THE HEALTH EFFECTS OF OLEUROPEIN, ONE OF THE MAJOR PHENOLIC COMPOUNDS OF OLIVES, OLEA EUROPAEA L
Main Article Content
Keywords
olive, phenolic compounds, oleuropein, pharmacological effects, Olea europaea, extract
Abstract
Olives (Olea europaea L.) and olive oils have a significant place in the daily diet in the Mediterranean Region and contain significant amounts of polyphenolic compounds, of which. oleuropein, hydroxytyrosol and tyrosol are dominant. Harvest time, geographical region and climate all affect the phenolic content. Experimental, clinical and epidemiological studies show the beneficial effects of oleuropein, such as antioxidant, antimicrobial, anticancer anti-inflammatory, antineuropathic and other properties. In particular, olive, leaves, roots, virgin olive oil and olive mill waste (vegetation and wastewater) are potential sources of oleuropein.This review focuses on the pharmacological effects of oleuropein and extraction procedures for oleuropein
References
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Allouche N, Fki I, Sayadi S. 2004. Toward a high- yield recovery of antioxidant and purified hydroxytyrosol from oil mill wastewater. J. Agric. Food Chem.52,267-273.
Altinyay C, Altun M. L. 2006. HPLC analysis of oleuropein in Olea europaea L. J. Fac. Pharm. 35,1-11.
Amiot M.J, Fleuriet A, Macheix J. J. 1986. Importance and evaluation of phenolic compounds in olive during growth and maturation. J Agric Food Chem. 34 (5), 822-826.
Ansari M, Kazemipour M, Fathi S. 2011. Development of a simple green extraction procedure and HPLC method for determination of oleuropein in olive extract applied to a multi-source comparative study. J. Iran Chem. Soc.8,38-47.
Arslan D, Ozcan M. M. 2011. Phenolic profile and antioxidant activity of olive fruits of the Turkish variety ‘sariulak’ from different locations. Grasas Y Aceites, 62 (4), 453-461.
Arslan D. 2012. Physico-chemical characteristics of olive fruits of Turkish varieties from the province of Hatay. Grasas Y Aceties, 63 (2), 158-166.
Aziz N. H, Farag S. F, Mousa L. A, Abo-Zaid M. A. 1998. Comparative antibacterial and antifungal effects of some phenolic compounds. Microbios. 93,43-54.
Barbaro B, Toitetta G, Maggio R, Arciello M, Tarocchi M, Galli A, Balsano C. 2014. Effects of the olive-derived polyphenol oleuropein on human health, Int. Journal of Molecular Sci. 15, 18508-18524.
Bazoti F. N, Bergquist J, Markides K, Tsarbopoulos A. 2006. Non-covalent interaction between amyloid-?-peptide (1-40) and oleuropein studies by electrospray ionization mass spectrometry. J Am. Soc. Mass Spectrom. 17, 568-575.
Bianco A, Lo Scalzo R, Scarpati M. L. 1993. Isolation of cornoside from Olea europaea and its transformation into halleridone. Phytochemistry. 32, 455-457.
Botia J. M, Ortuno A, Benavante_Garcia O, Baidez A. G, Frias J, Marcos D, Del Rio J. A. 2001. Modulation of the biosynthesis of some phenolic compounds in Olea europaea L. fruits: their influence on olive oil quality. J. Agric. Food Chem. 49, 355-358.
Cardeno A, Sanchez-hidalgo M, Rosillo M. A. 2013. Oleuropein, a secoiridoid derived from the olive tree, inhibits the proliferation of human colorectal cancer cell through down regulation fog HIF-1?, Nutrition and Cancer, 65 (1), 147-156.
Cicerale S, Lucas L J, Keast R S.2012. Antimicrobial, Antioxidant and Anti-inflammatory Phenolic Activities in Extra Virgin Olive Oil. Curr. Opin. Biotechnol. 23, 129-135.
Coni E,Di Benedetto R, Di Pasquale M, Masella R, Modesti D, Mattei R, Carlini E. A. 2000. Protective effect of oleuropein, an olive oil biophenol, on low density lipoprotein oxidizability in rabbits. Lipids. 35, 45-54.
