Dietary manipulation of precursor polyunsaturated fatty acids modulates eicosanoid and endocannabinoid synthesis: A potential tool to control tumor development

Current Nutrition and Food Science

Volumn 4, Issue 3, 2008, Pages 161-175

  Pasqualini, M E ^a   Berra, M A ^a   Yurawecz, M P ^b   Repossi, G ^a,c   Eynard, A R ^a,c  

^a FACULTAD DE CIENCIAS MÉDICAS   (Argentina)

^b CENTER FOR DRUG EVALUATION AND RESEARCH   (United States)

^c CONICET ^*  (Argentina)

Author keywords

Arachidonic acid; Cancer; Cyclooxygenases; Diet; Eicosanoids; Endocannabinoids; Lipoxygenases; PUFAs

Indexed keywords

12 HYDROXYICOSATETRAENOIC ACID; 15 HYDROXYICOSATETRAENOIC ACID; ARACHIDONATE LIPOXYGENASE; ARACHIDONIC ACID; ARACHIDONIC ACID DERIVATIVE; CONJUGATED LINOLEIC ACID; CORIOLIC ACID; CYTOCHROME P450; ENDOCANNABINOID; ICOSANOID; OMEGA 3 FATTY ACID; OMEGA 6 FATTY ACID; PHOSPHOLIPID DERIVATIVE; POLYUNSATURATED FATTY ACID; PROSTAGLANDIN DERIVATIVE; PROSTAGLANDIN SYNTHASE;

CANCER CONTROL; CARCINOGENESIS; CORRELATION ANALYSIS; DIET SUPPLEMENTATION; DIETARY INTAKE; FAT INTAKE; FATTY ACID METABOLISM; FATTY ACID SYNTHESIS; HUMAN; NEOPLASM; NUTRITIONAL ASSESSMENT; PRIORITY JOURNAL; REVIEW;

EID: 55249115079     PISSN: 15734013     EISSN: None     Source Type: Journal    
DOI: 10.2174/157340108785133356     Document Type: Review

References (146)

1. Potter JD. World Cancer Research Fund/American Institute for Cancer Research, USA Eds. Food, Nutrition and the Prevention of Cancer: a global perspective 1997; 13-17.
2. World Cancer Research Fund (WCRF)/American Institute for Cancer Research (AICR) Food, Nutrition, Physical Activity, and the Prevention of Cancer: A Global Perspective. AICR: Washington, DC, 2007.
3. Navarro A, Osella AR, Muñoz SE, Lantieri MJ, Fabro EA, Eynard AR. Fatty acids, fibres and colorectal cancer risk in Córdoba, Argentina. J Epid Biomol Biostat 1998; 3: 415-422.
4. Eynard AR. Role of dietary polyunsaturated fatty acids (PUFA) on tumorigenesis. Cancer J 1996; 9: 142-144.
5. Eynard AR. Is the risk of urinary tract tumorigenesis enhanced by a marginal chronic essential fatty acid deficiency (EFAD). Nutrition 1998; 14: 211-216.
6. Eynard AR. Potential of essential fatty acids as natural Therapeutic products for human tumors. Nutrition 2003; 4: 386-388.
7. Sinclair HM. In: Horrobin DF, Ed, And History of essential fatty acids. In Omega-6 Essential Fatty acids: Pathophysiology and roles in Clinical Medicine.: Alan R Liss, Inc. 1990; 1-20.
8. Simopoulous AP. Evolutionary aspects of diet, the omega-6/omega-3 ratio and genetic variation: nutritional implications for chronic diseases. Biomed Pharmacother 2006; 60: 502-507.
9. Connolly JM, Gilhooly EM, Rose DP. Effects of reduced dietary linoleic acid intake, alone or combined with an Algal Source of Docosahexaenoic acid, on MDA-MB-231 Breast cancer cell Growth and apoptosis in need mice. Nutrit Cancer 1999; 35: 44-49.
10. Comba A, Maestri DM, Berra MA, Labuckas D, Eynard AR, Pasqualini ME. Lipids modulate cell eicosanoids release, apoptosis and proliferation in a murine breast carcinoma. Biocell (Suppl) 2007; 31: 87.
11. Muñoz SE, Navarro A, Lantieri MJ, et al. Alcohol, methyl xanthine-containing beverages and colorrectal cancer in Córdoba, Argentina. Eur J Cancer Prev 1988; 7: 207-213.
