Oleocanthal is a phenylethanoid, a type of natural phenolic compound
found in extra-virgin olive oil. It appears to be responsible for the
burning sensation that occurs in the back of the throat when consuming
Oleocanthal is a tyrosol ester and its chemical structure is
related to oleuropein, also found in olive oil.
2 Alzheimer's disease
4 See also
6 External links
Oleocanthal has been found to have anti-inflammatory and antioxidant
properties in vitro. Similar to classical non-steroidal
anti-inflammatory drugs, it is a non-selective inhibitor of
cyclooxygenase (COX). 50 g (more than three and a half tablespoons) of
a typical extra virgin olive oil per day contains an amount of
oleocanthal with similar in vitro anti-inflammatory effect as 1/10 of
the adult ibuprofen dose. It is therefore suggested that long-term
consumption of small quantities may be responsible in part for the low
incidence of heart disease and
Alzheimer's disease associated with a
Mediterranean diet. However, 50 g is a great deal of olive oil
for most consumers; moreover, the absorption, metabolism, and
distribution of oleocanthal is not well characterized, and it is not
known whether these in vitro effects actually occur in the body.
"Against this background, the in vivo anti-inflammatory effects of
dietary oleocanthal cannot be as relevant as hypothesized by Beauchamp
Oleocanthal is an activator of the TRPA1 ion channel, which is
activated by ibuprofen. This appears to be responsible for the burning
sensation when consuming extra-virgin olive oil.
Recently it has been demonstrated that oleocanthal shows potential as
a therapeutic agent in the treatment of inflammatory degenerative
Oleocanthal inhibits LPS-induced NO production in
J774 macrophages, without affecting cell viability. Moreover, it
inhibits MIP-1α and IL-6 mRNA expression, as well as protein
synthesis, in both ATDC5 chondrocytes and J774 macrophages.
Oleocanthal also inhibits IL-1β, TNF-α and GM-CSF protein synthesis
from LPS-stimulated macrophages.
Oleocanthal can reduce the accumulation of β-amyloid proteins
involved in Alzheimer's Disease, via up-regulation of P-glycoprotein
Oleocanthal is capable of killing a variety of human cancer cells in
vitro while leaving healthy cells unharmed. While apoptosis
requires between 16 and 24 hours, oleocanthal operated within 30
minutes to one hour.
Oleocanthal pierces cancer cells' lysosomes, the
containers that store the cell's waste products, releasing enzymes
that kill the cell. In healthy cells, the application of oleocanthal
caused a temporary halt in their life cycles, but after 24 hours they
returned to normal.
Oleocanthal inhibits the enzymatic activity of mammalian target of
rapamycin (mTOR) with an IC50 value of 708 nM. Oleocanthal
inhibits the growth of several breast cancer cell lines at low
micromolar concentration in a dose-dependent manner. Oleocanthal
treatment caused a marked downregulation of phosphorylated mTOR in
metastatic breast cancer cell line (MDA-MB-231). These results
strongly indicate that mTOR inhibition is at least one of the factors
of the reported anticancer and neuroprotective properties of
^ "Extra-virgin olive oil mimics painkiller". Nature Publishing Group.
31 August 2005.
^ Beauchamp GK, Keast RS, Morel D, et al. (September 2005).
"Phytochemistry: ibuprofen-like activity in extra-virgin olive oil".
Nature. 437 (7055): 45–6. doi:10.1038/437045a.
^ a b Abuznait, AH; Qosa, H; Busnena, BA; El Sayed, KA; Kaddoumi, A
(Feb 25, 2013). "Olive-Oil-Derived
Oleocanthal Enhances β-Amyloid
Clearance as a Potential Neuroprotective Mechanism against Alzheimer's
Disease: In Vitro and in Vivo Studies". ACS Chemical Neuroscience. 4
(6): 973–82. doi:10.1021/cn400024q. PMC 3689195 .
^ a b Fogliano, Vincenzo; Raffaele Sacchi (January 2006). "Oleocanthal
in olive oil: Between myth and reality". Molecular Nutrition &
Food Research. 50 (1): 5–6. doi:10.1002/mnfr.200690002.
^ Catherine Peyrot des Gachons; Kunitoshi Uchida; Bruce Bryant; Asako
Shima; Jeffrey B. Sperry; Luba Dankulich-Nagrudny; Makoto Tominaga;
Amos B. Smith III; Gary K. Beauchamp; Paul A. S. Breslin (January
2011). "Unusual pungency from extra-virgin olive oil is attributable
to restricted spatial expression of the receptor of oleocanthal". J.
Neurosci. 31 (3): 999–1009. doi:10.1523/JNEUROSCI.1374-10.2011.
PMC 3073417 . PMID 21248124.
^ Cicerale, Sara; Paul A.S. Breslin; Gary K. Beauchamp; Russell S.J.
Keast (May 2009). "Sensory characterization of the irritant properties
of oleocanthal, a natural anti-inflammatory agent in extra virgin
olive oils". Chem Senses. 34 (4): 333–9. doi:10.1093/chemse/bjp006.
PMC 4357805 . PMID 19273462.
^ Iacono, A; Gómez, R; Sperry, J; Conde, J; Bianco, G; Meli, R;
Gómez-Reino, JJ; Smith Ab, 3rd; Gualillo, O (2010). "Effect of
oleocanthal and its derivatives on inflammatory response induced by
lipopolysaccharide in a murine chondrocyte cell line". Arthritis and
Rheumatism. 62 (6): 1675–82. doi:10.1002/art.27437.
^ Scotece, Morena; Gómez, Rodolfo; Conde, Javier; Lopez, Verónica;
Gómez-Reino, Juan J.; Lago, Francisca; Smith, Amos B.; Gualillo,
Oreste (2012). "Further evidence for the anti-inflammatory activity of
oleocanthal: Inhibition of MIP-1α and IL-6 in J774 macrophages and in
ATDC5 chondrocytes". Life Sciences. 91 (23–24): 1229–35.
doi:10.1016/j.lfs.2012.09.012. PMID 23044226.
^ Mihai, Andrei (February 20, 2015). "Olive Oil Compound Kills Cancer
Cells Within an Hour". ZME Science. Retrieved February 22, 2015.
^ Lavars, Nick (February 19, 2015). "
Olive oil ingredient leads cancer
cells to their death". Retrieved February 2015. Check date
values in: access-date= (help)
^ a b Khanfar, Mohammad A.; Bardaweel, Sanaa K.; Akl, Mohamed R.; El
Sayed, Khalid A. (2015-01-01). "Olive Oil-derived
Potent Inhibitor of Mammalian Target of Rapamycin: Biological
Evaluation and Molecular Modeling Studies". Phytotherapy Research. 29:
1776–1782. doi:10.1002/ptr.5434. ISSN 1099-1573.
Article about oleocanthal and extra virgin olive oil in Scientific
Smith, Amos B., III; Han, Qiang; Breslin, Paul A. S.; Beauchamp, Gary
K. (2005). "Synthesis and Assignment of Absolute Configuration of
(−)-Oleocanthal: A Potent, Naturally Occurring Non-steroidal
Anti-inflammatory and Anti-oxidant Agent Derived from Extra Virgin
Olive Oils". Organic Letters. 7 (22): 5075–5078.
doi:10.1021/ol052106a. PMID 16235961. CS1 maint: Multiple
names: authors list (link)
Alpha-lipoic acid (ALA)
Ascorbic acid (vitamin C)
Carotenoids (vitamin A)
Tocopherols (vitamin E)
Tocotrienols (vitamin E)
Ubiquinone (coenzyme Q)