The effect of natural and synthetic fatty acids on membrane structure, microdomain organization, cellular functions and human health

Biochimica et Biophysica Acta - Biomembranes

Volumn 1838, Issue 6, 2014, Pages 1518-1528

  Ibarguren, Maitane ^a,b   López, David J ^a,b   Escribá, Pablo V ^a  

^a UNIVERSITAT DE LES ILLES BALEARS   (Spain)

^b Lipopharma Therapeutics SL   (Spain)

Author keywords

2 Hydroxylated fatty acid; Fatty acid; Membrane domains; Membrane structure

Indexed keywords

2-HYDROXYLATED FATTY ACID; FATTY ACID; MEMBRANE DOMAINS; MEMBRANE STRUCTURE;

CELL MEMBRANE STRUCTURES; CELL PHYSIOLOGICAL PHENOMENA; FATTY ACIDS; HUMANS; MEMBRANE MICRODOMAINS;

EID: 84899454624     PISSN: 00052736     EISSN: 18792642     Source Type: Journal    
DOI: 10.1016/j.bbamem.2013.12.021     Document Type: Review

References (158)

1. G.O. Burr, and M.M. Burr A new deficiency disease produced by the rigid exclusion of fat from the diet J. Biol. Chem. 82 1929 345 367
2. C.A. Demopoulos, R.N. Pinckard, and D.J. Hanahan Platelet-activating factor. Evidence for 1-O-alkyl-2-acetyl-sn-glyceryl-3-phosphorylcholine as the active component (a new class of lipid chemical mediators) J. Biol. Chem. 254 19 1979 9355 9358 (Pubitemid 10248704)
3. S.J. Baum, P.M. Kris-Etherton, W.C. Willett, A.H. Lichtenstein, L.L. Rudel, K.C. Maki, J. Whelan, C.E. Ramsden, and R.C. Block Fatty acids in cardiovascular health and disease: a comprehensive update J. Clin. Lipidol. 6 2012 216 234
4. S. Terés, G. Barceló-Coblijn, M. Benet, R. Alvárez, R. Bressani, J.E. Halver, and P.V. Escribá Oleic acid content is responsible for the reduction in blood pressure induced by olive oil Proc. Natl. Acad. Sci. 105 2008 13811 13816
5. C.J. Lavie, R.V. Milani, M.R. Mehra, and H.O. Ventura Omega - 3 polyunsaturated fatty acids and cardiovascular diseases J. Am. Coll. Cardiol. 54 2009 585 594
6. R. Kapoor, and Y.S. Huang Gamma linolenic acid: an antiinflammatory omega - 6 fatty acid Curr. Pharm. Biotechnol. 7 2006 531 534 (Pubitemid 46017544)
7. U.N. Das Essential fatty acids: biochemistry, physiology and pathology Biotechnol. J. 1 2006 420 439
8. A.K. El-Ansary, A.G. Bacha, and L.Y. Al-Ayahdi Plasma fatty acids as diagnostic markers in autistic patients from Saudi Arabia Lipids Health Dis. 10 2011 62
9. L.Y. Wang, F. Le, N. Wang, L. Li, X.Z. Liu, Y.M. Zheng, H.Y. Lou, X.R. Xu, Y.L. Chen, X.M. Zhu, H.F. Huang, and F. Jin Alteration of fatty acid metabolism in the liver, adipose tissue, and testis of male mice conceived through assisted reproductive technologies: fatty acid metabolism in ART mice Lipids Health Dis. 12 2013 5
10. M. Mally, P. Peterlin, and S. Svetina Partitioning of oleic acid into phosphatidylcholine membranes is amplified by strain J. Phys. Chem. B 117 2013 12086 12094
11. M. Ibarguren, D.J. López, J.A. Encinar, J.M. González-Ros, X. Busquets, and P.V. Escribá 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
12. M. Igarashi, L. Chang, K. Ma, and S.I. Rapoport Kinetics of eicosapentaenoic acid in brain, heart and liver of conscious rats fed a high n-3 PUFA containing diet Prostaglandins Leukot. Essent. Fatty Acids 89 2013 403 412
13. M.L. Martin, G. Barceló-Coblijn, R.F. de Almeida, M.A. Noguera-Salva, S. Terés, M. Higuera, G. Liebisch, G. Schmitz, X. Busquets, and P.V. Escribá The role of membrane fatty acid remodeling in the antitumor mechanism of action of 2-hydroxyoleic acid Biochim. Biophys. Acta 1828 2013 1405 1413
14. A.W. Eliasz, D. Chapman, and D.F. Ewing Phospholipid phase transitions. Effects of n-alcohols, n-monocarboxylic acids, phenylalkyl alcohols and quaternary ammonium compounds Biochim. Biophys. Acta 448 1976 220 230
15. S. Mabrey, and J.M. Sturtevant Incorporation of saturated fatty acids into phosphatidylcholine bilayers Biochim. Biophys. Acta 486 1977 444 450 (Pubitemid 8054528)
16. H.L. Kantor, and J.H. Prestegard Fusion of phosphatidylcholine bilayer vesicles: role of free fatty acid Biochemistry 17 1978 3592 3597 (Pubitemid 8405389)
17. S.E. Schullery, T.A. Seder, D.A. Weinstein, and D.A. Bryant Differential thermal analysis of dipalmitoylphosphatidylcholine-fatty acid mixtures Biochemistry 20 1981 6818 6824 (Pubitemid 12185943)
