Membrane composition and dynamics: A target of bioactive virgin olive oil constituents

Biochimica et Biophysica Acta - Biomembranes

Volumn 1838, Issue 6, 2014, Pages 1638-1656

  Lopez, Sergio ^a   Bermudez, Beatriz ^a   Montserrat De La Paz, Sergio ^a   Jaramillo, Sara ^a   Varela, Lourdes M ^a   Ortega Gomez, Almudena ^a   Abia, Rocio ^a   Muriana, Francisco J G ^a  

^a INSTITUTO DE LA GRASA   (Spain)

Author keywords

Health disease; Membrane; Minor constituent; Oleic acid; Phospholipid; Virgin olive oil

Indexed keywords

ALPHA TOCOTRIENOL; BETA CAROTENE; CAMPESTEROL; DELTA 5 AVENASTEROL; ERYTHRODIOL; FLAVONOID; HYDROXYISOCHROMAN; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; ISOCHROMAN DERIVATIVE; LIGNAN; MASLINIC ACID; MEMBRANE LIPID; OLEANOLIC ACID; OLEIC ACID; OLIVE OIL; PHENYL GROUP; SECOIRIDOID; SITOSTEROL; SQUALENE; STEROL; TOCOPHEROL; UNCLASSIFIED DRUG; UVAOL; VIRGIN OLIVE OIL; XANTHOPHYLL;

CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; DOWN REGULATION; FATTY ACID ANALYSIS; HEATING; HUMAN; HYDROPHOBICITY; LIPID ABSORPTION; LIPID BILAYER; LIPID COMPOSITION; LIPOPHILICITY; MEMBRANE STRUCTURE; MOLECULAR DYNAMICS; MOLECULAR EVOLUTION; NONHUMAN; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN EXPRESSION; PROTEIN LOCALIZATION; REVIEW; TEMPERATURE SENSITIVITY;

HEALTH/DISEASE; MEMBRANE; MINOR CONSTITUENT; OLEIC ACID; PHOSPHOLIPID; VIRGIN OLIVE OIL;

ANIMALS; CELL MEMBRANE; HUMANS; LIPID BILAYERS; MEMBRANE LIPIDS; PLANT OILS;

EID: 84899011555     PISSN: 00052736     EISSN: 18792642     Source Type: Journal    
DOI: 10.1016/j.bbamem.2014.01.007     Document Type: Review

References (300)

1. G. Buckland, N. Travier, A. Agudo, A. Fonseca-Nunes, C. Navarro, P. Lagiou, C. Demetriou, P. Amiano, M. Dorronsoro, M.D. Chirlaque, J.M. Huerta, E. Molina, M.J. Perez, E. Ardanaz, C. Moreno-Iribas, J.R. Quiros, A. Naska, D. Trichopoulos, M.C. Giurdanella, R. Tumino, C. Agnoli, S. Grioni, S. Panico, A. Mattiello, G. Masala, C. Sacerdote, S. Polidoro, D. Palli, A. Trichopoulou, and C.A. Gonzalez Olive oil intake and breast cancer risk in the Mediterranean countries of the European Prospective Investigation into Cancer and Nutrition study Int. J. Cancer 131 2012 2465 2469
2. G. Buckland, N. Travier, A. Barricarte, E. Ardanaz, C. Moreno-Iribas, M.J. Sanchez, E. Molina-Montes, M.D. Chirlaque, J.M. Huerta, C. Navarro, M.L. Redondo, P. Amiano, M. Dorronsoro, N. Larranaga, and C.A. Gonzalez Olive oil intake and CHD in the European Prospective Investigation into Cancer and Nutrition Spanish cohort Br. J. Nutr. 108 2012 2075 2082
3. S. Lopez, B. Bermudez, L.M. Varela, A. Ortega, S. Jaramillo, R. Abia, and F.J. Muriana Olives and olive oil: diet and health impacts CAB Rev. 7 2012 1 10
4. J.M. Lou-Bonafonte, C. Arnal, M.A. Navarro, and J. Osada Efficacy of bioactive compounds from extra virgin olive oil to modulate atherosclerosis development Mol. Nutr. Food Res. 56 2012 1043 1057
5. E. Ros Olive oil and CVD: accruing evidence of a protective effect Br. J. Nutr. 108 2012 1931 1933
6. R. Estruch, E. Ros, J. Salas-Salvado, M.I. Covas, D. Corella, F. Aros, E. Gomez-Gracia, V. Ruiz-Gutierrez, M. Fiol, J. Lapetra, R.M. Lamuela-Raventos, L. Serra-Majem, X. Pinto, J. Basora, M.A. Munoz, J.V. Sorli, J.A. Martinez, M.A. Martinez-Gonzalez, and P.S. Investigators Primary prevention of cardiovascular disease with a Mediterranean diet N. Engl. J. Med. 368 2013 1279 1290
7. C. Feart, C. Samieri, B. Alles, and P. Barberger-Gateau Potential benefits of adherence to the mediterranean diet on cognitive health Proc. Nutr. Soc. 72 2013 140 152
8. A. Giacosa, R. Barale, L. Bavaresco, P. Gatenby, V. Gerbi, J. Janssens, B. Johnston, K. Kas, C. La Vecchia, P. Mainguet, P. Morazzoni, E. Negri, C. Pelucchi, M. Pezzotti, and M. Rondanelli Cancer prevention in Europe: the Mediterranean diet as a protective choice Eur. J. Cancer Prev. 22 2013 90 95
9. B. Bermudez, S. Lopez, A. Ortega, L.M. Varela, Y.M. Pacheco, R. Abia, and F.J. Muriana Oleic acid in olive oil: from a metabolic framework toward a clinical perspective Curr. Pharm. Des. 17 2011 831 843
10. International Olive Oil Council http://www.internationaloliveoil.org/ estaticos/view/131-world-olive-oil-figures
11. C.A. de la Lastra An up-date of olive oil and bioactive constituents in health: molecular mechanisms and clinical implications Curr. Pharm. Des. 17 2011 752 753
12. A. Ortega, L.M. Varela, B. Bermudez, S. Lopez, R. Abia, and F.J. Muriana Dietary fatty acids linking postprandial metabolic response and chronic diseases Food Funct. 3 2012 22 27
13. A. Cardeno, M. Sanchez-Hidalgo, and C.A. de la Lastra An up-date of olive oil phenols in inflammation and cancer: molecular mechanisms and clinical implications Curr. Med. Chem. 20 2013 4758 4776
14. S. Martin-Pelaez, M.I. Covas, M. Fito, A. Kusar, and I. Pravst Health effects of olive oil polyphenols: recent advances and possibilities for the use of health claims Mol. Nutr. Food Res. 57 2013 760 771
15. H. Sales-Campos, P.R. Souza, B.C. Peghini, J.S. da Silva, and C.R. Cardoso An overview of the modulatory effects of oleic acid in health and disease Mini Rev. Med. Chem. 13 2013 201 210
16. P. Inglese, F. Famiani, F. Galvano, M. Servili, S. Esposto, and S. Urbani Factors Affecting Extra-virgin Olive Oil Composition 2010 John Wiley & Sons Inc.
17. T.A. Lagace, and N.D. Ridgway The role of phospholipids in the biological activity and structure of the endoplasmic reticulum Biochim. Biophys. Acta 1833 2013 2499 2510
18. L. Hodson, and B.A. Fielding Stearoyl-CoA desaturase: rogue or innocent bystander? Prog. Lipid Res. 52 2013 15 42
19. A. Kotronen, T. Seppanen-Laakso, J. Westerbacka, T. Kiviluoto, J. Arola, A.L. Ruskeepaa, H. Yki-Jarvinen, and M. Oresic Comparison of lipid and fatty acid composition of the liver, subcutaneous and intra-abdominal adipose tissue, and serum Obesity 18 2010 937 944
20. A. Andersson, C. Nalsen, S. Tengblad, and B. Vessby Fatty acid composition of skeletal muscle reflects dietary fat composition in humans Am. J. Clin. Nutr. 76 2002 1222 1229
21. G. Rocquelin, L. Guenot, P.O. Astorg, and M. David Phospholipid content and fatty acid composition of human heart Lipids 24 1989 775 780
22. G. Bahrami, M. Masoumi, and Z. Rahimi Co-existence of fatty acids changes in aorta artery and adipose tissue; comparison between CAD and non CAD patients J. Thromb. Thrombolysis 27 2009 185 190
23. T. Fraser, H. Tayler, and S. Love Fatty acid composition of frontal, temporal and parietal neocortex in the normal human brain and in Alzheimer's disease Neurochem. Res. 35 2010 503 513
24. J. Guest, M. Garg, A. Bilgin, and R. Grant Relationship between central and peripheral fatty acids in humans Lipids Health Dis. 12 2013 79
25. Y. Min, C. Lowy, S. Islam, F.S. Khan, and R. Swaminathan Relationship between red cell membrane fatty acids and adipokines in individuals with varying insulin sensitivity Eur. J. Clin. Nutr. 65 2011 690 695
26. E. Frankel, A. Bakhouche, J. Lozano-Sanchez, A. Segura-Carretero, and A. Fernandez-Gutierrez Literature review on production process to obtain extra virgin olive oil enriched in bioactive compounds. Potential use of byproducts as alternative sources of polyphenols J. Agric. Food Chem. 61 2013 5179 5188
27. V.A. Ngo, R.K. Kalia, A. Nakano, and P. Vashishta Molecular mechanism of flip-flop in triple-layer oleic-acid membrane: correlation between oleic acid and water J. Phys. Chem. B 116 2012 13416 13423
28. Y.M. Pacheco, R. Abia, J.S. Perona, M. Reina, V. Ruiz-Gutierrez, E. Montero, and F.J. Muriana Triacylglycerol-rich lipoproteins interact with human vascular cells in a lipid-dependent fashion J. Agric. Food Chem. 49 2001 5653 5661
29. L.M. Varela, A. Ortega, B. Bermudez, S. Lopez, Y.M. Pacheco, J. Villar, R. Abia, and F.J. Muriana A high-fat meal promotes lipid-load and apolipoprotein B-48 receptor transcriptional activity in circulating monocytes Am. J. Clin. Nutr. 93 2011 918 925
30. B. Bermudez, S. Lopez, L.M. Varela, A. Ortega, Y.M. Pacheco, W. Moreda, R. Moreno-Luna, R. Abia, and F.J. Muriana Triglyceride-rich lipoprotein regulates APOB48 receptor gene expression in human THP-1 monocytes and macrophages J. Nutr. 142 2012 227 232
