Active-Italia: Oleocanthal from Olea europaea

The Virgin Olive Oil phenolic compounds include about 30 molecules from different chemical classes: phenolic alcohols, such as hydroxytyrosol and tyrosol, phenolic acids (e.g., caffeic and vanillic), flavones (luteolin and apigenin), lignans, and secoiridoids. The latter group represents the largest fraction. The principal ones are the aglycon forms of oleuropein and ligstroside, the dialdehydic forms of their decarboxymethylated derivatives, known as oleacein and oleocanthal. A protective role against cardiovascular, metabolic diseases, and human cancer has been attributed to hydroxytyrosol, oleocanthal, and oleacein -

In 1993 oleocanthal was first isolated from Extra Virgin Olive Oil along with other secoiridoids by Montedoro and colleagues. Subsequently, Beauchamp and coworkers demonstrated the antiinflammatory activity of oleocanthal in 2005.

“It is about a fortuitous discovery that occurred in the United States. In 1999 the American scientist Gary Beauchamp ( considered one of the world’s leading experts on chemosensory science) attended a world meeting on the island of Sicily accompanying other scientists to an organo – sensory conference on molecular nutrition organized by the marriage of physicists Massimo Ugo Palma and his wife Marie Beatrice Voltarelli.

In the course of the meeting, the couple invited a meal at their home on the island of Erice in which, among other things, extra virgin olive oil was served. Dr. Gary Beauchamp expert in organolepsy had no history of having tested the aforementioned oil in his life. He drank several sips and realized that it had a special flavor, when it was drunk, there was an itch in the backpacking that not all olive oils have. He repeated the operation and could see that it had the same taste as a syrup they were experiencing in his laboratory at the University of Philadelphia. Upon returning to the United States, they were able to confirm that the typical taste similar to ibuprofen came from a molecule that they later named Oleocanthal (Beauchamp and Cols, they called it OLEOCANTHAL, by the word «OLEO» Oil, CANTH from «ACANTHOS» Itching and AL of Aldehido).

The team of Professor Gary Beauchamp discovered something else, the substance was a powerful anti-inflammatory, four tablespoons of this oil rich in Oleocanthal, was the equivalent to approximately 250 mg of ibuprofen in vitro.”

Other chemical names of oleocanthal include decarboxymethyl ligstroside aglycone, dialdehydic form of deacetoxy-ligstroside aglycone, deacetoxy-dialdehydic ligstroside aglycone, and p-hydroxyphenylethanol-elenolic acid dialdehyde (p-HPEA-EDA). Naturally existing oleocanthal is presented in the S-configuration of chiral carbon, while synthetic oleocanthal is presented in the R-configuration.

Oleocanthal has several biological activities. Oleocanthal exerts antiinflammatory, antioxidant, anticancer, and neuroprotective pharmacologic activities. Despite structural dissimilarity, oleocanthal showed similar antiinflammatory properties to ibuprofen, a nonsteroidal antiinflammatory drug.

Italy, Spain, Greece, Tunisia, the United States, and France were the pioneer countries to research on olive phenolic content. According to the literature searches, four olive biophenols, including tyrosol, hydroxytyrosol, oleuropein, and oleocanthal, were the most studied olive oil biophenols. Unfortunately, studies on the pharmacokinetics and bioavailability of oleocanthal are still limited today.


Umberto Berti, PM Active-Italia

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