Selective Lipophilization of Natural Phenolic Alcohols Induced by In Situ Choline Chloride-Based Natural Deep Eutectic Solvents

IF 6.2 1区农林科学 Q1 AGRICULTURE, MULTIDISCIPLINARY

Journal of Agricultural and Food Chemistry Pub Date : 2024-12-09 DOI:10.1021/acs.jafc.4c09446

Sonia Bonacci, Erika Cione, Mario Coscarella, Monica Nardi, Rosa Scarpelli, Svilen Simeonov, Antonio Procopio

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Abstract

In this scientific work, a novel and green method for selective lipophilization of EVOO’s bioactive phenolic alcohols (PAs), namely, tyrosol, hydroxytyrosol, and its metabolite homovanillyl alcohol as fatty acid esters, is elucidated. The PAs have been employed as hydrogen bond donors in the formation of natural deep eutectic solvents (NADES) with choline chloride (ChCl). The fast and cheap esterification method by in situ formation of choline chloride-based deep eutectic solvents promotes the derivatization of PAs with various fatty acids as acylating agents in the absence of organic solvents and catalysts. Furthermore, given the growing interest in the application of NADES formed by bioactive molecules in the pharmacological and cosmetic fields, we analyzed the activity of antioxidant enzymes, superoxide dismutase, and glutathione S-transferase of three chemical formulations obtained after the formation of PA-oleate in the H₂O₂-treated HaCat human keratinocytes cell line, assessing also their toxicity via the MTT assay.

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原位氯化胆碱基天然深共晶溶剂诱导天然酚醇的选择性脂化作用

在这项科学工作中，阐述了一种新的绿色方法，用于选择性脂化EVOO的生物活性酚醇（PAs），即酪醇，羟基酪醇及其代谢产物纯香草醇作为脂肪酸酯。在与氯化胆碱（ChCl）形成天然深共晶溶剂（NADES）时，PAs被用作氢键供体。在没有有机溶剂和催化剂的情况下，原位形成氯化胆碱基深度共晶溶剂的快速廉价酯化方法促进了各种脂肪酸作为酰化剂的PAs衍生化。此外，鉴于生物活性分子形成的NADES在药理学和化妆品领域的应用越来越受到关注，我们分析了在h2o2处理的HaCat人角化细胞细胞系中形成pa -油酸酯后获得的三种化学制剂的抗氧化酶、超氧化物歧化酶和谷胱甘肽s -转移酶的活性，并通过MTT试验评估了它们的毒性。

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来源期刊

Journal of Agricultural and Food Chemistry 农林科学-农业综合

CiteScore

9.90

自引率

8.20%

发文量

1375

审稿时长

2.3 months

期刊介绍： The Journal of Agricultural and Food Chemistry publishes high-quality, cutting edge original research representing complete studies and research advances dealing with the chemistry and biochemistry of agriculture and food. The Journal also encourages papers with chemistry and/or biochemistry as a major component combined with biological/sensory/nutritional/toxicological evaluation related to agriculture and/or food.