Oleuropein mediated targeting of signaling network in cancer

Current Topics in Medicinal Chemistry

Volumn 16, Issue 22, 2016, Pages 2477-2483

  Fayyaz, Sundas ^a   Aydin, Tuba ^b   Cakir, Ahmet ^c   Gasparri, Maria Luisa ^d   Panici, Pierluigi Benedetti ^d   Farooqi, Ammad Ahmad ^a  

^a RASHID LATIF MEDICAL COLLEGE   (Pakistan)

^b AGRI IBRAHIM CECEN UNIVERSITY   (Turkey)

^c KILIS 7 ARALIK UNIVERSITY   (Turkey)

^d SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

Cancer cell apoptosis; HER2; MAPK pathway; Oleuropein; PI3K AKT

Indexed keywords

EPIDERMAL GROWTH FACTOR RECEPTOR 2; G PROTEIN COUPLED RECEPTOR 30; HYDROXYTYROSOL; MITOGEN ACTIVATED PROTEIN KINASE; OLEUROPEIN; PROTEIN BCL 2; PROTEIN P53; PROTEIN TYROSINE KINASE; TRASTUZUMAB; IRIDOID; PROTEIN KINASE B; REACTIVE OXYGEN METABOLITE;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; BREAST CANCER; BREAST CANCER CELL LINE; CANCER GROWTH; CANCER INHIBITION; CELL HETEROGENEITY; ENZYME ACTIVITY; ENZYME LINKED IMMUNOSORBENT ASSAY; GENE OVEREXPRESSION; GENE TARGETING; HIGH THROUGHPUT SCREENING; HUMAN; INTRACELLULAR SIGNALING; METASTASIS; NEOPLASM; NONHUMAN; OXIDATIVE STRESS; PHYTOCHEMISTRY; SPATIOTEMPORAL ANALYSIS; TRANSLATION REGULATION; TUMOR SUPPRESSOR GENE; ANIMAL; DRUG EFFECTS; METABOLISM; MOUSE; PATHOLOGY; SIGNAL TRANSDUCTION;

ANIMALS; APOPTOSIS; HUMANS; IRIDOIDS; MICE; NEOPLASMS; PROTO-ONCOGENE PROTEINS C-AKT; REACTIVE OXYGEN SPECIES; SIGNAL TRANSDUCTION;

EID: 84978997484     PISSN: 15680266     EISSN: 18734294     Source Type: Journal    
DOI: 10.2174/1568026616666160212123706     Document Type: Article

References (52)