31. L.M. Varela, A. Ortega-Gomez, S. Lopez, R. Abia, F.J. Muriana, and B. Bermudez The effects of dietary fatty acids on the postprandial triglyceride-rich lipoprotein/apoB48 receptor axis in human monocyte/macrophage cells J. Nutr. Biochem. 24 2013 2031 2039
32. V. Ruiz-Gutierrez, F.J. Muriana, A. Guerrero, A.M. Cert, and J. Villar Plasma lipids, erythrocyte membrane lipids and blood pressure of hypertensive women after ingestion of dietary oleic acid from two different sources J. Hypertens. 14 1996 1483 1490
33. R. Alemany, J.S. Perona, J.M. Sanchez-Dominguez, E. Montero, J. Canizares, R. Bressani, P.V. Escriba, and V. Ruiz-Gutierrez G protein-coupled receptor systems and their lipid environment in health disorders during aging Biochim. Biophys. Acta 1768 2007 964 975
34. E. Escrich, M. Solanas, R. Moral, and R. Escrich Modulatory effects and molecular mechanisms of olive oil and other dietary lipids in breast cancer Curr. Pharm. Des. 17 2011 813 830
35. P.V. Escriba, J.M. Gonzalez-Ros, F.M. Goni, P.K. Kinnunen, L. Vigh, L. Sanchez-Magraner, A.M. Fernandez, X. Busquets, I. Horvath, and G. Barcelo-Coblijn Membranes: a meeting point for lipids, proteins and therapies J. Cell. Mol. Med. 12 2008 829 875
36. A. Nohturfft, and S.C. Zhang Coordination of lipid metabolism in membrane biogenesis Annu. Rev. Cell Dev. Biol. 25 2009 539 566
37. P.V. Escriba Membrane-lipid therapy: a new approach in molecular medicine Trends Mol. Med. 12 2006 34 43
38. S.S. Funari, F. Barcelo, and P.V. Escriba Effects of oleic acid and its congeners, elaidic and stearic acids, on the structural properties of phosphatidylethanolamine membranes J. Lipid Res. 44 2003 567 575
39. J. Prades, S.S. Funari, P.V. Escriba, and F. Barcelo Effects of unsaturated fatty acids and triacylglycerols on phosphatidylethanolamine membrane structure J. Lipid Res. 44 2003 1720 1727
40. T.N. Engelbrecht, A. Schroeter, T. Hauss, and R.H. Neubert Lipophilic penetration enhancers and their impact to the bilayer structure of stratum corneum lipid model membranes: neutron diffraction studies based on the example oleic acid Biochim. Biophys. Acta 1808 2011 2798 2806
41. S. Leekumjorn, H.J. Cho, Y. Wu, N.T. Wright, A.K. Sum, and C. Chan The role of fatty acid unsaturation in minimizing biophysical changes on the structure and local effects of bilayer membranes Biochim. Biophys. Acta 1788 2009 1508 1516
42. R.N. Weijers Lipid composition of cell membranes and its relevance in type 2 diabetes mellitus Curr. Diabetes Rev. 8 2012 390 400
43. M. Ibarguren, D.J. Lopez, J.A. Encinar, J.M. Gonzalez-Ros, X. Busquets, and P.V. Escriba Partitioning of liquid-ordered/liquid-disordered membrane microdomains induced by the fluidifying effect of 2-hydroxylated fatty acid derivatives Biochim. Biophys. Acta 1828 2013 2553 2563
44. J. Prades, S.S. Funari, M. Gomez-Florit, O. Vogler, and F. Barcelo Effect of a 2-hydroxylated fatty acid on cholesterol-rich membrane domains Mol. Membr. Biol. 29 2012 333 343
45. S.R. Shaikh, A.C. Dumaual, A. Castillo, D. LoCascio, R.A. Siddiqui, W. Stillwell, and S.R. Wassall Oleic and docosahexaenoic acid differentially phase separate from lipid raft molecules: a comparative NMR, DSC, AFM, and detergent extraction study Biophys. J. 87 2004 1752 1766
46. J. Ye, and R.A. DeBose-Boyd Regulation of cholesterol and fatty acid synthesis Cold Spring Harb. Perspect. Biol. 3 2011 a004754
47. J.N. Lee, X. Zhang, J.D. Feramisco, Y. Gong, and J. Ye Unsaturated fatty acids inhibit proteasomal degradation of Insig-1 at a postubiquitination step J. Biol. Chem. 283 2008 33772 33783
48. Y. Gong, J.N. Lee, P.C. Lee, J.L. Goldstein, M.S. Brown, and J. Ye Sterol-regulated ubiquitination and degradation of Insig-1 creates a convergent mechanism for feedback control of cholesterol synthesis and uptake Cell Metab. 3 2006 15 24
49. X.Y. Dong, and S.Q. Tang Insulin-induced gene: a new regulator in lipid metabolism Peptides 31 2010 2145 2150
50. R. Ehehalt, R. Sparla, H. Kulaksiz, T. Herrmann, J. Fullekrug, and W. Stremmel Uptake of long chain fatty acids is regulated by dynamic interaction of FAT/CD36 with cholesterol/sphingolipid enriched microdomains (lipid rafts) BMC Cell Biol. 9 2008 45
51. E.J. Grasso, M.B. Scalambro, and R.O. Calderon Differential response of the urothelial V-ATPase activity to the lipid environment Cell Biochem. Biophys. 61 2011 157 168
52. M.C. Berman Slippage and uncoupling in P-type cation pumps; implications for energy transduction mechanisms and regulation of metabolism Biochim. Biophys. Acta 1513 2001 95 121
53. O. Vogler, J.M. Barcelo, C. Ribas, and P.V. Escriba Membrane interactions of G proteins and other related proteins Biochim. Biophys. Acta 1778 2008 1640 1652
54. A. Krishnan, M.S. Almen, R. Fredriksson, and H.B. Schioth The origin of GPCRs: identification of mammalian like rhodopsin, adhesion, glutamate and frizzled GPCRs in fungi PLoS One 7 2012 e29817
55. A.J. Venkatakrishnan, X. Deupi, G. Lebon, C.G. Tate, G.F. Schertler, and M.M. Babu Molecular signatures of G-protein-coupled receptors Nature 494 2013 185 194
56. O. Vogler, J. Casas, D. Capo, T. Nagy, G. Borchert, G. Martorell, and P.V. Escriba The Gbetagamma dimer drives the interaction of heterotrimeric Gi proteins with nonlamellar membrane structures J. Biol. Chem. 279 2004 36540 36545
57. V.D. Dixit, E.M. Schaffer, R.S. Pyle, G.D. Collins, S.K. Sakthivel, R. Palaniappan, J.W. Lillard Jr., and D.D. Taub Ghrelin inhibits leptin- and activation-induced proinflammatory cytokine expression by human monocytes and T cells J. Clin. Invest. 114 2004 57 66
58. A.D. Howard, S.D. Feighner, D.F. Cully, J.P. Arena, P.A. Liberator, C.I. Rosenblum, M. Hamelin, D.L. Hreniuk, O.C. Palyha, J. Anderson, P.S. Paress, C. Diaz, M. Chou, K.K. Liu, K.K. McKee, S.S. Pong, L.Y. Chaung, A. Elbrecht, M. Dashkevicz, R. Heavens, M. Rigby, D.J. Sirinathsinghji, D.C. Dean, D.G. Melillo, A.A. Patchett, R. Nargund, P.R. Griffin, J.A. DeMartino, S.K. Gupta, J.M. Schaeffer, R.G. Smith, and L.H. Van der Ploeg A receptor in pituitary and hypothalamus that functions in growth hormone release Science 273 1996 974 977
59. P.J. Delhanty, A. van Kerkwijk, M. Huisman, B. van de Zande, M. Verhoef-Post, C. Gauna, L. Hofland, A.P. Themmen, and A.J. van der Lely Unsaturated fatty acids prevent desensitization of the human growth hormone secretagogue receptor by blocking its internalization Am. J. Physiol. Endocrinol. Metab. 299 2010 E497 E505
60. G.L. Alberts, C.L. Chio, and W.B. Im Allosteric modulation of the human 5-HT(7A) receptor by lipidic amphipathic compounds Mol. Pharmacol. 60 2001 1349 1355
61. S. Teres, G. Barcelo-Coblijn, M. Benet, R. Alvarez, R. Bressani, J.E. Halver, and P.V. Escriba Oleic acid content is responsible for the reduction in blood pressure induced by olive oil Proc. Natl. Acad. Sci. U. S. A. 105 2008 13811 13816
62. R. Alemany, S. Teres, C. Baamonde, M. Benet, O. Vogler, and P.V. Escriba 2-hydroxyoleic acid: a new hypotensive molecule Hypertension 43 2004 249 254
63. Q. Yang, R. Alemany, J. Casas, K. Kitajka, S.M. Lanier, and P.V. Escriba Influence of the membrane lipid structure on signal processing via G protein-coupled receptors Mol. Pharmacol. 68 2005 210 217
64. R. Alemany, O. Vogler, S. Teres, C. Egea, C. Baamonde, F. Barcelo, C. Delgado, K.H. Jakobs, and P.V. Escriba Antihypertensive action of 2-hydroxyoleic acid in SHRs via modulation of the protein kinase A pathway and Rho kinase J. Lipid Res. 47 2006 1762 1770
65. P.V. Escriba, J.M. Sanchez-Dominguez, R. Alemany, J.S. Perona, and V. Ruiz-Gutierrez Alteration of lipids, G proteins, and PKC in cell membranes of elderly hypertensives Hypertension 41 2003 176 182
66. L.A. Ferrara, A.S. Raimondi, L. d'Episcopo, L. Guida, A. Dello Russo, and T. Marotta Olive oil and reduced need for antihypertensive medications Arch. Intern. Med. 160 2000 837 842
67. M. Mueckler, and B. Thorens The SLC2 (GLUT) family of membrane transporters Mol. Aspects Med. 34 2013 121 138
68. Y. Tsuchiya, H. Hatakeyama, N. Emoto, F. Wagatsuma, S. Matsushita, and M. Kanzaki Palmitate-induced down-regulation of sortilin and impaired GLUT4 trafficking in C2C12 myotubes J. Biol. Chem. 285 2010 34371 34381
69. S. Lopez, B. Bermudez, Y.M. Pacheco, J. Villar, R. Abia, and F.J. Muriana Distinctive postprandial modulation of beta cell function and insulin sensitivity by dietary fats: monounsaturated compared with saturated fatty acids Am. J. Clin. Nutr. 88 2008 638 644
