What are the trans fatty acids issues in foods after discontinuation of industrially produced trans fats? Ruminant products, vegetable oils, and synthetic supplements

European Journal of Lipid Science and Technology

Volumn 115, Issue 12, 2013, Pages 1378-1401

  Aldai, Noelia ^a   de Renobales, Mertxe ^a   Barron, Luis Javier R ^a   Kramer, John K G ^b  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^b AGRICULTURE AND AGRI FOOD CANADA   (Canada)

Author keywords

Conjugated fatty acids; GC; Health; Labeling; Partial hydrogenation; Ruminant; Trans fatty acids

Indexed keywords

EID: 84890629601     PISSN: 14387697     EISSN: 14389312     Source Type: Journal    
DOI: 10.1002/ejlt.201300072     Document Type: Article

References (187)

1. Mozaffarian, D., Aro, A., Willett, W. C., Health effects of trans-fatty acids: Experimental and observational evidence. Eur. J. Clin. Nutr. 2009, 63, S5-S21.
2. Gebauer, S. K., Chardigny, J. M., Jakobsen, M. U., Lamarche, B., et al., Effects of ruminant trans fatty acids on cardiovascular disease and cancer: A comprehensive review of epidemiological, clinical, and mechanistic studies. Adv. Nutr. 2011, 2, 332-354.
3. World Health Organization, Diet, nutrition and the prevention of chronic diseases, in: Report of a Joint WHO/FAO Expert Consultation, WHO Technical Report Series 916, Geneva, Switzerland 2003.
4. World Health Organization, A comprehensive global monitoring framework including indicators and a set of voluntary global targets for the prevention and control of noncommunicabale diseases, in: Second WHO Discussion Paper, Geneva, Switzerland 2012. http://www.who.int/nmh/events/2012/discussion_paper2_20120322.pdf
5. Ratnayake, W. M. N., Zehaluk, C., in: Akoh, C. C., Lai, O. M., (Eds.), Healthful Lipids, AOCS Press, Champaign, IL 2005, pp. 1-32.
6. Duhem, K., in: Destaillats, F., Sébédio, S. L., Dionisi, F., Chardigny, J. M. (Eds.), Trans Fatty Acids in Human Nutrition, 2nd Edn, The Oily Press, Bridgwater, UK 2009, pp. 381-394.
7. International Margarine Association of the Countries of Europe (IMACE) Code of Practice on Trans Fatty Acids, February 2013. http://www.imace.org/files/files/public-website/European-Margarine-Sector-Code-of-Practice-on-Trans-Fatty-Acids.pdf (accessed June 4, 2013).
8. Downs, S. M., Thow, A. M., Leeder, S. R., The effectiveness of policies for reducing dietary trans fat: A systematic review of the evidence. Bull. World Health Organ. 2103, 91, 262-269H.
9. Brouwer, I. A., Wanders, A. J., Katan, M. B., Trans fatty acids and cardiovascular health: Research completed? Eur. J. Clin. Nutr. 2013, 67, 541-547.
10. Precht, D., Molkentin, J., Frequency distributions of conjugated linoleic acid and trans fatty acid contents in European bovine milk fats. Milchwissenschaft 2000, 55, 687-691.
11. Field, C. J., Blewett, H. H., Proctor, S., Vine, D., Human health benefits of vaccenic acid. Appl. Physiol. Nutr. Metab. 2009, 34, 979-991.
12. Wang, Y., Jacome-Sosa, M. M., Proctor, S. D., The role of ruminant trans fat as a potential nutraceutical in the prevention of cardiovascular disease. Food Res. Int. 2012, 46, 460-468.
13. Sébédio, J. L., Catte, M., Boudier, M. A., Prevost, J., Grandgirard, A., Formation of fatty acid geometric isomers and cyclic fatty acid monomers during the finish frying of frozen prefried potatoes. Food Res. Int. 1996, 29, 109-116.
14. Harfoot, C. G., Hazlewood, G. P., in: Hobson, P. N., Stewart, C. S. (Eds.), The Rumen Microbial Ecosystem, Chapman & Hall, London, UK 1997, pp. 382-426.
15. Shingfield, K. J., Bernard, L., Leroux, C., Chilliard, Y., Role of trans fatty acids in the nutritional regulation of mammary lipogenesis in ruminants. Animal 2010, 4, 1140-1166.
16. Cruz-Hernandez, C., Deng, Z., Zhou, J., Hill, A. R. et al., Methods to analyze conjugated linoleic acids (CLA) and trans-18:1 isomers in dairy fats using a combination of GC, silver ion TLC-GC, and silver ion HPLC. J. AOAC Int. 2004, 87, 545-562.
17. Cruz-Hernandez, C., Kramer, J. K. G., Kennelly, J. J., Sorensen, B. M. et al., Evaluating the CLA and trans 18:1 isomers in milk fat of dairy cows fed increasing amounts of sunflower oil. J. Dairy Sci. 2007, 90, 3786-3801.
18. Shingfield, K. J., Reynolds, C. K., Lupoli, B., Toivonen, V. et al., Effect of forage type and proportion of concentrate in the diet on milk fatty acid composition in cows given sunflower oil and fish oil. Anim. Sci. 2005, 80, 225-238.
19. Roy, A., Ferlay, A., Shingfield, K. J., Chilliard, Y., Examination of the persistency of milk fatty acid composition responses to plant oils in cows given different basal diets, with particular emphasis on trans-C18:1 fatty acids and isomers of conjugated linoleic acid. Anim. Sci. 2006, 82, 479-492.
20. Hristov, A. N., Kennington, L. R., McGuire, M. A., Hunt, C. W., Effects of diets containing linoleic acid- or oleic acid-rich oils on ruminal fermentation and nutrient digestibility, and performance and fatty acid composition of adipose tissue and muscle tissues of finishing cattle. J. Anim. Sci. 2005, 83, 1312-1321.
21. Dugan, M. E. R., Kramer, J. K. G., Robertson, W. M., Meadus, W. J. et al., Comparing subcutaneous adipose tissue in beef and muskox with emphasis on trans 18:1 and conjugated linoleic acids. Lipids 2007, 42, 509-518.