18. J.R. Usher, R.M. Epand, and D. Papahadjopoulos The effect of free fatty acids on the thermotropic phase transition of dimyristoyl glycerophosphocholine Chem. Phys. Lipids 22 1978 245 253
19. R.D. Klausner, A.M. Kleinfeld, R.L. Hoover, and M.J. Karnovsky Lipid domains in membranes. Evidence derived from structural perturbations induced by free fatty acids and lifetime heterogeneity analysis J. Biol. Chem. 255 1980 1286 1295
20. M.J. Karnovsky, A.M. Kleinfeld, R.L. Hoover, and R.D. Klausner The concept of lipid domains in membranes J. Cell Biol. 94 Jul. 1982 1 6
21. F. Podo, and J.K. Blasie Proton magnetic relaxation studies of mixed phosphatidylcholine/fatty acid and mixed phosphatidylcholine bimolecular bilayers Biochim. Biophys. Acta 419 1976 1 18
22. 31P NMR spectroscopy and X-ray diffraction Biochim. Biophys. Acta 690 1982 117 123
23. J.M. Kremer, and P.H. Wiersema Exchange and aggregation in dispersions of dimyristoyl phosphatidylcholine vesicles containing myristic acid Biochim. Biophys. Acta 471 1977 348 360 (Pubitemid 8226320)
24. H. Hauser, W. Guyer, and K. Howell Lateral distribution of negatively charged lipids in lecithin membranes. Clustering of fatty acids Biochem. 18 1979 3285 3291
25. K. Peter Pauls, M.L. Alex, and B. Myer Deuterium nuclear magnetic resonance study of the effects of palmitic acid on dipalmitoylphosphatidylcholine bilayers Biochemistry 22 1983 8
26. D. Fodor, and R.M. Epand A densitometric study of the effects of free fatty acids on the phase transition of dimyristoylphosphatidylcholine bilayers Chem. Phys. Lipids 28 1981 159 164
27. R.M. Epand, R.F. Epand, N. Ahmed, and R. Chen Promotion of hexagonal phase formation and lipid mixing by fatty acids with varying degrees of unsaturation Chem. Phys. Lipids 57 1991 75 80
28. E.A. Lapshina, I.B. Zavodnik, and M. Bryszewska Effect of free fatty acids on the structure and properties of erythrocyte membrane Scand. J. Clin. Lab. Invest. 55 1995 391 397
29. Y. Onuki, M. Morishita, Y. Chiba, S. Tokiwa, and K. Takayama Docosahexaenoic acid and eicosapentaenoic acid induce changes in the physical properties of a lipid bilayer model membrane Chem. Pharm. Bull. (Tokyo) 54 2006 68 71 (Pubitemid 43036752)
30. G. Lenaz Lipid fluidity and membrane protein dynamics Biosci. Rep. 7 1987 823 837 (Pubitemid 18073276)
31. I.B. Zavodnik, A. Zaborowski, A. Niekurzak, and M. Bryszewska Effect of free fatty acids on erythrocyte morphology and membrane fluidity Biochem. Mol. Biol. Int. 42 1997 123 133 (Pubitemid 28173821)
32. I.B. Zavodnik, E.A. Lapshina, D. Palecz, and M. Bryszewska The effects of palmitate on human erythrocyte membrane potential and osmotic stability Scand. J. Clin. Lab. Invest. 56 1996 401 407 (Pubitemid 26266005)
33. D.J. López, M. Egido-Gabas, I. López-Montero, J.V. Busto, J. Casas, M. Garnier, F. Monroy, B. Larijani, F.M. Goñi, and A. Alonso Accumulated bending energy elicits neutral sphingomyelinase activity in human red blood cells Biophys. J. 102 2012 2077 2085
34. S.S. Funari, F. Barceló, and P.V. Escribá 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 (Pubitemid 37279706)
35. J. Prades, S.S. Funari, P.V. Escribá, and F. Barceló Effects of unsaturated fatty acids and triacylglycerols on phosphatidylethanolamine membrane structure J. Lipid Res. 44 2003 1720 1727 (Pubitemid 37203342)
36. F. Barceló, J. Prades, S.S. Funari, J. Frau, R. Alemany, and P.V. Escribá The hypotensive drug 2-hydroxyoleic acid modifies the structural properties of model membranes Mol. Membr. Biol. 21 2004 261 268 (Pubitemid 39208301)
37. A. Cordomi, J. Prades, J. Frau, O. Vögler, S.S. Funari, J.J. Pérez, P.V. Escribá, and F. Barceló Interactions of fatty acids with phosphatidylethanolamine membranes: X-ray diffraction and molecular dynamics studies J. Lipid Res. 51 2010 1113 1124
38. R. Jenske, F. Lindstrom, G. Grobner, and W. Vetter Impact of free hydroxylated and methyl-branched fatty acids on the organization of lipid membranes Chem. Phys. Lipids 154 2008 26 32
39. N. Muranushi, N. Takagi, S. Muranishi, and H. Sezaki Effect of fatty acids and monoglycerides on permeability of lipid bilayer Chem. Phys. Lipids 28 1981 269 279