Corona G, Deiana M, Incani A,Vauzour D, Dessi M. A. 2007.Inhibition p38/CREB phosphorylyation and COX-2 expression by olive oil polyphenols underlies their anti-proliferative effects. Biochem. Biophys. Res. Commun. 362, 606-611.
De la Puerta R, Martinez Domingez M. E, Ruiz-Gutierrez V, Flavill, J.A, Hoult J R. 2001. Effects of virgin olive oil phenolics on scavenging of reactive nitrogen species and upon n?trergic neurotransmission. Life Sci. 69, 1213-1222.
Damtoft S, Franzyk H, Jensen S. R. 1992. Excelsioside, a secoiridoid glucoside from Fraxinus excelsior. Phytochemistry. 31, 4197-4201.
Damtoft S, Franzyk H, Jensen S. R. 1993. Biosynthesis of secoiridoid glucosides in Oleaceae. Phytochemistry.34, 1291-1299.
Dogaka. 2011. Region of TR 63, Report on olives production and the work on feasibility. Development Agency of Southern Region of Mediterranean.
Daccache A, Lion C, Sibille N, Gerard M, Slomianny C, Lippens G, Cotelle P. 2011. Oleuropein and derivatives from olives as Tau aggregation inhibitors. Neurochem. Int.58, 700-707.
Esti M, Cinquanta L, La Notte E.1998. Phenolic compunds in different olive varieties. J. Agric.Food Chem. 46, 32-35.
FAO, 2011. Faostat Statistical Database, http://www.fao.org
Fredrickson W.R, Group S. 2000. Methods and composition for antiviral therapy with olive leaves. 6,117-124.
Furneri P. M, Marino A, Saija A, Uccella N,Bisignio G. 2002. In vitro antimycoplasmal activity of oleuropein. Int. J. Antimicrob. Agents. 20,293-296.
Golde T. E, Eckman C. B. 2001. Cholesterol modulation as an emerging strategy for the treatment of alzheimer’s disease. Drug Discov. Today. 6,1049-1055.
Goldsmith C. D, Statopoulos C. E,Golding J. B,Roach P. D. 2014. Fate of the phenolic compounds during olive oil production with the traditional press method. Int. Food Res.J. 21,101-109.
Gonzales-Hidalgo I, Banon S, Maria Rose J. 2012. Evaluation of the table olive by-products as a source of natural antioxidants. Int. J of Food Sci&Tech.47,674-681.
Hamdi H. K, Castellon R. 2005. Oleuropein, a non-toxic olive iridoid, is an anti-tumor agent and cytoskeleton disruptor. Biochem. Biophys.Res.Commun. 334,769-778.
Hofman A, Ott A, Breteler M. M, Bots M. L, Slooter A. J, van Harskamp F, van D?jin C. N, van Broeckhoven C, Grobbe D.E. 1997. Atherosclerosis, apolipoprotein E and prevalence of dementia and aAlzheimer’s disease in the Rotterdam Study. 349,151-154.
Japon-Lujan R, Luque de Castro M. D. 2006. J Chromatogr. ,1136,185.
Kimura Y, Sumiyoshi M. 2009. Olive leaf extract and its main component oleuropein prevent chronic ultraviolet B radiation-induced skin damage and carcinogenesis in hairless mice. The Journal of Nutrition, 139,2079-2086.
Kockar F, Turkoglu-Aydogan S, Ayd?n M. 2010. Determination of the anti-tumor effects of oleuropein in prostate (PC-3), breast (MCF-7) and hepatoma (HEP3B) cells. J of Bio. Sci.Res. 3 (2), 185-190.
Le Tutour B, Guedon D. 1992. Antioxidant activities of Olea europaea leaves and related phenolic compounds. Phytochemistry. 31,1173-1178.
Malik N. S. A,Bradford J. M. 2006. Changes in oleuropein levels during differentiation and development of floral buds in ‘arbequina’ olives.Sci. Hortic. 110,274-278.
Malik N. S. A, Bradford J. M. 2008. Recovery and stability of oleuropein and other phenolic compounds during extraction and processing of olive (Olea europaea L.) leaves. J of Food Agric & Environment, 6(2),8-13.
Mafra I, Baros A.S. 2006. Effect of black oxidizing table olive process on the cell wall polysaccharides of olive pulp (Olea europaea L. var). Carbohydr. Polym 65;1-8.