22. Aldai, N., Dugan, M. E. R., Juárez, M., Martínez, A., Osoro, K., Double-muscling character influences the trans-18:1 and conjugated linoleic acid profiles in concentrate-fed yearling bulls. Meat Sci. 2010, 85, 59-65.
23. Leheska, J. M., Thompson, L. D., Howe, J. C., Hentges, E. et al., Effects of conventional and grass feeding systems on the nutrient composition of beef. J. Anim. Sci. 2008, 88, 3575-3585.
24. Aldai, N., Dugan, M. E. R., Rolland, D. C., Kramer, J. K. G., Survey of the fatty acid composition of Canadian beef: 1. Backfat and longissimus lumborum muscle. Can. J. Anim. Sci. 2009, 89, 315-329.
25. Aldai, N., Kramer, J. K. G., Dugan, M. E. R., Fatty acid composition of North American beef: Backfat, in: Proceeding of the 55th International Congress of Meat Science and Technology (ICoMST), Copenhagen, Denmark 2009, pp. 1598-1603, http://www.icomst2009.dk/index.php?id=4048 (accessed June 14, 2013).
26. Ackman, R. G., Has a long-term coexistence adapted us to cope with trans fatty acids? J. Food Lipids 1997, 4, 295-318.
27. Pariza, M. W., Park, Y., Cook, M. E., The biologically active isomers of conjugated linoleic acid. Prog. Lipid Res. 2001, 40, 283-298.
28. Rajakangas, J., Basu, S., Salminen, I., Mutanen, M., Adenoma growth stimulation by the trans-10, cis-12 isomer of conjugated linoleic acid (CLA) is associated with changes in mucosal NF-κB and cyclin D1 protein levels in the Min mouse. J. Nutr. 2003, 133, 1943-1948.
29. Gebauer, S. K., Psota, T. L., Kris-Etherton, P. M., The diversity of health effects of individual trans fatty acid isomers. Lipids 2007, 42, 787-799.
30. Stubbs, C. D., Smith, A. D., The modification of mammalian membrane polyunsaturated fatty acid composition in relation to membrane fluidity and function. Bichim. Biophs. Acta 1984, 779, 89-137.
31. Yoshimoto, N., Nakamura, T., Suzuki, M., Sato, K., Phase properties of binary mixtures of petroselenic acid/oleic acid and asclepic acid/oleic acid. J. Phys. Chem. 1991, 95, 3384-3390.
32. Kalscheur, K. F., Teter, B. B., Piperova, L. S., Erdman, R. A., Effect of dietary forage concentration and buffer addition on duodenal flow of trans-18:1 fatty acids and milk fat production in dairy cows. J. Dairy Sci. 1997, 80, 2104-2114.
33. Griinari, J. M., Dwyer, D. A., McGuire, M. A., Bauman, D. E. et al., Trans-octadecenoic acids and milk fat depression in lactating dairy cows. J. Dairy Sci. 1998, 81, 1251-1261.
34. Kadegowda, A. K. G., Piperova, L. S., Erdman, R. A., Principal component and multivariate analysis of milk long-chain fatty acid composition during diet induced milk fat depression. J. Dairy Sci. 2008, 91, 749-759.
35. Bessa, R. J. B., Portugal, P. V., Mendes, I. A., Santos-Silva, J., Effect of lipid supplementation on growth performance, carcass and meat quality and fatty acid composition of intramuscular lipids of lambs fed dehydrated Lucerne or concentrate. Livest. Prod. Sci. 2005, 96, 185-194.
36. Shingfield, K. J., Bonnet, M., Scollan, N. D., Recent developments in altering the fatty acid composition of ruminant-derived foods. Animal 2013, 7, 132-162.
37. Morán, L., Giráldez, F. J., Panseri, S., Aldai, N. et al., Effect of dietary carnosic acid on the fatty acid profile and flavour stability of meat from fattening lambs. Food Chem. 2013, 138, 2407-2414.
38. Ha, Y. L., Grimm, N. K., Pariza, M. W., Anticarcinogens from fried ground beef: Heat-altered derivatives of linoleic acid. Carcinogenesis 1987, 8, 1881-1887.
39. Sehat, N., Kramer, J. K. G., Mossoba, M. M., Yurawecz, M. P. et al., Identification of conjugated linoleic acid isomers in cheese by gas chromatography, silver ion high performance liquid chromatography and mass spectral reconstructed ion profiles. Comparison of chromatographic elution sequences. Lipids 1998, 33, 963-971.
40. Kramer, J. K. G., Parodi, P. W., Jensen, R. G., Mossoba, M. M. et al., Rumenic acid: A proposed common name for the major conjugated linoleic acid isomer found in natural products. Lipids 1998, 33, 835.
41. Gunstone, F. D., Harwood, J. L., Padley, F. B., The Lipid Handbook, 2nd Edn, Chapman & Hall, London, UK 1994.
42. Yurawecz, M. P., Roach, J. A. G., Sehat, N., Mossoba, M. M. et al., A new conjugated linoleic acid isomer, 7trans, 9cis-octadecadienoic acid, in cow milk, cheese, beef and human milk and adipose tissue. Lipids 1998, 33, 803-809.
43. Bauman, D. E., Corl, B. A., Peterson, D. G., in: Sébédio, J.-L., Christie, W. W., Adlof, R. O., (Eds.), Advances in Conjugated Linoleic Acid Research, Vol. 2, AOCS Press, Champaign, IL 2003, pp. 146-173.
44. Kraft, J., Collomb, J. M., Möckel, P., Sieber, R., Jahreis, G., Differences in CLA isomer distribution of cow's milk lipids. Lipids 2003, 38, 657-664.
45. Mohammed, R., Stanton, C. S., Kennelly, J. J., Kramer, J. K. G. et al., Grazing cows are more efficient than zero-grazed and grass silage-fed cows in milk rumenic acid production. J. Dairy Sci. 2009, 92, 3874-3893.
46. Aldai, N., Lavín, P., Kramer, J. K. G., Jaroso, R., Mantecón, A. R., Breed effect on quality veal production in mountain areas: Emphasis on meat fatty acid composition. Meat Sci. 2012, 92, 687-696.