40. D. Marsh, A. Watts, and P.F. Knowles Evidence for phase boundary lipid. Permeability of tempo-choline into dimyristoylphosphatidylcholine vesicles at the phase transition Biochemistry 15 1976 3570 3578
41. M. Langner, and S. Hui Effect of free fatty acids on the permeability of 1,2-dimyristoyl-sn-glycero-3-phosphocholine bilayer at the main phase transition Biochim. Biophys. Acta 1463 2000 439 447 (Pubitemid 30081801)
42. W. Ehringer, D. Belcher, S.R. Wassall, and W. Stillwell A comparison of the effects of linolenic (18:3 omega 3) and docosahexaenoic (22:6 omega 3) acids on phospholipid bilayers Chem. Phys. Lipids 54 1990 79 88 (Pubitemid 20169121)
43. W. Stillwell, W. Ehringer, and L.J. Jenski Docosahexaenoic acid increases permeability of lipid vesicles and tumor cells Lipids 28 1993 103 108 (Pubitemid 23066768)
44. O.G. Mouritsen Lipids, curvature, and nano-medicine Eur. J. Lipid Sci. Technol. 113 2011 1174 1187
45. J.A. Lucy The fusion of biological membranes Nature 227 1970 815 817
46. Q.F. Ahkong, D. Fisher, W. Tampion, and J.A. Lucy The fusion of erythrocytes by fatty acids, esters, retinol and alpha-tocopherol Biochem. J. 136 1973 147 155
47. S. Massari, P. Arslan, A. Nicolussi, and R. Colonna Phospholipid exchange and size enlargement in sonicated vesicles induced by a 'critical' fatty acid concentration Biochim. Biophys. Acta 599 1980 118 126
48. C.E. Creutz cis-Unsaturated fatty acids induce the fusion of chromaffin granules aggregated by synexin J. Cell Biol. 91 1981 247 256 (Pubitemid 12252786)
49. E. Connell, F. Darios, K. Broersen, N. Gatsby, S.Y. Peak-Chew, C. Rickman, and B. Davletov Mechanism of arachidonic acid action on syntaxin-Munc18 EMBO Rep. 8 2007 414 419 (Pubitemid 46511044)
50. C. Rickman, and B. Davletov Arachidonic acid allows SNARE complex formation in the presence of Munc18 Chem. Biol. 12 2005 545 553 (Pubitemid 40727929)
51. F. Darios, and B. Davletov Omega - 3 and omega - 6 fatty acids stimulate cell membrane expansion by acting on syntaxin 3 Nature 440 2006 813 817
52. V.T. Armstrong, M.R. Brzustowicz, S.R. Wassall, L.J. Jenski, and W. Stillwell Rapid flip-flop in polyunsaturated (docosahexaenoate) phospholipid membranes Arch. Biochem. Biophys. 414 2003 74 82 (Pubitemid 36555447)
53. W. Stillwell, and S.R. Wassall Docosahexaenoic acid: membrane properties of a unique fatty acid Chem. Phys. Lipids 126 2003 1 27 (Pubitemid 37297962)
54. W. Stillwell, L.J. Jenski, M. Zerouga, and A.C. Dumaual Detection of lipid domains in docasahexaenoic acid-rich bilayers by acyl chain-specific FRET probes Chem. Phys. Lipids 104 2000 113 132 (Pubitemid 30009874)
55. W. Stillwell, S.R. Shaikh, M. Zerouga, R. Siddiqui, and S.R. Wassall Docosahexaenoic acid affects cell signaling by altering lipid rafts Reprod. Nutr. Dev. 45 2005 559 579 (Pubitemid 41511882)
56. W. Helfrich Elastic properties of lipid bilayers: theory and possible experiments Z. Naturforsch. C 28 1973 693 703
57. M. Edidin The state of lipid rafts: from model membranes to cells Annu. Rev. Biophys. Biomol. Struct. 32 2003 257 283 (Pubitemid 37056230)
58. M. Edidin Lipid microdomains in cell surface membranes Curr. Opin. Struct. Biol. 7 1997 528 532 (Pubitemid 27371298)
59. K. Simons, and E. Ikonen Functional rafts in cell membranes Nature 387 1997 569 572 (Pubitemid 27248754)
60. D.A. Brown, and E. London Structure and function of sphingolipid- and cholesterol-rich membrane rafts J. Biol. Chem. 275 2000 17221 17224 (Pubitemid 30430750)
61. D. Lichtenberg, F.M. Goñi, and H. Heerklotz Detergent-resistant membranes should not be identified with membrane rafts Trends Biochem. Sci. 30 2005 430 436 (Pubitemid 41033238)
62. M.B. Shah, and P.B. Sehgal Nondetergent isolation of rafts Methods Mol. Biol. 398 2007 21 28
63. S.C. Kuo, and M.P. Sheetz Optical tweezers in cell biology Trends Cell Biol. 2 1992 116 118
64. M.J. Saxton, and K. Jacobson Single-particle tracking: applications to membrane dynamics Annu. Rev. Biophys. Biomol. Struct. 26 1997 373 399 (Pubitemid 27255378)
