Oleocanthal: the natural Ibuprofen found in Extra Virgin Olive Oil

Consuming 3 tablespoons of raw Extra Virgin Olive oil (EVOO) on a daily basis provides a good amount of oleocanthal, a potent anti-inflammatory compound that is to blame for the low incidence of chronic inflammatory conditions in Mediterranean populations.  

Oleocanthal is a phenolic antioxidant compound with a highly similar mechanism of action to the Non-steroidal anti-inflammatory drug (NSAID) ibuprofen. In order to benefit from oleocanthal, the EVOO must be consumed raw, since cooking destroys the antioxidant. Oleocanthal is responsible for the burning feeling on the throat when EVOO is swallowed.


Figure 1. Although oleocanthal and ibuprofen are structurally different, both have been shown to have highly similar pharmacological actions. From http://pubs.acs.org/cen/news/83/i36/8336notw8.html

NSAID’s are commonly used to reduce inflammation and for pain relief, but they also appear to help in chronic inflammatory conditions. Ibuprofen achieves its anti-inflammatory potential by blocking the actions (inhibiting) of an enzyme known as cyclooxygenase (COX). There are 2 forms of this enzyme, simply referred to as COX-1 and COX-2, which synthesise prostaglandins from a molecule called arachidonic acid. COX-1 is found in most tissues, while COX-2 is predominantly found at sites of inflammation. Both enzymes are involved in production of pro-inflammatory-prostaglandins which result in pain and inflammation. Oleocanthal has been shown to inhibit COX enzymes, just like ibuprofen, but the good news is that EVOO consumption does not cause any of the side effects associated with taking NSAID’s.

Researchers have found that oleocanthal was far more potent at inhibiting COX than ibuprofen when both compounds were tested at the same concentration: 25µM of ibuprofen inhibited the activity of COX by 13-18%, while 25µM oleocanthal inhibited the activity of COX by 41-57%. Researchers estimate that consuming 3 tablespoons of EVOO per day roughly corresponds to 10% of the pain relieving dose of Ibuprofen. Due to its powerful inhibitory effects on COX, oleocanthal is now considered as a natural NSAID.


Figure 2. Ibuprofen and oleocanthal achieve their powerful anti-inflammatory actions by blocking COX-1 and COX-2 activity. Unfortunately, inhibiting COX-1 is undesirable as this enzyme also produces beneficial prostaglandins that help to regulate platelet function and protect the stomach mucosa. The severe side effects of ibuprofen are due to its inhibition of COX-1. Meanwhile, moderate consumption of EVOO provides small amounts of the natural NSAID oleocanthal, without any reported side effects. Based on http://www.medscape.com/viewarticle/553966_2

Oleocanthal in EVOO is believed to be responsible for the lower incidence of chronic inflammatory conditions within individuals consuming a Mediterranean style diet. Inflammation has been shown to play a key role in the development of joint-degenerative diseases such as rheumatoid arthritis (RA). NSAID’s appear to improve the outcome of these conditions by reducing inflammation. However, serious side effects e.g. stomach bleeding and stomach ulcers have been attributed to the daily use of ibuprofen due to its ability to inhibit COX-1, which is also involved in the production of beneficial prostaglandins that protect the stomach lining. On the other hand, moderate daily consumption of EVOO provides oleocanthal without any of ibuprofen’s side effects. Experts suggest that the benefits of oleocanthal in RA extend beyond COX inhibition.

Certain chemical messengers (cytokines) produced by white blood cells, such as Interleukin 1 (IL-1) and TNF alpha, induce COX-2 to synthesise pro-inflammatory prostaglandins. In RA, IL-1 and TNF alpha are over-expressed, contributing to the excessive inflammation. Oleocanthal has been shown to reduce the expression of both these cytokines and as a consequence it is likely to be helpful in RA by decreasing inflammation. Additionally, oleocanthal inhibits Interleukin-6 production, a cytokine that is responsible for cartilage destruction in RA.


Figure 3. In RA, interleukin-1 and TNF-alpha levels are excessively high. These two cytokines contribute to the ongoing chronic inflammation in the disease by inducing the expression of COX-2. Oleocanthal not only inhibits COX-2 directly (2), but it reduces its expression by decreasing the levels of IL-1 and TNF-alpha (1). Based on http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4139846/

Consuming raw EVOO on a daily basis from a young age appears to modulate the production of inflammatory compounds, helping to lower the risk of suffering from chronic inflammatory conditions. Oleocanthal is not only involved in helping to control inflammation, but it appears to have anti-cancer properties associated with its ability to inhibit COX-2.


Parkinson, L. & Keast, R. (2014). Oleocanthal, a Phenolic Derived from Virgin Olive Oil: A Review of the Beneficial Effects on Inflammatory Disease. International Journal of Molecular Sciences15(7), 12323–12334. http://doi.org/10.3390/ijms150712323

Beauchamp, G.K., Keast, R.S., Morel, D., Lin, J., Pika, J., Han, Q., Lee, C.H., Smith, A.B. & Breslin, P.A. (2005). Phytochemistry: ibuprofen-like activity in extra-virgin olive oil. Nature, 437(7055), 45-6.


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