47. Ratnayake, W. M. N., Overview of methods for the determination of trans fatty acids by gas chromatography, silver-ion thin-layer chromatography, silver-ion liquid chromatography, and gas chromatography/mass spectrometry. J. AOAC. Int. 2004, 87, 523-539.
48. Precht, D., Hagemeister, H., Kanitz, W., Voigt, J., Trans fatty acids and conjugated linoleic acids in milk fat from dairy cows fed a rumen-protected linoleic acid rich diet. Kieler Milchw. Forsch. 2002, 54, 225-242.
49. Kramer, J. K. G., Hernandez, M., Cruz-Hernandez, C., Kraft, J., Dugan, M. E. R., Combining results of two GC separations partly achieves determination of all cis and trans 16:1, 18:1, 18:2, 18: 3 and CLA isomers of milk fat as demonstrated using Ag-ion SPE fractionation. Lipids 2008, 43, 259-273.
50. Delmonte, P., Fardin Kia, A. R., Kramer, J. K. G., Mossoba, M. M. et al., Evaluation of highly polar ionic liquid gas chromatographic column for the determination of the fatty acids in milk fat. J. Chromatogr. A 2012, 1233, 137-146.
51. Baylin, A., Kabagambe, E. K., Ascherio, A., Spiegelman, D., Campos, H., High 18:2 trans-fatty acids in adipose tissue are associated with increased risk of nonfatal acute myocardial infarction in Costa Rican adults. J. Nutr. 2003, 133, 1186-1191.
52. Lemaitre, R. N., King, I. B., Mozaffarian, D., Sotoodehnia, N. et al., Plasma phospholipid trans fatty acids, fatal ischemic heart disease, and sudden cardiac death in older adults: The cardiovascular health study. Circulation 2006, 114, 209-215.
53. Kramer, J. K. G., Cruz-Hernandez, C., Or-Rashid, M., Dugan, M. E. R., The use of total trans-11 containing FA, rather than total 'n-7' FA, is recommended to assess the content of A with a positive health image in ruminant fats. Lipids 2004, 39, 693-695.
54. Destaillats, F., Trottier, J. P., Galvez, J. M. G., Angers, P., Analysis of α-linolenic acid biohydrogenation intermediates in milk fat with emphasis on conjugated linolenic acids. J. Dairy Sci. 2005, 88, 3231-3239.
55. Hopkins, C. Y., Chisholm, M. J., A survey of the conjugated fatty acids of seed oils. J. Am. Oil. Chem. Soc. 1968, 45, 176-182.
56. Suzuki, R., Nogushi, R., Ota, T., Masayuki, A. et al., Cytotoxic effect of conjugated trienoic fatty acids on mouse tumor and monocytic leukemia cells. Lipids 2001, 36, 477-482.
57. Igarashi, M., Miyazawa, T., Preparation and fractionation of conjugated trienes from a-linolenic acid and their growth-inhibitory effects on human tumor cells and fibroblasts. Lipids 2005, 40, 109-113.
58. Craig-Schmidt, M. C., Rong, Y., in: Destaillats, F., Sébédio, J. L., Dionisi, F., Chardigny, J. M. (Eds.), Trans Fatty Acids in Human Nutrition, 2nd Edn, The Oily Press, Bridgwater, UK 2009, pp. 329-380.
59. Fritsche, J., Steinhart, H., Contents of trans fatty acids (TFA) in German foods and estimation of daily intake. Fett/Lipid 1997, 99, 314-318.
60. Cruz-Hernandez, C., Kramer, J. K. G., Kraft, J., Santercole, V. et al., in: Yurawecz, M. P., Kramer, J. K. G., Gudmundsen, O., Pariza, M. P., Banni, S., (Eds.), Advances in Conjugated Linoleic Acid Research, Vol. 3, AOCS Press Champaign, IL 2006, pp. 45-93.
61. Precht, D., Molkentin, J., Trans-geometrical and positional isomers of linoleic acid including conjugated linoleic acid (CLA) in German milk and vegetable fats. Fett/Lipid 1997, 99, 319-326.
62. Precht, D., Molkentin, J., Recent trends in the fatty acid composition of German sunflower margarines, shortenings and cooking fats with emphasis on individual C16:1, C18:1, C18:2, C18:3 and C20:1 trans isomers, Nahrung 2000, 44, 222-228.
63. Ratnayake, W. M. N., Cruz-Hernandez, C., in: Destaillats, F., Sébédio, J. L., Dionisi, F., Chardigny, J. M. (Eds.), Trans Fatty Acids in Human Nutrition, 2nd Edn, The Oily Press, Bridgwater, UK 2009, pp. 105-146.
64. Precht, D., Molkentin, J., Vergleiche der Fettsären und der isomerenverteilung der trans-C18:1-Fettsären von Milchfett, Margarine, Back-, Brat- und Diätfetten. Kieler Milchw. Forsch. 1997, 49, 17-34.
65. Ratnayake, W. M. N., Hansen, S. L., Kennedy, M. P., Evaluation of the CP-Sil 88 and SP-2560 GC columns used in the recently approved AOCS official method Ce 1h-05: Determination of cis-, trans-, saturated, monounsaturated, and polyunsaturated fatty acids in vegetable or non-ruminant animal oils and fats by capillary GLC method. J. Am. Oil Chem. Soc. 2006, 83, 475-488.
66. Richter, E. K., Shawish, K. A., Scheeder, M. R. L., Colombani, P. C., Trans fatty acid content of selected Swiss foods: The Trans Swiss Pilot study. J. Food Comp. Anal. 2009, 22, 479-484.
67. Lehner, P., Entwicklung der Gehalte an trans-Fettsäuren in ausgewählten Produkten des Österreichischen Marktes - Folgestudie der AK-Transfett-Studie 2005. Arbeitskammer. Wien. 2007, 44, 1-22.
68. Fritsche, J., Petersen, K. D., Jahreis, G., Trans octadecenoic fatty acid (TFA) isomers in German foods and bakery goods. Eur. J. Lipid Sci. Technol. 2010, 112, 1363-1368.