65. G.J. Schutz, G. Kada, V.P. Pastushenko, and H. Schindler Properties of lipid microdomains in a muscle cell membrane visualized by single molecule microscopy EMBO J. 19 2000 892 901 (Pubitemid 30119815)
66. A. Kusumi, H. Ike, C. Nakada, K. Murase, and T. Fujiwara Single-molecule tracking of membrane molecules: plasma membrane compartmentalization and dynamic assembly of raft-philic signaling molecules Semin. Immunol. 17 2005 3 21 (Pubitemid 39575978)
67. M.J. Karnovsky Lipid domains in biological membranes: their structural and functional perturbation by free fatty acids and the regulation of receptor mobility. Co-presidential address Am. J. Pathol. 97 1979 212 221
68. R.D. Klausner, D.K. Bhalla, P. Dragsten, R.L. Hoover, and M.J. Karnovsky Model for capping derived from inhibition of surface receptor capping by free fatty acids Proc. Natl. Acad. Sci. U. S. A. 77 1980 437 441
69. D.E. MacIntyre, R.L. Hoover, M. Smith, M. Steer, C. Lynch, M.J. Karnovsky, and E.W. Salzman Inhibition of platelet function by cis-unsaturated fatty acids Blood 63 1984 848 857 (Pubitemid 14141306)
70. W.D. Sweet, and F. Schroeder Polyunsaturated fatty acids alter sterol transbilayer domains in LM fibroblast plasma membrane FEBS Lett. 229 1988 188 192 (Pubitemid 18058764)
71. F. Schroeder, J.R. Jefferson, A.B. Kier, J. Knittel, T.J. Scallen, W.G. Wood, and I. Hapala Membrane cholesterol dynamics: cholesterol domains and kinetic pools Proc. Soc. Exp. Biol. Med. 196 1991 235 252
72. E. Dusserre, T. Pulcini, M.C. Bourdillon, M. Ciavatti, and F. Berthezene Omega - 3 fatty acids in smooth muscle cell phospholipids increase membrane cholesterol efflux Lipids 30 1995 35 41
73. W. Stillwell The role of polyunsaturated lipids in membrane raft function Scand. J. Food Nutr. 50 S2 2006 107 113 (Pubitemid 46018387)
74. H. Ahyayauch, M. Raab, J.V. Busto, N. Andraka, J.L. Arrondo, M. Masserini, I. Tvaroska, and F.M. Goñi Binding of beta-amyloid (1-42) peptide to negatively charged phospholipid membranes in the liquid-ordered state: modeling and experimental studies Biophys. J. 103 2012 453 463
75. T. Kawarabayashi, M. Shoji, L.H. Younkin, L. Wen-Lang, D.W. Dickson, T. Murakami, E. Matsubara, K. Abe, K.H. Ashe, and S.G. Younkin Dimeric amyloid beta protein rapidly accumulates in lipid rafts followed by apolipoprotein E and phosphorylated tau accumulation in the Tg2576 mouse model of Alzheimer's disease J. Neurosci. 24 2004 3801 3809 (Pubitemid 38509410)
76. A.H. van der Luit, M. Budde, P. Ruurs, M. Verheij, and W.J. van Blitterswijk Alkyl-lysophospholipid accumulates in lipid rafts and induces apoptosis via raft-dependent endocytosis and inhibition of phosphatidylcholine synthesis J. Biol. Chem. 277 2002 39541 39547 (Pubitemid 35190932)
77. B.M. Castro, A. Fedorov, V. Hornillos, J. Delgado, A.U. Acuna, F. Mollinedo, and M. Prieto Edelfosine and miltefosine effects on lipid raft properties: membrane biophysics in cell death by antitumor lipids J. Phys. Chem. B 117 2013 7929 7940
78. A.B. Awad, C.S. Fink, and P.J. Horvath Alteration of membrane fatty acid composition and inositol phosphate metabolism in HT-29 human colon cancer cells Nutr. Cancer 19 1993 181 190 (Pubitemid 23131435)
79. S. Jayadev, C.M. Linardic, and Y.A. Hannun Identification of arachidonic acid as a mediator of sphingomyelin hydrolysis in response to tumor necrosis factor alpha J. Biol. Chem. 269 1994 5757 5763 (Pubitemid 24242948)
80. T.A. Chan, P.J. Morin, B. Vogelstein, and K.W. Kinzler Mechanisms underlying nonsteroidal antiinflammatory drug-mediated apoptosis Proc. Natl. Acad. Sci. U. S. A. 95 1998 681 686 (Pubitemid 28083803)
81. A. Mullen, C.E. Loscher, and H.M. Roche Anti-inflammatory effects of EPA and DHA are dependent upon time and dose-response elements associated with LPS stimulation in THP-1-derived macrophages J. Nutr. Biochem. 21 2010 444 450
82. J.M. Huang, H. Xian, and M. Bacaner Long-chain fatty acids activate calcium channels in ventricular myocytes Proc. Natl. Acad. Sci. U. S. A. 89 1992 6452 6456
83. Y. Katsuta, T. Iida, S. Inomata, and M. Denda Unsaturated fatty acids induce calcium influx into keratinocytes and cause abnormal differentiation of epidermis J. Invest. Dermatol. 124 2005 1008 1013 (Pubitemid 40629103)
