Evaluating acid and base catalysts in the methylation of milk and rumen fatty acids with special emphasis on conjugated dienes and total trans fatty acids

Lipids

Volumn 32, Issue 11, 1997, Pages 1219-1228

  Kramer, John K G ^a   Fellner, Vivek ^a   Dugan, Michael E R ^a   Sauer, Frank D ^a   Mossoba, Magdi M ^b   Yurawecz, Martin P ^b  

^a AGRICULTURE AND AGRI FOOD CANADA   (Canada)

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

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ALKADIENE; BASE; FATTY ACID; FATTY ACID ESTER; HEXANE;

ANALYTIC METHOD; ARTICLE; ARTIFACT; CATALYST; GAS LIQUID CHROMATOGRAPHY; INFRARED SPECTROSCOPY; LIPID ANALYSIS; LIPID COMPOSITION; METHYLATION; MILK; NONHUMAN; RUMINANT STOMACH; THIN LAYER CHROMATOGRAPHY;

EID: 0030661916     PISSN: 00244201     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11745-997-0156-3     Document Type: Article

References (58)

1. Christie, W.W. (1981) The Effects of Diet and Other Factors on the Lipid Composition of Ruminant Tissues and Milk, in Lipid Metabolism in Ruminant Animals (Christie, W.W., ed.) pp. 193-226, Pergamon Press, Oxford.
2. Sutton, J.D., and Morant, S.V. (1989) A Review of the Potential of Nutrition to Modify Milk Fat and Protein, Livest. Prod. Sci. 23, 219-237.
3. Henninger, M., and Ulberth, F. (1994) Trans Fatty Acid Content of Bovine Milk Fat, Milkwissenschaft 49, 555-558.
4. Wolff, R.L. (1994) Contribution of trans-18:1 Acids from Dairy Fat to European Diets, J. Am. Oil Chem. Soc. 71, 277-283.
5. Chen, Z.-Y, Pelletier, G., Hollywood, R., and Ratnayake, W.M.N. (1995) Trans Fatty Acid Isomers in Canadian Human Milk, Lipids 30, 15-21.
6. Wolff, R.L. (1995) Content and Distribution of trans-18:1 Acids in Ruminant Milk and Meat Fats. Their Importance in European Diets and Their Effect on Human Milk, J. Am. Oil Chem. Soc. 72, 259-272.
7. Precht, D. (1995) Variation of trans Fatty Acids in Milk Fats, Z. Ernährungswiss. 34, 27-29.
8. Chardigny, J.-M., Wolff, R.L., Mager, E., Bayard, C.C., Sébédio, J.-L., Martine, L., and Ratnayake, W.M.N. (1996) Fatty Acid Composition of French Infant Formulas with Emphasis on the Content and Detailed Profile of trans Fatty Acids, J. Am. Oil Chem. Soc. 73, 1595-1601.
9. Fogerty, A.C., Ford, G.L., and Svoronos, D. (1988) Octadeca-9,11-dienoic Acid in Foodstuffs and in the Lipids of Human Blood and Breast Milk, Nutr. Rep. Internat. 38, 937-944.
10. Ha, Y.L., Grimm, N.K., and Pariza, M.W. (1989) Newly Recognized Anticarcinogenic Fatty Acids: Identification and Quantitation in Natural and Processed Cheeses, J. Agr. Food Chem. 37, 75-81.
11. Shantha, N.C., Decker, E.A., and Ustunol, Z. (1992) Conjugated Linoleic Acid Concentration in Processed Cheese, J. Am. Oil Chem. Soc. 69, 425-428.
12. Werner, S.A., Luedecke, L.O., and Shultz, T.D. (1992) Determination of Conjugated Linoleic Acid and Isomer Distribution in Three Cheddar-Type Cheeses: Effects of Cheese Cultures, Processing, and Aging, J. Agric. Food Chem. 40, 1817-1821.
13. Shantha, N.C., Ram, L.N., O'Leary, J., Hicks, C.L., and Decker, E.A. (1995) Conjugated Linoleic Acid Concentrations of Dairy Products as Affected by Processing and Storage, J. Food Sci. 60, 695-697, 720.
14. Banni, S., Gianfranca, C., Contini, M.S., Angioni, E., Deiana, M., Dessì, M.A., Melis, M.P., and Corongiu, F.P. (1996) Characterization of Conjugated Diene Fatty Acids in Milk, Dairy Products, and Lamb Tissues, Nutr. Biochem. 7, 150-155.
15. Jiang, J., Bjoerck, L., Fondén, R., and Emanuelson, M. (1996) Occurrence of Conjugated cis-9, trans-11-Octadecadienoic Acid in Bovine Milk: Effects of Feed and Dietary Regimen, J. Dairy Sci. 79, 438-445.
16. Ha, Y.L., Storkson, J., and Pariza, M.W. (1990) Inhibition of Benzo(a)pyrene-induced Mouse Forestomach Neoplasia by Conjugated Dienoic Derivatives of Linoleic Acid, Cancer Res. 50, 1097-1101.