69. Khunt, K., Baehr, M., Rohrer, C., Jahreis, G., Trans fatty acid isomers and the trans-9/trans-11 index in fat containing foods. Eur. J. Lipid Sci. Technol. 2011, 113, 1281-1292.
70. Mossoba, M. M., Moss, J., Kramer, J. K. G., Trans fat labeling and levels in U.S. foods: Assessment of gas chromatographic and infrared spectroscopic techniques for regulatory compliance. J. AOAC Int. 2009, 92, 1284-1300.
71. Doell, D., Folmer, D., Lee, H., Honigfort, M., Carberry, S., Updated estimate of trans fat intake by the US population. Food Addit. Contam. 2012, 29, 861-874.
72. Ratnayake, W. M. N., L'Abbe, M. R., Farnworth, S., Dumais, L. et al., Trans fatty acids: Current contents in Canadian foods and estimated intake levels for the Canadian population. J. AOAC Int. 2009, 92, 1258-1276.
73. Ansorena, D., Echarte, A., Ollé, R., Astiasarán, I., 2012: No trans fatty acids in Spanish bakery products. Food Chem. 2013, 138, 422-429.
74. Ackman, R. G., Hooper, S. N., Hooper, D. L., Linolenic acid artifacts from the deodorization of oils. J. Am. Oil Chem. Soc. 1974, 51, 42-49.
75. Bezelgues, J. B., Destaillats, F., in: Destaillats, F., Sébédio, J. L., Dionisi, F., Chardigny, J. M. (Eds.), Trans Fatty Acids in Human Nutrition, 2nd Edn, The Oily Press, Bridgwater, UK 2009, pp. 65-75.
76. Wolff, R. L., trans-Polyunsaturated fatty acids in French edible rapeseed and soybean oils. J. Am. Oil Chem. Soc. 1992, 69, 106-110.
77. Regulations Amending the Food and Drug Regulations (Nutrition Labeling, Nutrient Content Claims and Health Claims), Department of Health, Canada Gazette, Part 11. January 1, 2003. http://canadagazette.gc.ca/partII/2003/20030101/html/sor11-e.html
78. Brühl, L., Determination of trans fatty acids in cold pressed oils and in dried seeds. Fett/Lipid 1996, 98, 380-383.
79. Sébédio, J. L., Ratnayake, W. M. N., Ackman, R. G., Prevost, J., Stability of polyunsaturated omega-3 fatty acids during deep fat frying of Atlantic mackerel (Scomber scombrus L.). Food Res. Int. 1993, 26, 163-173.
80. Juanéda, P., Brac de la Pérrière, S., Sébédio, J. L., Grégoire, S., Influence of heat and refining on formation of CLA isomers in sunflower oil. J. Am. Oil. Chem. Soc. 2003, 80, 937-940.
81. Azizian, H., Kramer, J. K. G., A rapid method for the quantification of fatty acids in fats and oils with emphasis on trans fatty acids using Fourier transform near infrared spectroscopy (FT-NIR). Lipids 2005, 40, 855-867.
82. Li, J., Fan, Y., Zhang, Z., Yu, H. et al., Evaluating the trans fatty acid, CLA, PUFA and erucic acid diversity in human milk from five regions in China. Lipids 2009, 44, 257-271.
83. Mohammed, R., Kennelly, J. J., Kramer, J. K. G., Beauchemin, K. A. et al., Effect of grain type and processing method on rumen fermentation and milk rumenic acid production. Animal 2010, 4, 1425-1444.
84. Piperova, L. S., Teter, B. B., Bruckental, I., Sampugna, J. et al., Mammary lipogenic enzyme activity, trans fatty acids and conjugated linoleic acids are altered in lactating dairy cows fed a milk fat-depressing diet. J. Nutr. 2000, 130, 2568-2574.
85. Aldai, N., Dugan, M. E. R., Kramer, J. K. G., Martínez, A. et al., Length of concentrate finishing affects the fatty acid composition of grass-fed and genetically lean beef: An emphasis on trans-18:1 and conjugated linoleic acid profiles. Animal 2011, 5, 1643-1652.
86. Kramer, R., Wolf, S., Petri, T., von Soosten, D. et al., A commonly used rumen-protected conjugated linoleic acid supplement marginally affects fatty acid distribution of body tissues and gene expression of mammary gland in heifers during early lactation. Lipids Health Dis. 2013, 12, 96.
87. Jain, V. P., Proctor, A., Lall, R., Pilot-scale production of conjugated linoleic acid-rich soy oil by photoirradiation. J. Food Sci. 2008, 73, E183-E192.
88. Shah, U., Proctor, A., Lay, J. O., Moon, K., Determination of CLA trans, trans positional isomerism in CLA-rich soy oil by GC and silver ion HPLC. J. Am. Oil Chem. Soc. 2012, 89, 979-985.
89. Tricon, S., Burdge, G. C., Kew, S., Banerjee, T. et al., Opposing effects of cis-9, trans-11 and trans-10, cis-12 conjugated linoleic acid on blood lipids in healthy humans. Am. J. Clin. Nutr. 2004, 80, 614-620.
90. Wallace, R. J., McKain, N., Shingfield, K. J., Devillard, E., Isomers of conjugated linoleic acids are synthesized via different mechanisms in ruminal digesta and bacteria. J. Lipid Res. 2007, 48, 2247-2254.
91. Destaillats, F., Wolff, R. L., Precht, D., Molkentin, J., Study of individual trans- and cis-16:1 isomers in cow, goat, and ewe cheese fats by gas-liquid chromatography with emphasis on the trans-Δ3 isomer. Lipids 2000, 35, 1027-1032.
92. Leat, W. M. F., Kemp, P., Lysons, R. J., Alexander, T. J. L., Fatty acid composition of depot fats from gnotobiotic lambs. J. Agric. Sci. Camb. 1977, 88, 175-179.
93. Gómez-Cortés, P., Frutos, P., Mantecón, A. R., Juárez, M. et al., Addition of olive oil to dairy ewe diets: Effect on milk fatty acid profile and animal performance. J. Dairy Sci. 2008, 91, 3119-3127.
94. Glasser, F., Schmidely, P., Sauvant, D., Doreau, M., Digestion of fatty acids in ruminants: A meta-analysis of flows and variation factors: 2. C18 fatty acids. Animal 2008, 2, 691-704.
