Phenolic compounds found in Extra Virgin Olive Oil (EVOO) have been associated with various health benefits. Bioavailability studies indicate that the phase I and II metabolites of these phenolic compounds can be detected in human urine and plasma following EVOO consumption. To contribute to the understanding of the biological potential of these phenolic compounds and their metabolites, this study delves into the synthesis, stability, and biological activities of hydroxytyrosol (HT), tyrosol (Tyr), and homovanillic alcohol (HVA), as well as their glucuronide, sulfate, and acetylated metabolites. For the first time, an effective synthesis was developed to allow the selective obtention of 3′- and 4′-glucuronides, as well as sulfates of HT. HT and its acetylated derivative emerged as the most potent compounds across antioxidant assessments, antiproliferative studies against human colorectal adenocarcinoma cell lines, and antimicrobial assays.

中文翻译：

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探索羟基酪醇及其衍生物的生物学潜力：抗增殖、抗氧化和抗菌活性的合成策略和评价


特级初榨橄榄油 （EVOO） 中发现的酚类化合物与各种健康益处有关。生物利用度研究表明，食用 EVOO 后，可以在人类尿液和血浆中检测到这些酚类化合物的 I 期和 II 期代谢物。为了帮助了解这些酚类化合物及其代谢物的生物学潜力，本研究深入研究了羟基酪醇 （HT）、酪醇 （Tyr） 和高香草醇 （HVA） 的合成、稳定性和生物活性，以及它们的葡萄糖醛酸苷、硫酸盐和乙酰化代谢物。首次开发了一种有效的合成，允许选择性获得 3'- 和 4'-葡萄糖醛酸苷酸，以及 HT 的硫酸盐。HT 及其乙酰化衍生物在抗氧化评估、针对人结直肠腺癌细胞系的抗增殖研究和抗菌测定中成为最有效的化合物。