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oleocanthal (Hyeda)
phenolic compound in extra virgin olive oil in amounts up to 200 ug/mL [4]
Indications:
- transdermal olive oil formulation for relief of inflammation [2]
Adverse effects:
- responsible for the burning sensation that occurs in the back of the throat when consuming extra virgin olive oil
Mechanism of action:
- in vitro activity of 10-20 uM oleocanthal
- inhibits COX1 & COX2
- 9-10 mg of oleocanthal contains 10% of anti-inflammatory activity of 200-400 mg of ibuprofen [4]
- amount in 50 g (4 tbsp) of extra virgin olive oil
- inhibits cell proliferation, cell migration, & invasion of breast cancer & prostate cancer cells via inhibition of c-Met
- inhibits AMPK in colon cancer cells
- inhibits macrophage inflammatory protein-1-alpha in multiple myeloma
- induces cell death of cancer cells in vitro
- induces both necrosis & apoptosis of cancer cells in vitro via induction of lysosomal membrane permeabilization
- cancer cells have fragile lysosomal membranes compared to non-cancerous cells
- in the absence of serum, oleocanthal induces necrosis of cancer cells (does not induce cleavage of caspase-3)
- suppresses proliferation of non-cancer cells by inhibiting Rb protein phosphorylation at Ser608
- normal cells resume proliferation 72 hours after oleocanthal treatment
- induces a reversible cell cycle arrest in non-cancerous cells that retain their viability
- inhibits acid sphingomyelinase which destabilizes the lysosomal membrane
- cancer cells overcome lysosomal membrane fragility by overexpression of HSP70 which enhances acid sphingomyelinase activity
Interactions
drug interactions
drug adverse effects of NSAIDs
monitor with non steroidal anti-inflammatory agents (NSIADs)
General
aldehyde
alkene; olefin
ester
non-steroidal anti-inflammatory agent (NSAID)
phenol
Properties
INHIBITS: cyclooxygenase
Database Correlations
PUBCHEM correlations
References
- LeGendre O, Breslin PA, Foster DA
(-)-Oleocanthal rapidly and selectively induces cancer cell
death via lysosomal membrane permeabilization (LMP).
Molecular & Cellular Oncology. 23 Jan 2015.
http://dx.doi.org/10.1080/23723556.2015.1006077
- PubChem: 16681728
- Wikipedia: Oleocanthal
http://en.wikipedia.org/wiki/Oleocanthal
- Beauchamp GK, Keast RSJ, Morel D et al
Phytochemistry: Ibuprofen-like activity in extra-virgin olive
oil.
Nature 437, 45-46 (1 September 2005)
http://www.nature.com/nature/journal/v437/n7055/full/437045a.html
- Akl MR, Ayoub NM, Mohyeldin MM et al
Olive phenolics as c-Met inhibitors: (-)-Oleocanthal attenuates
cell proliferation, invasiveness, and tumor growth in breast
cancer models.
PLoS One. 2014 May 21;9(5):e97622
PMID: 24849787