95. Duckett, S. K., Andrae, J. G., Owens, F. N., Effect of high-oil corn or added corn oil on ruminal biohydrogenation of fatty acids and conjugated linoleic acid formation in beef steers fed finishing diets. J. Anim. Sci. 2002, 80, 3353-3360.
96. Bauchart, D., Bispo Villar, E., Thomas, A., Lyan, B. et al., Linseed and rapeseed supplements diversely altered trans 18:1 isomers in total lipids of Longissimus thoracis muscle of finishing Normand cows. Archiva Zootechnica 2010, 13, 5-11.
97. Habeanu, M., Thomas, A., Bispo, E., Gobert, M. et al., Extruded linseed and rapeseed both influenced fatty acid composition of total lipids and their polar and neutral fractions in longissimus thoracis and semitendinosus muscles of finishing Normand cows. Meat Sci. 2013, 96, 99-107.
98. Juárez, M., Dugan, M. E. R., Aalhus, J. L., Aldai, N. et al., Dietary vitamin E inhibits the trans 10-18:1 shift in beef backfat. Can. J. Anim. Sci. 2010, 90, 9-12.
99. Humada, M. J., Serrano, E., Sañudo, C., Rolland, D. C., Dugan, M. E. R., Production system and slaughter age effects on intramuscular fatty acids from young Tudanca bulls. Meat Sci. 2011, 90, 678-685.
100. Aldai, N., Najera, A. L., Dugan, M. E. R., Celaya, R., Osoro, K., Characterization of intramuscular, intermuscular and subcutaneous adipose tissues in yearling bulls of different generic groups. Meat Sci. 2007, 76, 682-691.
101. Griinari, J. M., Bauman, D. E., in: Yurawecz, M. P., Mossoba, M. M., Kramer, J. K. G., Pariza, M. W., Nelson, G. J., (Eds.), Advances in Conjugated Linoleic Acid Research, Vol. 1, AOCS Press, Champaign, IL 1999, pp. 180-200.
102. Aldai, N., Dugan, M. E. R., Kramer, J. K. G., Can the trans-18:1 and conjugated linoleic acid profiles in retail ground beef be healthier than steak? J. Food Comp. Anal. 2010, 23, 326-332.
103. Dugan, M. E. R., Rolland, D. C., Aalhus, J. L., Aldai, N., Kramer, J. K. G., Subcutaneous fat composition of youthful and mature Canadian beef: Emphasis on individual conjugated linoleic acid and trans-18:1 isomers. Can. J. Anim. Sci. 2008, 88, 591-599.
104. Body, D. R., The occurrence of cis-octadec-15-enoic acid as a major biohydrogenation product from methyl linolenate in bovine rumen liquor. Biochem. J. 1976, 157, 741-744.
105. Rego, O. A., Alves, S. P., Antunes, M. S., Rosa, H. J. D. et al., Rumen biohydrogenation-derived fatty acids in milk fat from grazing dairy cows supplemented with rapeseed, sunflower, or linseed oils. J. Dairy Sci. 2009, 92, 4530-4540.
106. Bessa, R. J. B., Alves, S. P., Jerónimo, E., Alfaia, C. M. et al., Effect of lipid supplements on ruminal biohydrogenation intermediates and muscle fatty acids in lambs. Eur. J. Lipid Sci. Technol. 2007, 109, 868-878.
107. Nassu, R. T., Dugan, M. E. R., He, M. L., McAllister, T. A. et al., The effects of feeding flaxseed to beef cows given forage based diets on fatty acids of longissimus thoracis muscle and backfat. Meat Sci. 2011, 89, 469-477.
108. Shingfield, K. J., Lee, M. R. F., Humphries, D. J., Scollan, N. D. et al., Effect of linseed oil and fish oil alone or as an equal mixture on ruminal fatty acid metabolism in growing steers fed maize silage-based diets. J. Anim. Sci. 2011, 89, 3728-3741.
109. Bernard, L., Shingfield, K. J., Rouel, J., Ferlay, A., Chilliard, Y., Effect of plant oils in the diet on performance and milk fatty acid composition in goats fed diets based on grass hay or maize silage. Br. J. Nutr. 2009, 101, 213-224.
110. Chilliard, Y., Doreau, F. M., Effect of different types of forages, animal fat or marine oils in cow's diet on milk fat secretion and composition, especially conjugated linoleic acid (CLA) and polyunsaturated fatty acids. Livest. Prod. Sci. 2001, 70, 31-48.
111. Toral, P. G., Shingfield, K. J., Hervás, G., Toivonen, V., Frutos, P., Effect of fish oil and sunflower oil on rumen fermentation characteristics and fatty acid composition of digesta in ewes fed a high concentrate diet. J. Dairy Sci. 2010, 93, 4804-4817.
112. Kairenius, P., Toivonen, V., Shingfield, K. J., Identification and ruminal outflow of long-chain fatty acid biohydrogenation intermediates in cows fed diets containing fish oil. Lipids 2011, 46, 587-606.
113. Aldai, N., Hervás, G., Belenguer, A., Frutos, P. et al., Evaluating the in vitro metabolism of docosahexaenoic acid in sheep rumen fluid. Lipids 2012, 47, 821-825.
114. Klein, C. M., Jenkins, T. C., Docosahexaenoic acid elevates trans-18:1 isomers but is not directly converted into trans-18:1 isomers in ruminal batch cultures. J. Dairy Sci. 2011, 94, 4676-4683.
115. Wa{ogonek}sowska, I., Maia, M. R. G., Niedźwiedzka, K. M., Czauderna, M. et al., Influence of fish oil on ruminal biohydrogenation of C18 unsaturated fatty acids. Br. J. Nutr. 2006, 95, 1199-1211.
116. AbuGhazaleh, A. A., Jenkins, T. C., Short communication: Docosahexaenoic acid promotes vaccenic acid accumulation in mixed ruminal cultures when incubated with linoleic acid. J. Dairy Sci. 2004, 87, 1047-1050.