17. Ip, C., Chin, S.F., Scimeca, J.A., and Pariza, M.W. (1991) Mammary Cancer Prevention by Conjugated Dienoic Derivative of Linoleic Acid, Cancer Res. 51, 6118-6124.
18. Belury, M.A. (1995) Conjugated Dienoic Linoleate: A Polyunsaturated Fatty Acid with Unique Chemoprotective Properties, Nutr. Rev. 53, 83-89.
19. Jensen, R.G., Ferris, A.M., and Lammi-Keefe, C.J. (1991) The Composition of Milk Fat, J. Dairy Sci. 74, 3228-3243.
20. Jensen, R.G. (1996) The Lipids in Human Milk, Prog. Lipid Res. 35, 53-92.
21. Harfoot, C.G. (1981) Lipid Metabolism in the Rumen, in Lipid Metabolism in Ruminant Animals (Christie, W.W., ed.) pp. 21-55, Pergamon Press, Oxford.
22. 18 cis- and trans-Fatty Acids of Margarine on the SP-2340 Capillary Column, J. Chromatogr. Sci. 28, 633-639.
23. Ratnayake, W.M.N., and Pelletier, G. (1992) Positional and Geometric Isomers of Linoleic Acid in Partially Hydrogenated Oils, J. Am. Oil Chem. Soc. 69, 95-105.
24. Wolff, R.L., Bayard, C.C., and Fabien, R.J. (1995) Evaluation of Sequential Methods for the Determination of Butterfat Fatty Acid Composition with Emphasis on trans-18:1 Acids. Application of the Study of Seasonal Variations in French Butters, J. Am. Oil Chem. Soc. 72, 1471-1483.
25. Molkentin, J., and Precht, D. (1995) Optimized Analysis of trans-Octadecenoic Acids in Edible Oils, Chromatographia 41, 267-272.
26. Christie, W.W. (1982) Lipid Analysis, 2nd edn., Pergamon Press, Oxford.
27. Shantha, N.C., Decker, E.A., and Hennig, B. (1993) Comparison of Methylation Methods for the Quantitation of Conjugated Linoleic Acid Isomers, J. AOAC Internat. 76, 644-649.
28. van den Berg, J.J.M., Cook, N.E., and Tribble, D.L. (1995) Reinvestigation of the Antioxidant Properties of Conjugated Linoleic Acid, Lipids 30, 599-605.
29. Koritala, S., and Rohwedder, W.K. (1972) Formation of an Artifact During Methylation of Conjugated Fatty Acids, Lipids 7, 274.
30. Bannon, C.D., Craske, J.D., and Hilliker, A.E. (1985) Analysis of Fatty Acid Methyl Esters with High Accuracy and Reliability. IV. Fats with Fatty Acids Containing Four or More Atoms, J. Am. Oil Chem. Soc. 62, 1501-1507.
31. Craske, J.D., Bannon, C.D., and Norman, L.M. (1988) Limitations of Ambient Temperature Methods for the Methanolysis of Triacylglycerols in the Analysis of Fatty Acid Methyl Esters with High Accuracy and Reliability, J. Am. Oil Chem. Soc. 65, 262-266.
32. Wolff, R.L., and Fabien, R.J. (1989) Utilisation de l'isopropanol pour l'extraction de la matière grasse de produits laiters et pour l'estérification subséquente des acides gras, Le Lait 69, 33-46.
33. Stoffel, W., Chu, F., and Ahrens, E.H. (1959) Analysis of Long-Chain Fatty Acids by Gas-Liquid Chromatography. Micromethod for Preparation of Methyl Esters, Anal. Chem. 31, 307-308.
34. Morrison, W.R., and Smith, L.M. (1964) Preparation of Fatty Acid Methyl Esters and Dimethylacetals from Lipids with Boron Fluoride-Methanol, J. Lip. Res. 5, 600-608.
35. Lepage, G., and Roy, C.C. (1986) Direct Transesterification of all Classes of Lipid in a One-Step Reaction, J. Lip. Res. 27, 114-120.
36. Christopherson, S.W., and Glass, R.L. (1970) Preparation of Milk Fat Methyl Esters by Alcoholysis in an Essentially Nonalcoholic Solution, J. Dairy Sci. 52, 1289-1290.
37. Schuchardt, U., and Lopes, O.C. (1988) Tetramethylguanidine-Catalyzed Transesterification of Fats and Oils: A New Method for Rapid Determination of Their Composition, J. Am. Oil Chem. Soc. 65, 1940-1941.
38. Fellner, V., Sauer, F.D., and Kramer, J.K.G. (1995) Steady-State Rates of Linoleic Acid Biohydrogenation by Ruminai Bacteria in Continuous Culture, J. Dairy Sci. 78, 1815-1823.