12. Mattson MP. Energy intake, meal frequency, and health: a neurobiological perspective. Anuu Rev Nutr 2005; 25: 237-60.
13. Duffy PH, Lewis SM, Mayhug MA, et al. The effects of different levels of dietary restriction on neoplastic pathology in the male Sprague-Dawley rat. Aging Clin Exp Res 2005; 16: 448-56.
14. Navarro A, Muñoz SE, Lantieri MJ, et al. Meat Cooking Habits and Risk of colorectal cancer in Córdoba, Argentina. Nutrition 2004; 20: 873-877.
15. Das UN. Can essential fatty acids reduce the burden of disease(s)? Lipids Health Dis 2008; 7: 9-27.
16. Dailey A, Imming P. 12-Lipoxigenase: Classification, possible therapeutic benefits from inhibition, and inhibitors. Curr Med Chem 1999; 6: 389-398.
17. Longtin R. Far tissue organization theory of cancer, a difficult road to acceptance. J Natl Cancer Inst 2005; 97: 11-12.
18. Larsson SC, Kumlin M, Ingelman-Sunderg M, Wolk A. Dietary long-chain n-3 fatty acids for prevention of cancer: a review of potential mechanisms. Am J Clin Nutr 2004; 79: 935-945.
19. Sprecher H, Luthria DL, Mohammed BS, Baykousheva SP. Reevaluation of the pathways for the biosynthesis of polyunsaturated fatty acids. J Lipid Res 1995; 36: 20471-2477.
20. Horrobin DF, Manku MS. In: Horrobin DF. Ed Clinical biochemistry of essential fatty acids. Omega-6 Essential Fatty acids: Pathophysiology and roles in Clinical Medicine Alan R. Liss, Inc. 1990; 21-53.
21. Risé P, Marangoni F, Galli C. Regulation of PUFA metabolism: pharmacological and toxicological aspects. Prost Leuk Essent Fatty Acids 2002; 67: 85-89.
22. Di Marzo V. Endocannabinoids in the new millennium. Prost Leuk Essent Fatty Acids 2002; 66: 91-92.
23. Lynch DL, Reggio PH. Molecular dynamics simulations of the endocannabinoid N-arachidonoylethanolamine (anandamide) in a phospholipid bilayer: probing structure and dynamics. J Med Chem 2005; 48: 4824-4833.
24. De Marchi N, De Petrocellis L, Orlando P, Daniele F, Fezza F, Di Marzo V. Endocannabinoid signalling in the blood of patients with schizophrenia. Lipids Health Dis 2003; 2: 1-9.
25. Jiang W, Zhang Y, Xiao L, et al. Cannabinoids promote embryonic and adult hippocampus neurogenesis and produce anxiolytic- and antidepressant-like effects. J Clin Invest 2005; 115: 3104-16.
26. Arenos JD, Musty RE, Bucci DJ. Blockade of cannabinoid CB1 receptors alters contextual learning and memory. Eur J Pharmacol 2006; 539: 177-83.
27. Kirkham TC, Tucci SA. Endocannabinoidz in appetite control and the treatment of obesity. CNS Neurol Disord Drug Targets 2006; 5: 272-92.
28. Laezza C, Pisanti S, Crescenzi E, Bifulco M. Anandamide inhibits Cdk2 and activates Chk1 leading to cell cycle arrest in human breast cancer cells. FEBS Lett 2006; 580: 6076-6082.
29. Good CH. Endocannabinoid-dependent regulation of feedforward inhibition in cerebellar Purkinje cells. J Neurosci 2007; 27: 1-3.
30. Stengel PW, Cockerham SL, Silbaugh SA. Inhaled anandamide reduces leukotriene D4-induced airway obstruction in guinea pigs. Eur J Pharmacol 2007; 557: 66-68.
31. Sun X, Dey SK. Aspects of endocannabinoid signaling in periimplantation biology. Mol Cell Endocrinol 2008; in Press.
32. Bab I, Zimmer A. Cannabinoid receptors and the regulation of bone mass. Br J Pharmacol 2008; 153:182-8.
33. Berger A, Crozier G, Bisogno T, Cavaliere P, Innis S, Di Marzo V. Anandamide and diet: Inclusion of dietary arachidonate and docosahexaenoate leads to increased brain levels of the corresponding. Proc Natl Acad Sci USA 2001; 98: 6402-6406.
