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| Names | |
|---|---|
| Preferred IUPAC name 2-(4-Hydroxyphenyl)ethyl (3S,4E)-4-formyl-3-(2-oxoethyl)hex-4-enoate | |
| Identifiers | |
3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
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| UNII | |
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| Properties | |
| C17H20O5 | |
| Molar mass | 304.34 g/mol |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Oleocanthal is aphenylethanoid, or a type ofnatural phenolic compound found in extra-virginolive oil. It appears to be responsible for the burning sensation that occurs in the back of the throat when consuming such oil. Oleocanthal is atyrosolester and itschemical structure is related tooleuropein, also found in olive oil.
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Oleocanthal has been found to haveanti-inflammatory andantioxidant propertiesin vitro. Similar to the classicalnon-steroidal anti-inflammatory drugibuprofen, it is a non-selective inhibitor ofcyclooxygenase (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 similarin vitro anti-inflammatory effect as 1/10 of the adultibuprofen dose.[1] It is therefore suggested that long-term consumption of small quantities may be responsible in part for the low incidence ofheart disease andAlzheimer's disease associated with aMediterranean diet.[2][3] 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 thesein vitro effects actually occur in the body.[4] "Against this background, thein vivo anti-inflammatory effects of dietary oleocanthal cannot be as relevant as hypothesized by Beauchampet al.."[4]
Oleocanthal is an activator of theTRPA1 ion channel, which is activated by ibuprofen. Oleocanthal is found to be responsible for the burning sensation when consuming extra-virgin olive oil.[5][6]
Recently it has been demonstrated that oleocanthal shows potential as a therapeutic agent in the treatment of inflammatory degenerative joint diseases.[7] Oleocanthal inhibits LPS-induced NO production in J774macrophages, without affecting cell viability. Moreover, it inhibits MIP-1α and IL-6mRNA expression, as well asprotein synthesis, in both ATDC5chondrocytes and J774 macrophages. Oleocanthal also inhibits IL-1β, TNF-α and GM-CSF protein synthesis from LPS-stimulated macrophages.[8]
Studies in ananimal model suggest that oleocanthal can reduce the accumulation ofβ-amyloid proteins via up-regulation ofP-glycoprotein andLRP1.[3]
Oleocanthal is capable of killing a variety of human cancer cellsin vitro while leaving healthy cells unharmed.[9] Whileapoptosis 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.[10]
Cell apoptosis is tested by treating the lysosomal membrane with acridine orange. Acridine orange radiates a red fluorescent color at an increased concentration in a lysosome that is undamaged. Oleocanthal weakens the red fluorescent color indicating apoptosis; however, non-cancerous cells will not experience apoptosis. This is a result of lysosome membrane permeabilization promoting cancer cell death. Lysosomal membrane permeabilization is not activated by oleocanthal in non-cancerous cells.[11]
Oleocanthal has also been shown in vitro to inhibit c-met, an important tyrosine kinase receptor which is responsible for proliferation of many cell types. The same study that found these results also showed that oleocanthal had no deleterious effects on healthy control cells over a span of 48 hours, the same amount of time that it took for inhibition of c-met in MB-231 breast cancer cells. Cells are forced into cell cycle arrest during G1 phase, effectively decreasing the viability of this highly invasive cell line.[12]
Although it is not being administered as a drug currently, many strategies are being studied to use oleocanthal as a small drug inhibitor ofC-Met, as well a potential monoclonal antibody againsthereditary gingival fibromatosis (HGF) and C-Met.
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