Oleocanthal
| Oleocanthal | |
|---|---|
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| IUPAC name 2-(4-hydroxyphenyl)ethyl (3S,4E) | |
| Identifiers | |
| CAS number | 289030-99-5  |
| ChemSpider | 9827154 |
| Jmol-3D images | {{#if:O=CC[C@H](C(=C/C)\C=O)CC(=O)OCCc1ccc(O)cc1|Image 1 |
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| Properties | |
| Molecular formula | C17H20O5 |
| Molar mass | 304.34 g mol−1 |
(verify) (what is: / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| Infobox references | |
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 extra-virgin olive oil. Oleocanthal is a tyrosol ester and its chemical structure is related to oleuropein that is also found in olive oil.
Oleocanthal has been found to be have anti-inflammatory and antioxidant properties in vitro. Similar to classical NSAIDs, it is a non-selective inhibitor of cyclooxygenase (COX). 50g (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.[1] It is therefore suggested that long-term consumption of small quantities of oleocanthal from olive oil may be responsible in part for the low incidence of heart disease and Alzheimer's disease associated with a Mediterranean 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 yet well-characterized, and it is not known whether these in vitro effects actually occur in the body.[4] "Against this background, the in vivo anti-inflammatory effects of dietary oleocanthal cannot be as relevant as hypothesized by Beauchamp et al."[4]
Furthermore, oleocanthal was shown to be an activator of the TRPA1 ion channel, which is activated by ibuprofen. Activation of the TRPA1 ion channel by the oleocanthal appears to be responsible for the burning sensation that occurs in the back of the throat when consuming extra-virgin olive oil.[5][6]
Recently it has been demonstrated that oleocanthal shows potential as a therapeutic weapon for the treatment of inflammatory degenerative joint diseases.[7] 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.[8] Another recent finding has been the ability of oleocanthal to reduce the accumulation of β-amyloid proteins involved in Alzheimer's Disease, via up-regulation of P-glycoprotein and LRP1.[3]
See also
References
- ↑ "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. PMID 16136122.
- ↑ 3.0 3.1 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. PMID 23414128.
- ↑ 4.0 4.1 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. PMID 16397870.
- ↑ 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, and 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; e, Paul A.S. Breslin, Gary K. Beauchamp, and 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. 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. PMID 20201078.
- ↑ 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.
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. doi:10.1021/ol052106a. PMID 16235961.
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