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天然深共晶溶剂对 - 白藜芦醇光化学诱导异构化和 2,4,6-三羟基二苯并呋喃电化学环形成的影响。

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

机构信息

Department of Biochemical Sciences "A. Rossi Fanelli", Sapienza University of Roma, p.le Aldo Moro 5, 00185 Rome, Italy.

Active-Italia S.r.l., Via delle Terme Deciane 10, 00153 Rome, Italy.

出版信息

Molecules. 2022 Apr 6;27(7):2348. doi: 10.3390/molecules27072348.

Abstract

-Resveratrol is a natural bioactive compound with well-recognized health promoting effects. When exposed to UV light, this compound can undergo a photochemically induced / 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 -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.

摘要

白藜芦醇是一种天然生物活性化合物,具有公认的促进健康的作用。当暴露在紫外线下时,这种化合物可以经历光诱导的/异构化和 6π电化学环化,随后形成 2,4,6-三羟基二苯并噻吩(THP)。THP 是一种潜在的有害化合物,可产生遗传毒性作用。在这项工作中,我们使用非商业的五氟苯基固定相改进了两种白藜芦醇异构体和 THP 的色谱分离和测定。我们通过在不同的紫外光暴露条件下评估天然深共晶溶剂(NaDES)作为可能的光保护剂的效果,来评估-Resveratrol 异构体和 THP 的形成,目的是增强 Resveratrol 的光稳定性并抑制 THP 的产生。我们的结果表明,甘油基 NaDES 表现出明显的光保护作用,特别是脯氨酸/甘油基 NaDES 对 Resveratrol 的光化学异构化具有很强的抑制作用,并显著限制了有毒衍生物 THP 的形成。考虑到各种商业产品中都含有白藜芦醇,鉴于其光化学降解产物可能带来的遗传毒性风险,以及需要开发绿色、生态可持续和生物相容的白藜芦醇光稳定配方,这些结果值得注意。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cd3b/9000676/a8b6ed25f069/molecules-27-02348-g001.jpg

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