34. Pertwee RG, Ross RA. Cannabinoid receptors and their ligands Prostaglandins Leukot Essent Fatty Acids 2002; 66: 101-121.
35. Burstein S. The elmiric acids: Biologically active anandamide analogs. Neuropharmacology 2008; in Press.
36. Muccioli GG, Nephi S. Microglia produce and hydrolyze, palmitoylethanolamide. Neuropharmacology 2008; 54: 16-22.
37. Okamoto Y, Morishita J, Tsuboi K, Tonai T, Ueda N. Molecular characterization of a phospholipase D generating anandamide and its congeners. J Biol Chem 2004; 279: 5298-5305.
38. Liu J, Wang L, Harvey-White J, et al. A biosyn-thetic pathway for anandamide. Proc Natl Acad Sci USA 2006; 103:13345-13350.
39. Leung D, Saghatelian A, Simon GM, Cravatt BF. Inactivation of N-acy1 phosphatidylethanolamine phospholipase D reveals multiple mechanisms for the biosynthesis of endocannabinoids. Biochemistry 2006; 45: 4720-4726.
40. Pazos MR, Nunez E, Benito C, Tolon RM, Romero J. Functional neuroanatomy of the endocannabinoid system. Pharmacol Biochem Behav 2005; 81:239-247.
41. Burstein S, Raz A. Inhibition of PGE, biosynthesis by A′-THC. Prostaglandins 1972; 2: 369-374.
42. Burstein S. In: Murphy L and Bartke A Eds, Eicosanoids as mediators of cannabinoid action. Marijuanal Cannabinoids CRC Press, Boca Raton FL 1992; 73-91.
43. Kozak KR, Marnett LJ. Oxidative metabolism of Endocannabinoids. Prostaglandins Leukot Essent Fatty Acids 2002; 66: 211-220
44. Yang H, Zhang J, Andreasson K, Chen C. COX-2 oxidative metabolism of endocannabinoids augments hippocampal synaptic plasticity. Mol Cell Neurosci 2008; 37: 682-695.
45. Needleman P, Turk J, Jakschik BA, Morrison AR, Lefkowith JB. Arachidonic acid metabolism. Ann Rev Biochem 1986; 55: 69-102.
46. Ara G, Teicher DA. Cyclooxygenase and lipoxygenase inhibitors in cancer therapy. Prost Leak Essent Fatty Acids 1996; 54: 3-16.
47. Yoshimoto A, Kasahara K, Kawashima A, Fujimura M, Nakao S. Characterization of the prostaglandin biosynthetic pathway in non-small cell lung cancer: a comparison with small cell lung cancer and correlation with angiogenesis, angiogenic factors and metastases. Oncol Rep 2005. 13: 1049-1057.
48. Funk CD. Prostaglandins and Leukotrienes: Advances in eicosanoid biology. Science 2001; 294: 1871-1875.
49. Tapiero H, Ba GN, Couvreur P, Tew KD. Polyunsaturated fatty acids (PUFA) and eicosanoids in human health and pathologies. Biomed Pharmacother 2002; 56: 215-222.
50. Xie W, Chipmman JG, Robertson DL, Erickson RL, Simmonds DL. Expression of a mitogen-responsive gene encoding prostaglandin synthase is regulated by mRNA Splicing. Proc Natl Acad Sci USA 1991; 88: 2692-2696.
51. Kubuju DA, Fletcher BS, Varnum BC, Lim RW, Herschman HR. TIS10 a phorbol ester tumor promoter-inducible mRNA from Swiss 3T3 cells encoded avel prostaglandin synthase/oxygenase homologue. J Biol Chem 1991; 266: 12866-12872.
52. Ristimaki A, Honkanen N, Jankala H, Sipponen P, Harkonen M. Expression of cyclooxygenase-2 in human gastric carcinoma. Cancer Res 1997; 57: 1276-1280.
53. Zimmerman KC, Sarbia M, Weber A, Bochard F, Gabbert HE, Sehror K. Ciclooxygenase-2 expression in human esophageal carcinoma. Cancer Res 1999; 59:198-204.