Mao W, Shi H, Chen X, Yin Y, Yang T, Ge M, Luo M, Chen D, Qian X. 2012. Anti-proliferation and migration effects of oleuropein on human A549 lung carcinoma cells. Lat.Am.J.Pharm. 31,1217-1221.
Menendez J. A, Vazquez-Martin A, Colomer R, Brunet J, Carrasco-Pancarbo A, Garcia-Villalba R,Fernandez-Gutierrez A, Segura-Carretero A. 2007. Olive oils’s bitter principle reverses acquired autoresistance to trastuzumab (Herceptin) in HER2-over expressing breast cancer cells. BMC Cancer, 7,80.
Mousa M. Y, Gerosopoulos D, Metzidakis I, Kiritsakis A.1996. Effect of altitude on the fruit and quality characteristics of ‘mastoides’ olives. J. Sci.Food Agric. 71,345-350.
Othman N. B, Roblain D, Thonart P, Hamdi M. 2008. Tunisian table olive phenolic compunds and their antioxidant capacity. Journal of Food Science; Food Chemistry, 73(4),235-240.
Psaltopoulou T, Kosti R. I, Haidopoulos M, Bartsch H. 2011. Olive oil intake is inversely related to cancer prevalence: a systematic review and a meta-analysis of 13800 patients and 23340 Controls in 19 Observational Studies. Lipids Health Dis. 10,127.
Rice-Evans C. A, Miller N. T, Paganga G. 1997. Antioxidant properties of phenolic compounds. Trends Plant Sci. 2(4),152-159.
Romero P. M, Jesus T. M, Ramo T, Jose Moltiva M. 2003. Effect of crop season on the composition virgin olive oil with protected designation of origin ‘les garrigues’. J Am.Oil Chem.Soc.80,423-430.
Sahin S, Bilgin M, Dramur M. U. 2011. Investigation of oleuropein content in olive leaf extract obtained by supercritical fluid extraction and soxhlet methods. Separation Science and Tech. 46,1829-1837.
Saija A,Uccela N. 2001. Olive biphenols: functional effects on human well-being. Trends Food Sci.Technol. 11,357-363.
Savournin C, Baghdikian B, Elias R, Dargouth-Kesraoui F, Boukef K, Balansard G. 2001. Rapid high performance liquid chromaotography analysis for the quantitive determination of oleuropein in Olea europaea leaves. J. Agric. Food Chem. 49,618-621.
Soler-Rivas C, Espin J. C, Wichers H. J. 2000. Oleuropein and related compounds. J. Sci. Food Agric. 80,1013-1023.
Stamatopoulos K, Katsoyannos E, Chatzilazarou, Konteles S. J. 2012. Improvement of oleuropein extractability by optimising steam blanching process, a pre-treatment of olive leaf extraction via response surface methodology. Food Chemistry, 133,344-351.
Sudjana A. N, D’orazio C, Ryan V, Rasool N, Ng J, Islam N, Riley T. V, Hammer K. A. 2009. Antimicrobial activity of commercial Olea europaea (olive) leaf extract. Int. J. Antimicrob. Agents. 33,461-463.
Tayoub G, Sulaiman H, Hassan A. H, Alorfi M. 2012. Determination of oleuropein in leaves and fruits of some Syrian olive varieties. Int. J. Med. Arom. Plants. 2,428-433.
Tripoli E, Giammanco M, Tabacchi G, Di Majo D, Giammanco S, La Guardia M. 2005. The phenolic composition of olive oil:structure, biological activity and beneficial effects on human health. Nutr. Res. Rev. 18,98-112
Tovar M. J, Romero M. P, Alegre S, Girona J, Motilva M. J. 2002. Composition and organoleptic characteristics of oil from Arbequina olive (Olea europaea L.) trees under deficit irrigation. J. Sci. Food Agric. 82,1755-1763.
Visioli F, Poli A, Galli C. 2002. Antioxidant and other biological activities of phenols from olives and olive oil. Med. Res. Rev. 22,65-75.
Visioli F, Bellosta S, Galli C.1998. Oleuropein, the bitter principles of olives, enhances nitric oxide production by mouse macrophages. Life Sci. 62,541-546.
