Extra Virgin Olive Oil Extract Exceeds Ibuprofen's Anti-Inflammatory Properties

Researchers from the University of Teramo and Sapienza University in Rome devel­oped a new method to sus­tain­ably extract oleo­can­thal and olea­cein from extra vir­gin olive oil, obtain­ing a highly con­cen­trated solu­tion.

These extracts could pro­vide more effec­tive anti-inflam­ma­tory results than well-known drugs such as Ibuprofen. While phe­nol extrac­tion has been typ­i­cally expen­sive, the new extracts can be pro­duced at a frac­tion of the cost.

One rea­son phe­nol extrac­tion is so costly is the required chem­i­cals. The new process elim­i­nates the need for these chem­i­cals, rely­ing entirely on water as a sol­vent.

Additionally, this water-based process pro­duces no chem­i­cal waste and does not affect the edi­bil­ity of the processed olive oil.

“We have devel­oped a water-based, eco-friendly and bio­com­pat­i­ble method­ol­ogy,” said Antonio Francioso, co-author of the study and researcher at the University of Teramo’s Bioscience and Technology for Food, Agriculture and Environment Department.

“Oleocanthal and olea­cein are nat­ural, edi­ble prod­ucts formed dur­ing olive oil pro­duc­tion. They are derived from plant pre­cur­sors, ligstro­side and oleu­ropein,” he added. ​“They are espe­cially notable for their anti-inflam­ma­tory and antiox­i­dant effects.”

The researchers devel­oped a method to syn­the­size two oleo­can­thal and olea­cein deriv­a­tives, thio­can­thal and thio­can­thol.

They also explored how oleo­can­thal, oleacin and their new deriv­a­tives could inhibit cyclooxy­ge­nase activ­ity. Cyclooxygenase inhibitors, like Ibuprofen, are com­monly used to reduce inflam­ma­tion.

“We con­firmed exist­ing data by using Ibuprofen as the gold stan­dard in our tests,” said Luciana Mosca, co-author of the study and researcher at Sapienza University’s bio­chem­i­cal sci­ences depart­ment.

“Oleocanthal, olea­cein and the new mol­e­cules demon­strated sig­nif­i­cantly stronger activ­ity than Ibuprofen as cyclooxy­ge­nase inhibitors,” she added.

The new mol­e­cules dif­fer from oleo­can­thal and olea­cein due to a process known as sul­fona­tion, which could poten­tially make them far more effec­tive for med­ical appli­ca­tions.

“Oleocanthal and oleacin, though well-stud­ied, have shown great activ­ity in vitro and in cel­lu­lar sys­tems,” Mosca said. ​“However, they face a sig­nif­i­cant phar­ma­co­ki­netic issue: they are unsta­ble mol­e­cules.”

When oleo­can­thal and olea­cein are ingested, they degrade rapidly as the body iden­ti­fies the com­pounds as poten­tially harm­ful and employs var­i­ous bio­log­i­cal sys­tems, includ­ing enzymes, to break them down.

“The extreme reac­tiv­ity of these mol­e­cules is due to their chem­i­cal struc­ture. By using this sul­fona­tion reac­tion, we can make them much less reac­tive,” Mosca said. ​“That’s why we believe that in vivo, these mol­e­cules could demon­strate greater phar­ma­co­log­i­cal activ­ity.”

“However, this still needs to be con­firmed from a sci­en­tific per­spec­tive,” she added. ​“We have early evi­dence, and we’re con­tin­u­ing to con­duct tests. There’s more to come in the next chap­ter.”

Although dozens of phe­nols are present in extra vir­gin olive oils, not all extra vir­gin olive oil con­tains the same amount and pro­por­tion of these com­pounds. Interestingly, these dif­fer­ences impact the pro­duc­tion process of the new extracts.

“It’s impor­tant to select cul­ti­vars that pro­duce olive oils par­tic­u­larly rich in these two polyphe­nols, as not all cul­ti­vars can yield high amounts of oleo­can­thal and olea­cein in the oil,” said Roberto Mattioli, co-author of the study and researcher at Sapienza University’s bio­chem­i­cal sci­ences depart­ment.

For this rea­son, the researchers focused their ini­tial study on Coratina, an Apulian cul­ti­var known for pro­duc­ing extra vir­gin olive oil in which 70 to 80 per­cent of the phe­nols are oleo­can­thal and olea­cein.

“Even with such rich cul­ti­vars, tra­di­tional extrac­tion meth­ods rely on lengthy processes involv­ing organic sol­vents, which must be removed after­ward, pos­ing risks to both the envi­ron­ment and work­ers,” Mattioli said.

Mattioli and his col­leagues said they had devel­oped a method using bio­com­pat­i­ble mol­e­cules instead of organic sol­vents to obtain highly con­cen­trated extracts, reach­ing about 50 mil­ligrams of polyphe­nols per mil­li­liter.

“These mol­e­cules can be safely ingested, poten­tially admin­is­tered directly to ani­mals, or used in vitro on tis­sues or cells in cul­ture because they are entirely bio­com­pat­i­ble,” he said. ​“With such high con­cen­tra­tions, the sub­stances can be appro­pri­ately diluted in var­i­ous cul­ture media and admin­is­tered directly, with­out fur­ther purifi­ca­tion steps or sol­vent evap­o­ra­tion.”

“Currently, five mil­ligrams of oleo­can­thal can cost €250, mak­ing it unsus­tain­able for large-scale pro­duc­tion,” Francioso added.

According to the researchers, the new process might turn the tables.

“Starting with par­tic­u­larly rich oils, we use an extremely eco­nom­i­cal method… to con­cen­trate polyphe­nols by a fac­tor of 100 in a bio­log­i­cal and lipid sol­vent,” said Rodolfo Federico, co-author of the study and co-founder of the startup Active-Italia.

“For the first time, we have raw mate­ri­als that can be used as health-pro­mot­ing agents. Until now, no sup­ple­ments con­tain­ing oleo­can­thal and olea­cein have existed,” he added, ​“only their pre­cur­sors.”

He believes extracts of these two mol­e­cules will have far-reach­ing ben­e­fits beyond the proven anti-inflam­ma­tory prop­er­ties attrib­uted to their cyclooxy­ge­nase-inhibit­ing behav­ior.

“In vivo evi­dence from clin­i­cal stud­ies in patients shows that olive oil with high oleo­can­thal and olea­cein con­tent inhibits the syn­the­sis of pro-inflam­ma­tory cytokines,” he said. ​“The mech­a­nism of action could be much broader, poten­tially address­ing mul­ti­ple patholo­gies. It’s truly quite fas­ci­nat­ing.”

Hundreds of stud­ies have linked con­sum­ing extra vir­gin olive oil to var­i­ous health ben­e­fits.