84. A. El-Yassimi, A. Hichami, P. Besnard, and N.A. Khan Linoleic acid induces calcium signaling, Src kinase phosphorylation, and neurotransmitter release in mouse CD36-positive gustatory cells J. Biol. Chem. 283 2008 12949 12959
85. M. Musashi, S. Ota, and N. Shiroshita The role of protein kinase C isoforms in cell proliferation and apoptosis Int. J. Hematol. 72 2000 12 19
86. A.B. Awad, A.L. Young, and C.S. Fink The effect of unsaturated fatty acids on membrane composition and signal transduction in HT-29 human colon cancer cells Cancer Lett. 108 1996 25 33 (Pubitemid 26393556)
87. P.V. Escribá, M. Sastre, and J.A. García-Sevilla Disruption of cellular signaling pathways by daunomycin through destabilization of nonlamellar membrane structures Proc. Natl. Acad. Sci. U. S. A. 92 1995 7595 7599
88. Q. Yang, R. Alemany, J. Casas, K. Kitajka, S.M. Lanier, and P.V. Escribá Influence of the membrane lipid structure on signal processing via G protein-coupled receptors Mol. Pharmacol. 68 2005 210 217 (Pubitemid 41002960)
89. M. Asano, K. Masuzawa, T. Matsuda, and T. Asano Reduced function of the stimulatory GTP-binding protein in beta adrenoceptor-adenylate cyclase system of femoral arteries isolated from spontaneously hypertensive rats J. Pharmacol. Exp. Ther. 246 1988 709 718
90. R. Alemany, S. Terés, C. Baamonde, M. Benet, O. Vögler, and P.V. Escribá 2-hydroxyoleic acid: a new hypotensive molecule Hypertension 43 2004 249 254 (Pubitemid 38174183)
91. R. Alemany, O. Vögler, S. Terés, C. Egea, C. Baamonde, F. Barceló, C. Delgado, K.H. Jakobs, and P.V. Escribá 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 (Pubitemid 44222827)
92. J. Martínez, O. Vögler, J. Casas, F. Barceló, R. Alemany, J. Prades, T. Nagy, C. Baamonde, P.G. Kasprzyk, S. Terés, C. Saus, and P.V. Escribá Membrane structure modulation, protein kinase C alpha activation, and anticancer activity of Minerval Mol. Pharmacol. 67 2005 531 540 (Pubitemid 40216746)
93. V. Lladó, A. Gutiérrez, J. Martínez, J. Casas, S. Terés, M. Higuera, A. Galmes, C. Saus, J. Besalduch, X. Busquets, and P.V. Escribá Minerval induces apoptosis in Jurkat and other cancer cells J. Cell. Mol. Med. 14 2010 659 670
94. V. Lladó, S. Terés, M. Higuera, R. Álvarez, M.A. Noguera-Salva, J.E. Halver, P.V. Escribá, and X. Busquets Pivotal role of dihydrofolate reductase knockdown in the anticancer activity of 2-hydroxyoleic acid Proc. Natl. Acad. Sci. U. S. A. 106 2009 13754 13758
95. J. Martínez, A. Gutiérrez, J. Casas, V. Llado, A. Lopéz-Bellan, J. Besalduch, A. Dopazo, and P.V. Escribá The repression of E2F-1 is critical for the activity of Minerval against cancer J. Pharmacol. Exp. Ther. 315 2005 466 474 (Pubitemid 41380543)
96. S. Terés, V. Lladó, M. Higuera, G. Barceló-Coblijn, M.L. Martin, M.A. Noguera-Salva, A. Marcilla-Etxenike, J.M. García- Verdugo, M. Soriano-Navarro, C. Saus, U. Gómez-Pinedo, X. Busquets, and P.V. Escribá 2-Hydroxyoleate, a nontoxic membrane binding anticancer drug, induces glioma cell differentiation and autophagy Proc. Natl. Acad. Sci. 109 2012 8489 8494
97. M.L. Martin, G. Liebisch, S. Lehneis, G. Schmitz, M. Alonso-Sande, J. Bestard-Escalas, D.H. López, J.M. García-Verdugo, M. Soriano-Navarro, X. Busquets, P.V. Escribá, and G. Barceló-Coblijn Sustained activation of sphingomyelin synthase by 2-hydroxyoleic acid induces sphingolipidosis in tumor cells J. Lipid Res. 54 2013 1457 1465
98. G. Barceló-Coblijn, M.L. Martin, R.F. de Almeida, M.A. Noguera-Salva, A. Marcilla-Etxenike, F. Guardiola-Serrano, A. Luth, B. Kleuser, J.E. Halver, and P.V. Escribá Sphingomyelin and sphingomyelin synthase (SMS) in the malignant transformation of glioma cells and in 2-hydroxyoleic acid therapy Proc. Natl. Acad. Sci. 108 2011 19569 19574
99. M. Soderberg, C. Edlund, K. Kristensson, and G. Dallner Fatty acid composition of brain phospholipids in aging and in Alzheimer's disease Lipids 26 1991 421 425
100. W.J. Lukiw, J.G. Cui, V.L. Marcheselli, M. Bodker, A. Botkjaer, K. Gotlinger, C.N. Serhan, and N.G. Bazan A role for docosahexaenoic acid-derived neuroprotectin D1 in neural cell survival and Alzheimer disease J. Clin. Invest. 115 2005 2774 2783 (Pubitemid 41434404)