54. Hida T, Yatabe Y, Achiwa H, et al. Increased expression of cyclooxygenase-2 occurs frequently in human lung cancers, specifically in adenocarcinomas. Cancer Res 1998; 58: 3761-3764.
55. Eberhart CE, Coffy RJ, Radhika A, Giardiello FM, Ferrenbach S, Dubois RN. Up-regulation of cyclooxygenase-2 gene expression in human colo-rectal adenomas and adeno-carcinomas. Gastroenterology 1994; 107: 1183-1188.
56. Half E, Tang XM, Gwyn K, Sahin A, Wathen K, Sinicrope FA. Cyclooxygenase-2 expression in human breast cancers and adjacent ductal carcinoma in situ. Cancer Res 2002; 62: 1676-1681.
57. Smith WL, Dewitt DL, Garavito RM. Cyclooxygenases: structural, cellular and molecular biology. Annu Rev Biochem 2000; 69: 145-182.
58. Das UN. COX-2 inhibitors and metabolism of essential fatty acids. Med Sci Monit 2005; 11: 233-237.
59. Das UN. Essential fatty acids: biochemistry, physiology and pathology. Biotechnol J 2006; 1: 420-39.
60. Das UN. Gamma-linolenic acid therapy of human glioma-a review of in vitro, in vivo, and clinical studies. Med Sci Monit 2007; 13: 119-31.
61. Lim JW, Kim H, Kim KH. Nuclear factor-kappa B regulates cyclooxygenase-2 expression and cell proliferation in human gastric cancer cells. Lab Invest 2001; 81: 349-360.
62. Kojima M, Morisaki T, Uchiyama A, et al. Association of enhanced cyclooxygenase-2 expression with possible local immunosuppression in human colorectal carcinomas. Ann Surg Oncol 2001; 8: 458-465.
63. Plastaras JP, Guengerich FP, Nebert DW, Marnett LJ. Xenobiotic-metabolizing Cytochromes P450 convert Prostaglandin endoperoxide to Hydroxyheptadecatrienoic acid and the mutagen, Malondialdehyde. J Biol Chem 2000; 275: 11784-11790.
64. Emery J, Lucassen A, Murphy M. Common hereditary cancers and implications for primary care. Lancet 2001; 358: 56-63.
65. Subbaramaiah K, Zakin D, Weksler BB, Dannenberg AJ. Inhibition of cyclooxygenase: a novel approach in cancer prevention. Proc Soc Exp Biol Med 1997; 216: 201-210.
66. Harris RE, Beebe-Donk J, Alshafie GA. Reduction in the risk of human breast cancer by selective cyclooxygenase-2 (COX-2) inhibitors. BMC Cancer 2006; 6: 27.
67. Go VL, Wong DA, Wang Y, Butrum RR, Norman HA, Willkerson L. Diet and cancer prevention: evidence-based medicine to genomic medicine. J Nutr 2004; 134: 3513S-3516S.
68. Subbarayan V, Xu XC, Kim J, et al. Inverse relationship between 15-lipoxygenase-2 and PPAR-gamma gene expression in normal epithelia compared with tumor epithelia. Neoplasia 2005; 7: 280-293.
69. Hansen-Petrik MB, McEntee MF, Juli B, Shi H, Zemel MB, Whelan J. Prostaglandin E(2) protect intestinal tumors from nonsteroidal anti-inflamatory drug-induced regression in Apc(Min/+) mice. Cancer Res 2002; 62: 403-408.
70. Cutler NS, Graves-Deal R, LaFleur BJ, et al. Stromal production of prostacyclin confers an antiapoptotic effect to colonic epithelial cells. Cancer Res 2003; 63: 1748-1751.
71. Gupta RA, Wang D, Katkuri S, Wang H, Dey SK, Du Bois RN. Activation of nuclear hormone receptor peroxisome proliferator-activated receptor-delta accelerates intestinal adenoma growth. Nat Med 2004; 10: 245-247.
72. Zeidler R, Csanady M, Gires O, Lang S, Schmitt B, Wollenberg B. Tumor cell-derived prostaglandin E2 inhibits monocyte function by interfering with CCR5 and Mac-1. FASEB J 2000; 17: 661-668.
73. O' Byrne KJ, Dalgleish AG. Chronic immune activation and inflammation as the cause od malignancy. Br J Cancer 2001; 85: 473-483.
