Effect of Natural Deep Eutectic Solvents on <i>trans</i>-Resveratrol Photo-Chemical Induced Isomerization and 2,4,6-Trihydroxyphenanthrene Electro-Cyclic Formation
Roberto Mattioli,
Daniel Di Risola,
Rodolfo Federico,
Alessia Ciogli,
Francesco Gasparrini,
Claudio Villani,
Mario Fontana,
Anna Maggiore,
Maria d’Erme,
Luciana Mosca,
Antonio Francioso
Affiliations
Roberto Mattioli
Department of Biochemical Sciences “A. Rossi Fanelli”, Sapienza University of Roma, p.le Aldo Moro 5, 00185 Rome, Italy
Daniel Di Risola
Department of Biochemical Sciences “A. Rossi Fanelli”, Sapienza University of Roma, p.le Aldo Moro 5, 00185 Rome, Italy
Rodolfo Federico
Active-Italia S.r.l., Via delle Terme Deciane 10, 00153 Rome, Italy
Alessia Ciogli
Department of Chemistry and Technology of Drugs, Sapienza University, p.le Aldo Moro 5, 00185 Rome, Italy
Francesco Gasparrini
Department of Chemistry and Technology of Drugs, Sapienza University, p.le Aldo Moro 5, 00185 Rome, Italy
Claudio Villani
Department of Chemistry and Technology of Drugs, Sapienza University, p.le Aldo Moro 5, 00185 Rome, Italy
Mario Fontana
Department of Biochemical Sciences “A. Rossi Fanelli”, Sapienza University of Roma, p.le Aldo Moro 5, 00185 Rome, Italy
Anna Maggiore
Department of Biochemical Sciences “A. Rossi Fanelli”, Sapienza University of Roma, p.le Aldo Moro 5, 00185 Rome, Italy
Maria d’Erme
Department of Biochemical Sciences “A. Rossi Fanelli”, Sapienza University of Roma, p.le Aldo Moro 5, 00185 Rome, Italy
Luciana Mosca
Department of Biochemical Sciences “A. Rossi Fanelli”, Sapienza University of Roma, p.le Aldo Moro 5, 00185 Rome, Italy
Antonio Francioso
Department of Biochemical Sciences “A. Rossi Fanelli”, Sapienza University of Roma, p.le Aldo Moro 5, 00185 Rome, Italy
trans-Resveratrol is a natural bioactive compound with well-recognized health promoting effects. When exposed to UV light, this compound can undergo a photochemically induced trans/cis isomerization and a 6π electrochemical cyclization with the subsequent formation of 2,4,6-trihydroxyphenanthrene (THP). THP is a potentially harmful compound which can exert genotoxic effects. In this work we improved the chromatographic separation and determination of the two resveratrol isomers and of THP by using a non-commercial pentafluorophenyl stationary phase. We assessed the effect of natural deep eutectic solvents (NaDES) as possible photo-protective agents by evaluating cis-resveratrol isomer and THP formation under different UV-light exposure conditions with the aim of enhancing resveratrol photostability and inhibiting THP production. Our results demonstrate a marked photoprotective effect exerted by glycerol-containing NaDES, and in particular by proline/glycerol NaDES, which exerts a strong inhibitory effect on the photochemical isomerization of resveratrol and significantly limits the formation of the toxic derivative THP. Considering the presence of resveratrol in various commercial products, these results are of note in view of the potential genotoxic risk associated with its photochemical degradation products and in view of the need for the development of green, eco-sustainable and biocompatible resveratrol photo-stable formulations.