70. S. Lopez, B. Bermudez, A. Ortega, L.M. Varela, Y.M. Pacheco, J. Villar, R. Abia, and F.J. Muriana Effects of meals rich in either monounsaturated or saturated fat on lipid concentrations and on insulin secretion and action in subjects with high fasting triglyceride concentrations Am. J. Clin. Nutr. 93 2011 494 499
71. A. Chabowski, M. Zendzian-Piotrowska, A. Nawrocki, and J. Gorski Not only accumulation, but also saturation status of intramuscular lipids is significantly affected by PPARgamma activation Acta Physiol. 205 2012 145 158
72. J. Hwang, Y.H. Chang, J.H. Park, S.Y. Kim, H. Chung, E. Shim, and H.J. Hwang Dietary saturated and monounsaturated fats protect against acute acetaminophen hepatotoxicity by altering fatty acid composition of liver microsomal membrane in rats Lipids Health Dis. 10 2011 184
73. R.I. Bello, C. Gomez-Diaz, M.I. Buron, P. Navas, and J.M. Villalba Differential regulation of hepatic apoptotic pathways by dietary olive and sunflower oils in the aging rat Exp. Gerontol. 41 2006 1174 1184
74. V. Martin, N. Fabelo, G. Santpere, B. Puig, R. Marin, I. Ferrer, and M. Diaz Lipid alterations in lipid rafts from Alzheimer's disease human brain cortex J. Alzheimer's Dis. 19 2010 489 502
75. E. Evangelisti, D. Wright, M. Zampagni, R. Cascella, C. Fiorillo, S. Bagnoli, A. Relini, D. Nichino, T. Scartabelli, B. Nacmias, S. Sorbi, and C. Cecchi Lipid rafts mediate amyloid-induced calcium dyshomeostasis and oxidative stress in Alzheimer's disease Curr. Alzheimer Res. 10 2013 143 153
76. B.P. Head, H.H. Patel, and P.A. Insel Interaction of membrane/lipid rafts with the cytoskeleton: impact on signaling and function: membrane/lipid rafts, mediators of cytoskeletal arrangement and cell signaling Biochim. Biophys. Acta 1838 2013 532 545
77. A.M. Sebastiao, M. Colino-Oliveira, N. Assaife-Lopes, R.B. Dias, and J.A. Ribeiro Lipid rafts, synaptic transmission and plasticity: impact in age-related neurodegenerative diseases Neuropharmacology 64 2013 97 107
78. A. Tabernero, E.M. Lavado, B. Granda, A. Velasco, and J.M. Medina Neuronal differentiation is triggered by oleic acid synthesized and released by astrocytes J. Neurochem. 79 2001 606 616
79. R.A. Rodriguez-Rodriguez, A. Tabernero, A. Velasco, E.M. Lavado, and J.M. Medina The neurotrophic effect of oleic acid includes dendritic differentiation and the expression of the neuronal basic helix-loop-helix transcription factor NeuroD2 J. Neurochem. 88 2004 1041 1051
80. A. Bento-Abreu, A. Tabernero, and J.M. Medina Peroxisome proliferator-activated receptor-alpha is required for the neurotrophic effect of oleic acid in neurons J. Neurochem. 103 2007 871 881
81. X. Yang, S. Askarova, and J.C. Lee Membrane biophysics and mechanics in Alzheimer's disease Mol. Neurobiol. 41 2010 138 148
82. Z. Amtul, D. Westaway, D.F. Cechetto, and R.F. Rozmahel Oleic acid ameliorates amyloidosis in cellular and mouse models of Alzheimer's disease Brain Pathol. 21 2011 321 329
83. A. Bolognesi, A. Chatgilialoglu, L. Polito, and C. Ferreri Membrane lipidome reorganization correlates with the fate of neuroblastoma cells supplemented with fatty acids PLoS One 8 2013 e55537
84. J.J. Ochoa, R. Pamplona, M.C. Ramirez-Tortosa, S. Granados-Principal, P. Perez-Lopez, A. Naudi, M. Portero-Otin, M. Lopez-Frias, M. Battino, and J.L. Quiles Age-related changes in brain mitochondrial DNA deletion and oxidative stress are differentially modulated by dietary fat type and coenzyme Q(10) Free Radic. Biol. Med. 50 2011 1053 1064
85. M. Svensson, A. Hakansson, A.K. Mossberg, S. Linse, and C. Svanborg Conversion of alpha-lactalbumin to a protein inducing apoptosis Proc. Natl. Acad. Sci. U. S. A. 97 2000 4221 4226
86. A. Fontana, B. Spolaore, and P. Polverino de Laureto The biological activities of protein/oleic acid complexes reside in the fatty acid Biochim. Biophys. Acta 1834 2013 1125 1143
87. J.C. Ho, P. Storm, A. Rydstrom, B. Bowen, F. Alsin, L. Sullivan, I. Ambite, K.H. Mok, T. Northen, and C. Svanborg Lipids as tumoricidal components of human alpha-lactalbumin made lethal to tumor cells (HAMLET): unique and shared effects on signaling and death J. Biol. Chem. 288 2013 17460 17471
88. T. Nakamura, T. Aizawa, R. Kariya, S. Okada, M. Demura, K. Kawano, K. Makabe, and K. Kuwajima Molecular mechanisms of the cytotoxicity of human alpha-lactalbumin made lethal to tumor cells (HAMLET) and other protein-oleic acid complexes J. Biol. Chem. 288 2013 14408 14416
89. Z. Xiao, A. Mak, K. Koch, and R.B. Moore A molecular complex of bovine milk protein and oleic acid selectively kills cancer cells in vitro and inhibits tumour growth in an orthotopic rat bladder tumour model BJU Int. 112 2013 E201 E210
90. H. Wen, W.R. Glomm, and O. Halskau Cytotoxicity of bovine alpha-lactalbumin: oleic acid complexes correlates with the disruption of lipid membranes Biochim. Biophys. Acta 1828 2013 2691 2699
91. C. Duringer, A. Hamiche, L. Gustafsson, H. Kimura, and C. Svanborg HAMLET interacts with histones and chromatin in tumor cell nuclei J. Biol. Chem. 278 2003 42131 42135
92. E. Psomiadou, and M. Tsimidou Stability of virgin olive oil. 1. Autoxidation studies J. Agric. Food Chem. 50 2002 716 721
93. E. Psomiadou, and M. Tsimidou Stability of virgin olive oil. 2. Photo-oxidation studies J. Agric. Food Chem. 50 2002 722 727
94. C. De Luca, and G. Valacchi Surface lipids as multifunctional mediators of skin responses to environmental stimuli Mediators Inflamm. 2010 2010 321494
95. X.Y. Dong, S.Q. Tang, and J.D. Chen Dual functions of Insig proteins in cholesterol homeostasis Lipids Health Dis. 11 2012 173
96. S. Gill, J. Stevenson, I. Kristiana, and A.J. Brown Cholesterol-dependent degradation of squalene monooxygenase, a control point in cholesterol synthesis beyond HMG-CoA reductase Cell Metab. 13 2011 260 273
97. M. Spanova, and D. Günther Squalene - biochemistry, molecular biology, process biotechnology, and applications Eur. J. Lipid Sci. Technol. 113 2011 1299 1320
98. T. Hauss, S. Dante, N.A. Dencher, and T.H. Haines Squalane is in the midplane of the lipid bilayer: implications for its function as a proton permeability barrier Biochim. Biophys. Acta 1556 2002 149 154
99. J.S. Hansen, A. Vararattanavech, T. Vissing, J. Torres, J. Emneus, and C. Helix-Nielsen Formation of giant protein vesicles by a lipid cosolvent method Chembiochem 12 2011 2856 2862
100. M. Spanova, D. Zweytick, K. Lohner, L. Klug, E. Leitner, A. Hermetter, and G. Daum Influence of squalene on lipid particle/droplet and membrane organization in the yeast Saccharomyces cerevisiae Biochim. Biophys. Acta 1821 2012 647 653
101. S.F. Gilmore, A.I. Yao, Z. Tietel, T. Kind, M.T. Facciotti, and A.N. Parikh Role of squalene in the organization of monolayers derived from lipid extracts of Halobacterium salinarum Langmuir 29 2013 7922 7930
102. P. Couvreur, L.H. Reddy, S. Mangenot, J.H. Poupaert, D. Desmaele, S. Lepetre-Mouelhi, B. Pili, C. Bourgaux, H. Amenitsch, and M. Ollivon Discovery of new hexagonal supramolecular nanostructures formed by squalenoylation of an anticancer nucleoside analogue Small 4 2008 247 253
103. A. Ambike, V. Rosilio, B. Stella, S. Lepetre-Mouelhi, and P. Couvreur Interaction of self-assembled squalenoyl gemcitabine nanoparticles with phospholipid-cholesterol monolayers mimicking a biomembrane Langmuir 27 2011 4891 4899
104. D. Desmaele, R. Gref, and P. Couvreur Squalenoylation: a generic platform for nanoparticular drug delivery J. Control. Release 161 2012 609 618
105. H.M. Ali, A. Maksimenko, G. Urbinati, H. Chapuis, M. Raouane, D. Desmaele, H. Yasuhiro, H. Harashima, P. Couvreur, and L. Massaad-Massade Effects of silencing RET/PTC1 oncogene in papillary thyroid carcinoma by siRNA-squalene nanoparticles with and without fusogenic companion GALA-Cholesterol Thyroid 2013 10.1089/thy.2012.0544 (Epub ahead of print)
106. A. Wei, and T. Shibamoto Antioxidant activities of essential oil mixtures toward skin lipid squalene oxidized by UV irradiation Cutan. Ocul. Toxicol. 26 2007 227 233
107. S. Cho, C.W. Choi, D.H. Lee, C.H. Won, S.M. Kim, S. Lee, M.J. Lee, and J.H. Chung High-dose squalene ingestion increases type I procollagen and decreases ultraviolet-induced DNA damage in human skin in vivo but is associated with transient adverse effects Clin. Exp. Dermatol. 34 2009 500 508