74. Rita M, Young I. Eicosanoids and the immunology of cancer. Cancer Metastasis Rev 1994; 113: 337-384.
75. Yu M, Ives D, Ramesha CS. Synthesis of prostaglandin E2 ethanolamide from anandamide by cyclooxygenase-2. J Biol Chem 1997; 272: 21181-21186.
76. Cristino L, Starowicz K, De Petrocellis L, et al. Immunohistochemical localization of anabolic and catabolic enzymes for anandamide and other putative endovanilloids in the hippocampus and cerebellar cortex of the mouse brain. Neuroscience 2008; 151: 955-968.
77. Kühn H. Biosynthesis, metabolization and biological importance of the primary 15-Lipoxygenase metabolites 15-Hydro(pero)xy-5Z, 8Z, 11Z, 13E-Eicosatetraenoic acid and 13-hydro(pero)xy-9Z, 11E-octadecadienoic acid. Prog Lipid Res 1996; 35: 203-226.
78. Spiteller G. Are lipid peroxidation processes induced by changes in the cell wall structure and how are these processes connected with diseases? Med Hypothesis 2003; 60: 69-83.
79. Tang DG, La E, Kern J, Kehrer JP. Fatty Acid Oxidation and signaling in apoptosis. Biol Chem 2002. 383: 425-442.
80. Le May C, Pineau T, Bigot K, Kohl C, Girard J, Pegorier JP. Reduced hepatic fatty acid oxidation in fasting PPAR alpha-null mice is due to impaired mitochondrial hydroxymethylglutaryl-CoA synthase gene expression. FEBS Lett 2002; 475: 163-166.
81. Sun Y, Alexander SP, Garle MJ, et al. Cannabinoid activation of PPAR alpha: a novel neuroprotective mechanism. Br J Pharmacol 2007; 152: 734-743.
82. Ide T, Kobayashi H, Ashakumary L, et al. Comparative effects of perilla and fish oils on the activity and gene expression of fatty acid oxidation enzymes in rat liver. Biochim Biophys Acts 2000; 1485: 23-35.
83. Grommes C, Landreth GE, Heneka MT. Antineoplastic effects of peroxisome proliferator-activated receptor γ agonists. Lancet Oncol 2004; 5: 119-129.
84. Hadjiagapiou C, Spector AA. 12-hydroxieicosatetraenoic acid reduces prostacyclin production by endothelial cells. Prostaglandins 1986; 31: 1135-1144.
85. Sekiya F, Takagi J, Usui T, et al. 12 S-hidroxyeicosatetraenoic acid plays a central role in the regulation of platelet activation. Biochem Biophys Res Commun 1991; 179: 345-351.
86. Schroeder CP, Yang P, Newman RA, Lotan R. Eicosanoid metabolism in squamous cell carcinoma cell lines derived from primary and metastatic head and neck cancer and its modulation by celecoxib. Cancer Biol Ther 2004; 3: 847-852.
87. Bortuzzo C, Hanif R, Kashfi K, Staiano-Coico L, Shiff SJ, Rigas B. The effect of leukotrienes B and selected HETEs on the proliferation of colon cancer cells. Biochim Biophys Acta 1996; 1300: 240-246.
88. Chang WC, Liu YW, Ming CC, Suzuki H, Yoshimoto TS. Induction of arachidonate 12-lipoxygenase m RNA by epidermal growth factor in A431 cells. J Biol Chem 1993; 268: 18734-18739.
89. Kandouz M, Nie D, Pidgeon GP. Krishnamoorthy S, Maddipati KR, Honn KV. Platelet-type 12-lipoxygenase activates NF-kappa B in prostate cancer cells. Prostaglandins Other Lipid Mediat 2003; 71: 189-204.
90. Tong WG, Ding XZ, Adrian TE. The mechanisms of lipoxygenase inhibitor-induced apoptosis in human breast cancer cells. Biochem Biophys Res Commun 2002; 296: 942-948.
91. Ding XZ, Tong WG, Adrian TE. 12-lipoxygenase metabolite 12(S)-HETE stimulates human pancreatic cancer cell proliferation via protein tyrosine phosphorylation and ERK activation. Int J Cancer 2001; 94: 630-636.
92. Wong BCY, Wang WP, Cho CH, et al. 12-lipoxygenase inhibition induced apoptosis in human gastric cancer cells. Carcinogenesis 2001; 22: 1349-1354.
