Oleocanthal, also known as deacetoxydialdehydic ligstroside aglycone, is a type of natural phenolic compound found in extra-virgin olive oil and is responsible for its bitter and pungent taste. It was mentioned in the literature in 1993 as a compound found in virgin olive oil. 1 Dr. Gary Beauchamp discovered olecanthal by accident when he discovered that he tasted something in olive oil that was similar to ibuprofen, the anti-inflammatory that he was studying. Upon further research, Dr. Beauchamp discovered the nonsteroidal anti-inflammatory molecule called olecanthal.
The polyphenols that are contained in extra virgin olive oil are responsible for the key sensory characteristics of bitterness, pungency, and astringency. Oleocanthal produces a strong peppery stinging and burning pungent sensation at the back of the throat. 2 Oleocanthal is aptly named since oleo means olive and canth means sting and al stands for aldehyde. 3
Figure 1: Olecanthal 3-D molecule
Oleocanthal has been demonstrated to have potential neuroprotective properties and contribute to preventing cognitive decline due to neurodegenerative diseases. Numerous clinical and preclinical studies have shown that the neuroprotective properties of oleocanthal are obtained by consuming high phenolic extra virgin olive oil.
The role that oleocanthal plays in the reduced incidence of Alzheimer’s disease has been examined in the following five studies:
Study 1 August 2009
The reserachers demonstrate that oleocanthal abrogates fibrillization of tau by locking tau into the naturally unfolded state. They demonstrate oleocanthal forms an adduct with the lysine via initial Schiff base formation. Structure and function studies demonstrate that the two aldehyde groups of oleocanthal are required for the inhibitory activity. These two aldehyde groups show certain specificity when titrated with free lysine and oleocanthal does not significantly affect the normal function of tau. 4
Study 2 October 2009
This study showed that oleocanthal increased the immunoreactivity of soluble Abeta species, when assayed with both sequence- and conformation-specific Abeta antibodies, indicating changes in oligomer structure. Analysis of oligomers in the presence of oleocanthal showed an upward shift in MW and a ladder-like distribution of SDS-stable ADDL subspecies. Amyloid beta-derived diffusible ligands (ADDLs) comprise the neurotoxic subset of soluble Abeta(1-42) oligomers, now widely considered to be the molecular cause of memory malfunction and neurodegeneration in Alzheimer’s disease.
The study from October 2009 is very important because it shows that oleocanthal changes the protein Amyloid beta-derived diffusible ligands (ADDLs). Amyloid beta-derived diffusible ligands (ADDLs) comprise the neurotoxic subset of soluble Abeta(1-42) oligomers, now widely considered to be the molecular cause of memory malfunction and neurodegeneration in Alzheimer’s disease. ADDLs adhere to synapses in the brain and close them off. Oleocantahal alters and changes ADDLs to where it cannot bind to the synapse. The result is a a slow down of the advancement of Alzheimer’s disease. Oleocanthal also augments antibody clearance of ADDLs, therefore protecting hippocampal neurons from ADDL toxicity. 5
Additionally, treatment with oleocanthal improved antibody clearance of ADDLs. 6
Study 3 July 2011
This study investigated the mechanism by which oleocanthal inhibits tau fibrillization and aggregation in vitro via covalent chemical interaction with the fibrillogenic fragment of tau proteins. 7
Study 4 June 2013
The authors of this study applied different concentrations of oleocanthal over three days to mouse brain cell cultures. They also administered oleocanthal to live mice every day for two weeks. In both trials, levels of two proteins that play major roles in transporting beta-amyloid out of the brain as well as enzymes that degrade beta-amyloid increased significantly after administering oleocanthal. oleocanthal enhances the clearance of amyloid-beta from the brain by increasing two major amyloid-beta transport proteins at the blood-brain barrier. 8 The results from the researchers demonstrated significant increase in 125I-Aβ40 degradation as a result of the up-regulation of amyloid-beta degrading enzymes following oleocanthal treatment. In conclusion, these findings provide experimental support that potential reduced risk of Alzheimer’s disease associated with extra-virgin olive oil could be mediated by enhancement of amyloid-beta clearance from the brain.
Figure 2: Oleocanthal
Study 5 November 2015
In this study, the researchers investigated the effect of oleocanthal on pathological hallmarks of Alzheimer’s disease in TgSwDI, an animal model of Alzheimer’s disease. Mice treatment for 4 weeks with oleocanthal significantly decreased amyloid load in the hippocampal parenchyma and microvessels. This reduction was associated with enhanced cerebral clearance of amyloid-beta across the blood-brain barrier (BBB). Further mechanistic studies demonstrated oleocanthal to increase the expression of important amyloid clearance proteins at the BBB including P-glycoprotein and LRP1, and to activate the ApoE-dependent amyloid clearance pathway in the mice brains. Their conclusion was that findings from in vivo and in vitro studies provide further support for the protective effect of oleocanthal against the progression of Alzheimer’s disease. 9
Figure 3: Oleocanthal Enhances Amyloid-Beta Clearance
Extra Virgin Olive Oil
Extra Virgin Olive Oil contains many polyphenols (at least 30) other than olecanthal, including:
- elenolic acid
The grade of olive oil will determine the amount of polyphenols contained in the oil. Ordinary grades of olive oil contain 50 ppm or less of polyphenols, depending on their percentage of refined olive oil. With Extra Virgin Olive Oil, the polyphenol content typically ranges between 100 to 250 ppm. Exceptional grades of Extra Virgin Olive Oil may be as high as 500 ppm. This higher content of polyphenols will depend on a number of factors such as:
- age of the oil
- degree of ripeness
- olive cultivar
- production and extraction technologies employed
Extra virgin olive oil generally falls into three categories:
The robust olive oils tend to have the highest levels of polyphenols. This can be indicated by the olive oil having a strong peppery finish, a distinct bitterness and very intense flavors on the front end of the palate.
One company in Northern California that produces exceptional extra virgin olive oil is Apollo Olive Oil. They utilize a state-of-the-art method of olive oil extraction that uses milling under vacuum, which dramatically improves the extraction of polyphenols and provides much more quality control over the entire milling process. This vacuum technology greatly reduces oxidation of the olive oil and thus produces excellent Extra Virgin olive oil with roughly triple the amounts of polyphenols, compared to conventional milling technologies. Only five such vacuum mills exist in the world, and Apollo Olive Oil was privileged to obtain one in 2005.
The graph below demonstrates the higher polyphenols (in ppm) content of Apollo Olive Oils, known as Exceptional EVOOs.
Source: Apollo Olive Oil
The Table below lists the varieties of EVOO produced by Apollo Olive Oil and the their polyphenol, tocopherol and total antioxidant content:
Polyphenols, Tocopherol and Total Antioxidant Content of Apollo Olive Oil Varieties
Name of Olive Oil Polyphenols Tocopherols (Vitamin E) Total antioxidants
Mistral Organic 398 mg/Kg 258 mg/Kg 656 mg/Kg
Sierra Organic 430 mg/Kg 256 mg/Kg 686 mg/Kg
Grossane Organic 472 mg/Kg 278 mg/Kg 750 mg/Kg
Aglandau Organic 500 mg/Kg 258 mg/Kg 758 mg/Kg
Barouni 683 mg/Kg 230 mg/Kg 913 mg/Kg
Coratina Organic 650 mg/Kg 301 mg/Kg 951 mg/Kg
Source: Apollo Olive Oil
Apollo Olive Oil is the leader in polyphenol extraction from extra virgin olive oil. It truly may be the healthiest olive oil you can find in the United States.