Advertisement

Metabolism of R,S Enantiomers of 3-Phenylamino-1,2-Propanediol, a Compound Associated with the Toxic Oil Syndrome, in C57BL/6- and A/J-Strain Mice

  • Margarita G. Ladona
  • Jordi Bujons
  • Angel Messeguer
  • Coral Ampurdanés
  • Anna Morató
Part of the Advances in Experimental Medicine and Biology book series (AEMB, volume 500)

Abstract

The Toxic Oil Syndrome (TOS) appeared in Spain in spring 1981 as a massive food-borne intoxication in the central and northwestern areas of the country. A huge population of over 20,000 people was afflicted and over 400 deaths occurred1. The clinical features of TOS resembled an allergic-toxic syndrome in the acute phase and an autoimmune condition in the chronic phase1,2. Although some patients recovered after a long period of time (several months), many continue to suffer severe sequel or mild symptoms.

Keywords

Aniline Derivative Aniline Hydrochloride World Health Organization Regional Intestinal Hydrolysis Radioactivity Clearance 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    P. Gradjean, and S. Tarkowski eds. Toxic Oil Syndrome: mass food poisoning in Spain. Report of a WHO Meeting: Madrid 21–25 March 1983. World Health Organization Regional office for Europe, Copenhagen (1984).Google Scholar
  2. 2.
    J.M. Tabuenca. Toxic allergic syndrome caused by ingestion of rapeseed oil denatured with aniline. Lancet 2, 567–568 (1981).PubMedCrossRefGoogle Scholar
  3. 3.
    J. Nadal and S. Tarkowski. Toxic Oil Syndrome: current knowledge and future perspectives. WHO Regional Publications, European series no 42, Copenhagen (1992).Google Scholar
  4. 4.
    A. Vázquez-Roncero, C. Janer del Valle, R. Maestro-Duran and E. Graciane-Constante. New aniline derivatives in cooking oils associated with the toxic oil syndrome. Lancet ii, 1024–1025 (1983).CrossRefGoogle Scholar
  5. 5.
    J.T. Bernert, E.M. Kilbourne, J.R. Akins, M. Posada de la Paz, N.K. Meredith, I. Abaitua-Borda and S. Wages. Compositional analysis of oil samples implicated in the Spanish toxic oil syndrome. J. Food Sci. 52, 1562–1569 (1987).CrossRefGoogle Scholar
  6. 6.
    M. Posada de la Paz, R.M. Philen, I. Abaitua Borda, J.T. Bernert, J.C. Bada-Gancedo, P.J. DuClos, E.M. Kilbourne. Toxic Oil Syndrome: traceback of the toxic oil and evidence for a point source epidemic. Food. Chem. Toxicol. 34, 251–257 (1996).CrossRefGoogle Scholar
  7. 7.
    H.H. Schurz, R.H. Hill, M. Posada de la Paz, R.M. Philen, I. Abaitua-Borda, S.L. Bailey and L.L. Needham. Products of aniline and triglycerides in oil samples associated with the Toxic Oil Syndrome. Chem. Res. Toxicol. 9, 1001–1006 (1996).PubMedCrossRefGoogle Scholar
  8. 8.
    M. Posada de la Paz, R.M. Philen, H.H. Schurz, R.H. Hill, O. Gimenez-Ribota, A. Gómez de la Cámara, E.M. Kilbourne, I. Abaitua-Borda. Epidemiologic evidence for a new class of compounds associated with Toxic Oil Syndrome. Epidemiology 10 130 –134 (1999).CrossRefGoogle Scholar
  9. 9.
    A. Vázquez-Roncero, R. Maestro-Duran and V. Ruiz-Gutierrez. New aniline derivatives in oils related to the Toxic Syndrome. Toxicity in mice of 3-phenylamino-1,2- propanediol and its fatty acid mono-and diesters. Grasas y Aceites 35, 330–331 (1984).Google Scholar
  10. 10.
    V. Ruiz-Gutierrez and R. Maestro-Duran. Lymphatic absorption of 3-phenyalmino-1,2propanediol and its esters. Exp. Toxic. Pathol. 44, 29–33 (1992).Google Scholar
  11. 11.
    C. Berking, M.V. Hobbs, R. Chatelain, M. Meurer and S.A. Bell. Strain-dependent cytokine profile and susceptibility to oleic acid anilide in a murine model of the Toxic Oil Syndrome. Toxicol. Appl. Pharmacol. 148, 222–228 (1998).PubMedCrossRefGoogle Scholar
  12. 12.
    V. del Pozo, B. de Andrés, S. Gallardo, B. Cardaba, E. de Arruda-Chaves, I. Cortegano, A. Jurado, P. Palomino, H. Oliva, B. Aguilera, M. Posada and C. Lahoz. Cytokine mRNA expression in lung tissue from Toxic Oil Syndrome patients: a Th2 immunological mechanism. Toxicology 118, 61–70 (1997).PubMedCrossRefGoogle Scholar
  13. 13.
    M.G. Ladona, J. Bujons, A. Messeguer, C. Ampurdanés, A. Morató and J. Corbella. Biotransformation and clearance of 3-(phenylamino)propane-1,2-diol, a compound present in samples related to Toxic Oil Syndrome in C57BL/6 and A/J mice. Chem. Res. Toxicol. 12, 1127–1137 (1999).PubMedCrossRefGoogle Scholar
  14. 14.
    M. Ferrer, M. Galceran, F. Sanchez-Baeza, J. Casas and A. Messeguer. Synthesis of aniline derivatives with potential toxicological implications to the Spanish Toxic Oil Syndrome. Liebigs Ann. Chem. 507 –511 (1993).Google Scholar

Copyright information

© Springer Science+Business Media New York 2001

Authors and Affiliations

  • Margarita G. Ladona
    • 1
  • Jordi Bujons
    • 1
  • Angel Messeguer
    • 1
  • Coral Ampurdanés
    • 1
  • Anna Morató
    • 1
  1. 1.Consejo Superior de Investigaciones Científicas (CSIC)BarcelonaSpain

Personalised recommendations