108. P. Viola, and M. Viola Virgin olive oil as a fundamental nutritional component and skin protector Clin. Dermatol. 27 2009 159 165
109. K. Wolosik, M. Knas, A. Zalewska, M. Niczyporuk, and A.W. Przystupa The importance and perspective of plant-based squalene in cosmetology J. Cosmet. Sci. 64 2013 59 66
110. L.H. Reddy, and P. Couvreur Squalene: a natural triterpene for use in disease management and therapy Adv. Drug Deliv. Rev. 61 2009 1412 1426
111. H.N. Bhilwade, N. Tatewaki, H. Nishida, and T. Konishi Squalene as novel food factor Curr. Pharm. Biotechnol. 11 2010 875 880
112. S.K. Kim, and F. Karadeniz Biological importance and applications of squalene and squalane Adv. Food Nutr. Res. 65 2012 223 233
113. M.A. Tegenge, and R.J. Mitkus A physiologically-based pharmacokinetic (PBPK) model of squalene-containing adjuvant in human vaccines J. Pharmacokinet. Pharmacodyn. 40 2013 545 556
114. I. Domonkos, M. Kis, Z. Gombos, and B. Ughy Carotenoids, versatile components of oxygenic photosynthesis Prog. Lipid Res. 52 2013 539 561
115. B. Gandul-Rojas, and M.I. Minguez-Mosquera Chlorophyll and carotenoid composition in virgin olive oils from various Spanish olive varieties J. Sci. Food Agric. 72 1996 31 39
116. L. Gallardo-Guerrero, M. Roca, and I. Minguez-Mosquera Distribution of chlorophylls and carotenoids in ripening olives and between oil and alperujo when processed using a two-phase extraction system J. Am. Chem. Soc. 79 2002 105 109
117. R. Aparicio-Ruiz, and B. Gandul-Rojas Thermal degradation kinetics of neoxanthin, violaxanthin, and antheraxanthin in virgin olive oils J. Agric. Food Chem. 60 2012 5180 5191
118. J. Paik, A. During, E.H. Harrison, C.L. Mendelsohn, K. Lai, and W.S. Blaner Expression and characterization of a murine enzyme able to cleave beta-carotene. The formation of retinoids J. Biol. Chem. 276 2001 32160 32168
119. T. Kowatz, D. Babino, P. Kiser, K. Palczewski, and J. von Lintig Characterization of human beta, beta-carotene-15,15′-monooxygenase (BCMO1) as a soluble monomeric enzyme Arch. Biochem. Biophys. 539 2013 214 222
120. E.H. Harrison Mechanisms involved in the intestinal absorption of dietary vitamin A and provitamin A carotenoids Biochim. Biophys. Acta 1821 2012 70 77
121. J.A. Novotny, S.R. Dueker, L.A. Zech, and A.J. Clifford Compartmental analysis of the dynamics of beta-carotene metabolism in an adult volunteer J. Lipid Res. 36 1995 1825 1838
122. B. Gleize, M. Steib, M. Andre, and E. Reboul Simple and fast HPLC method for simultaneous determination of retinol, tocopherols, coenzyme Q(10) and carotenoids in complex samples Food Chem. 134 2012 2560 2564
123. A. Perez-Galvez, Y.M. Pacheco, B. Bermudez, S. Lopez, R. Abia, F.J. Muriana, J. Villar, and J. Garrido-Fernandez Postprandial evolution of the carotenoid content in the triacylglycerol-rich lipoprotein fraction after a single ingestion of virgin olive oil in humans Food Res. Int. 38 2005 1097 1102
124. G.P. Lobo, S. Hessel, A. Eichinger, N. Noy, A.R. Moise, A. Wyss, K. Palczewski, and J. von Lintig ISX is a retinoic acid-sensitive gatekeeper that controls intestinal beta, beta-carotene absorption and vitamin A production FASEB J. 24 2010 1656 1666
125. A. Sujak, W. Okulski, and W.I. Gruszecki Organisation of xanthophyll pigments lutein and zeaxanthin in lipid membranes formed with dipalmitoylphosphatidylcholine Biochim. Biophys. Acta 1509 2000 255 263
126. J. Cerezo, J. Zuniga, A. Bastida, A. Requena, J.P. Ceron-Carrasco, and L.A. Eriksson Antioxidant properties of beta-carotene isomers and their role in photosystems: insights from ab initio simulations J. Phys. Chem. A 116 2012 3498 3506
127. J. Cerezo, J. Zuniga, A. Bastida, A. Requena, and J.P. Ceron-Carrasco Conformational changes of beta-carotene and zeaxanthin immersed in a model membrane through atomistic molecular dynamics simulations Phys. Chem. Chem. Phys. 15 2013 6527 6538
128. W.I. Gruszecki, A. Sujak, K. Strzalka, A. Radunz, and G.H. Schmid Organisation of xanthophyll-lipid membranes studied by means of specific pigment antisera, spectrophotometry and monomolecular layer technique lutein versus zeaxanthin Z. Naturforsch. C 54 1999 517 525
129. A. Sujak, J. Gabrielska, W. Grudzinski, R. Borc, P. Mazurek, and W.I. Gruszecki Lutein and zeaxanthin as protectors of lipid membranes against oxidative damage: the structural aspects Arch. Biochem. Biophys. 371 1999 301 307
130. A. Wisniewska, J. Widomska, and W.K. Subczynski Carotenoid-membrane interactions in liposomes: effect of dipolar, monopolar, and nonpolar carotenoids Acta Biochim. Pol. 53 2006 475 484
131. W.I. Gruszecki, and K. Strzalka Carotenoids as modulators of lipid membrane physical properties Biochim. Biophys. Acta 1740 2005 108 115
132. A. Martinez, M.A. Rodriguez-Girones, A. Barbosa, and M. Costas Donator acceptor map for carotenoids, melatonin and vitamins J. Phys. Chem. A 112 2008 9037 9042
133. R.M. Han, J.P. Zhang, and L.H. Skibsted Reaction dynamics of flavonoids and carotenoids as antioxidants Molecules 17 2012 2140 2160
134. B. Li, P. Vachali, J.M. Frederick, and P.S. Bernstein Identification of StARD3 as a lutein-binding protein in the macula of the primate retina Biochemistry 50 2011 2541 2549
135. A. Wisniewska-Becker, G. Nawrocki, M. Duda, and W.K. Subczynski Structural aspects of the antioxidant activity of lutein in a model of photoreceptor membranes Acta Biochim. Pol. 59 2012 119 124
136. G. Horvath, E. Szoke, A. Kemeny, T. Bagoly, J. Deli, L. Szente, S. Pal, K. Sandor, J. Szolcsanyi, and Z. Helyes Lutein inhibits the function of the transient receptor potential A1 ion channel in different in vitro and in vivo models J. Mol. Neurosci. 46 2012 1 9
137. T. Aslam, C. Delcourt, R. Silva, F.G. Holz, A. Leys, A. Garcia-Layana, and E. Souied Micronutrients in age-related macular degeneration Ophthalmologica 229 2013 75 79
138. E. Yonova-Doing, P.G. Hysi, C. Venturini, K.M. Williams, A. Nag, S. Beatty, S.H. Liew, C.E. Gilbert, and C.J. Hammond Candidate gene study of macular response to supplemental lutein and zeaxanthin Exp. Eye Res. 115C 2013 172 177
139. J. Feeney, C. Finucane, G.M. Savva, H. Cronin, S. Beatty, J.M. Nolan, and R.A. Kenny Low macular pigment optical density is associated with lower cognitive performance in a large, population-based sample of older adults Neurobiol. Aging 34 2013 2449 2456
140. Y.H. Cui, C.X. Jing, and H.W. Pan Association of blood antioxidants and vitamins with risk of age-related cataract: a meta-analysis of observational studies Am. J. Clin. Nutr. 98 2013 778 786
141. E.J. Johnson, R. Vishwanathan, M.A. Johnson, D.B. Hausman, A. Davey, T.M. Scott, R.C. Green, L.S. Miller, M. Gearing, J. Woodard, P.T. Nelson, H.Y. Chung, W. Schalch, J. Wittwer, and L.W. Poon Relationship between serum and brain carotenoids, alpha-tocopherol, and retinol concentrations and cognitive performance in the oldest old from the Georgia Centenarian Study J. Aging Res. 2013 2013 951786
142. J. Karppi, S. Kurl, T.H. Makikallio, K. Ronkainen, and J.A. Laukkanen Low levels of plasma carotenoids are associated with an increased risk of atrial fibrillation Eur. J. Epidemiol. 28 2013 45 53
143. Z. Dai, R. Wang, L.W. Ang, Y.L. Low, J.M. Yuan, and W.P. Koh Protective effects of dietary carotenoids on risk of hip fracture in men: the Singapore Chinese health study J. Bone Miner. Res. 2013 10.1002/jbmr.2041 (Epub ahead of print)
144. T. Wolak, and E. Paran Can carotenoids attenuate vascular aging? Vasc. Pharmacol. 59 2013 63 66
145. R.A. Moreau, B.D. Whitaker, and K.B. Hicks Phytosterols, phytostanols, and their conjugates in foods: structural diversity, quantitative analysis, and health-promoting uses Prog. Lipid Res. 41 2002 457 500
146. M. Fuentes de Mendoza, C. De Miguel Gordillo, J. Marin Expoxito, J. Sanchez Casas, M. Martinez Cano, D. Martin Vertedor, and M.N. Franco Baltasar Chemical composition of virgin olive oils according to the ripening in olives Food Chem. 141 2013 2575 2581
147. M. Lukic, I. Lukic, M. Krapac, B. Sladonja, and V. Pilizota Sterols and triterpene diols in olive oil as indicators of variety and degree of ripening Food Chem. 136 2013 251 258
148. D. Garcia-Gonzalez, M. Viera, N. Tena, and R. Aparicio Evaluation of the methods based on triglycerides and sterols for the detection of hazelnut oil in olive oil Grasas Aceites 58 2007 344 350
