Tuesday, 5 November 2013

Phytochemicals in Foods - 7 Health Benefits of Oleocanthal

Oleocanthal is the phytochemical in the Tyrosol esters, belonging to The class of Flavonoids found a abundantly in olive oil.

Health benefits
Antiinflammatory activity
In the investigation of the anti inflammatory effect of Oleocantha of olive oil against chronic inflammation, a critical factor in the pathogenesis of many inflammatory disease states including cardiovascular disease, cancer, diabetes, degenerative joint diseases and neurodegenerative diseases., found that This pharmacological similarity has provoked interest in oleocanthal and the few studies conducted thus far have verified its anti-inflammatory and potential therapeutic actions. A review of the health benefits of the Mediterranean diet and anti-inflammatory properties of virgin olive oil is presented with the additional emphasis on the pharmacological and anti-inflammatory properties of the phenolic compound oleocanthal, according to "Molecular mechanisms of inflammation. Anti-inflammatory benefits of virgin olive oil and the phenolic compound oleocanthal" by Lucas L, Russell A, Keast R."(1)

2. Breast and prostate cancers
In the investigation of the effect of extra-virgin olive oil (EVOO), containing a variety of minor phenolic compounds with beneficial properties. (-)-Oleocanthal (1) against metastatic breast and prostate cancers, found that Oleocanthal inhibited the proliferation, migration, and invasion of the epithelial human breast and prostate cancer cell lines MCF7, MDA-MB-231, and PC-3, respectively, with an IC (50) range of 10-20 µM, and demonstrated anti-angiogenic activity via downregulating the expression of the microvessel density marker CD31 in endothelial colony forming cells with an IC (50) of 4.4 µM, according to "(-)-Oleocanthal as a c-Met inhibitor for the control of metastatic breast and prostate cancers" by Elnagar AY, Sylvester PW, El Sayed KA.(2)

3. Colon Cancer
In the evaluation of the effect of p-HPEA-EDA, a phenolic compound of virgin olive oil against cancers, found that dialdehydic form of decarboxymethyl ligstroside aglycone (p-HPEA-EDA), a phenolic compound of virgin olive oil, inhibits tumor promoter-induced cell transformation in JB6 Cl41 cells and suppress cyclooxygenase-2 (COX-2) and tumorigenicity by adenosine monophosphate-activated protein kinase (AMPK) activation in HT-29 cells. p-HPEA-EDA inhibited 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced phosphorylation of extracellular signal-regulated kinases 1/2 and p90RSK in JB6 Cl41 cells, resulting in the inhibition of cell proliferation, activator protein-1 transactivation and cell transformation promoted by TPA. Moreover, p-HPEA-EDA strongly inhibited the cell viability and COX-2 expression by activation of AMPK activity in HT-29 cells, according to "p-HPEA-EDA, a phenolic compound of virgin olive oil, activates AMP-activated protein kinase to inhibit carcinogenesis" by
Khanal P, Oh WK, Yun HJ, Namgoong GM, Ahn SG, Kwon SM, Choi HK, Choi HS.(3)

4. Osteoarthritis (OA)
In the comparison of the effect on the therapeutic management of joint inflammatory diseases as of that of that of ibuprofen, a drug widely used in the therapeutic management of joint inflammatory diseases, found that Oleocanthal and its derivatives decreased lipopolysaccharide-induced NOS2 synthesis in chondrocytes without significantly affecting cell viability at lower concentrations. Among the derivatives we examined, derivative 231 was the most interesting, since its inhibitory effect on NOS2 was devoid of cytotoxicity even at higher concentrations, according to "Effect of oleocanthal and its derivatives on inflammatory response induced by lipopolysaccharide in a murine chondrocyte cell line" by Iacono A, Gómez R, Sperry J, Conde J, Bianco G, Meli R, Gómez-Reino JJ, Smith AB 3rd, Gualillo O.(4)

5. Antioxidant activity
In the investigation of the effect of total syntheses and the assignment of absolute configurations of both the (+)- and (-)-enantiomers of oleocanthal 1 (a.k.a. deacetoxy ligstroside aglycon)
found that the absolute and relative stereochemistry of the naturally occurring enantiomer (-)-1 proved to be 3S,4E. Both syntheses begin with d-(-)-ribose, proceed in 12 steps, and are achieved with an overall yield of 7%. Both enantiomers proved to be non-steroidal anti-inflammatory and anti-oxidant agents, according to "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" by Smith AB 3rd, Han Q, Breslin PA, Beauchamp GK.(5)

6. NSAID ibuprofen
In the assessment of Phenolic compounds extracted from extra virgin olive oil, One of the components, (-)-oleocanthal (1), an inhibitor of the COX-1 and COX-2 enzymes, possesses similar potency as the NSAID ibuprofen, found that the first- and now second-generation syntheses of both enantiomers of the oleocanthals, as well as the first synthesis of the closely related (-)-deacetoxy-oleuropein aglycone and a series of related analogues for structure activity studies. To demonstrate the utility of the second-generation synthesis, multigram quantities of (-)-oleocanthal were prepared in 10 steps (14% overall yield) from commercially available D-lyxose, according to "Syntheses of (-)-oleocanthal, a natural NSAID found in extra virgin olive oil, the (-)-deacetoxy-oleuropein aglycone, and related analogues" by Smith AB 3rd, Sperry JB, Han Q.(6)

7. Immunoreactivity and synaptotoxicity
In the investigation of the effect of oleocanthal (OC), a naturally-occurring phenolic compound found in extra-virgin olive oil on the immunoreactivity of soluble Abeta species, found that oleocanthal is capable of altering the oligomerization state of ADDLs while protecting neurons from the synaptopathological effects of ADDLs and suggest OC as a lead compound for development in AD therapeutics, according to "Alzheimer's-associated Abeta oligomers show altered structure, immunoreactivity and synaptotoxicity with low doses of oleocanthal" by Pitt J, Roth W, Lacor P, Smith AB 3rd, Blankenship M, Velasco P, De Felice F, Breslin P, Klein WL.(7)

8. Etc.

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(1) http://www.ncbi.nlm.nih.gov/pubmed/21443487
(2) http://www.ncbi.nlm.nih.gov/pubmed/21328179
(3) http://www.ncbi.nlm.nih.gov/pubmed/21216846
(4) http://www.ncbi.nlm.nih.gov/pubmed/20201078
(5) http://www.ncbi.nlm.nih.gov/pubmed/16235961
(6) http://www.ncbi.nlm.nih.gov/pubmed/17685574
(7) http://www.ncbi.nlm.nih.gov/pubmed/19631677

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