Yildiz G, Uylaser V. 2011.Natural an antioxidants: oleuropein. J of Agricultural Faculty of Uludag University.25,1,131-142.
Yorulmaz A, Erinc H, Tekin A. 2013.Changes in olive oil characteristics during maturation. J.Am. Oil Soc. 90,647-658.
Yousfi K, Cert R. M, Garcia J. M. 2006. Changes in quality and phenolic compounds of virgin olive oils during objectively described fruit maturation, Eur.Food Res.Tech. 223,117-124.
Allouche N, Fki I, Sayadi S. 2004. Toward a high- yield recovery of antioxidant and purified hydroxytyrosol from oil mill wastewater. J. Agric. Food Chem.52,267-273.
Altinyay C, Altun M. L. 2006. HPLC analysis of oleuropein in Olea europaea L. J. Fac. Pharm. 35,1-11.
Amiot M.J, Fleuriet A, Macheix J. J. 1986. Importance and evaluation of phenolic compounds in olive during growth and maturation. J Agric Food Chem. 34 (5), 822-826.
Ansari M, Kazemipour M, Fathi S. 2011. Development of a simple green extraction procedure and HPLC method for determination of oleuropein in olive extract applied to a multi-source comparative study. J. Iran Chem. Soc.8,38-47.
Arslan D, Ozcan M. M. 2011. Phenolic profile and antioxidant activity of olive fruits of the Turkish variety ‘sariulak’ from different locations. Grasas Y Aceites, 62 (4), 453-461.
Arslan D. 2012. Physico-chemical characteristics of olive fruits of Turkish varieties from the province of Hatay. Grasas Y Aceties, 63 (2), 158-166.
Aziz N. H, Farag S. F, Mousa L. A, Abo-Zaid M. A. 1998. Comparative antibacterial and antifungal effects of some phenolic compounds. Microbios. 93,43-54.
Barbaro B, Toitetta G, Maggio R, Arciello M, Tarocchi M, Galli A, Balsano C. 2014. Effects of the olive-derived polyphenol oleuropein on human health, Int. Journal of Molecular Sci. 15, 18508-18524.
Bazoti F. N, Bergquist J, Markides K, Tsarbopoulos A. 2006. Non-covalent interaction between amyloid-?-peptide (1-40) and oleuropein studies by electrospray ionization mass spectrometry. J Am. Soc. Mass Spectrom. 17, 568-575.
Bianco A, Lo Scalzo R, Scarpati M. L. 1993. Isolation of cornoside from Olea europaea and its transformation into halleridone. Phytochemistry. 32, 455-457.
Botia J. M, Ortuno A, Benavante_Garcia O, Baidez A. G, Frias J, Marcos D, Del Rio J. A. 2001. Modulation of the biosynthesis of some phenolic compounds in Olea europaea L. fruits: their influence on olive oil quality. J. Agric. Food Chem. 49, 355-358.
Cardeno A, Sanchez-hidalgo M, Rosillo M. A. 2013. Oleuropein, a secoiridoid derived from the olive tree, inhibits the proliferation of human colorectal cancer cell through down regulation fog HIF-1?, Nutrition and Cancer, 65 (1), 147-156.
Cicerale S, Lucas L J, Keast R S.2012. Antimicrobial, Antioxidant and Anti-inflammatory Phenolic Activities in Extra Virgin Olive Oil. Curr. Opin. Biotechnol. 23, 129-135.
Coni E,Di Benedetto R, Di Pasquale M, Masella R, Modesti D, Mattei R, Carlini E. A. 2000. Protective effect of oleuropein, an olive oil biophenol, on low density lipoprotein oxidizability in rabbits. Lipids. 35, 45-54.
Corona G, Deiana M, Incani A,Vauzour D, Dessi M. A. 2007.Inhibition p38/CREB phosphorylyation and COX-2 expression by olive oil polyphenols underlies their anti-proliferative effects. Biochem. Biophys. Res. Commun. 362, 606-611.
De la Puerta R, Martinez Domingez M. E, Ruiz-Gutierrez V, Flavill, J.A, Hoult J R. 2001. Effects of virgin olive oil phenolics on scavenging of reactive nitrogen species and upon n?trergic neurotransmission. Life Sci. 69, 1213-1222.