149. B. Mathison, and D. Holstege A rapid method to determine sterol, erythrodiol, and uvaol concentrations in olive oil J. Agric. Food Chem. 61 2013 4506 4513
150. K. Matsuoka, E. Rie, S. Yui, C. Honda, and K. Endo Competitive solubilization of cholesterol and beta-sitosterol with changing biliary lipid compositions in model intestinal solution Chem. Phys. Lipids 165 2012 7 14
151. S.W. Park Intestinal and hepatic Niemann-Pick c1-like 1 Diabetes Metab. J. 37 2013 240 248
152. L. Jia, J.L. Betters, and L. Yu Niemann-Pick C1-like 1 (NPC1L1) protein in intestinal and hepatic cholesterol transport Annu. Rev. Physiol. 73 2011 239 259
153. V. Escurriol, M. Cofan, M. Serra, M. Bullo, J. Basora, J. Salas-Salvado, D. Corella, I. Zazpe, M.A. Martinez-Gonzalez, V. Ruiz-Gutierrez, R. Estruch, and E. Ros Serum sterol responses to increasing plant sterol intake from natural foods in the Mediterranean diet Eur. J. Nutr. 48 2009 373 382
154. Y. Park, and T.P. Carr Unsaturated fatty acids and phytosterols regulate
155. K. Hac-Wydro Studies on beta-sitosterol and ceramide-induced alterations in the properties of cholesterol/sphingomyelin/ganglioside monolayers Biochim. Biophys. Acta 1828 2013 2460 2469
156. K. Hac-Wydro The effect of beta-sitosterol on the properties of cholesterol/phosphatidylcholine/ganglioside monolayers - the impact of monolayer fluidity Colloids Surf. B: Biointerfaces 110 2013 113 119
157. J. Aittoniemi, T. Rog, P. Niemela, M. Pasenkiewicz-Gierula, M. Karttunen, and I. Vattulainen Tilt: major factor in sterols' ordering capability in membranes J. Phys. Chem. B 110 2006 25562 25564
158. T. Rog, M. Pasenkiewicz-Gierula, I. Vattulainen, and M. Karttunen Ordering effects of cholesterol and its analogues Biochim. Biophys. Acta 1788 2009 97 121
159. S. Rozner, L. Verkhovski, Y. Nissimov, A. Aserin, R. Vilensky, D. Danino, C.C. Zouboulis, Y. Milner, and N. Garti Inhibition of cholesterol transport into skin cells in cultures by phytosterol-loaded microemulsion Chem. Phys. Lipids 153 2008 109 118
160. K.K. Halling, and J.P. Slotte Membrane properties of plant sterols in phospholipid bilayers as determined by differential scanning calorimetry, resonance energy transfer and detergent-induced solubilization Biochim. Biophys. Acta 1664 2004 161 171
161. K. Hac-Wydro, P. Wydro, P. Dynarowicz-Latka, and M. Paluch Cholesterol and phytosterols effect on sphingomyelin/phosphatidylcholine model membranes - thermodynamic analysis of the interactions in ternary monolayers J. Colloid Interface Sci. 329 2009 265 272
162. F. Marangoni, and A. Poli Phytosterols and cardiovascular health Pharmacol. Res. 61 2010 193 199
163. S.P. Choudhary, and L.S. Tran Phytosterols: perspectives in human nutrition and clinical therapy Curr. Med. Chem. 18 2011 4557 4567
164. J. Plat, D. Mackay, S. Baumgartner, P.M. Clifton, H. Gylling, and P.J. Jones Progress and prospective of plant sterol and plant stanol research: report of the Maastricht meeting Atherosclerosis 225 2012 521 533
165. H. Cederberg, H. Gylling, T.A. Miettinen, J. Paananen, J. Vangipurapu, J. Pihlajamaki, T. Kuulasmaa, A. Stancakova, U. Smith, J. Kuusisto, and M. Laakso Non-cholesterol sterol levels predict hyperglycemia and conversion to type 2 diabetes in finnish men PLoS One 8 2013 e67406
166. S. Staubach, and F.G. Hanisch Lipid rafts: signaling and sorting platforms of cells and their roles in cancer Expert Rev. Proteomics 8 2011 263 277
167. N. Defamie, and M. Mesnil The modulation of gap-junctional intercellular communication by lipid rafts Biochim. Biophys. Acta 1818 2012 1866 1869
168. K.S. George, and S. Wu Lipid raft: a floating island of death or survival Toxicol. Appl. Pharmacol. 259 2012 311 319
169. P.G. Bradford, and A.B. Awad Modulation of signal transduction in cancer cells by phytosterols Biofactors 36 2010 241 247
170. P.J. Jansen, D. Lutjohann, K. Abildayeva, T. Vanmierlo, T. Plosch, J. Plat, K. von Bergmann, A.K. Groen, F.C. Ramaekers, F. Kuipers, and M. Mulder Dietary plant sterols accumulate in the brain Biochim. Biophys. Acta 1761 2006 445 453
171. T. Vanmierlo, O. Weingartner, S. van der Pol, C. Husche, A. Kerksiek, S. Friedrichs, E. Sijbrands, H. Steinbusch, M. Grimm, T. Hartmann, U. Laufs, M. Bohm, H.E. de Vries, M. Mulder, and D. Lutjohann Dietary intake of plant sterols stably increases plant sterol levels in the murine brain J. Lipid Res. 53 2012 726 735
172. J. Wang, F. Wu, and C. Shi Substitution of membrane cholesterol with beta-sitosterol promotes nonamyloidogenic cleavage of endogenous amyloid precursor protein Neuroscience 247 2013 227 233
173. C. Shi, J. Liu, F. Wu, X. Zhu, D.T. Yew, and J. Xu β-sitosterol inhibits high cholesterol-induced platelet β-amyloid release J. Bioenerg. Biomembr. 43 2011 691 697
174. C. Shi, F. Wu, and J. Xu Incorporation of β-sitosterol into mitochondrial membrane enhances mitochondrial function by promoting inner mitochondrial membrane fluidity J. Bioenerg. Biomembr. 45 2013 301 305
175. N. Stiti, S. Triki, and M.-A. Hartmann Formation of triterpenoids throughout Olea europaea fruit ontogeny Lipids 42 2007 55 67
176. A. Guinda, M. Rada, T. Delgado, P. Gutierrez-Adanez, and J.M. Castellano Pentacyclic triterpenoids from olive fruit and leaf J. Agric. Food Chem. 58 2010 9685 9691
177. J. Peragon Time course of pentacyclic triterpenoids from fruits and leaves of olive tree (Olea europaea L.) cv. picual and cv. cornezuelo during ripening J. Agric. Food Chem. 61 2013 6671 6678
178. Y. Allouche, A. Jimenez, M. Uceda, M.P. Aguilera, J.J. Gaforio, and G. Beltran Triterpenic content and chemometric analysis of virgin olive oils from forty olive cultivars J. Agric. Food Chem. 57 2009 3604 3610
179. J. Prades, O. Vogler, R. Alemany, M. Gomez-Florit, S.S. Funari, V. Ruiz-Gutierrez, and F. Barcelo Plant pentacyclic triterpenic acids as modulators of lipid membrane physical properties Biochim. Biophys. Acta 1808 2011 752 760
180. A.C. Teixeira, A.R. Garcia, L.M. Ilharco, A.M. Goncalves da Silva, and A.C. Fernandes Phase behaviour of oleanolic acid, pure and mixed with stearic acid: interactions and crystallinity Chem. Phys. Lipids 163 2010 655 666
181. M. Bayer, P. Proksch, I. Felsner, H. Brenden, Z. Kohne, R. Walli, T.N. Duong, C. Gotz, J. Krutmann, and S. Grether-Beck Photoprotection against UVAR: effective triterpenoids require a lipid raft stabilizing chemical structure Exp. Dermatol. 20 2011 955 958
182. M.B. Sporn, K.T. Liby, M.M. Yore, L. Fu, J.M. Lopchuk, and G.W. Gribble New synthetic triterpenoids: potent agents for prevention and treatment of tissue injury caused by inflammatory and oxidative stress J. Nat. Prod. 74 2011 537 545
183. F.M. Goni, and A. Alonso Effects of ceramide and other simple sphingolipids on membrane lateral structure Biochim. Biophys. Acta 1788 2009 169 177
184. S. Grether-Beck, M. Salahshour-Fard, A. Timmer, H. Brenden, I. Felsner, R. Walli, J. Fullekrug, and J. Krutmann Ceramide and raft signaling are linked with each other in UVA radiation-induced gene expression Oncogene 27 2008 4768 4778
185. Y. Uchida Ceramide signaling in mammalian epidermis Biochim. Biophys. Acta 1841 2013 453 462
186. W.J. van Blitterswijk, A.H. van der Luit, R.J. Veldman, M. Verheij, and J. Borst Ceramide: second messenger or modulator of membrane structure and dynamics? Biochem. J. 369 2003 199 211
187. Y. Allouche, G. Beltran, J.J. Gaforio, M. Uceda, and M.D. Mesa Antioxidant and antiatherogenic activities of pentacyclic triterpenic diols and acids Food Chem. Toxicol. 48 2010 2885 2890
188. M.P. Montilla, A. Agil, M.C. Navarro, M.I. Jimenez, A. Garcia-Granados, A. Parra, and M.M. Cabo Antioxidant activity of maslinic acid, a triterpene derivative obtained from Olea europaea Planta Med. 69 2003 472 474
189. J.S. Perona, R. Cabello-Moruno, and V. Ruiz-Gutierrez The role of virgin olive oil components in the modulation of endothelial function J. Nutr. Biochem. 17 2006 429 445
190. L.I. Somova, F.O. Shode, P. Ramnanan, and A. Nadar Antihypertensive, antiatherosclerotic and antioxidant activity of triterpenoids isolated from Olea europaea, subspecies africana leaves J. Ethnopharmacol. 84 2003 299 305
191. L.O. Somova, A. Nadar, P. Rammanan, and F.O. Shode Cardiovascular, antihyperlipidemic and antioxidant effects of oleanolic and ursolic acids in experimental hypertension Phytomedicine 10 2003 115 121
