Entry #: 1
Date: 5 June 2017
Topic: Oleocanthal and NSAIDs
Type: Original Paper
OliveNetTM Journal Club
Expert review of literature related to olives and olive oil
D. Elizabeth McCord, Nancy B. Ray and Tom C. Karagiannis
Beauchamp et al.
Citation / Year
(1) / 2005
oleocanthal, ibuprofen, inflammation, COX-1, COX-2, lipoxygenase
This is a landmark publication, highlighting that a throat irritating phenolic compound derived from olive oil, oleocanthal, inhibits the cyclooxygenase (COX)-1 and COX-2 enzymes in a concentration-dependent manner. A much earlier observation indicating a correlation between bitterness and pharmacological activity for certain compounds provided the basis for this study (2). Due to the similar pungent, throat irritating properties, the authors hypothesised that the pharmacological effects namely, modulation of inflammation and analgesic properties, of ibuprofen may overlap with those of oleocanthal.
Using commercially available ELISA-based assays for COX-1, COX-2 and 15-lipoxygense (15-LO), the findings indicated that the activity of oleocanthal was akin to that of the well-known non-steroidal anti-inflammatory drug, ibuprofen. Although less potent than the positive control, indomethacin, both the natural (-)oleocanthal (IC50 23 μM and 28 μM for COX-1 and COX-2, respectively ) and (+)oleocanthal (IC50 25 μM and 40 μM, respectively) enantiomers inhibited the COX-1 and COX-2 enzymes non-selectively. For comparison ibuprofen inhibits COX-1 and COX-2 enzymes with IC50 values previously calculated to be, 5 μM and 223 μM, respectively (3). It was shown that oleocanthal and ibuprofen do not inhibit lipoxygenase; another key enzyme involved in the arachidonic acid-mediated inflammation pathways (nor-dihydroguaiaretic acid [NDGA] and caffeic acid were used as positive controls).
Key points and implications
Assuming consumption of 50 g extra-virgin olive oil per day the authors performed approximate calculations to estimate daily intake of oleocanthal. Using previously published data indicating 200 μg/mL (4) of which 60-90% is absorbed (5, 6)a dietary daily intake of up to 9 mg of oleocanthal, was calculated. This represents approximately 10% of the recommended adult dose of ibuprofen for relief of pain. Overall, as eluded to by the authors, the findings highlighted that regular consumption of extra-virgin olive oil provides a long-term low dose of oleocanthal which may confer beneficial cardiovascular, anticancer and anti-inflammatory effects observed with classical NSAIDs including aspirin and ibuprofen. More generally, this publication provides a potential molecular link between a Mediterranean diet rich in olive oil and beneficial health effects.
- G. K. Beauchamp et al., Phytochemistry: ibuprofen-like activity in extra-virgin olive oil. Nature 437, 45-46 (2005).
- R. Fischer, F. Griffin, R. C. Archer, S. C. Zinsmeister, P. S. Jastram, Weber ratio in gustatory chemoreception; an indicator of systemic (drug) reactivity. Nature 207, 1049-1053 (1965).
- J. A. Mitchell, P. Akarasereenont, C. Thiemermann, R. J. Flower, J. R. Vane, Selectivity of nonsteroidal antiinflammatory drugs as inhibitors of constitutive and inducible cyclooxygenase. Proc Natl Acad Sci U S A 90, 11693-11697 (1993).
- F. B. Hu, The Mediterranean diet and mortality–olive oil and beyond. N Engl J Med 348, 2595-2596 (2003).
- E. Miro-Casas et al., Hydroxytyrosol disposition in humans. Clin Chem 49, 945-952 (2003).
- K. L. Tuck, M. P. Freeman, P. J. Hayball, G. L. Stretch, I. Stupans, The in vivo fate of hydroxytyrosol and tyrosol, antioxidant phenolic constituents of olive oil, after intravenous and oral dosing of labeled compounds to rats. J Nutr 131, 1993-1996 (2001).