Oleocanthal
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Preferred IUPAC name
2-(4-Hydroxyphenyl)ethyl (3S,4E)-4-formyl-3-(2-oxoethyl)hex-4-enoate | |
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CompTox Dashboard (EPA)
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Properties | |
C17H20O5 | |
Molar mass | 304.34 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Oleocanthal is a
Potential biological effects
This section needs more primary sources. (May 2018) |
Anti-inflammatory
Oleocanthal has been found to have
Oleocanthal is an activator of the
Recently it has been demonstrated that oleocanthal shows potential as a therapeutic agent in the treatment of inflammatory degenerative joint diseases.
Beta-amyloid
Studies in an
Selective cytotoxicity
Oleocanthal is capable of killing a variety of human cancer cells in vitro while leaving healthy cells unharmed.[9] 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.[10]
Oleocanthal inhibits the enzymatic activity of mammalian target of rapamycin (mTOR) with an IC50 value of 708 nM.
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.[12]
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.[13]
Potential medical uses
Although it is not being administered as a drug currently, many strategies are being studied to use oleocanthal as a small drug inhibitor of
See also
References
- S2CID 205033514.
- S2CID 205033514.
- ^ PMID 23414128.
- ^ PMID 16397870.
- PMID 21248124.
- PMID 19273462.
- PMID 20201078.)
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: CS1 maint: numeric names: authors list (link - 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 19, 2015.
- ^ PMID 26248874.
- PMID 26380379. Retrieved 3 May 2018.
- PMID 24849787.
External links
- Article about oleocanthal and extra virgin olive oil in Scientific American
- 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. PMID 16235961.)
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: CS1 maint: multiple names: authors list (link