117. Lee, M. R. F., Tweed, J. K. S., Moloney, A. P., Scollan, N. D., The effects of fish oil supplementation on rumen metabolism and the biohydrogenation of unsaturated fatty acids in beef steers given diets containing sunflower oil. Anim. Sci. 2005, 80, 361-367.
118. Boeckaert, C., Vlaeminc, B., Mestdagh, J., Fievez, V., In vitro examination of DHA-edible micro algae: 1. Effect on rumen lipolysis and biohydrogenation of linoleic and linolenic acid. Anim. Feed Sci. Technol. 2006, 136, 63-79.
119. Cruz-Hernandez, C., Kramer, J. K. G., Kennelly, J. J., Okine, E. K., Weselake, R. J., Effect of sunflower oil and Monensin on the CLA and 18:1 isomers composition of milk fat in dairy cows, in: 4th Euro Fed Lipid Congress, Workshop on rumen biohydrogenation, Madrid, Spain 2006, Abstract 5860_0434, http://www.eurofedlipid.org/meetings/archive/madrid/5860/5860_0434.pdf (accessed June 15, 2013).
120. Fellner, V., Sauer, F. D., Kramer, J. K. G., Steady-state rates of linoleic acid biohydrogenation by ruminal bacteria in continuous culture. J. Dairy Sci. 1995, 78, 1815-1823.
121. Eifert, E. C., Lana, R. P., Lanna, D. P. D., Leopoldino, W. M. et al., Milk fatty acid profile of cows fed monensin and soybean oil in early lactation. Rev. Bras. Zootecn. 2006, 35, 219-228.
122. Aldai, N., Dugan, M. E. R., Kramer, J. K. G., Mir, P. S., McAllister, T. A., Nonionophore antibiotics do not affect the trans-18:1 and conjugated linoleic acid composition in beef adipose tissue. J. Anim. Sci. 2008, 86, 3522-3532.
123. Jenkins, T. C., Fellner, V., McGuffey, R. K., Monensin by fat interactions on trans fatty acids in cultures of mixed ruminal microorganisms grown in continuous fermentors fed corn or barley. J. Dairy Sci. 2003, 86, 324-330.
124. Mosley, E. E., Powell, G. L., Riley, M. B., Jenkins, T. C., Microbial biohydrogenation of oleic acid to trans isomers in vitro. J. Lipid Res. 2002, 43, 290-296.
125. Proell, J. M., Mosley, E. E., Powell, G. L., Jenkins, T. C., Isomerization of stable isotopically labeled elaidic acid to cis and trans monoenes by ruminal microbes. J. Lipid Res. 2002, 43, 2072-2076.
126. Jenkins, T. C., Wallace, R. J., Moate, P. J., Mosley, E. E., Board-invited review: Recent advances in biohydrogenation of unsaturated fatty acids within the rumen microbial ecosystem. J. Anim. Sci. 2008, 86, 397-412.
127. Horrocks, L. A., in: Snyder, F. (Ed.), Ether Lipids, Chemistry and Biology, Academic Press, New York 1972, pp. 177-272.
128. Wolff, R. L., Characterization of trans-monounsaturated alkenyl chains in total plasmalogens (1-O-alk-1-enyl-2-acyl glycerophospholipids) from sheep heart. Lipids 2002, 37, 811-816.
129. Dannenberger, D., Lorenz, S., Nuernberg, G., Scollan, N. et al., Analysis of fatty aldehyde composition, including 12-methyltridecanal, in plasmalogens from longissimus muscle of concentrate- and pasture-fed bulls. J. Agric. Food Chem. 2006, 54, 182-188.
130. Santercole, V., Mazzette, R., De Santis, E. P. L., Banni, S. et al., Total lipids of Sarda sheep meat that include the fatty acid and alkenyl composition and the CLA and trans-18:1 isomers. Lipids 2007, 42, 361-382.
131. Kraft, J., Kramer, J. K. G., Schoene, F., Chambers, J. R., Jahreis, G., Extensive analysis of long-chain polyunsaturated fatty acids, CLA, trans-18:1 isomers, and plasmalogenic lipids in different retail beef types. J. Agric. Food Chem. 2008, 56, 4775-4782.
132. Alves, S. P., Santos-Silva, J., Cabrita, A. R. J., Fonseca, A. J. M., Bessa, R. J. B., Detailed dimethylacetal and fatty acid composition of rumen content from lambs fed lucerne or concentrate supplemented with soybean oil. PLoS ONE 2013, 8, e58386.
133. Snyder, F. (Ed.), Ether Lipids, Chemistry and Biology. Academic Press, New York 1972, pp. 121-156.
134. Alves, S. P., Bessa, R. J. B., Identification of cis-12, cis-15 octadecadienoic acid and other minor polyenoic fatty acids in ruminant fat. Eur. J. Lipid Sci. Technol. 2007, 109, 879-883.
135. Alves, S. P., Tyburczy, C., Lawrence, P., Bessa, R. J. B., Brenna, J. T., Acetonitrile covalent adduct chemical ionization tandem mass spectrometry of non-methylene-interrupted pentaene fatty acid methyl esters. Rapid Commun. Mass Spectrom. 2011, 25, 1933-1941.
136. Werner, L. B., Hellgren, L. I., Raff, M., Jensen, S. K. et al., Effects of butter from mountain-pasture grazing cows on risk markers of the metabolic syndrome compared with conventional Danish butter: A randomized controlled study. Lipids Health Dis. 2013, 12, 99.
137. Department of Health and Human Services, Food and Drug Administration, Food labeling; trans fatty acids in nutrition labeling; nutrient content claims, and health claims; Final rule, July 11, 2003. Federal Register 68 (No. 133): 41434-41506.
138. Larsen, T. M., Toubro, S., Astrup, A., Efficiency and safety of dietary supplements containing CLA for the treatment of obesity: Evidence from animal and human studies. J. Lipid Res. 2003, 44, 2234-2241.
139. Tholstrup, T., Raff, M., Straarup, E. M., Lund, P. et al., An oil mixture with trans-10, cis-12 conjugated linoleic acid increases markers of inflammation and in vivo lipid peroxidation compared with cis-9, trans-11 conjugated linoleic acid in postmenopausal women. J. Nutr. 2008, 138, 1445-1451.