39. Fellner, V., Sauer, F.D., and Kramer, J.K.G. (1997) Effect of Ionophores with Different Binding Selectivity for Cations on Fermentation and Lipid Metabolism by a Continuous Culture of Ruminal Bacteria, J. Dairy Sci. 80, 921-928.
40. Sauer, F.D., Fellner, V., Kinsman, R., Kramer, J.K.G., Jackson, H.A., Lee, A.J., and Chen, S. (1997) Methane Output and Lactation Response in Holstein Cattle with Monensin or Unsaturated Fat Added to the Diet, J. Amin. Sci., in press.
41. Jensen, R.G. (1989) The Lipids of Human Milk, pp. 30, CRC Press Inc., Boca Raton.
42. Bligh, E.G., and Dyer, W.J. (1959) A Rapid Method of Total Lipid Extraction and Purification, Can. J. Biochem. Physiol. 37, 911-917.
43. Official Methods and Recommended Practices of the American Oil Chemists' Society, (1989) Preparation of Methyl Esters of Long-Chain Fatty Acids (Ce 2-66), 4th edn., American Oil Chemists' Society, Champaign.
44. 18 Triene and Conjugated Diene Isomers in Hydrogenated Soybean Oil and Margarine by GC-MI-FT-IR Spectroscopy, J. Chromatogr. Sci., 29, 324-330.
45. Mossoba, M.M., Yurawecz, P.M., and McDonald, R.E. (1996) Rapid Determination of the Total trans Content of Neat Hydrogenated Oils by Attenuated Total Reflection Spectroscopy, J. Am. Oil Chem. Soc. 73, 1003-1009.
46. Ali, L.H., Angyal, G., Weaver, C.M., Rader, J.I., and Mossoba, M.M. (1996) Determination of Total trans Fatty Acids in Foods: Comparison of Capillary-Column Gas Chromatography and Single-Bounce Horizontal Attenuated Total Reflection Infrared Spectroscopy, J. Am. Oil Chem. Soc. 73, 1699-1705.
47. Official Methods and Recommended Practices of the American Oil Chemists' Society, (1996-1997) Isolated trans Isomers - Infrared Spectroscopic Methods (Cd 14d-96), 4th edn. with additions and revisions, American Oil Chemists' Society, Champaign.
48. Wolff, R.L. (1994) Analysis of Alpha-Linolenic Acid Geometric Isomers in Deodorized Oils by Capillary Gas-Liquid Chromatography on Cyanoalkyl Polysiloxane Stationary Phases: A Note of Caution, J. Am. Oil Chem. Soc. 71, 907-909.
49. Yurawecz, M.P., Hood, J.K., Roach, J.A.G., Mossoba, M.M., Daniels, D.H., Ku, Y., Pariza, M.W., and Chin, S.F. (1994) Conversion of Allylic Hydroxy Oleate to Conjugated Linoleic Acid and Methoxy Oleate by Acid-Catalyzed Methylation Procedures, J. Am. Oil Chem. Soc. 71, 1149-1155.
50. Bitman, J., and Wood, D.L. (1987) Comparison of Direct Transesterification of Fatty Acids with Procedures Applied to Extracts of Human and Cow Milk Fat, J. Am. Oil Chem. Soc. 64, 637.
51. Smith, G.N., Taj, M., and Braganza, J.M. (1991) On the Identification of a Conjugated Diene Component of Duodenal Bile as 9Z,11E-Octadecadienoic Acid, Free Rad. Biol. Med. 10, 13-21.
52. Kepler, C.R., Hirons, K.P., McNeill, J.J., and Tove, S.B. (1966) Intermediates and Products of the Biohydrogenation of Linoleic Acid by Butyrivibrio fibrisolvens, J. Biol. Chem. 241, 1350-1354.
53. Hughes, P.E., Hunter, W.J., and Tove, S.B. (1982) Biohydrogenation of Unsaturated Fatty Acids, J. Biol. Chem. 257, 3643-3649.
54. Fujimoto, K., Kimoto, H., Shishikura, M., Endo, Y., and Ogimoto, K. (1993) Biohydrogenation of Linoleic Acid by Anaerobic Bacteria Isolated from Rumen, Biosci. Biotech. Biochem. 57, 1026-1027.
55. Cawood, P., Wickens, D.G., Iversen, S.A., Braganza, J.M., and Dormandy, T.L. (1983) The Nature of Diene Conjugation in Human Serum, Bile and Duodenal Juice, FEBS Lett. 162, 239-243.
56. Iversen, S.A., Cawood, P., Madigan, M.J., Lawson, A.M., and Dormandy, T.L. (1984) Identification of a Diene Conjugated Component of Human Lipid as Octadeca-9,11-dienoic Acid, FEBS Lett. 171, 320-324.
57. Dormandy, T.L., and Wickens, D.G. (1987) The Experimental and Clinical Pathology of Diene Conjugation, Chem. Phys. Lipids 45, 353-364.
58. Belury, M.A., and Kempa-Steczko, A. (1997) Conjugated Linoleic Acid Modulates Hepatic Lipid Composition in Mice, Lipids 32, 199-204.