101. M. Akbar, F. Calderon, Z. Wen, and H.Y. Kim Docosahexaenoic acid: a positive modulator of Akt signaling in neuronal survival Proc. Natl. Acad. Sci. U. S. A. 102 2005 10858 10863 (Pubitemid 41105957)
102. C.M. Borghese, R.A. Gomez, and O.A. Ramirez Phosphatidylserine increases hippocampal synaptic efficacy Brain Res. Bull. 31 1993 697 700 (Pubitemid 23137789)
103. K.S. Panickar, and S.J. Bhathena Control of fatty acid intake and the role of essential fatty acids in cognitive function and neurological disorders J.P. Montmayeur, J. le Coutre, Fat Detection: Taste, Texture, and Post Ingestive Effects 2010 CRC Press Boca Raton (FL)
104. H. Sprecher Metabolism of highly unsaturated n - 3 and n - 6 fatty acids Biochim. Biophys. Acta 1486 2000 219 231 (Pubitemid 30618862)
105. S.J. Carlson, E.M. Fallon, B.T. Kalish, K.M. Gura, and M. Puder The role of the omega - 3 fatty acid DHA in the human life cycle JPEN J. Parenter. Enteral Nutr. 37 2013 15 22
106. C. Agostoni Role of long-chain polyunsaturated fatty acids in the first year of life J. Pediatr. Gastroenterol. Nutr. 47 Suppl. 2 2008 S41 S44
107. D. Estadella, C.M. da Penha Oller do Nascimento, L.M. Oyama, E.B. Ribeiro, A.R. Damaso, and A. de Piano Lipotoxicity: effects of dietary saturated and transfatty acids Mediat. Inflamm. 2013 2013 137579
108. P.C. Calder Long chain fatty acids and gene expression in inflammation and immunity Curr. Opin. Clin. Nutr. Metab. Care 16 2013 425 433
109. G. Siegel, and E. Ermilov Omega - 3 fatty acids: benefits for cardio-cerebro-vascular diseases Atherosclerosis 225 2012 291 295
110. D.F. Horrobin Low prevalences of coronary heart disease (CHD), psoriasis, asthma and rheumatoid arthritis in Eskimos: are they caused by high dietary intake of eicosapentaenoic acid (EPA), a genetic variation of essential fatty acid (EFA) metabolism or a combination of both? Med. Hypotheses 22 1987 421 428 (Pubitemid 17140104)
111. J.N. Kiage, P.D. Merrill, C.J. Robinson, Y. Cao, T.A. Malik, B.C. Hundley, P. Lao, S.E. Judd, M. Cushman, V.J. Howard, and E.K. Kabagambe Intake of trans fat and all-cause mortality in the Reasons for Geographical and Racial Differences in Stroke (REGARDS) cohort Am. J. Clin. Nutr. 97 2013 1121 1128
112. M. Ochiai, K. Fujii, H. Takeuchi, and T. Matsuo Effects of dietary trans fatty acids on fat accumulation and metabolic rate in rat J. Oleo Sci. 62 2013 57 64
113. G.M. Hinnouho, S. Czernichow, A. Dugravot, G.D. Batty, M. Kivimaki, and A. Singh-Manoux Metabolically healthy obesity and risk of mortality: does the definition of metabolic health matter? Diabetes Care 36 2013 2294 2300
114. E. Granstrom The arachidonic acid cascade. The prostaglandins, thromboxanes and leukotrienes Inflammation 8 Suppl. 1984 S15 S25
115. A.P. Simopoulos The importance of the omega - 6/omega - 3 fatty acid ratio in cardiovascular disease and other chronic diseases Exp. Biol. Med. (Maywood) 233 2008 674 688
116. A.P. Simopoulos Evolutionary aspects of diet, the omega - 6/omega - 3 ratio and genetic variation: nutritional implications for chronic diseases Biomed. Pharmacother. 60 2006 502 507
117. A. Ambring, M. Johansson, M. Axelsen, L. Gan, B. Strandvik, and P. Friberg Mediterranean-inspired diet lowers the ratio of serum phospholipid n - 6 to n - 3 fatty acids, the number of leukocytes and platelets, and vascular endothelial growth factor in healthy subjects Am. J. Clin. Nutr. 83 2006 575 581 (Pubitemid 44699202)
118. C. Samieri, F. Grodstein, B.A. Rosner, J.H. Kang, N.R. Cook, J.E. Manson, J.E. Buring, W.C. Willett, and O.I. Okereke Mediterranean diet and cognitive function in older age Epidemiol. 24 2013 490 499
119. P.V. Escribá, J.M. Sánchez-Domínguez, R. Alemany, J.S. Perona, and V. Ruíz-Gutiérrez Alteration of lipids, G proteins, and PKC in cell membranes of elderly hypertensives Hypertension 41 2003 176 182 (Pubitemid 36056811)
120. C. Carrillo, M. Cavia Mdel, and S.R. Alonso-Torre Antitumor effect of oleic acid; mechanisms of action: a review Nutr. Hosp. 27 2012 1860 1865
121. C.R. Brinkmann, S. Thiel, and D.E. Otzen Protein-fatty acid complexes: biochemistry, biophysics and function FEBS J. 280 2013 1733 1749