140. AOCS Official Method Ce 1h-05, Determination of cis-, trans-, saturated, monounsaturated and polyunsaturated fatty acids in vegetable or non-ruminant animal oils and fats by capillary GLC. Approved 2005.
141. Mossoba, M. M., Kramer, J. K. G., Official Methods for the Determination of Trans Fat, 2nd Edn, AOCS Press, Urbana, IL 2009.
142. Delmonte, P., Fardin Kia, A. R., Kramer, J. K. G., Mossoba, M. M. et al., Separation characteristics of fatty acid methyl esters using SLB-1L111, a new ionic liquid coated capillary gas chromatographic column. J. Chromatogr. A 2011, 1218, 545-554.
143. Fardin-Kia, A. R., Delmonte, P., Kramer, J. K. G., Jahreis, G. et al., Separation of the fatty acids in menhaden oil as methyl esters with a highly polar ionic liquid gas chromatographic column and identification by time of flight mass spectrometry. Lipids 2013, 48, 1279-1295.
144. Health Canada, 2006. Food and Nutrition, TRANSforming the food supply. Report of the Trans Far Task Force Submitted to the Minister or Health. Available online: http://www.hc-sc.gc.caJfn-an/aiLformats/hpfb-dgpsa/pdf/nutrition/tf-gr_reprap-eng.pdf (2013 July 15).
145. Ledoux, M., Juanéda, P., Sébédio, J.-L., Trans fatty acids: Definition and occurrence in foods. Eur. J. Lipid Sci. Technol. 2007, 109, 891-900.
146. Wang, Y., Proctor, S. D., Current issues surrounding the definition of trans-fatty acids: Implications for health, industry and food labels. Br. J. Nutr. 2013, doi: 10.1017/S0007114513001086
147. Tholstrup, T., Raff, M., Basu, S., Nonboe, P. et al., Effects of butter high in ruminant trans and monounsaturated fatty acids on lipoproteins, incorporation of fatty acids into lipid classes, plasma C-reactive protein, oxidative stress, hemostatic variables, and insulin in healthy young men. Am. J. Clin. Nutr. 2006, 83, 237-243.
148. Chardigny, J. M., Destaillats, F., Malpuech-Brugère, C., Moulin, J. et al., Do trans fatty acids from industrially produced sources and from natural sources have the same effect on cardiovascular disease risk factors in healthy subjects? Results of the trans Fatty Acids Collaboration (TRANSFACT) study. Am. J. Clin. Nutr. 2008, 87, 558-566.
149. Motard-Bélanger, A., Charest, A., Grenier, G., Paquin, P. et al., Study of the effect of trans fatty acids from ruminants on blood lipids and other risk factors for cardiovascular disease. Am. J. Clin. Nutr. 2008, 87, 593-599.
150. Tardy, A. L., Lambert-Porcheron, S., Malpuech-Brugere, C., Giraudet, C. et al., Dairy and industrial sources of trans fat do not impair peripheral insulin sensitivity in overweight women. Am. J. Clin. Nutr. 2009, 90, 88-94.
151. Bauchart, D., Roy, A., Lorenz, S., Chardigny, J. M. et al., Butters varying in trans 18:1 and cis-9, trans-11 conjugated linoleic acid modify plasma lipoproteins in the hypercholesterolemic rabbit. Lipids 2007, 42, 123-133.
152. Roy, A., Chardigny, J. M., Bauchart, D., Ferlay, A. et al., Butters rich either in trans-10-C18:1 or in trans-11-C18:1 plus cis-9, trans-11 CLA differentially affect plasma lipids and aortic fatty streak in experimental atherosclerosis in rabbits Animal 2007, 1, 467-476.
153. Dupasquier, C. M. C., Patenaude, A. F., Blackwood, D. P., Chouinard, Y. et al., Elaidic and vaccenic trans fatty acids have different effects on atherosclerotic development in low density lipoprotein receptor deficient (LDLr2/2) mice. Ann. Nutr. Metab. 2007, 51, 266.
154. Wolff, R. L., Precht, D., A critique of 50-m CP-Sil 88 capillary columns used alone to assess trans-unsaturated FA in foods: The case of the TRANSFAIR study. Lipids 2002, 37, 627-629.
155. -/- mice. Eur. J. Lipid Sci. Technol. 2011, 113, 572-583.
156. Christie, W. W., Lipid Analysis: Isolation, Separation, Identification and Structural Analysis of Lipids, 3rd Edn, The Oily Press, Barnes & Associates, Bridgewater, UK 2003.
157. Aldai, N., Murray, B. E., Najera, A. I., Troy, D. J., Osoro, K., Derivatization of fatty acids and its application for conjugated linoleic acid studies in ruminant meat lipids. J. Sci. Food Agric. 2005, 85, 1073-1083.
158. Aldai, N., Kramer, J. K. G., Cruz-Hernandez, C., Santercole, V. et al., in: Cherian, G., Poureslami, R. (Eds.), Fats and Fatty Acids in Poultry Nutrition and Health, Context Products Ltd, Leicestershire, UK 2012, pp. 249-290.
159. Jensen, R. G., Ferris, A. M., Lammi-Keefe, C. L., The composition of milk fat. J. Dairy Sci. 1991, 74, 3228-3243.
160. Schröder, M., Vetter, W., Detection of 430 fatty acid methyl esters from a transesterified butter sample. J. Am. Oil Chem. Soc. 2013, 90, 771-790.
161. Kramer, J. K. G., Feller, V., Dugan, M. E. R., Sauer, F. D. et al., 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 1997, 32, 1219-1228.
162. AOCS Official Method Ce 1j-07, Determination of cis-, trans-, saturated, monounsaturated, and polyunsaturated fatty acids in extracted fats by capillary GLC. Amended 2013.
163. Kramer, J. K. G., Blackadar, C. B., Zhou, J., Evaluation of two GC columns (60-m SUPELCOWAX 10 and 100-m CP Sil 88) for analysis of milkfat with emphasis on CLA, 18:1, 18:2, and 18:3 isomers, and short- and long-chain FA. Lipids 2002, 37, 823-835.
