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.

Effect of natural deep eutectic solvents on trans-resveratrol photo-chemical induced isomerization and 2,4,6-trihydroxyphenanthrene electro-cyclic formation / Mattioli, R.; Di Risola, D.; Federico, R.; Ciogli, A.; Gasparrini, F.; Villani, C.; Fontana, M.; Maggiore, A.; D'Erme, M.; Mosca, L.; Francioso, A.. - In: MOLECULES. - ISSN 1420-3049. - 27:7(2022), pp. 2348-2360. [10.3390/molecules27072348]

Effect of natural deep eutectic solvents on trans-resveratrol photo-chemical induced isomerization and 2,4,6-trihydroxyphenanthrene electro-cyclic formation

Mattioli R.;Di Risola D.;Federico R.;Ciogli A.;Gasparrini F.;Villani C.;Fontana M.;Maggiore A.;d'Erme M.;Mosca L.
;
Francioso A.
2022

Abstract

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.
2,4,6-trihydroxyphenanthrene; chromatographic separation; isomerization and 6π photochemical electrocyclization; natural deep eutectic solvents; pentafluorophenyl stationary phase; photo-stability; photochemistry; trans/cis-resveratrol; UV light; Isomerism; Phenanthrenes; Resveratrol; Solvents; Deep Eutectic Solvents; Glycerol
01 Pubblicazione su rivista::01a Articolo in rivista
Effect of natural deep eutectic solvents on trans-resveratrol photo-chemical induced isomerization and 2,4,6-trihydroxyphenanthrene electro-cyclic formation / Mattioli, R.; Di Risola, D.; Federico, R.; Ciogli, A.; Gasparrini, F.; Villani, C.; Fontana, M.; Maggiore, A.; D'Erme, M.; Mosca, L.; Francioso, A.. - In: MOLECULES. - ISSN 1420-3049. - 27:7(2022), pp. 2348-2360. [10.3390/molecules27072348]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/1629608
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