192. R. Rodriguez-Rodriguez, J.S. Perona, M.D. Herrera, and V. Ruiz-Gutierrez Triterpenic compounds from "orujo" olive oil elicit vasorelaxation in aorta from spontaneously hypertensive rats J. Agric. Food Chem. 54 2006 2096 2102
193. R. Rodriguez-Rodriguez, M.D. Herrera, M.A. de Sotomayor, and V. Ruiz-Gutierrez Pomace olive oil improves endothelial function in spontaneously hypertensive rats by increasing endothelial nitric oxide synthase expression Am. J. Hypertens. 20 2007 728 734
194. A. Marquez-Martin, R. De La Puerta, A. Fernandez-Arche, V. Ruiz-Gutierrez, and P. Yaqoob Modulation of cytokine secretion by pentacyclic triterpenes from olive pomace oil in human mononuclear cells Cytokine 36 2006 211 217
195. L.I. Somova, F.O. Shode, and M. Mipando Cardiotonic and antidysrhythmic effects of oleanolic and ursolic acids, methyl maslinate and uvaol Phytomedicine 11 2004 121 129
196. J. Martinez-Gonzalez, R. Rodriguez-Rodriguez, M. Gonzalez-Diez, C. Rodriguez, M.D. Herrera, V. Ruiz-Gutierrez, and L. Badimon Oleanolic acid induces prostacyclin release in human vascular smooth muscle cells through a cyclooxygenase-2-dependent mechanism J. Nutr. 138 2008 443 448
197. X. Wang, R. Liu, W. Zhang, X. Zhang, N. Liao, Z. Wang, W. Li, X. Qin, and C. Hai Oleanolic acid improves hepatic insulin resistance via antioxidant, hypolipidemic and anti-inflammatory effects Mol. Cell. Endocrinol. 376 2013 70 80
198. W. Lee, E.J. Yang, S.K. Ku, K.S. Song, and J.S. Bae Anti-inflammatory effects of oleanolic acid on LPS-induced inflammation in vitro and in vivo Inflammation 36 2013 94 102
199. R.S. Santos, P.L. Silva, G.P. de Oliveira, C.L. Santos, F.F. Cruz, E.F. de Assis, H.C. de Castro-Faria-Neto, V.L. Capelozzi, M.M. Morales, P. Pelosi, C.R. Gattass, and P.R. Rocco Oleanolic acid improves pulmonary morphofunctional parameters in experimental sepsis by modulating oxidative and apoptotic processes Respir. Physiol. Neurobiol. 189 2013 484 490
200. V. Stepanov, K. Stankov, and M. Mikov The bile acid membrane receptor TGR5: a novel pharmacological target in metabolic, inflammatory and neoplastic disorders J. Recept. Signal Transduct. Res. 33 2013 213 223
201. D.D. Jensen, C.B. Godfrey, C. Niklas, M. Canals, M. Kocan, D.P. Poole, J.E. Murphy, F. Alemi, G.S. Cottrell, C. Korbmacher, N.A. Lambert, N.W. Bunnett, and C.U. Corvera The bile acid receptor TGR5 does not interact with beta-arrestins or traffic to endosomes but transmits sustained signals from plasma membrane rafts J. Biol. Chem. 288 2013 22942 22960
202. J.M. Castellano, A. Guinda, T. Delgado, M. Rada, and J.A. Cayuela Biochemical basis of the antidiabetic activity of oleanolic acid and related pentacyclic triterpenes Diabetes 62 2013 1791 1799
203. Y. Allouche, F. Warleta, M. Campos, C. Sanchez-Quesada, M. Uceda, G. Beltran, and J.J. Gaforio Antioxidant, antiproliferative, and pro-apoptotic capacities of pentacyclic triterpenes found in the skin of olives on MCF-7 human breast cancer cells and their effects on DNA damage J. Agric. Food Chem. 59 2011 121 130
204. S.Y. Park, C.W. Nho, D.Y. Kwon, Y.H. Kang, K.W. Lee, and J.H. Park Maslinic acid inhibits the metastatic capacity of DU145 human prostate cancer cells: possible mediation via hypoxia-inducible factor-1alpha signalling Br. J. Nutr. 109 2013 210 222
205. F.J. Reyes-Zurita, E.E. Rufino-Palomares, P.P. Medina, L. Garcia-Salguero, J. Peragon, M. Cascante, and J.A. Lupianez Antitumour activity on extrinsic apoptotic targets of the triterpenoid maslinic acid in p53-deficient Caco-2 adenocarcinoma cells Biochimie 95 2013 2157 2167
206. E.E. Rufino-Palomares, F.J. Reyes-Zurita, L. Garcia-Salguero, K. Mokhtari, P.P. Medina, J.A. Lupianez, and J. Peragon Maslinic acid, a triterpenic anti-tumoural agent, interferes with cytoskeleton protein expression in HT29 human colon-cancer cells J. Proteomics 83 2013 15 25
207. J. Wang, M. Yu, L. Xiao, S. Xu, Q. Yi, and W. Jin Radiosensitizing effect of oleanolic acid on tumor cells through the inhibition of GSH synthesis in vitro Oncol. Rep. 30 2013 917 924
208. G. Guo, W. Yao, Q. Zhang, and Y. Bo Oleanolic acid suppresses migration and invasion of malignant glioma cells by inactivating MAPK/ERK signaling pathway PLoS One 8 2013 e72079
209. J. Wei, H. Liu, M. Liu, N. Wu, J. Zhao, L. Xiao, L. Han, E. Chu, and X. Lin Oleanolic acid potentiates the antitumor activity of 5-fluorouracil in pancreatic cancer cells Oncol. Rep. 28 2012 1339 1345
210. S.M. Kim, M.K. Chae, M.S. Yim, I.H. Jeong, J. Cho, C. Lee, and E.K. Ryu Hybrid PET/MR imaging of tumors using an oleanolic acid-conjugated nanoparticle Biomaterials 34 2013 8114 8121
211. R. Martin, M. Hernandez, C. Cordova, and M.L. Nieto Natural triterpenes modulate immune-inflammatory markers of experimental autoimmune encephalomyelitis: therapeutic implications for multiple sclerosis Br. J. Pharmacol. 166 2012 1708 1723
212. A. Bendini, L. Cerretani, A. Carrasco-Pancorbo, A.M. Gomez-Caravaca, A. Segura-Carretero, A. Fernandez-Gutierrez, and G. Lercker Phenolic molecules in virgin olive oils: a survey of their sensory properties, health effects, antioxidant activity and analytical methods. An overview of the last decade Molecules 12 2007 1679 1719
213. S. Christophoridou, and P. Dais Detection and quantification of phenolic compounds in olive oil by high resolution 1H nuclear magnetic resonance spectroscopy Anal. Chim. Acta. 633 2009 283 292
214. C. Romero, and M. Brenes Analysis of total contents of hydroxytyrosol and tyrosol in olive oils J. Agric. Food Chem. 60 2012 9017 9022
215. T.A. Enache, A. Amine, C.M. Brett, and A.M. Oliveira-Brett Virgin olive oil ortho-phenols-electroanalytical quantification Talanta 105 2013 179 186
216. S. Cicerale, L.J. Lucas, and R.S. Keast Antimicrobial, antioxidant and anti-inflammatory phenolic activities in extra virgin olive oil Curr. Opin. Biotechnol. 23 2012 129 135
217. A. Dagdelen, G. Tumen, M. Ozcan, and E. Dundar Phenolics profiles of olive fruits (Olea europaea L.) and oils from AyvalIk, Domat and Gemlik varieties at different ripening stages Food Chem. 136 2013 41 45
218. L. Rubio, M.J. Motilva, A. Macia, T. Ramo, and M.P. Romero Development of a phenol-enriched olive oil with both its own phenolic compounds and complementary phenols from thyme J. Agric. Food Chem. 60 2012 3105 3112
219. M. Suarez, R.M. Valls, M.P. Romero, A. Macia, S. Fernandez, M. Giralt, R. Sola, and M.J. Motilva Bioavailability of phenols from a phenol-enriched olive oil Br. J. Nutr. 106 2011 1691 1701
220. M. de Bock, E.B. Thorstensen, J.G. Derraik, H.V. Henderson, P.L. Hofman, and W.S. Cutfield Human absorption and metabolism of oleuropein and hydroxytyrosol ingested as olive (Olea europaea L.) leaf extract Mol. Nutr. Food Res. 57 2013 2079 2085
221. M.N. Vissers, P.L. Zock, A.J. Roodenburg, R. Leenen, and M.B. Katan Olive oil phenols are absorbed in humans J. Nutr. 132 2002 409 417
222. A. Serra, L. Rubio, X. Borras, A. Macia, M.P. Romero, and M.J. Motilva Distribution of olive oil phenolic compounds in rat tissues after administration of a phenolic extract from olive cake Mol. Nutr. Food Res. 56 2012 486 496
223. F. Paiva-Martins, M.H. Gordon, and P. Gameiro Activity and location of olive oil phenolic antioxidants in liposomes Chem. Phys. Lipids 124 2003 23 36
224. G.I. Togna, A.R. Togna, M. Franconi, C. Marra, and M. Guiso Olive oil isochromans inhibit human platelet reactivity J. Nutr. 133 2003 2532 2536
225. N. Caturla, L. Perez-Fons, A. Estepa, and V. Micol Differential effects of oleuropein, a biophenol from Olea europaea, on anionic and zwiterionic phospholipid model membranes Chem. Phys. Lipids 137 2005 2 17
226. H.A. Scheidt, and D. Huster The interaction of small molecules with phospholipid membranes studied by 1H NOESY NMR under magic-angle spinning Acta Pharmacol. Sin. 29 2008 35 49
227. P. Kosinova, K. Berka, M. Wykes, M. Otyepka, and P. Trouillas Positioning of antioxidant quercetin and its metabolites in lipid bilayer membranes: implication for their lipid-peroxidation inhibition J. Phys. Chem. B 116 2012 1309 1318
228. A. Bendini, L. Cerretani, S. Vecchi, A. Carrasco-Pancorbo, and G. Lercker Protective effects of extra virgin olive oil phenolics on oxidative stability in the presence or absence of copper ions J. Agric. Food Chem. 54 2006 4880 4887