Damtoft S, Franzyk H, Jensen S. R. 1992. Excelsioside, a secoiridoid glucoside from Fraxinus excelsior. Phytochemistry. 31, 4197-4201.
Damtoft S, Franzyk H, Jensen S. R. 1993. Biosynthesis of secoiridoid glucosides in Oleaceae. Phytochemistry.34, 1291-1299.
Dogaka. 2011. Region of TR 63, Report on olives production and the work on feasibility. Development Agency of Southern Region of Mediterranean.
Daccache A, Lion C, Sibille N, Gerard M, Slomianny C, Lippens G, Cotelle P. 2011. Oleuropein and derivatives from olives as Tau aggregation inhibitors. Neurochem. Int.58, 700-707.
Esti M, Cinquanta L, La Notte E.1998. Phenolic compunds in different olive varieties. J. Agric.Food Chem. 46, 32-35.
FAO, 2011. Faostat Statistical Database, http://www.fao.org
Fredrickson W.R, Group S. 2000. Methods and composition for antiviral therapy with olive leaves. 6,117-124.
Furneri P. M, Marino A, Saija A, Uccella N,Bisignio G. 2002. In vitro antimycoplasmal activity of oleuropein. Int. J. Antimicrob. Agents. 20,293-296.
Golde T. E, Eckman C. B. 2001. Cholesterol modulation as an emerging strategy for the treatment of alzheimer’s disease. Drug Discov. Today. 6,1049-1055.
Goldsmith C. D, Statopoulos C. E,Golding J. B,Roach P. D. 2014. Fate of the phenolic compounds during olive oil production with the traditional press method. Int. Food Res.J. 21,101-109.
Gonzales-Hidalgo I, Banon S, Maria Rose J. 2012. Evaluation of the table olive by-products as a source of natural antioxidants. Int. J of Food Sci&Tech.47,674-681.
Hamdi H. K, Castellon R. 2005. Oleuropein, a non-toxic olive iridoid, is an anti-tumor agent and cytoskeleton disruptor. Biochem. Biophys.Res.Commun. 334,769-778.
Hofman A, Ott A, Breteler M. M, Bots M. L, Slooter A. J, van Harskamp F, van D?jin C. N, van Broeckhoven C, Grobbe D.E. 1997. Atherosclerosis, apolipoprotein E and prevalence of dementia and aAlzheimer’s disease in the Rotterdam Study. 349,151-154.
Japon-Lujan R, Luque de Castro M. D. 2006. J Chromatogr. ,1136,185.
Kimura Y, Sumiyoshi M. 2009. Olive leaf extract and its main component oleuropein prevent chronic ultraviolet B radiation-induced skin damage and carcinogenesis in hairless mice. The Journal of Nutrition, 139,2079-2086.
Kockar F, Turkoglu-Aydogan S, Ayd?n M. 2010. Determination of the anti-tumor effects of oleuropein in prostate (PC-3), breast (MCF-7) and hepatoma (HEP3B) cells. J of Bio. Sci.Res. 3 (2), 185-190.
Le Tutour B, Guedon D. 1992. Antioxidant activities of Olea europaea leaves and related phenolic compounds. Phytochemistry. 31,1173-1178.
Malik N. S. A,Bradford J. M. 2006. Changes in oleuropein levels during differentiation and development of floral buds in ‘arbequina’ olives.Sci. Hortic. 110,274-278.
Malik N. S. A, Bradford J. M. 2008. Recovery and stability of oleuropein and other phenolic compounds during extraction and processing of olive (Olea europaea L.) leaves. J of Food Agric & Environment, 6(2),8-13.
Mafra I, Baros A.S. 2006. Effect of black oxidizing table olive process on the cell wall polysaccharides of olive pulp (Olea europaea L. var). Carbohydr. Polym 65;1-8.
Mao W, Shi H, Chen X, Yin Y, Yang T, Ge M, Luo M, Chen D, Qian X. 2012. Anti-proliferation and migration effects of oleuropein on human A549 lung carcinoma cells. Lat.Am.J.Pharm. 31,1217-1221.
