Exploring the Biological\nPotential of Hydroxytyrosol\nand Derivatives: Synthetic Strategies and Evaluation of Antiproliferative,\nAntioxidant, and Antimicrobial Activities

Phenolic\ncompounds found in Extra Virgin Olive Oil (EVOO)\nhave\nbeen associated with various health benefits. Bioavailability studies\nindicate that the phase I and II metabolites of these phenolic compounds\ncan be detected in human urine and plasma following EVOO consumption.\nTo contribute to the understanding of the biological potential of\nthese phenolic compounds and their metabolites, this study delves\ninto the synthesis, stability, and biological activities of hydroxytyrosol\n(HT), tyrosol (Tyr), and homovanillic alcohol (HVA), as well as their\nglucuronide, sulfate, and acetylated metabolites. For the first time,\nan effective synthesis was developed to allow the selective obtention\nof 3′- and 4′-glucuronides, as well as sulfates of HT.\nHT and its acetylated derivative emerged as the most potent compounds\nacross antioxidant assessments, antiproliferative studies against\nhuman colorectal adenocarcinoma cell lines, and antimicrobial assays.