229. M. Pazos, M.L. Andersen, I. Medina, and L.H. Skibsted Efficiency of natural phenolic compounds regenerating alpha-tocopherol from alpha-tocopheroxyl radical J. Agric. Food Chem. 55 2007 3661 3666
230. F. Paiva-Martins, J. Fernandes, S. Rocha, H. Nascimento, R. Vitorino, F. Amado, F. Borges, L. Belo, and A. Santos-Silva Effects of olive oil polyphenols on erythrocyte oxidative damage Mol. Nutr. Food Res. 53 2009 609 616
231. J. Li, G. Yang, S. Wang, L. Jiang, X. Liu, C. Geng, L. Zhong, and M. Chen The protective effects of hydroxytyrosol against ortho-phenylphenol-induced DNA damage in HepG2 cells Toxicol. Mech. Methods 22 2012 432 437
232. X. Zou, Z. Feng, Y. Li, Y. Wang, K. Wertz, P. Weber, Y. Fu, and J. Liu Stimulation of GSH synthesis to prevent oxidative stress-induced apoptosis by hydroxytyrosol in human retinal pigment epithelial cells: activation of Nrf2 and JNK-p62/SQSTM1 pathways J. Nutr. Biochem. 23 2012 994 1006
233. F. Shahidi, and M. Naczk Phenolics in Food and Nutraceuticals: Sources, Applications and Health Effects 2004 CRC Press
234. S. Rigacci, V. Guidotti, M. Bucciantini, M. Parri, C. Nediani, E. Cerbai, M. Stefani, and A. Berti Oleuropein aglycon prevents cytotoxic amyloid aggregation of human amylin J. Nutr. Biochem. 21 2010 726 735
235. K. Pillay, and P. Govender A direct fluorescence-based technique for cellular localization of amylin Biotechnol. Appl. Biochem. 60 2013 384 392
236. M. Caruana, J. Neuner, T. Hogen, F. Schmidt, F. Kamp, C. Scerri, A. Giese, and N. Vassallo Polyphenolic compounds are novel protective agents against lipid membrane damage by alpha-synuclein aggregates in vitro Biochim. Biophys. Acta 1818 2012 2502 2510
237. L. Diomede, S. Rigacci, M. Romeo, M. Stefani, and M. Salmona Oleuropein aglycone protects transgenic C. elegans strains expressing Abeta42 by reducing plaque load and motor deficit PLoS One 8 2013 e58893
238. B. Luzon-Toro, A. Geerlings, and S. Hilfiker Hydroxytyrosol increases norepinephrine transporter function in pheochromocytoma cells Nucl. Med. Biol. 35 2008 801 804
239. M.I. Covas Bioactive effects of olive oil phenolic compounds in humans: reduction of heart disease factors and oxidative damage Inflammopharmacology 16 2008 216 218
240. J. Lopez-Miranda, F. Perez-Jimenez, E. Ros, R. De Caterina, L. Badimon, M.I. Covas, E. Escrich, J.M. Ordovas, F. Soriguer, R. Abia, C.A. de la Lastra, M. Battino, D. Corella, J. Chamorro-Quiros, J. Delgado-Lista, D. Giugliano, K. Esposito, R. Estruch, J.M. Fernandez-Real, J.J. Gaforio, C. La Vecchia, D. Lairon, F. Lopez-Segura, P. Mata, J.A. Menendez, F.J. Muriana, J. Osada, D.B. Panagiotakos, J.A. Paniagua, P. Perez-Martinez, J. Perona, M.A. Peinado, M. Pineda-Priego, H.E. Poulsen, J.L. Quiles, M.C. Ramirez-Tortosa, J. Ruano, L. Serra-Majem, R. Sola, M. Solanas, V. Solfrizzi, R. de la Torre-Fornell, A. Trichopoulou, M. Uceda, J.M. Villalba-Montoro, J.R. Villar-Ortiz, F. Visioli, and N. Yiannakouris Olive oil and health: summary of the II international conference on olive oil and health consensus report, Jaen and Cordoba (Spain) 2008 Nutr. Metab. Cardiovasc. Dis. 20 2010 284 294
241. E.K. Pauwels The protective effect of the Mediterranean diet: focus on cancer and cardiovascular risk Med. Princ. Pract. 20 2011 103 111
242. F. Visioli, and E. Bernardini Extra virgin olive oil's polyphenols: biological activities Curr. Pharm. Des. 17 2011 786 804
243. S.M. Ross Effects of extra virgin olive oil phenolic compounds and the Mediterranean diet on cardiovascular health Holist. Nurs. Pract. 27 2013 303 307
244. E. Escrich, R. Moral, and M. Solanas Olive oil, an essential component of the Mediterranean diet, and breast cancer Public Health Nutr. 14 2011 2323 2332
245. I. Casaburi, F. Puoci, A. Chimento, R. Sirianni, C. Ruggiero, P. Avena, and V. Pezzi Potential of olive oil phenols as chemopreventive and therapeutic agents against cancer: a review of in vitro studies Mol. Nutr. Food Res. 57 2013 71 83
246. M.J. Oliveras-Lopez, J.J. Molina, M.V. Mir, E.F. Rey, F. Martin, and H.L. de la Serrana Extra virgin olive oil (EVOO) consumption and antioxidant status in healthy institutionalized elderly humans Arch. Gerontol. Geriatr. 57 2013 234 242
247. R.J. Widmer, M.A. Freund, A.J. Flammer, J. Sexton, R. Lennon, A. Romani, N. Mulinacci, F.F. Vinceri, L.O. Lerman, and A. Lerman Beneficial effects of polyphenol-rich olive oil in patients with early atherosclerosis Eur. J. Nutr. 52 2013 1223 1231
248. D. Palmieri, B. Aliakbarian, A.A. Casazza, N. Ferrari, G. Spinella, B. Pane, G. Cafueri, P. Perego, and D. Palombo Effects of polyphenol extract from olive pomace on anoxia-induced endothelial dysfunction Microvasc. Res. 83 2012 281 289
249. J. Makino, R. Nakanishi, T. Kamiya, H. Hara, M. Ninomiya, M. Koketsu, and T. Adachi Luteolin suppresses the differentiation of THP-1 cells through the inhibition of NOX2 mRNA expression and the membrane translocation of p47phox J. Nat. Prod. 76 2013 1285 1290
250. C. Manna, D. Napoli, G. Cacciapuoti, M. Porcelli, and V. Zappia Olive oil phenolic compounds inhibit homocysteine-induced endothelial cell adhesion regardless of their different antioxidant activity J. Agric. Food Chem. 57 2009 3478 3482
251. H.K. Obied, P.D. Prenzler, I. Konczak, A.U. Rehman, and K. Robards Chemistry and bioactivity of olive biophenols in some antioxidant and antiproliferative in vitro bioassays Chem. Res. Toxicol. 22 2009 227 234
252. L. Zambonin, C. Caliceti, F. Vieceli Dalla Sega, D. Fiorentini, S. Hrelia, L. Landi, and C. Prata Dietary phenolic acids act as effective antioxidants in membrane models and in cultured cells, exhibiting proapoptotic effects in leukaemia cells Oxid. Med. Cell. Longev. 2012 2012 839298
253. P. Pratheeshkumar, Y.O. Son, A. Budhraja, X. Wang, S. Ding, L. Wang, A. Hitron, J.C. Lee, D. Kim, S.P. Divya, G. Chen, Z. Zhang, J. Luo, and X. Shi Luteolin inhibits human prostate tumor growth by suppressing vascular endothelial growth factor receptor 2-mediated angiogenesis PLoS One 7 2012 e52279
254. X. Cai, W. Lu, T. Ye, M. Lu, J. Wang, J. Huo, S. Qian, X. Wang, and P. Cao The molecular mechanism of luteolin-induced apoptosis is potentially related to inhibition of angiogenesis in human pancreatic carcinoma cells Oncol. Rep. 28 2012 1353 1361
255. Q. Chen, S. Liu, J. Chen, Q. Zhang, S. Lin, Z. Chen, and J. Jiang Luteolin induces mitochondria-dependent apoptosis in human lung adenocarcinoma cell Nat. Prod. Commun. 7 2012 29 32
256. P.S. Rao, A. Satelli, M. Moridani, M. Jenkins, and U.S. Rao Luteolin induces apoptosis in multidrug resistant cancer cells without affecting the drug transporter function: involvement of cell line-specific apoptotic mechanisms Int. J. Cancer 130 2012 2703 2714
257. S. Karthikeyan, G. Kanimozhi, N.R. Prasad, and R. Mahalakshmi Radiosensitizing effect of ferulic acid on human cervical carcinoma cells in vitro Toxicol. In Vitro 25 2011 1366 1375
258. J.A. Menendez, A. Vazquez-Martin, C. Oliveras-Ferraros, R. Garcia-Villalba, A. Carrasco-Pancorbo, A. Fernandez-Gutierrez, and A. Segura-Carretero Analyzing effects of extra-virgin olive oil polyphenols on breast cancer-associated fatty acid synthase protein expression using reverse-phase protein microarrays Int. J. Mol. Med. 22 2008 433 439
259. J.A. Menendez, A. Vazquez-Martin, R. Garcia-Villalba, A. Carrasco-Pancorbo, C. Oliveras-Ferraros, A. Fernandez-Gutierrez, and A. Segura-Carretero tabAnti-HER2 (erbB-2) oncogene effects of phenolic compounds directly isolated from commercial extra-virgin olive oil (EVOO) BMC Cancer 8 2008 377
260. Y.Z. Hashim, I.R. Rowland, H. McGlynn, M. Servili, R. Selvaggini, A. Taticchi, S. Esposto, G. Montedoro, L. Kaisalo, K. Wahala, and C.I. Gill Inhibitory effects of olive oil phenolics on invasion in human colon adenocarcinoma cells in vitro Int. J. Cancer 122 2008 495 500
261. L. Fini, E. Hotchkiss, V. Fogliano, G. Graziani, M. Romano, E.B. De Vol, H. Qin, M. Selgrad, C.R. Boland, and L. Ricciardiello Chemopreventive properties of pinoresinol-rich olive oil involve a selective activation of the ATM-p53 cascade in colon cancer cell lines Carcinogenesis 29 2008 139 146
262. C. Romero, E. Medina, J. Vargas, M. Brenes, and A. De Castro In vitro activity of olive oil polyphenols against Helicobacter pylori J. Agric. Food Chem. 55 2007 680 686