164. Sehat, N., Rickert, R., Mossoba, M. M., Kramer, J. K. G. et al., Improved separation of conjugated fatty acid methyl esters by silver ion-high-performance liquid chromatography. Lipids 1999, 34, 407-413.
165. Turner, T., Rolland, D. C., Aldai, N., Dugan, M. E. R., Short communication: Rapid separation of cis9, trans11- and trans7, cis9-18:2 (CLA) isomers from ruminant tissue using a 30m SLB-IL111 ionic column. Can. J. Anim. Sci. 2011, 91, 711-713.
166. Santercole, V., Delmonte, P., Kramer, J. K. G., Comparison of separations of fatty acids from fish products using a 30-m Supelcowax-10 and a 100-m SP-2560 column. Lipids 2012, 47, 329-344.
167. Lawrence, P., Brenna, J. T., Acetonitrile covalent adduct chemical ionization mass spectrometry or double bond localization in non-methylene-interrupted polyene fatty acid methyl esters. Anal. Chem. 2006, 78, 1312-1317.
168. Bertram, S. H., Die Vaccensäure (Eine neue Fettsäure aus Rind-, Schaf- und Butterfett). Biochem Z. 1928, 197, 433-441.
169. Gómez-Cortés, P., Tyburczy, C., Brenna, J. T., Juárez, M., de la Fuente, M. A., Characterization of cis-9 trans-11 trans-15 C18:3 in milk fat by GC and covalent adduct chemical ionization tandem MS. Lipid Res. 2009, 50, 2412-2420.
170. Precht, D., Molkentin, J., Rapid analysis of the isomers of trans-octadecenoic acid in milk fat. Int. Dairy J. 1996, 6, 791-809.
171. Precht, D., Molkentin, J., C18:1, C18:2 and C18:3 trans and cis fatty acid isomers including conjugated cis-9, trans-11 linoleic acid (CLA) as well as total fat composition of German human milk lipids. Nahrung 1999, 43, 233-244.
172. Precht, D., Molketin, J., Identification and quantitation of cis/trans C16:1 and C17:1 fatty acid positional isomers in German human milk lipids by thin-layer chromatography and gas chromatography/mass spectrometry. Eur. J. Lipid Sci. Technol. 2000, 102, 102-113.
173. Kramer, J. K. G., Cruz-Hernandez, C., Zhou, J., Conjugated linoleic acids and octadecenoic acids: Analysis by GC. Eur. J. Lipid Sci. Technol. 2001, 103, 600-609.
174. Ratnayake, W. M., Plouffe, L. J., Pasquier, E., Gagnon, C., Temperature-sensitive resolution of cis- and trans-fatty acid isomers of partially hydrogenated vegetable oils on SP-2560 and CP-Sil 88 Capillary Columns. J. AOAC Int. 2002, 85, 1112-1118.
175. Precht, D., Molkentin, J., Overestimation of linoleic acid and trans-C18:2 isomers in milk fats with emphasis on trans Δ9, trans Δ12-octadecadienoic acid. Milchwissenschaft 2003, 58, 30-34.
176. Shingfield, K. J., Ahvenjärvi, S., Toivonen, V., Ärölä, A. et al., Effect of dietary fish oil on biohydrogenation of fatty acids and milk fatty acid content in cows. Anim. Sci. 2003, 77, 165-179.
177. Golay, P. A., Dionisi, F., Hug, B., Giuffrida, F., Destaillats, F., Direct quantification of fatty acids in dairy powders with special emphasis on trans fatty acid content. Food Chem. 2006, 101, 1115-1120.
178. Shingfield, K. J., Reynolds, C. K., Hervas, G., Griinari, J. M. et al., Examination of the persistency of milk fatty acid composition responses to fish oil and sunflower oil in the diet of dairy cows. J. Dairy Sci. 2006, 89, 714-732.
179. Alves, S. P., Bessa, R. J. B., Comparison of two gas-liquid chromatography columns for the analysis of fatty acids in ruminant meat. J. Chromatogr. A 2009, 1216, 5130-5139.
180. Delmonte, P., Fardin-Kia, A. R., Hu, Q., Rader, J. I., Review of methods for preparation and gas chromatographic separation of trans and cis reference fatty acids. J. AOAC Int. 2009, 92, 1310-1326.
181. Golay, P. A., Giuffrida, F., Dionisi, F., Destaillats, F., Streamlined methods for the resolution and quantification of fatty acids including trans fatty acid isomers in food products by gas chromatography. J. AOAC Int. 2009, 92, 1301-1309.
182. Dugan, M. E. R., Aldai, N., Aalhus, J. L., Rolland, D. C., Kramer, J. K. G., Review: Trans-forming beef to provide healthier fatty acid profiles. Can. J. Anim. Sci. 2011, 91, 545-556.
183. Halmemies-Beauchet-Filleau, A., Kokkonen, T., Lampi, A. M., Toivonen, V. et al., Effect of plant oils and camelina expeller on milk fatty acid composition in lactating cows fed diets based on red clover silage. J. Dairy Sci. 2011, 94, 4413-4430.
184. Jerónimo, E., Alves, S. P., Alfaia, C. M., Prates, J. A. M. et al., Biohydrogenation intermediates are differently deposited between polar and neutral intramuscular lipids of lambs. Eur. J. Lipid Sci. Technol. 2011, 113, 924-934.
185. Honkanen, A. M., Griinari, J. M., Vanhatalo, A., Ahvenjärvi, S. et al., Characterization of the disappearance and formation of biohydrogenation intermediates during incubations of linoleic acid with rumen fluid in vitro. J. Dairy Sci. 2012, 95, 1376-1394.
186. Destaillats, F., Guitard, M., Cruz-Hernandez, C., Identification of Δ6-monounsaturated fatty acids in human hair and nail samples by gas-chromatography-mass-spectrometry using ionic-liquid coated capillary column. J. Chromatogr. A 2011, 1218, 9384-9389.
187. Wolff, R. L., Combe, N. A., Destaillats, F., Boue, C. et al., Follow-up of the Δ4 to Δ16 trans-18:1 isomer profile and content in French processed foods containing partially hydrogenated vegetable oils during the period 1995-1999. Analytical and nutritional implications. Lipids 2000, 35, 815-825.