marconi 446, 00146 Rome, Italy
Elena Mattoni
Centro Interdipartimentale per la Didattica Chimica (CeDiC), Via della Vasca Navale 79, 00146 Roma, Italy
Paolo Lupattelli
Department of Science, University of Basilicata, Via dell’Ateneo Lucano 10, 85100 Potenza, Italy
Seyed Sepehr Moeini
Department of Science, Roma Tre University, Viale G. Marconi 446, 00146 Rome, Italy
Tecla Gasperi
Department of Science, Roma Tre University, Viale G. Marconi 446, 00146 Rome, Italy
Roberta Bernini
Department of Agriculture and Forest Sciences (DAFNE), University of Tuscia, Via S. Camillo de Lellis, 01100 Viterbo, Italy
Sandra Incerpi
Department of Science, Roma Tre University, Viale G. Marconi 446, 00146 Rome, Italy
Daniela Tofani
Department of Science, Roma Tre University, Viale G. Marconi 446, 00146 Rome, Italy
New dihydroxytyrosyl esters 2a, 2c–2j of dicarboxylic acids were synthesized from methyl orthoformate protected hydroxytyrosol 3 and diacyl chlorides. New compounds were characterized (HRMS, FT-IR, 1H- and 13C-NMR), and tested for antioxidant activity both in vitro (ABTS) and on L6 myoblasts and THP1 leukemic monocytes cell culture by DCF assay. According to the ABTS assay, compounds 2a, 2c–2j showed a TEAC value of antioxidant capacity up to twice that of Trolox. Very high or complete ROS protections were obtained in the cell environment where lipophilicity and rigidity of dicarboxylic structure seem to facilitate the antioxidant effect. MTT assay and proliferation test were used for assessment of cell viability. These compounds can be envisaged as a new class of preservatives for food or cosmetic products.
