Effect of Natural Deep Eutectic Solvents on trans-Resveratrol Photo-Chemical Induced Isomerization and 2,4,6-Trihydroxyphenanthrene Electro-Cyclic Formation

• Main Authors: Ciogli, A. (Author), d'Erme, M. (Author), Di Risola, D. (Author), Federico, R. (Author), Fontana, M. (Author), Francioso, A. (Author), Gasparrini, F. (Author), Maggiore, A. (Author), Mattioli, R. (Author), Mosca, L. (Author), Villani, C. (Author)
• Format: Article
• Language: English
• Published: NLM (Medline) 2022
• Subjects: 2,4,6-trihydroxyphenanthrene; chemistry; chromatographic separation; Deep Eutectic Solvents; glycerol; Glycerol; isomerism; Isomerism; isomerization and 6π photochemical electrocyclization; natural deep eutectic solvents; pentafluorophenyl stationary phase; phenanthrene derivative; Phenanthrenes; photochemistry; photo-stability; resveratrol; Resveratrol; solvent; Solvents; trans/cis-resveratrol; UV light
• Online Access: View Fulltext in Publisher
• ISBN: 14203049 (ISSN)
• DOI: 10.3390/molecules27072348

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.