122. C.R. Brinkmann, S. Thiel, M.K. Larsen, T.E. Petersen, J.C. Jensenius, and C.W. Heegaard Preparation and comparison of cytotoxic complexes formed between oleic acid and either bovine or human alpha-lactalbumin J. Dairy Sci. 94 2011 2159 2170
123. W. Fischer, L. Gustafsson, A.K. Mossberg, J. Gronli, S. Mork, R. Bjerkvig, and C. Svanborg Human alpha-lactalbumin made lethal to tumor cells (HAMLET) kills human glioblastoma cells in brain xenografts by an apoptosis-like mechanism and prolongs survival Cancer Res. 64 2004 2105 2112 (Pubitemid 38339460)
124. A.K. Mossberg, M. Puchades, O. Halskau, A. Baumann, I. Lanekoff, Y. Chao, A. Martinez, C. Svanborg, and R. Karlsson HAMLET interacts with lipid membranes and perturbs their structure and integrity PLoS One 5 2010 e9384
125. K.H. Weylandt, C.Y. Chiu, B. Gomolka, S.F. Waechter, and B. Wiedenmann Omega - 3 fatty acids and their lipid mediators: towards an understanding of resolvin and protectin formation Prostaglandins Other Lipid Mediat. 97 2012 73 82
126. B. Gomolka, E. Siegert, K. Blossey, W.H. Schunck, M. Rothe, and K.H. Weylandt Analysis of omega - 3 and omega - 6 fatty acid-derived lipid metabolite formation in human and mouse blood samples Prostaglandins Other Lipid Mediat. 94 2011 81 87
127. J.X. Kang, J. Wang, L. Wu, and Z.B. Kang Transgenic mice: fat-1 mice convert n - 6 to n - 3 fatty acids Nature 427 2004 504 (Pubitemid 38209102)
128. D.T. Stark, and N.G. Bazan Neuroprotectin D1 induces neuronal survival and downregulation of amyloidogenic processing in Alzheimer's disease cellular models Mol. Neurobiol. 43 2011 131 138
129. C.N. Serhan, S. Hong, K. Gronert, S.P. Colgan, P.R. Devchand, G. Mirick, and R.L. Moussignac Resolvins: a family of bioactive products of omega - 3 fatty acid transformation circuits initiated by aspirin treatment that counter proinflammation signals J. Exp. Med. 196 2002 1025 1037 (Pubitemid 35231761)
130. J.S. Duffield, S. Hong, V.S. Vaidya, Y. Lu, G. Fredman, C.N. Serhan, and J.V. Bonventre Resolvin D series and protectin D1 mitigate acute kidney injury J. Immunol. 177 2006 5902 5911 (Pubitemid 44628803)
131. A.F. Bento, R.F. Claudino, R.C. Dutra, R. Marcon, and J.B. Calixto Omega - 3 fatty acid-derived mediators 17(R)-hydroxy docosahexaenoic acid, aspirin-triggered resolvin D1 and resolvin D2 prevent experimental colitis in mice J. Immunol. 187 2011 1957 1969
132. B.D. Levy Resolvin D1 and resolvin E1 promote the resolution of allergic airway inflammation via shared and distinct molecular counter-regulatory pathways Front. Immunol. 3 2012 390
133. P. Sapieha, A. Stahl, J. Chen, M.R. Seaward, K.L. Willett, N.M. Krah, R.J. Dennison, K.M. Connor, C.M. Aderman, E. Liclican, A. Carughi, D. Perelman, Y. Kanaoka, J.P. Sangiovanni, K. Gronert, and L.E. Smith 5-Lipoxygenase metabolite 4-HDHA is a mediator of the antiangiogenic effect of omega-3 polyunsaturated fatty acids Sci. Transl. Med. 3 2011 69ra12
134. E.K. Long, T.C. Murphy, L.J. Leiphon, J. Watt, J.D. Morrow, G.L. Milne, J.R. Howard, and M.J. Picklo Sr. Trans-4-hydroxy-2-hexenal is a neurotoxic product of docosahexaenoic (22:6; n - 3) acid oxidation J. Neurochem. 105 2008 714 724 (Pubitemid 351562721)
135. S. Banni Conjugated linoleic acid metabolism Curr. Opin. Lipidol. 13 2002 261 266 (Pubitemid 34592282)
136. G.S. Kelly Conjugated linoleic acid: a review Altern. Med. Rev. 6 2001 367 382 (Pubitemid 32826184)
137. J. Oleszczuk, L. Oleszczuk, A.K. Siwicki, and E. Skopinska-Skopinska Biological effects of conjugated linoleic acids supplementation Pol. J. Vet. Sci. 15 2012 403 408
138. T. Tanaka, M. Hosokawa, Y. Yasui, R. Ishigamori, and K. Miyashita Cancer chemopreventive ability of conjugated linolenic acids Int. J. Mol. Sci. 12 2011 7495 7509
139. B.F. Cravatt, O. Prospero-Garcia, G. Siuzdak, N.B. Gilula, S.J. Henriksen, D.L. Boger, and R.A. Lerner Chemical characterization of a family of brain lipids that induce sleep Science 268 1995 1506 1509
140. J.P. Huidobro-Toro, and R.A. Harris Brain lipids that induce sleep are novel modulators of 5-hydroxytrypamine receptors Proc. Natl. Acad. Sci. 93 1996 8078 8082
