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

• Published in: Journal of agricultural and food chemistry 2024-12, Vol.72 (50), p.27841-27849
• Main Authors: Bonacci, Sonia, Cione, Erika, Coscarella, Mario, Nardi, Monica, Scarpelli, Rosa, Simeonov, Svilen, Procopio, Antonio
• Format: Article
• Language: English
• Subjects: Agricultural and Environmental Chemistry; Antioxidants - chemistry; Antioxidants - pharmacology; Cell Line; Choline - chemistry; Choline - pharmacology; Deep Eutectic Solvents - chemistry; Esterification; Humans; Keratinocytes - drug effects; Phenols - chemistry; Phenols - pharmacology; Phenylethyl Alcohol - analogs & derivatives; Phenylethyl Alcohol - chemistry; Phenylethyl Alcohol - pharmacology; Superoxide Dismutase - chemistry; Superoxide Dismutase - metabolism
• ISSN: 0021-8561; 1520-5118; 1520-5118
• DOI: 10.1021/acs.jafc.4c09446

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.