1. Martini, M.; Vecchione, L.; Siena, S.; Tejpar, S.; Bardelli, A. Targeted therapies: how personal should we go? Nat. Rev. Clin. Oncol., 2011, 9(2),87-97.
2. Brown, R.; Curry, E.; Magnani, L.; Wilhelm-Benartzi, C.S.; Borley, J. Poised epigenetic states and acquired drug resistance in cancer. Nat. Rev. Cancer., 2014, 14(11),747-53.
3. Buchheit, C.L.; Weigel, K.J.; Schafer, Z.T. Cancer cell survival during detachment from the ECM: multiple barriers to tumour progression. Nat. Rev. Cancer, 2014, 14(9),632-41.
4. Jones, C.; Baker, S.J. Unique genetic and epigenetic mechanisms driving paediatric diffuse high-grade glioma. Nat. Rev. Cancer, 2014,14(10).
5. Visioli, F.; Poli, A.; Galli, C. Antioxidant and other biological activities of phenols from olives and olive oil. Med. Res. Rev., 2002, 22, 65-75.
6. Visioli, F.; Bellosta, S.; Galli, C. Oleuropein, the bitter principles of olives, enhances nitric oxide production by mouse macrophages. Life Sci., 1998, 62, 541-546.
7. Visioli, F.; Galli, C.; Galli, G.; Caruso D. Biological activities and metabolic fate of olive oil phenols. Eur. J. Lipid sci. Technol., 2002, 104, 667-684.
8. Omar, S.H. Oleuropein in Olive and its Pharmacological Effects. Sci. Pharm., 2010, 78, 133-154.
9. Soler-Rivas, C.; Espin, J. C.; Wichers, H. J. Oleuropein and related compounds. A review. J. Sci. Food Agric., 2000, 80, 1013-1023
10. Le Tutour, B.; Guedon, D. Antioxidative activities of Olea europaea leaves and related phenolic compounds. Phytochemistry, 1992, 31, 1173-1178.
11. Servili, M.; Baldioli, M.; Selvaggini, R.; Macchioni, A.; Montedoro, G.F. Phenolic compounds of olive fruit: one and twodimensional nuclear magnetic resonance characterization of Nüzhenide and its distribution in the constitutive parts of fruit. J. Agric. Food Chem., 1999, 47: 12-18.
12. Damtoft, S.; Franzyk, H.; Jensen, S.R. Biosynthesis of secoiridoid glucosides in Oleaceae. Phytochemistry, 1993, 34,1291-1299.
13. Calis, I.; Hosny, M.; Khalifa, T.; Nishibe, S. Secoiridoids from Fraxinus angustifolia. Phytochemistry, 1993, 33, 1453-1456.
14. Kuwajima, H.; Morita, M.; Takaishi, K.; Inoue, K.; Fujita, T.; He, Z.D.; Yang, C.R. Secoiridoid, coumarin and secoiridoid-coumarin glucosides from Fraxinus chinensis. Phytochemistry, 1992, 31, 1277-1280.
15. Terazawa, M. Phenolic compounds in living tissues of woods. VI. Ligustroside and oleuropein in the inner bark of Fraxinus mandshurica Rupr. var. japonica Maxim. and Ayringa vulgaris L. and their seasonal variation in them. Res. Bull College Exp. Forests, Hokkaido Univ., 1986, 43, 109-126.
16. Diak, J. Phytochemical study of privet (Ligustrum vulgare L.). Herba Polon, 1988, 34, 103-108.
17. Shen, Y.C.; Lin, S.L.; Chein, C.C. Jaspolyside, a secoiridoid glycoside from Jasminum polyanthum. Phytochemistry, 1996, 42, 1629-1631.
18. Tanahashi, T.; Takenaka, Y.; Nagakura, N. Two dimeric secoiridoid glucosides from Jasminum polyanthum. Phytochemistry, 1996, 41, 1341-1345.
19. Sugiyama, M.; Machida, K.; Matsuda, N.; Kikuchi, M. A Secoiridoid glycoside from Osmanthus asiaticus. Phytochemistry, 1993, 34, 1169-1170.
20. Pieme, C.; Santosh, G.; Tekwu, E.; Askun, T.; Aydeniz, H.; Ngogang, J.; Bhushan, S.; Saxena, A. Fruits and barks extracts of Zanthozyllum heitzii a spice from Cameroon induce mitochondrial dependent apoptosis and Go/G1 phase arrest in human leukemia HL-60 cells. Biol. Res., 2014, 47(1): 54.
21. Sahin, S.; Bilgin, M.; Dramur, M.U. Investigation of Oleuropein Content in Olive Leaf Extract Obtained by Supercritical Fluid Extraction and Soxhlet Methods. Separation Sci.Technol, 2011, 46, 1829-1837.
22. Xie, P.; Huang, L.; Zhang, C.; You, F.; Zhang, Y. Reduced pressure extraction of oleuropein from olive leaves (Olea europaea L.) with ultrasound assistance. Food Bioprod. Processing, 2015, 93, 29-38.
