abstract
Because of the close relation between oxidative stress and a plethora of inflammatory diseases, antioxidants have received an increased attention for incorporation into dermatological products. Their use and absorption are, however, limited by their low solubility in water-rich formulations. Herein, a set of novel cholinium-based salts, namely dicholinium ellagate and cholinium caffeate, syringate, vanillate, gallate, and salicylate, were synthesized and characterized. Their melting and decomposition temperatures, water solubility, and toxicological, antioxidant, cytotoxicity and pro-/anti-inflammatory activities were addressed. These new salts, exclusively composed of ions derived from natural sources, display a high thermal stability-up to 150 degrees C. The synthesized compounds are significantly more soluble in water (on average, 3 orders of magnitude higher) than the corresponding phenolic acids. Furthermore, they present not only similar but even higher antioxidant and anti-inflammatory activities, as well as comparable cytotoxicity and lower ecotoxicity profiles than their acidic precursors. Among all the investigated salts, dicholinium ellagate is the most promising synthesized salt when considering the respective antioxidant and anti-inflammatory activities. Because all the synthesized salts are based on the cholinium cation, they can further be envisaged as essential nutrients to be used in oral drugs.
keywords
CARBOXYLATE IONIC LIQUIDS; FISCHERI MARINE-BACTERIA; VIBRIO-FISCHERI; CAFFEIC ACID; OXIDATIVE STRESS; ELLAGIC ACID; IN-VITRO; TOXICITY; BIODEGRADATION; BIOMATERIALS
subject category
Chemistry; Science & Technology - Other Topics; Engineering
authors
Sintra, TE; Luis, A; Rocha, SN; Ferreira, AIMCL; Goncalves, F; Santos, LMNBF; Neves, BM; Freire, MG; Ventura, SPM; Coutinho, JAP
our authors
Andreia Veríssimo Luís
Research Fellowship
Mara Guadalupe Freire Martins
Coordinating Researcher
Sónia Patrícia Marques Ventura
Assistant Professor
Tânia Ereira Sintra
Post-Doc FellowshipGroups
G4 - Renewable Materials and Circular Economy
G5 - Biomimetic, Biological and Living Materials
acknowledgements
This work was developed in the scope of the project CICECO-Aveiro Institute of Materials (ref. FCT UID/CTM/50011/2013), financed by national funds through the FCT/MEC and when applicable, cofinanced by FEDER under the PT2020 Partnership Agreement. The authors are grateful for financial support from FCT for the doctoral grant SFRH/BD/85871/2012 of T. E. Sintra and postdoctoral grant SFRH/BPD/79263/2011 of S. P. M. Ventura. M. G. Freire acknowledges the European Research Council (ERC) for the Starting Grant ERC 2013-StG-337753.