Toward the Design and Synthesis of Novel Oleocanthal – Based compounds as Potential Anticancer Agents

Extra virgin olive oil (EVOO), a well-known source of polyphenols, has attracted considerable scientific attention in recent years because of their biological activities and health protective effects. Among them hydroxytyrosol, tyrosol and their corresponding EDA esters, oleacein and oleocanthal respectively, acknowledged as the key ingredients responsible for the health benefits of EVOO, are the subject of intense scientific study due to their important biological properties. The significant interest in these high-value natural compounds and the difficulty to isolate them in high amounts in pure form, has triggered the development of various synthetic approaches involving multistep total synthesis with low overall total yields.

In this regard herein we describe the development of a concise and scalable procedure, for the synthesis of various oleocanthal and iso-oleocanthal analogues. The synthesis is performed by a straightforward biomimetic and stereocontrolled approach, starting from oleuropein, an oleacein precursor highly abundant in olive leaves. Several oleocanthal analogs with improved cytotoxic activity against various cancer cell lines have been synthesized. The results so far indicate that oleuropein could serve as an excellent alternative starting material for promising oleocanthal active derivatives.

The authors declare no conflict of interest.

Funding

Ddiol, Τ1ΕDΚ-02 423

Publication History

Article published online:
12 December 2022