93. Chen YQ, Dunniec ZM, Liu B, et al. Endogenous 12 (S)-HETE production by tumor cells and its role in metastasis. Cancer Res 1994; 54: 1574-1579.
94. Tang DG, Grossi IM, Chen YQ, Diglio CA, Honn KV. 12 (S)-HETE promotes tumor-cell adhesion by increasing surface expression of αVβ3 integrins on endothelial cells. Int J Cancer 1993; 54: 102-111.
95. Honn KV, Tang DG, Gao X, et al. 12-lipoxygenases and 12 (S)-HETE: role in cancer metastasis. Cancer Metastasis Rev 1994; 13: 365-396.
96. Liu XH, Connolly JM, Rose DP. Eicosanoids as mediators of linoleic acid-stimulated invasion and type IV collagenase production by a metastatic human breast cancer cell line. Clin Exp Metastasis 1996; 14: 145-152.
97. Espada CE, Berra MA, Martinez MJ, Eynard AR, Pasqualini ME. Effect of chia oil (Salvia hispanica) rich in ω-3 fatty acids on the eicosanoid release, apoptosis and t-lymphocyte tumor infiltration in a murine mammary gland adenocarcinoma. Prostaglandins Leukot Essent Fatty Acids 2007; 77: 21-28.
98. Craib SJ, Ellington HC, Pertwee RG, Ross RA. A possible role of lipoxygenase in the activation of vanilloid receptors by anandamide in the guinea-pig bronchus. Br J Pharmacol 2001; 134: 30-37.
99. Edgemond WS, Hillard CJ, Falck JR, Kearn CS, Campbell WB. Human platelets and polymorphonuclear leukocytes synthesize oxygenated derivatives of arachidonylethanolamide (anandamide): their affinities for cannabinoid receptors and pathways of inactivation. Mol Pharmacol 1998; 54:80-88.
100. Buchanan MR, Horsewood P, Brister SJ. Regulation of endothelial cell and platelet receptor-ligand binding by 12- and 15-lipoxygenase monohydroxides, 12-, 15-HETE and 13-HODE. Prostaglandins Leukot Essent Fatty Acids 1998; 58: 339-346.
101. Fernandez Zapico M, Barotto N, Eynard A, Valentich M. Selenium antiproliferative effect on cultured osteosarcoma cells. International Proceeding Division. Moraes M, Brentani R, Bevilacqua R, Ed, Bolonga, Italia 1998; 381-384.
102. Jacobs ET, Jiang R, Alberts DS, et al. Selenium and colorectal adenoma. Results of a Pooled Analysis. J Natl Cancer Inst 2004; 96: 1669-1675.
103. Horrobin DF, Ziboh VA. The importance of linoleic acid metabolites in cancer metastasis and in the synthesis and actions of 13-HODE. In Sinzinger, et al. Eds, Recent Advances in Research on Prostaglandin, Thromboxane and Leukotrienes. Plenum Press, New York 1998; 291-294.
104. Spindler SA, Sarkar FH, Sakr WA, et al. Production of 13-hidroyoctadecadienoic acid (13-HODE) by prostate tumors and cell lines. Bichem Biophys Res Commun 1997; 239: 775-781.
105. Bastida E, Bertomeu MC, Haas TA, et al. Regulation of tumor cell adhesion by intracellular 13-HODE: 15-HETE ratio. J Lipid Mediat 1990; 2: 281-293.
106. Simpson AE. The cytochrome P450 4 (CYP4) family. Gen Pharmacol 1997; 28: 351-359.
107. Fitzpatrick FA, Murphy RC. Cytochrome P-450 metabolism of arachidonic acid: formation and biological actions of "epoxygenase"-derived eicosanoids. Pharmacol Rev 1989; 40: 229-241.
108. Brash AR. Arachidonic acid as a bioactive molecule. J Clin Invest 2001; 107: 1339-45.
109. Shappell SB, Gupta RA, Manning S, et al. 15 S-Hydroxyeicosatetraenoic acid activates peroxisome proliferator-activated receptor gamma and inhibits proliferation in PC3 prostate carcinoma cells. Cancer Res 2001; 61: 497-503.
110. Hong CC, Tang BK, Hammond GL, Tritchler D, Yaffe M, Boyd NF. Cytochrome P450 1A2 (CYP1A2) activity and risk factors for breast cancer: a cross-sectional study. Breast Cancer Res 2004; 6: 352-365.
