Abstract
A study was performed to examine the ability of dietary oleic anilide to alter 12-hydroxyeicosatetraenoic acid (12-HETE) production. The structure of oleic anilide, synthesized by reacting oleic acid with aniline, was confirmed by mass spectrometry. The purity of oleic anilide, 75%, was measured by gas chromatography. Oleic acid, which constituted the remaining 25%, is a major component of the rapeseed oil vehicle. Balb/c mice were fed oleic anilide as 0.75% of their diet by weight for three weeks. Their lungs were excised and examined for 12-HETE production in vitro. The 12-HETE levels were significantly (p<0.01) lower in mice fed oleic anilide than in mice fed the oleic acid control diet. This result illustrates eicosanoid production as a target of fatty acid anilide toxicity. The fatty acid composition, including arachidonic acid, of mouse lungs from both dietary groups was not different. This confirms the availability of substrate for 12-lipoxygenase in both groups. Spleen weights were higher in mice fed oleic anilide than in control mice (p<0.005). These observations are relevant to immunoregulation and the autoimmune syndromes noted in patients of the Toxic Oil Syndrome (TOS).
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Aldridge WN (1992) Experimental studies. In: Toxic oil syndrome: Current knowledge and future perspectives. WHO regional publications, European series no. 42, WHO, England, pp 67–97
Altmann HJ, Grunow W (1983) Distribution and excretion of orally administered oleic acid anilide in the rat. Toxicology 27:321–326
Bell SA, Hobbs MV, Rubin RL (1992) Isotype-restricted hyperimmunity in a murine model of the toxic oil syndrome. J Immunol 148:3369–3376
Berger A, German JB (1990) Phospholipid fatty acid composition of various mouse tissues after feeding a-linolenate (18:3n-3) or eicosatreinoate (20:3n-3). Lipids 25:473–480
Blasco R, Ruiz-Gutierrez V (1992) Effect of fatty acid anilides on immune responses of Swiss mice. Clin Exp Immunol 89:131–135
Borda IA, Posada de la Paz M (1992) Clinical findings. In: Toxic oil syndrome: Current knowledge and future perspectives. WHO regional publications, European series no. 42; WHO, England, pp 27–38
Brown-Galatoli CH, Hall ND (1992) Impaired suppressor cell activity due to surface sulphydryl oxidation in rheumatoid arthritis. Br J Rheumatol 31:599–603
de Castellarnau C, Pich I, Chanquia C, Vila L, Lagunas C, Fontcuberta J, Rutllant M (1993) Effects of linoleic and oleic acid anilides on prostacyclin synthesis and fibrinolytic profile of human endothelial cells in culture: Relevance to the toxic oil syndrome. Toxicology 81:181–194
Droge W, Eck H-P, Mihm S (1992) HIV-induced cysteine deficiency and T-cell dysfunction—A rationale for treatment with N-acetylcysteine. Immunology Today 13:211–214
Esterbauer H, Schaur RJ, Zollner H (1991) Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes. Free Radical Biol Med 11:81–128
Fitzsimmons BJ, Rokach J (1989) Enzyme inhibitors and leukotriene receptor antagonists. In: Rokach J (ed) Leukotrienes and lipoxygenases. Chemical, biological and clinical aspects. Elsevier, The Netherlands, pp 427–502
Fournier, E, Efthymiou M-L, Lecorsier A (1982) Spanish adulterated oil matter. An important discovery by Spanish toxicologists: The toxicity of anilides of unsaturated fatty acids. Toxicol Eur Res 4:107–112
German J.B., Hu M-H (1990) Oxidant stress inhibits the endogenous production of lipoxygenase metabolites in rat lungs and fish gills. Free Radical Biol Med 8:441–448
Glaser KB, Molilio D, Chang JY, Senko N (1993) Phospholipase A2 enzymes: Regulation and inhibition. Trends Pharmacol Sci 14:92–98
Gmunder H, Droge W (1991) Differential effects of glutathione depletion on T cell subsets. Cell Immunol 138:229–237
Goulding NJ, Guyre PM (1993) Glucocorticoids, lipocortins and the immune response. Curr Op Immunol 5:108–113
