Identification of conjugated fatty acids by gas chromatography-mass spectrometry of 4-methyl-1,2,4-triazoline-3,5-dione adducts

JAOCS, Journal of the American Oil Chemists' Society

Volumn 75, Issue 2, 1998, Pages 137-142

  Dobson, Gary ^a  

^a SCOTTISH CROP RESEARCH INSTITUTE   (United Kingdom)

Author keywords

4 methyl 1,2,4 triazoline 3,5 dione adducts; Conjugated fatty acids; Diels Alder adducts; Gas chromatography mass spectrometry

Indexed keywords

ADDITION REACTIONS; ELECTRON SPECTROSCOPY; ESTERS; GAS CHROMATOGRAPHY; HYDROGEN BONDS; KETONES; MASS SPECTROMETRY; NITROGEN COMPOUNDS;

DIELS ALDER CYCLOADDITION REACTION; ELECTRON IMPACT MASS SPECTROMETRY; FATTY ACID METHYL ESTER; METHYLTRIAZOLINONE; OCTADECADIENOATE; OCTADECATRIENOATE; STEREOISOMERS;

FATTY ACIDS;

EID: 0031999733     PISSN: 0003021X     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11746-998-0024-9     Document Type: Article

References (24)

1. Ha, Y.S., J. Storkson, and M.W. Pariza, Inhibition of Benzo[a]pyrene-Induced Mouse Forestomach Neoplasia by Conjugated Dienoic Derivatives of Linoleic Acid, Cancer Res. 50:1097-1101 (1990).
2. Ip, C., M. Singh, H.J. Thompson, and J.A. Scimeca, Conjugated Linoleic Acid Suppresses Mammary Carcinogenesis and Proliferative Activity of the Mammary Gland in the Rat, Ibid. 54:1212-1215 (1994).
3. Kepler, R.C., K.P. Hirons, J.J. McNeiil, and S.B. Tove. Intermediates and Products of the Biohydrogenation of Linoleic Acid by Butyrivibrio fibrisolvens, J. Biol. Chem. 247:1350-1358 (1966).
4. Banni, S., B.W. Day, R.W. Evans, F.P. Corongiu, and B. Lombardi, Liquid Chromatography-Mass Spectrometric Analysis of Conjugated Diene Fatty Acids in Partially Hydrogenated Fat, J. Am. Oil Chem. Soc. 71:1321-1325 (1994).
5. Parodi, P.W., Conjugated Octadecadienoic Acids of Milk Fat, J. Dairy Sci. 60:1550-1553 (1977).
6. Fogerty, A.C., G.L Ford, and D. Svoronos, Octadec-9,11-dienoic Acid in Foodstuffs and in the Lipids of Human Blood and Breast Milk, Nutr. Rep, Intl. 3S:937-944 (1988).
7. Chin, S.F., W. Liu J.M. Storkson, Y.L. Ha, and M.W. Pariza, Dietary Sources of Conjugated Dienoic Isomers of Linoleic Acid, a Newly Recognized Class of Anticarcinogens, J. Food Comp. Anal. 5:185-197 (1992).
8. Christie, W.W., The Effects of Diet and Other Factors on the Lipid Composition of Ruminant Tissues and Milk, Prog. Lipid Res. 17:245-277 (1979).
9. Ha, Y.L., N.K. Grimm, and M.W. Pariza, Anticarcinogens from Ground Beef: Heat-Altered Derivatives of Linoleic Acid, Carcinogenesis 8:1881-1887 (1987).
10. Banni, S., B.W. Day, R.W. Evans, F.P. Corongiu, and B. Lombardi, Detection of Conjugated Diene Isomers of Linoleic Acid in Liver Lipids of Rats Fed a Choline-Devoid Diet Indicates That the Diet Does Not Cause Lipoperoxidation, J. Nutr. Biochem. 6:281-289 (1995).
11. Sébédio, J.L., P. Juaneda, G. Dobson, I. Ramilison, J.C. Martin, J.M. Chardigny, and W.W. Christie, Metabolites of Conjugated Isomers of Linoleic Acid (CLA) in the Rat, Biochim. Biophys. Acta 1345:5-10 (1997).
12. Banni, S., G. Carta, M.S. Contini, E. Angioni, M. Deiana, M.A. Dessi, M.P. Melis, and F.P. Corongiu, Characterization of Conjugated Diene Fatty Acids in Milk, Dairy Products and Lamb Tissue, Nutr. Biochem. 7:150-155 (1996).
13. Hopkins, C.Y., Fatty Acids with Conjugated Unsaturation, in Topics in Lipid Chemistry, Vol. 3, edited by F.D. Gunstone, Elek Science, London, 1972, pp. 37-87.
14. Fairbank, J., J. Hollingworth, J. Griffin, E. Ridgeway, D. Wickens, A. Singer, and T. Dormandy, Octadec-9,11-dienoic Acid in Cervical Intraepithelial Neoplasia: A Colposcopic Study, Clin. Chim. Acta 186:53-58 (1989).
15. Parham, D.M., P.E. Ross, F.D. Gunstone, A.J. Robertson, and I.D. Duncan, Identification of Octadeca-9,11-dienoic Acid and Its Significance in the Diagnosis of Cervical Intraepithelial Neoplasia, Ibid. 182:289-294 (1989).
16. 18 Fatty Acids, J. Am. Oil Chem. Soc. 71:873-876 (1994).
17. Young, D.C., P. Vouros, B. Decosta, and M.F. Holick, Location of Conjugated Diene Position in an Aliphatic Chain by Mass Spectrometry of the 4-Phenyl-1,2,4-triazoline-3,5-dione Adduct, Anal. Chem. 59:1954-1957 (1987).
18. Young, D.C., P. Vouros, and M.F. Holick, Gas Chromatography-Mass Spectrometry of Conjugated Dienes by Derivatization with 4-Methyl-1,2,4-triazoline-3,5-dione, J. Chromatogr. 522:295-302 (1990).
19. Read, G., N.R. Richardson, and D.G. Wickens, Determination of Octadecadienoic Acids in Human Serum: A Critical Appraisal, Analyst 119:393-396 (1994).
20. Bligh, E.G., and W.J. Dyer, A Rapid Method of Total Lipid Extraction and Purification, Can. J. Biochem. Physiol. 37:911-917 (1959).
21. Christie, W.W., Gas Chromatography and Lipids, Oily Press, Ayr, 1989, p. 70.
22. Fay, L., and U. Richli, Location of Double Bonds in Polyunsaturated Fatty Acids by Gas Chromatography-Mass Spectrometry After 4,4-Dimethyloxazoline Derivatization, J. Chromatogr. 541:89-98 (1991).
23. Joh, Y.-G., S.-J. Kim, and W.W. Christie, The Structure of the Triacylglycerols, Containing Punicic Acid, in the Seed Oil of Trichosanthes kirilowii, J. Am. Oil Chem. Soc. 72:1037-1042 (1995).
24. Dobson, G., W.W. Christie, E.Y. Brechany, J.-L. Sébédio, and J.L. Le Quere, Silver Ion Chromatography and Gas Chromatography-Mass Spectrometry in the Structural Analysis of Cyclic Dienoic Acids Formed in Frying Oils, Chem. Phys. Lipids 75:171-182 (1995).