23. Capasso, R.; Evidente, A.; Scognamiglio, F. A simple thin layer chromatographic method to detect the main polyphenols occurring in olive oil vegetation waters. Phytochem. Anal, 1992, 3, 270-275.
24. Ficarra, P.; Ficarra,R.; de Pasquale, A.; Monforte, M.T.; Calabro, M.L. HPLC analysis of oleuropein and some flavonoids in leaf and bud of Olea europaea L. Farmaco, 1991, 46, 803-815.
25. De Laurentis, N.; Crescenzo, G.; Lai, O.R.; Milillo, M.A. Investigation on the extraction and concentration of oleuropein and flavonoids in Olea europaea L. based products. Pharm. Pharmacol. Lett., 1997, 7, 27-30.
26. Baracco, A.; Bertin, G.; Gnocco, E.; Legorati, M.; Sedocco, S.; Catinella, S.; Favretto, D.; Traldi, P. A comparison of the combination of fast-atom bombardment with tandem mass spectrometry and of gas chromatography with mass spectrometry in the analysis of a mixture of kaempferol, kaempferide, luteolin and oleuropein. Rapid Commun. Mass Spectrom, 1995, 9, 427-436.
27. Mylonaki, S.; Kiassos, E.; Makris, D.P.; Kefalas, P. Optimisation of the extraction of olive (Olea europaea) leaf phenolics using water/ ethanol-based solvent systems and response surface methodology. Anal Bioanal. Chem., 2008, 392, 977-985.
28. Savournin, C.; Baghdikian, B.; Elias, R.; Dargouth-Kesraoui F, Boukef K, Balansard G, Rapid high-performance liquid chromatography analysis for the quantitative determination of oleuropein in Olea europaea leaves. J. Agric. Food Chem., 2001, 49, 618-621.
29. Bouaziz, M.; Sayadi, S. Isolation and evaluation of antioxidants from leaves of a Tunisian cultivar olive tree. Eur. J. Lipid Sci. Technol., 2005, 107, 497-504.
30. Jàpon-Lujan, R.; Luque-Rodriguez, J.M.; de Castro, M.D.L. Dynamic ultrasoundassisted extraction of oleuropein and related biophenols from olive leaves. J. Chromatogr A, 2006, 1108 (1), 76-82.
31. Aouidi, F.; Dupuy, N.; Artaud, J.; Roussos, S.; Msallemd, M.; Gaimec, I.P.; Hamdi, M. Rapid quantitative determination of oleuropein in olive leaves (Olea europaea) using mid-infrared spectroscopy combined with chemometric analyses. Industrial Crops Prod., 2012, 37, 292-297.
32. Kefalas, P. Isolation of oleuropein from the leaves of olive tree. European Patent, EP 1795201, A1, 2007.
33. Andreadou, I.; Sigala, F.; Papaefthimiou, M.; Sigalas, C.; Aligiannis, N.; Savvari, P.; Gorgoulis, V.; Papalabros, E.; Kremastinos, D.T. Acute doxorubicin cardiotoxicity is successively treated with the phytochemical oleuropein through suppression of oxidative and nitrosative stress. J. Mol. Cell Cardiol., 2007, 42, 549-558. 136(8): 2213-9.
34. Fernández-Arroyo, S.; Gómez-Martínez, A.; Rocamora-Reverte, L.; Quirantes-Piné, R.; Segura-Carretero, A.; Fernández-Gutiérrez, A.; Ferragut, J.A. Application of nanoLC-ESI-TOF-MS for the metabolomic analysis of phenolic compounds from extra-virgin olive oil in treated colon-cancer cells. J. Pharm. Biomed. Anal, 2012, 63,128-34.
35. Quirantes-Piné, R.; Zurek, G.; Barrajón-Catalán, E.; Bäßmann, C.; Micol, V.; Segura-Carretero, A.; Fernández-Gutiérrez, A. A metabolite- profiling approach to assess the uptake and metabolism of phenolic compounds from olive leaves in SKBR3 cells by HPLCESI-QTOF-MS. J. Pharm. Biomed. Anal., 2013, 72: 121-6.
36. Corominas-Faja, B,; Santangelo, E.; Cuyàs, E.; Micol, V.; Joven, J.; Ariza, X.; Segura-Carretero, A.; García, J.; Menendez, J.A. Computer-aided discovery of biological activity spectra for antiaging and anti-cancer olive oil oleuropeins. Aging (Albany NY), 2014, 6(9), 731-41.
37. Menendez, J.A.; Vazquez-Martin, A.; Colomer, R.; Brunet, J.; Carrasco-Pancorbo, A.; Garcia-Villalba, R.; Fernandez-Gutierrez, A.; Segura-Carretero, A. Olive oil’s bitter principle reverses acquired autoresistance to trastuzumab (Herceptin) in HER2- overexpressing breast cancer cells. BMC Cancer, 2007, 9, 7,80.