141. C.R. Roe, L. Sweetman, D.S. Roe, F. David, and H. Brunengraber Treatment of cardiomyopathy and rhabdomyolysis in long-chain fat oxidation disorders using an anaplerotic odd-chain triglyceride J. Clin. Invest. 110 2002 259 269 (Pubitemid 34787363)
142. O. Vögler, A. López-Bellán, R. Alemany, S. Tofe, M. González, J. Quevedo, V. Pereg, F. Barceló, and P.V. Escribá Structure-effect relation of C18 long-chain fatty acids in the reduction of body weight in rats Int. J. Obes. (Lond) 32 2008 464 473 (Pubitemid 351414826)
143. I. Fedorova, A. Hashimoto, R.A. Fecik, M.P. Hedrick, L.O. Hanus, D.L. Boger, K.C. Rice, and A.S. Basile Behavioral evidence for the interaction of oleamide with multiple neurotransmitter systems J. Pharmacol. Exp. Ther. 299 2001 332 342 (Pubitemid 32905151)
144. C.R. Roe, T. Bottiglieri, M. Wallace, E. Arning, and A. Martin Adult Polyglucosan Body Disease (APBD): anaplerotic diet therapy (triheptanoin) and demonstration of defective methylation pathways Mol. Genet. Metab. 101 2010 246 252
145. K. Borges, and U. Sonnewald Triheptanoin - a medium chain triglyceride with odd chain fatty acids: a new anaplerotic anticonvulsant treatment? Epilepsy Res. 100 2012 239 244
146. Y. Kuramitsu, Y. Ohiro, K. Matsushita, M. Obara, M. Kobayashi, and M. Hosokawa The mechanism of locally enhanced production of tumor necrosis factor-alpha in tumor tissues by the administration of a new synthetic lipid A analog, ONO-4007, in hepatoma-bearing rats Anticancer Drugs 8 1997 886 893 (Pubitemid 27487803)
147. V. Foulon, M. Sniekers, E. Huysmans, S. Asselberghs, V. Mahieu, G.P. Mannaerts, P.P. Van Veldhoven, and M. Casteels Breakdown of 2-hydroxylated straight chain fatty acids via peroxisomal 2-hydroxyphytanoyl-CoA lyase: a revised pathway for the alpha-oxidation of straight chain fatty acids J. Biol. Chem. 280 2005 9802 9812 (Pubitemid 40395826)
148. F. Gelin, I. Boogers, A.A.M. Noordeloos, J.S. Sinninghe, R. Riegman, and J.W. de Leeuw Resistant biomacromolecules in marien microalgae of the classes Eustigmatophyceae and Chlorophyceae: geochemical implications Org. Geochem. 26 1997 659 675 (Pubitemid 28010284)
149. J.K. Volkman, R.B. Johns, F.T. Gillan, and G.J. Perry Microbial lipids of an intertidal sediment. Fatty acids and hydrocarbons Geochim. Cosmochim. Acta 44 1980 1133 1143
150. C.R. Smith Jr., and I.A. Wolff Characterization of naturally occurring alpha-hydroxylinolenic acid Lipids 4 1969 9 14
151. M.B. Bohannon, and R. Kleiman Unsaturated C18 α-hydroxy acids in Salvia nilotica Lipids 10 1975 703 706
152. P.V. Escribá (2010). Use of hydroxyoleic acid and related compounds in the manufacture of drugs. USA. US 7851507B2 Dec 14, 2010. Patent.
153. J. Prades, R. Alemany, J.S. Perona, S.S. Funari, O. Vögler, V. Ruíz-Gutiérrez, P.V. Escribá, and F. Barceló Effects of 2-hydroxyoleic acid on the structural properties of biological and model plasma membranes Mol. Membr. Biol. 25 2008 46 57
154. A phase I/IIA study of Minerval in adult patients with advanced solid tumours vol. 2013 2013
155. D.H. López, M.A. Fiol-deRoque, M.A. Noguera-Salva, S. Terés, F. Campana, S. Piotto, J.A. Castro, R.J. Mohaibes, P.V. Escribá, and X. Busquets 2-Hydroxy arachidonic acid: a new non-steroidal anti-inflammatory drug PLoS One 8 2013 e72052
156. M.A. Fiol-Deroque, R. Gutiérrez-Lanza, S. Terés, M. Torres, P. Barceló, R.V. Rial, A. Verkhratsky, P.V. Escribá, X. Busquets, and J.J. Rodríguez Cognitive recovery and restoration of cell proliferation in the dentate gyrus in the 5XFAD transgenic mice model of Alzheimer's disease following 2-hydroxy-DHA treatment Biogerontology 14 2013 763 775
157. M. Torres, S.L. Price, M.A. Fiol-deRoque, A. Marcilla-Etxenike, H. Ahyayauch, G. Barceló-Coblijn, S. Terés, L. Katsouri, M. Ordinas, D.J. López, M. Ibarguren, F.M. Goñi, X. Busquets, J. Vitorica, M. Sastre, and P.V. Escribá Membrane lipid modifications and therapeutic effects mediated by hydroxydocosahexaenoic acid on Alzheimer's disease Biochim. Biophys. Acta 1838 2014 1680 1692 (in this issue)
158. P.V. Escribá Membrane-lipid therapy: a new approach in molecular medicine Trends Mol. Med. 12 2006 34 43 (Pubitemid 43089654)