Producción CyT
Photosensitized isomerization of resveratrol: Evaluation of energy and electron transfer pathways

Artículo

Autoría
Neyra Recky, Jael Rhode ; Gaspar Tosato, Maira ; Buglak, Andrey A. ; DANTOLA, MARIA LAURA ; LORENTE, CAROLINA
Fecha
2024
Editorial y Lugar de Edición
Elsevier Inc.
Revista
Free Radical Biology and Medicine, vol. 216 (pp. 50-59) - ISSN 0891-5849
Elsevier Inc.
ISSN
0891-5849
Resumen Información suministrada por el agente en SIGEVA
Resveratrol (3,5,4?-trihydroxystilbene) is a natural stilbene synthetized as trans-isomer in plants exposed to oxidative stress. In order to understand the mechanism involvedduring photosensitized degradation of trans-resveratrol,steady-state and time-resolved experiments were performed and compared with quantum-chemical calculations using density functional theory (DFT). Pterin (Ptr), a well-known photosensitizer, under UV-A radiation induces the oxidation of several biomolecules mainly throug... Resveratrol (3,5,4?-trihydroxystilbene) is a natural stilbene synthetized as trans-isomer in plants exposed to oxidative stress. In order to understand the mechanism involvedduring photosensitized degradation of trans-resveratrol,steady-state and time-resolved experiments were performed and compared with quantum-chemical calculations using density functional theory (DFT). Pterin (Ptr), a well-known photosensitizer, under UV-A radiation induces the oxidation of several biomolecules mainly through electron-transfer mechanisms. On the one hand, it was observed that trans-RSV participates in an energy-transfer pathway with3Ptr*forming3trans-RSV*, which dissipates the energy by isomerization to cis-RSV. On the other hand, RSV neutral radical (trans-RSV(-H)•) was detected in laser flash photolysis experiments, indicating an electron-transfer mechanism. The electron-transfer from 3Ptr* to trans-RSV is a barely feasible reaction, however, more favorable is the formation of trans-RSV(-H)• in a reaction between trans-RSV and Ptr radical cation (Ptr•+), which is produced during irradiation. The combination of experimental and theoretical approaches evidences the capability of trans-RSV to undergo energy-transfer (feasible by DFT calculations) and/or one-electron transfer pathways with Ptr triplet excited state.These findings reveal the mechanisms involved in the interaction of trans-RSV and pterin excited states and provide information on the antioxidant action of resveratrol during photosensitized oxidation of biomolecules.
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Palabras Clave
electron-transferoxidative stressresveratrolenergy-transfer
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