263. M. Castro, C. Romero, A. de Castro, J. Vargas, E. Medina, R. Millan, and M. Brenes Assessment of Helicobacter pylori eradication by virgin olive oil Helicobacter 17 2012 305 311
264. M. Alirezaei, O. Dezfoulian, S. Neamati, M. Rashidipour, N. Tanideh, and A. Kheradmand Oleuropein prevents ethanol-induced gastric ulcers via elevation of antioxidant enzyme activities in rats J. Physiol. Biochem. 68 2012 583 592
265. N. Zoric, I. Horvat, N. Kopjar, A. Vucemilovic, D. Kremer, S. Tomic, and I. Kosalec Hydroxytyrosol expresses antifungal activity in vitro Curr. Drug Targets 14 2013 992 998
266. G. Eumkeb, S. Siriwong, and K. Thumanu Synergistic activity of luteolin and amoxicillin combination against amoxicillin-resistant Escherichia coli and mode of action J. Photochem. Photobiol. B 117 2012 247 253
267. W. Hur, S.W. Kim, Y.K. Lee, J.E. Choi, S.W. Hong, M.J. Song, S.H. Bae, T. Park, S.J. Um, and S.K. Yoon Oleuropein reduces free fatty acid-induced lipogenesis via lowered extracellular signal-regulated kinase activation in hepatocytes Nutr. Res. 32 2012 778 786
268. S. Sanchez-Fidalgo, L. Sanchez de Ibarguen, A. Cardeno, and C.A. de la Lastra Influence of extra virgin olive oil diet enriched with hydroxytyrosol in a chronic DSS colitis model Eur. J. Nutr. 51 2012 497 506
269. P. Dewapriya, S.W. Himaya, Y.X. Li, and S.K. Kim Tyrosol exerts a protective effect against dopaminergic neuronal cell death in in vitro model of Parkinson's disease Food Chem. 141 2013 1147 1157
270. N. Dragicevic, A. Smith, X. Lin, F. Yuan, N. Copes, V. Delic, J. Tan, C. Cao, R.D. Shytle, and P.C. Bradshaw Green tea epigallocatechin-3-gallate (EGCG) and other flavonoids reduce Alzheimer's amyloid-induced mitochondrial dysfunction J. Alzheimer's Dis. 26 2011 507 521
271. M. Ishisaka, K. Kakefuda, M. Yamauchi, K. Tsuruma, M. Shimazawa, A. Tsuruta, and H. Hara Luteolin shows an antidepressant-like effect via suppressing endoplasmic reticulum stress Biol. Pharm. Bull. 34 2011 1481 1486
272. P. Sunkireddy, S.N. Jha, J.R. Kanwar, and S.C. Yadav Natural antioxidant biomolecules promises future nanomedicine based therapy for cataract Colloids Surf. B: Biointerfaces 112 2013 554 562
273. C. Wall, R. Lim, M. Poljak, and M. Lappas Dietary flavonoids as therapeutics for preterm birth: luteolin and kaempferol suppress inflammation in human gestational tissues in vitro Oxid. Med. Cell. Longev. 2013 2013 485201
274. C. Agostini, J. Bresson, S. Fairweather-Tati, A. Flynn, I. Golly, H. Korhonen, P. Lagiou, M. Lovik, R. Marchelli, A. Martin, B. Moseley, M. Neuhauser-Berthold, H. Przyrembel, S. Salminen, Y. Sanz, S. Strain, S. Strobel, I. Tetens, D. Tome, H. van Loveren, and H. Verhagen Scientific Opinion on the substantiation of health claims related to polyphenols in olive and protection of LDL particles from oxidative damage (ID 1333, 1638, 1639, 1696, 2865), maintenance of normal blood HDL cholesterol concentrations (ID 1639), maintenance of normal blood pressure (ID 3781), "anti-inflammatory properties" (ID 1882), "contributes to the upper respiratory tract health" (ID 3468), "can help to maintain a normal function of gastrointestinal tract" (3779), and "contributes to body defences against external agents" (ID 3467) pursuant to Article 13(1) of Regulation (EC) No 1924/2006 EFSA J. 9 2011 2033 2058
275. M.L. Colombo An update on vitamin E, tocopherol and tocotrienol- perspectives Molecules 15 2010 2103 2113
276. E. Niki, and M.G. Traber A history of vitamin E Ann. Nutr. Metab. 61 2012 207 212
277. S.C. Cunha, J.S. Amaral, J.O. Fernandes, and M.B. Oliveira Quantification of tocopherols and tocotrienols in portuguese olive oils using HPLC with three different detection systems J. Agric. Food Chem. 54 2006 3351 3356
278. V. Papadimitriou, T.G. Sotiroudis, A. Xenakis, N. Sofikiti, V. Stavyiannoudaki, and N.A. Chaniotakis Oxidative stability and radical scavenging activity of extra virgin olive oils: an electron paramagnetic resonance spectroscopy study Anal. Chim. Acta. 573-574 2006 453 458
279. Y. Allouche, A. Jimenez, J.J. Gaforio, M. Uceda, and G. Beltran How heating affects extra virgin olive oil quality indexes and chemical composition J. Agric. Food Chem. 55 2007 9646 9654
280. S. Casal, R. Malheiro, A. Sendas, B.P. Oliveira, and J.A. Pereira Olive oil stability under deep-frying conditions Food Chem. Toxicol. 48 2010 2972 2979
281. A. Dagdelen, G. Tumen, M.M. Ozcan, and E. Dundar Determination of tocopherol contents of some olive varieties harvested at different ripening periods Nat. Prod. Res. 26 2012 1454 1457
282. K. Yousfi, C.M. Weiland, and J.M. Garcia Effect of harvesting system and fruit cold storage on virgin olive oil chemical composition and quality of superintensive cultivated 'Arbequina' olives J. Agric. Food Chem. 60 2012 4743 4750
283. M. Benito, J.M. Lasa, P. Gracia, R. Oria, M. Abenoza, L. Varona, and A.C. Sanchez-Gimeno Olive oil quality and ripening in super-high-density Arbequina orchard J. Sci. Food Agric. 93 2013 2207 2220
284. G. Rigane, M. Boukhris, R.B. Salem, S. Sayadi, and M. Bouaaziz Analytical evaluation of two monovarietal virgin olive oils cultivated in the south of Tunisia: Jemri-Bouchouka and Chemlali-Tataouin cultivars J. Sci. Food Agric. 93 2013 1242 1248
285. T.J. Sontag, and R.S. Parker Cytochrome P450 omega-hydroxylase pathway of tocopherol catabolism. Novel mechanism of regulation of vitamin E status J. Biol. Chem. 277 2002 25290 25296
286. E. Niki, and N. Noguchi Dynamics of antioxidant action of vitamin E Acc. Chem. Res. 37 2004 45 51
287. J. Atkinson, R.F. Epand, and R.M. Epand Tocopherols and tocotrienols in membranes: a critical review Free Radic. Biol. Med. 44 2008 739 764
288. J. Atkinson, T. Harroun, S.R. Wassall, W. Stillwell, and J. Katsaras The location and behavior of alpha-tocopherol in membranes Mol. Nutr. Food Res. 54 2010 641 651
289. L. Ulatowski, and D. Manor Vitamin E trafficking in neurologic health and disease Annu. Rev. Nutr. 33 2013 87 103
290. Y. Yoshida, Y. Saito, L.S. Jones, and Y. Shigeri Chemical reactivities and physical effects in comparison between tocopherols and tocotrienols: physiological significance and prospects as antioxidants J. Biosci. Bioeng. 104 2007 439 445
291. M.A. Kamal, and V.A. Raghunathan Modulated phases of phospholipid bilayers induced by tocopherols Biochim. Biophys. Acta 1818 2012 2486 2493
292. A.C. Howard, A.K. McNeil, and P.L. McNeil Promotion of plasma membrane repair by vitamin E Nat. Commun. 2 2011 597
293. Y. Yoshida, E. Niki, and N. Noguchi Comparative study on the action of tocopherols and tocotrienols as antioxidant: chemical and physical effects Chem. Phys. Lipids 123 2003 63 75
294. A.F. Sonnen, H. Bakirci, T. Netscher, and W.M. Nau Effect of temperature, cholesterol content, and antioxidant structure on the mobility of vitamin E constituents in biomembrane models studied by laterally diffusion-controlled fluorescence quenching J. Am. Chem. Soc. 127 2005 15575 15584
295. M. Nagao, Y. Moriyama, K. Yamagishi, H. Iso, A. Tamakoshi, and J.S. Group Relation of serum alpha- and gamma-tocopherol levels to cardiovascular disease-related mortality among Japanese men and women J. Epidemiol. 22 2012 402 410
296. S.J. Weinstein, U. Peters, J. Ahn, M.D. Friesen, E. Riboli, R.B. Hayes, and D. Albanes Serum alpha-tocopherol and gamma-tocopherol concentrations and prostate cancer risk in the PLCO Screening Trial: a nested case-control study PLoS One 7 2012 e40204
297. J.J. Sutachan, Z. Casas, S.L. Albarracin, B.R. Stab II, I. Samudio, J. Gonzalez, L. Morales, and G.E. Barreto Cellular and molecular mechanisms of antioxidants in Parkinson's disease Nutr. Neurosci. 15 2012 120 126
298. F. Mangialasche, E. Westman, M. Kivipelto, J.S. Muehlboeck, R. Cecchetti, M. Baglioni, R. Tarducci, G. Gobbi, P. Floridi, H. Soininen, I. Kloszewska, M. Tsolaki, B. Vellas, C. Spenger, S. Lovestone, L.O. Wahlund, A. Simmons, P. Mecocci AddNeuroMed consortium Classification and prediction of clinical diagnosis of Alzheimer's disease based on MRI and plasma measures of alpha-/gamma-tocotrienols and gamma-tocopherol J. Intern. Med. 273 2013 602 621
299. D.K. Das Tocotrienols: potential drug targets for cardiovascular, cancer and neurological diseases Curr. Pharm. Des. 17 2011 2145 2146
300. B. Aggarwal, and K. Nesaretnam Vitamin E tocotrienols: life beyond tocopherols Genes Nutr. 7 2012 1