111. Kivisto KT, Fritz P, Linder A, Friedel G, Beaune P, Kroemer HK. Immunohistochemical localization of cytochrome P450 3A in human pulmonary carcinomas and normal bronchial tissue. Histochem Cell Biol 1995; 103: 25-29.
112. Cheeseman KH, Burton GW, Ingold KV, Slater TF. Lipid peroxidation and lipid antioxidant in normal and tumor cells. Toxicol Pathol 1984; 12: 235-239.
113. Calderón RO, Glocker M, Eynard AR. Lipid and fatty acid composition of different fraction from rat urinary transitional epithelium. Lipids 1998; 33: 1017-1022.
114. Calderon RO, Eynard AR. Fatty acids specifically related to the anisotropic properties of plasma membrane from rat urothelium. Biochim Biophys Acta 2000; 1483: 174-184.
115. Calderon RO, Grasso EJ. Symmetric array of the urothelium surface controlled by the lipid lattice composition. Biochem Biophys Res Commun 2006; 339: 642-646.
116. Bongiovanni GA, Eynard AR, Calderon RO. Altered lipid profile and changes in uroplakin properties of rat urothelial plasma membrane with diets of different lipid composition. Mol Cell Biochem 2005; 271: 69-75.
117. Horrobin DF, Manku MS. Huang YS. Effects of essential fatty acids on prostaglandin biosynthesis. Biomed Biophys Acta 1984; 43: 114-120.
118. Ma DW, Field CJ, Clandinin MT. An enriched mixture of trans-10, cis-12-CLA inhibits linoleic acid metabolism and PGE2 synthesis in MDA-MB-231 cells. Nutr Cancer 2002; 44: 203-212.
119. Bannis S, Angioni E, Casu V, et al. Decrease in linoleic acid metabolites as a potential mechanism in cancer risk reduction by conjugated linoleic acid. Carcinogenesis 1999; 20: 1019-1024.
120. Belury MA. Inhibition of carcinogenesis by conjugated linoleic acid: Potential Mechanisms od Action. J Nutr 2002; 132: 2995-2998.
121. Ha YL, Grimm NK, Pariza MW. Anticarcinogens from fried ground beef: beat-altered Derivatives of Linoleic Acid. Carcinogenesis 1987; 8: 1881-1887.
122. Pariza MW, Hargraves WA. A beef derived mutagenesis modulator inhibits initiation of mouse epidermal tumors by 7, 12-dimethylbenz [a]anthracene. Carcinogenesis 1985; 6: 591-593.
123. Ha YL, Storkson J, Pariza MW. Inhibition of benzo(a)pyrene-induced mouse forestomach neoplasia by conjugated dienoic derivatives of linoleic acid. Cancer Res 1990; 50: 1097-1101.
124. Ip C, Chin SF, Scimeca JA, Pariza MW. Mammary cancer prevention by conjugated dienoic derivatives of linoleic acid. Cancer Res 1991; 51: 6118-6124.
125. Yurawecz MP, Roach JAG, Sehat N, et al. New conjugated linoleic acid (CLA) isomer, 7-trans,9-cis-octadecadienoic acid in cow milk, cheese, beef, and human milk and adipose tissue. Lipids 1998; 33: 803-809.
126. Griinari JM, Cori BA, Lacy SH, Chouinard PY, Nurmela KVV, Bauman DE. Conjugated linoleic acid is synthesized endogenously in lactating dairy cows by Delta (9)-desaturase. J Nutr 2000; 130: 2285-2291.
127. Corl BA, Baumgard LH, Dwye DA, Griinari JM, Phillips BS, Bauman DE. The role of delta (9)-desaturase in the production of cis-9, trans-11 CLA. J Nutr Biochem 2001; 12: 622-630.
128. Ip C, Scimeca JA, Thompson H. Effects of timing and duration of dietary conjugated linoleic acid on mammary cancer prevention. Nutr Cancer 1995; 24: 241-247.
129. Yin JJ, Kramer JKG, Yurawecz MP, Eynard AR, Mossoba L, Yu LL. Effects of Conjugated Linoleic Acid (CLA) isomers on Oxygen Diffusion- concentration products in liposomes and phospholipid solutions. J Agric Food Chem 2006; 54: 7287-7293.