Menendez J. A, Vazquez-Martin A, Colomer R, Brunet J, Carrasco-Pancarbo A, Garcia-Villalba R,Fernandez-Gutierrez A, Segura-Carretero A. 2007. Olive oils’s bitter principle reverses acquired autoresistance to trastuzumab (Herceptin) in HER2-over expressing breast cancer cells. BMC Cancer, 7,80.
Mousa M. Y, Gerosopoulos D, Metzidakis I, Kiritsakis A.1996. Effect of altitude on the fruit and quality characteristics of ‘mastoides’ olives. J. Sci.Food Agric. 71,345-350.
Othman N. B, Roblain D, Thonart P, Hamdi M. 2008. Tunisian table olive phenolic compunds and their antioxidant capacity. Journal of Food Science; Food Chemistry, 73(4),235-240.
Psaltopoulou T, Kosti R. I, Haidopoulos M, Bartsch H. 2011. Olive oil intake is inversely related to cancer prevalence: a systematic review and a meta-analysis of 13800 patients and 23340 Controls in 19 Observational Studies. Lipids Health Dis. 10,127.
Rice-Evans C. A, Miller N. T, Paganga G. 1997. Antioxidant properties of phenolic compounds. Trends Plant Sci. 2(4),152-159.
Romero P. M, Jesus T. M, Ramo T, Jose Moltiva M. 2003. Effect of crop season on the composition virgin olive oil with protected designation of origin ‘les garrigues’. J Am.Oil Chem.Soc.80,423-430.
Sahin S, Bilgin M, Dramur M. U. 2011. Investigation of oleuropein content in olive leaf extract obtained by supercritical fluid extraction and soxhlet methods. Separation Science and Tech. 46,1829-1837.
Saija A,Uccela N. 2001. Olive biphenols: functional effects on human well-being. Trends Food Sci.Technol. 11,357-363.
Savournin C, Baghdikian B, Elias R, Dargouth-Kesraoui F, Boukef K, Balansard G. 2001. Rapid high performance liquid chromaotography analysis for the quantitive determination of oleuropein in Olea europaea leaves. J. Agric. Food Chem. 49,618-621.
Soler-Rivas C, Espin J. C, Wichers H. J. 2000. Oleuropein and related compounds. J. Sci. Food Agric. 80,1013-1023.
Stamatopoulos K, Katsoyannos E, Chatzilazarou, Konteles S. J. 2012. Improvement of oleuropein extractability by optimising steam blanching process, a pre-treatment of olive leaf extraction via response surface methodology. Food Chemistry, 133,344-351.
Sudjana A. N, D’orazio C, Ryan V, Rasool N, Ng J, Islam N, Riley T. V, Hammer K. A. 2009. Antimicrobial activity of commercial Olea europaea (olive) leaf extract. Int. J. Antimicrob. Agents. 33,461-463.
Tayoub G, Sulaiman H, Hassan A. H, Alorfi M. 2012. Determination of oleuropein in leaves and fruits of some Syrian olive varieties. Int. J. Med. Arom. Plants. 2,428-433.
Tripoli E, Giammanco M, Tabacchi G, Di Majo D, Giammanco S, La Guardia M. 2005. The phenolic composition of olive oil:structure, biological activity and beneficial effects on human health. Nutr. Res. Rev. 18,98-112
Tovar M. J, Romero M. P, Alegre S, Girona J, Motilva M. J. 2002. Composition and organoleptic characteristics of oil from Arbequina olive (Olea europaea L.) trees under deficit irrigation. J. Sci. Food Agric. 82,1755-1763.
Visioli F, Poli A, Galli C. 2002. Antioxidant and other biological activities of phenols from olives and olive oil. Med. Res. Rev. 22,65-75.
Visioli F, Bellosta S, Galli C.1998. Oleuropein, the bitter principles of olives, enhances nitric oxide production by mouse macrophages. Life Sci. 62,541-546.
Yildiz G, Uylaser V. 2011.Natural an antioxidants: oleuropein. J of Agricultural Faculty of Uludag University.25,1,131-142.
Yorulmaz A, Erinc H, Tekin A. 2013.Changes in olive oil characteristics during maturation. J.Am. Oil Soc. 90,647-658.
Yousfi K, Cert R. M, Garcia J. M. 2006. Changes in quality and phenolic compounds of virgin olive oils during objectively described fruit maturation, Eur.Food Res.Tech. 223,117-124.
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