Grigolo B, Borzi RM, Mariani E, Monaco MCG, Cattini L, Porstmann T, Facchini A (1994) Intracellular Cu/Zn superoxide dismutase levels in T and non-T cells from normal aged subjects. Mech Ageing Development 73:27–37
Guitart R, Gelpi E (1992) Chemical composition of TOS-related oils. In: Toxic oil syndrome: Current knowledge and future perspectives. WHO regional publications, European series no. 42, WHO, England, pp 99–142
Ishii Y, Morita S, Murota S, Kitamura S (1993) Hyperoxia decreases cyclooxygenase activity in endothelial cells. Prost Leuk Ess Fatty Acids 48:455–461
Khan MF, Kaphalia BS, Palofox A, Jerrells TR, Ansari GAS (1991) Heated linoleic acid anilide: Toxicity and relevance to toxic oil syndrome. Toxicology 68:143–155
Kilbourne EM, de la Paz MP, Borda IA (1992) Epidemiological studies. In: Toxic oil syndrome: Current knowledge and future perspectives. WHO regional publications, European serie no. 42, WHO, England, pp 5–25
Lahoz C, Rose NR, Goter Robinson CJ (1992) Immunology. In: Toxic oil syndrome: Current knowledge and future perspectives. WHO regional publications, European series no. 42, WHO, England, pp 143–163
McKeown MJ, Hall ND, Corvalan JRF (1984) Defective monocyte accessory function due to surfaces sulphydryl (SH) oxidation in rheumatoid arthritis. Clin Exp Immunol 57:607–613
Mukherjee S, Ghosh S, Rodgers L, Nayyar T, Desai U, Das SK (1994) Toxic effects of fatty acid anilides on the oxygen defense systems of guinea pig lungs and erythrocytes. J Biochem Toxicology 9:1–7
Naiki M, Yoshida SH, Watanabe Y, Izui S, Ansari AA, Gershwin ME (1993) The contribution of I-Abm12 to phenotypic and functional alterations among T-cell subsets in NZB mice. J Autoimmunity 6:131–143
Percival MD, Denis D, Riendeau D, Gresser MJ (1992) Investigation of the mechanism of non-turnover-dependent inactivation of purified human 5-lipoxygenase. Inactivation by H2O2 and inhibition by metal ions. Eur J Biochem 210:109–11
Pestana A, Munoz E (1982) News and views. Anilides and the Spanish toxic oil syndrome. Nature 298:608
Pich I, Lopez S, Vila L, Lagunas C, De Castellarnau C (1993) Influence of fatty acid anilides present in toxic oils on the metabolism of exoenous arachidonic acid in cultured human endothelial cells. Toxicology 77:51–63
Roederer M, Staal FJT, Osada H, Herzenberg LA, Herzenberg LA (1991) CD4 and CD8 T cells with high intracellular glutathione levels are selectively lost as the HIV infection progresses. Int Immunol 9:933–937
Suarez A, Viloria MD, Garcia-Barreno P, Municio AM (1985) Toxic oil syndrome, Spain: Effect of oleoylanilide on the release of polyunsaturated fatty acids and lipid peroxidation in rats. Arch Environ Contam Toxicol 14:131–136
van der Donk EMM, Verhagen J, Veldink GA, Vliegenthart JFG (1991) 12-lipoxygenase from rat basophilic leukemia cells: Separation from 5-lipoxygenase and temperature-dependent inactivation by hydroperoxy fatty acid. Biochim Biophys Acta 1081:135–140
Veis DJ, Sorenson CM, Shutter JR, Korsmeyer SJ (1993) Bcl-2-deficient mice demonstrate fulminant lymphoid apoptosis, polycystic kidneys, and hypopigmented hair. Cell 75:229–240
Wheals BB, Whitehouse MJ, Curry CJ (1982) Application of liquid chromatographic and spectroscopic methods for the characterization of fatty acid anilides in contaminated cooking oils. J Chromatogr 238:203–215
Yoshida S, Dorshkind K, Bearer E, Castles JJ, Ahmed A, Gershwin ME (1987) Abnormalities of B lineage cells are demonstrable in long term lymphoid bone marrow cultures of New Zealand black mice. J Immunol 139:1454–1458
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Yoshida, S.H., Bruenner, B.A., German, J.B. et al. Decrease of 12-hydroxyeicosatetraenoic acid production in mouse lungs following dietary oleic anilide consumption: Implications for the toxic oil syndrome. Arch. Environ. Contam. Toxicol. 28, 524–528 (1995). https://doi.org/10.1007/BF00211637
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00211637