130. Banni S, Carta G, Contini MS, et al. Characterization of conjugated diene fatty acids in milk, dairy products, and lamb tissues. J Nutr Biochem 1996; 7: 150-155.
131. Yurawecz MP, Sehat N, Mossoba MM, Roach JAG, Kramer JKG, Ku Y. Variations in isomer distribution in commercially available conjugated linoleic acid. Fett Lipid 1999; 101: 277-282.
132. Banni S, Petroni A, Blasevich M, et al. Conjugated linoleic acids (CLA) as precursors of a distinct family of PUFA. Lipids 2004; 39: 1143-1146.
133. Ellen G, Elgersma A. Re: Nomenclature of trans-fatty acids plea for using the term n-7 fatty acids in place of C18:2cis-9, trans-11, and C18:1trans-11 or their trivial names rumenic acid and vaccenic acid rather than the generic term conjugated linoleic acids. Lipids 2004; 39: 693.
134. Kramer JKG, Cruz-Hernandez C, Or-Rashid M, Dugan MER. The use of Total trans-11 Containing FA, Rather than total "n-7" FA, Is recommended to assess the content of fa with a positive health image in rumiant fats. Lipids 2004; 39: 693-695.
135. Elgersma A, Ellen G. Response from Authors. Lipids 2004; 39: 695-696.
136. Banni S, Petroni A, Blasevich M, et al. Detection of conjugated C16 PUFAs in rat tissues as possible partial beta-oxidation products of naturally occurring conjugated linoleic acid and its metabolites. Biochim Biophys Acta 2004; 1682:120-127.
137. Muñoz SE, Silva RA, Lamarque A, Guzman CA, Eynard AR. Protective capability of dietary Zizyphus mistol seed oil, rich in 18:3, n-3, on the development of two murine mammary gland adenocarcinomas with high or low metastatic potential. Prostaglandins Leukot Essent Fatty Acids 1995; 53: 135-138.
138. Galloway JH, Cartwright IJ, Woodcok BE. Effects of dietary fish oil supplementation on the fatty acid composition of the human platelet membrane: demonstration of selectivity in the incorporation of eicosapentaenoic acid into memebrane phospholipids pools. Clin Sci 1985; 64: 449-54.
139. Honn KV, Tang DG. Adhesion molecules and tumor cell interaction with endothelium and subendothelial matrix. Cancer Metastasis Rev 1992; 11: 353-375.
140. Xia SH, Wang J, Kang JX. Decreased n-6/n-3 fatty acid ratio reduces the invasive potential of human lung cancer cells by down-regulation of cell adhesion/invasion-related genes. Carcinogenesis 2005; 26: 779-784.
141. Bagga D, Anders HJ, Glaspy JA. Long-chain n-3-to-n-6 polyunsaturated fatty acid ratios in breast adipose tissue from women with and without breast cancer. Nutr Cancer 2002; 42: 180-5.
142. Eynard AR, Jiang WG, Mansel RE. Eicosatrienoic acid (20:3 n-9) inhibits the expression of E-cadherin and desmoglein in human squamous cell carcinoma in vitro. Prostaglandins Leukot Essent Fatty Acids 1998; 59: 371-377.
143. Pasqualini ME, Heyd VL, Manzo P, Eynard AR. Association between E-cadherin expression by human colon, bladder and breast cancer cells and the 13-HODE: 15-HETE ratio. A possible role of their metastatic potential. Prostaglandins Leukot Essen Fatty Acids 2003; 68: 9-16.
144. Abel S, de Kock M, Smutus CM, de Villiers C, Swanevelder S, Gelderblom WC. Dietary modulation of fatty acid profiles and oxidative status of rat hepatocyte nodules: effect of different n-6/n-3 fatty acid ratios. Lipids 2004; 39: 963-76.
145. Sugiura T, Kobayashi Y, Oka S, Waku K. Biosynthesis and degradation of anandamide and 2-arachydonoylglycerol and their possible physiological significance. Prostaglandins Leukot Essent Fatty Acids 2002; 66: 173-192.
146. Kozak KR, Crews BC, Ray JL, Tai HH, Morrow JD, Marnett LJ. Metabolism of prostaglandin glycerol esters and prostaglandin ethanolamides in vitro and in vivo. J Biol Chem 2001; 276: 36993-36998.