Phenolic Compounds from Virgin Olive Oil: Approaches for Their Synthesis and Analogues

Abstract

Virgin olive oil (VOO) is the main fat consumed by populations in the Mediterranean basin, and phenolic compounds, minor components of this fat, are known to be responsible for diverse health benefits when consumed in a regular diet. According to numerous investigations, these benefits are mostly related to phenols such as tyrosol and hydroxytyrosol and secoiridoid derivatives such as ligstroside, oleuropein, oleocanthal and oleacein. These compounds are present in low concentrations, and for some of them, standards are not commercially available, hampering studies on the mechanisms underlying their biological activity. In order to contribute to a better knowledge of the bioactivity of these compounds and their metabolites, they must be available with high purity and in sufficient amounts for the assays. Chemical synthesis has been considered a convenient way to obtain these compounds. This Review will focus on the synthesis of representative VOO compounds, namely, ligstroside, oleuropein, oleocanthal, oleacein and analogues.

Properties and chemical compositions of monovarietal virgin olive oil at different ripening stages: A study on olive cultivation in Northwest China

“…Interestingly, they showed similar dynamics to hydroxytyrosol and tyrosol. The two phenolic alcohols, together with secologanin, could form oleuropein in the olive plant leaves and fruits (Rao et al., 2019), and then during the VOO preparation, the biotransformation from oleuropein to other secoiridoids might afford oleacein, oleocanthal, and so on (Martins et al., 2022; Sarikaki et al., 2020). Oleacein (0.02–26.27 mg/kg) and oleocanthal (0.09–58.09 mg/kg) were found to be much more than oleuropein aglycone (0.01–8.14 mg/kg).…”

Potential Therapeutic Properties of Olea europaea Leaves from Selected Cultivars Based on Their Mineral and Organic Profiles

“…HT has also been associated with innumerous favorable properties such as immuno-protective and antimicrobial activity [ 60 , 61 ], and anti-diabetic [ 62 ], anti-arrhythmic and cardioprotective [ 63 ], hypotensive and anti-atherosclerotic [ 64 ], anti-inflammatory [ 65 ], and antioxidant [ 66 , 67 , 68 ] effects. Besides HT, other phenolic compounds have shown to exhibit antibacterial effects against several strains of bacteria responsible for intestinal and respiratory infections in vitro [ 66 , 69 , 70 , 71 ], with promising results for applications as preservatives in food industry [ 23 , 62 , 72 , 73 ], in particular reducing the growth of Helicobacter pylori, which is associated with peptic ulcers and gastric cancer [ 66 ]. OLE polyphenols have also revealed antiviral and antiprotozoal activities [ 17 , 61 , 74 , 75 , 76 ].…”

Extra-Virgin Olive Oil in Alzheimer’s Disease: A Comprehensive Review of Cellular, Animal, and Clinical Studies

“…EVOO is renowned for its culinary virtues and its rich array of phenolic compounds, which are garnering increasing attention for their potential therapeutic implications in AD [30,33,34]. Central to this group of compounds are primary phenolics like OLE, HT, and tyrosol, which undergo dynamic changes during olive maturation and oil extraction, influencing EVOO's health properties [30,35,36]. OLE, a major phenolic in olive fruit and its derivative OLG, and HT, known for its potent antioxidant capacity, possess critical neuroprotective effects [34,36,37].…”

“…Central to this group of compounds are primary phenolics like OLE, HT, and tyrosol, which undergo dynamic changes during olive maturation and oil extraction, influencing EVOO's health properties [30,35,36]. OLE, a major phenolic in olive fruit and its derivative OLG, and HT, known for its potent antioxidant capacity, possess critical neuroprotective effects [34,36,37]. The minor polar compounds in EVOO, including the secoiridoids OC and OH-OC, and phenolic alcohols such as tyrosol and HT, add to this protective arsenal.…”