38. Menendez, J.A.; Vazquez-Martin, A.; Garcia-Villalba, R.; Carrasco-Pancorbo, A.; Oliveras-Ferraros, C.; Fernandez-Gutierrez, A.; Segura-Carretero, A. tabAnti-HER2 (erbB-2) oncogene effects of phenolic compounds directly isolated from commercial Extra-Virgin Olive Oil (EVOO). BMC Cancer, 2008, 18, 8,377.
39. Yao, J.; Wu, J.; Yang, X.; Yang, J.; Zhang, Y.; Du, L. Oleuropein induced apoptosis in HeLa cells via a mitochondrial apoptotic cascade associated with activation of the c-Jun NH2-terminal kinase. J. Pharmacol. Sci., 2014, 125(3),300-11.
40. Chimento, A.; Casaburi, I.; Rosano, C.; Avena, P.; De Luca, A.; Campana, C.; Martire, E.; Santolla, M.F.; Maggiolini, M.; Pezzi, V.; Sirianni, R. Oleuropein and hydroxytyrosol activate GPER/ GPR30-dependent pathways leading to apoptosis of ER-negative SKBR3 breast cancer cells. Mol. Nutr. Food Res., 2014, 58(3), 478-89.
41. Sirianni, R.; Chimento, A.; De Luca, A.; Casaburi, I.; Rizza, P.; Onofrio, A.; Iacopetta, D.; Puoci, F.; Andò, S.; Maggiolini, M.; Pezzi, V. Oleuropein and hydroxytyrosol inhibit MCF-7 breast cancer cell proliferation interfering with ERK1/2 activation. Mol. Nutr. Food Res., 2010, 54(6), 833-40.
42. Czabotar, P.E.; Lessene, G.; Strasser, A.; Adams, J.M. Control of apoptosis by the BCL-2 protein family: implications for physiology and therapy. Nat. Rev. Mol. Cell Biol., 2014, 15(1), 49-63.
43. Hassan, Z.K.; Elamin, M.H.; Omer, S.A.; Daghestani, M.H.; Al-Olayan, E.S.; Elobeid, M.A.; Virk, P. Oleuropein induces apoptosis via the p53 pathway in breast cancer cells. Asian Pac. J. Cancer Prev., 2014,14(11), 6739-42.
44. Yan, C.M.; Chai, E.Q.; Cai, H.Y.; Miao, G.Y.; Ma, W. Oleuropein induces apoptosis via activation of caspases and suppression of phosphatidylinositol 3-kinase/protein kinase B pathway in HepG2 human hepatoma cell line. Mol. Med. Rep., 2015, doi: 10.3892/mmr.2015.3266.
45. Bulotta, S.; Corradino, R.; Celano, M.; Maiuolo, J.; D’Agostino, M.; Oliverio, M.; Procopio, A.; Filetti, S.; Russo, D. Antioxidant and antigrowth action of peracetylated oleuropein in thyroid cancer cells. J. Mol. Endocrinol., 2013, 51(1), 181-9.
46. Acquaviva, R.; Di Giacomo, C.; Sorrenti, V.; Galvano, F.; Santangelo, R.; Cardile, V.; Gangia, S.; D’Orazio, N.; Abraham, N.G.; Vanella, L. Antiproliferative effect of oleuropein in prostate cell lines. Int. J. Oncol., 2012,(1),31-8.
47. Elamin, M.H.; Daghestani, M.H.; Omer, S.A.; Elobeid, M.A.; Virk, P.; Al-Olayan, E.M.; Hassan, Z.K.; Mohammed, O.B.; Aboussekhra, A. Olive oil oleuropein has anti-breast cancer properties with higher efficiency on ER-negative cells. Food. Chem. Toxicol., 2013, 53, 310-6.
48. Hamdi, H.K.; Castellon, R. Oleuropein, a non-toxic olive iridoid, is an anti-tumor agent and cytoskeleton disruptor. Biochem. Biophys. Res. Commun., 2005, 334(3), 769-78.
49. Kimura, Y.; Sumiyoshi, M. Olive leaf extract and its main component oleuropein prevent chronic ultraviolet B radiation-induced skin damage and carcinogenesis in hairless mice. J. Nutr., 2009, 139(11): 2079-86.
50. Tsarbopoulos, A.; Gikas, E.; Papadopoulos, N.; Aligiannis, N.; Kafatos, A. Simultaneous determination of oleuropein and its metabolites in plasma by high-performance liquid chromatography. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 2003, 785(1): 157-64.
51. de Bock, M.; Thorstensen, E.B.; Derraik, J.G.; Henderson, H.V.; Hofman, P.L.; Cutfield, W.S. Human absorption and metabolism of oleuropein and hydroxytyrosol ingested as olive (Olea europaea L.) leaf extract. Mol. Nutr. Food Res., 2013, 57(11): 2079-85.
52. García-Villalba, R.; Larrosa, M.; Possemiers, S.; Tomás-Barberán, F.A.; Espín, J.C. Bioavailability of phenolics from an oleuropeinrich olive (Olea europaea) leaf extract and its acute effect on plasma antioxidant status: comparison between pre- and postmenopausal women. Eur. J. Nutr., 2014, 53(4), 1015-27.