Trans fatty acid analyses in samples of marine origin: The risk of false positives

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 8, 2011, Pages 3520-3531

  Mjøs, Svein A ^a,b   Haugsgjerd, Bjørn Ole ^a  

^a NOFIMA   (Norway)

^b UNIVERSITY OF BERGEN   (Norway)

Author keywords

interferents; marine lipids; trans fatty acids

Indexed keywords

CHROMATOGRAPHIC CONDITIONS; COATED CAPILLARIES; FALSE POSITIVE; INTERFERENTS; MARINE LIPIDS; NATURALLY OCCURRING; RETENTION INDEX; TEMPERATURE CONDITIONS; TRANS FATTY ACID;

GAS CHROMATOGRAPHY; LIPIDS;

FATTY ACIDS;

FATTY ACID;

ARTICLE; GAS CHROMATOGRAPHY; LABORATORY DIAGNOSIS; MARINE BIOLOGY;

CHROMATOGRAPHY, GAS; FALSE POSITIVE REACTIONS; FATTY ACIDS; MARINE BIOLOGY;

EID: 79954988238     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf104156v     Document Type: Article

References (65)

1. Dijkstraa, A. Revisiting the formation of trans isomers during partial hydrogenation of triacylglycerol oils Eur. J. Lipid Sci. Technol. 2006, 108, 249-264
2. Schmidt, S. Formation of trans unsaturation during partial hydrogenation Eur. J. Lipid Sci. Technol. 2000, 102, 646-648
3. Grandgirard, A.; Sebedio, J. L.; Fleury, J. Geometrical isomerization of linoleinic acid during heat treatment of vegetable oils J. Am. Oil Chem. Soc. 1984, 61, 1563-1568
4. Wolff, R. L. Heat-induced geometrical isomerization of α-linolenic acid: effect of temperature and heating time on the appearance of individual isomers J. Am. Oil Chem. Soc. 1993, 70, 425-430
5. Hénon, G.; Kemény, Z.; Recseg, K.; Zwobada, F.; Kovari, K. Deodorization of vegetable oils. Part I: Modelling the geometrical isomerization of polyunsaturated fatty acids J. Am. Oil Chem. Soc. 1999, 75, 73-81 (Pubitemid 129676538)
6. Fritsche, J.; Steinhart, H. Analysis, occurence, and physiological properties of trans fatty acids (TFA) with particular ephasis on conjugated linoleic acid isomers (CLA) - a review Fett/Lipid 1998, 100, 190-210
7. Destaillats, F.; Golay, R. A.; Joffre, F.; de Wispelaere, M.; Huga, B.; Giuffrida, F.; Fauconnot, F.; Dionisi, F. Comparison of available analytical methods to measure trans -octadecenoic acid isomeric profile and content by gas-liquid chromatography in milk fat J. Chromatogr., A 2007, 1145, 222-228 (Pubitemid 46335800)
8. American Society for Clinical Nutrition and American Institute of Nutrition. Position paper on trans fatty acids. ASCN/AIN Task Force on Trans Fatty Acids. Am. J. Clin. Nutr. 1996, 63, 663 - 670.
9. Uauy, R.; Aro, A.; Clarke, R.; Ghafoorunissa, R.; LAbbe, M.; Mozaffarian, D.; Skeaff, M.; Stender, S.; Tavella, M. WHO Scientific Update on trans fatty acids: summary and conclusions Eur. J. Clin. Nutr. 2009, 63, S68-S75
10. 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
11. Bysted, A.; Mikkelsen, Å.; Leth, T. Substitution of trans fatty acids in foods on the Danish market Eur. J. Lipid Sci. Technol. 2009, 111, 574-583
12. Arshad, F.; Sundram, K. Trans fatty acids - an update on its regulatory status Palm Oil Dev. 2003, 39, 16-19
13. Friesen, R.; Innis, S. M. Trans fatty acids in human milk in canada declined with the introduction of trans fat food labeling J. Nutr. 2006, 136, 2558-2561 (Pubitemid 44521613)
14. Juanéda, P.; Ledoux, M.; Sébédio, J. L. Analytical methods for determination of trans fatty acid content in food Eur. J. Lipid Sci. Technol. 2007, 109, 901-907
15. Firestone, D., Ed. Official Methods and Recommended Practices of the American Oil Chemists Society, 4 th ed.; American Oil Chemists Society: Champaign, IL, 1997.
16. ISO 15304:2002 Animal and vegetable fats and oils - Determination of the content of trans fatty acid isomers - Gas chromatographic method; International Organization for Standardization: Geneva, Switzerland, 2002.
17. AOAC official method 994.15: total cis-and trans -octadecenoic isomers and general fatty acid composition in hydrogenated vegetable oils and animal fats. Official Methods of Analysis, 17 th ed.; AOAC International: Gaithersburg, MD, 2003.
18. Castello, G.; Vezzani, S.; DAmato, G. Effect of temperature on the polarity of some stationary phases for gas chromatography J. Chromatogr., A 1997, 779, 275-286 (Pubitemid 27402013)
19. Kiridena, W.; Qian, J.; Koziol, W. W.; Poole, C. F. Evaluation of the separation characteristics of application-specific (fatty acid methyl esters) open-tubular columns for gas chromatography J. Sep. Sci. 2007, 30, 740-745 (Pubitemid 46542084)
20. Mjøs, S. A. Identification of fatty acids in gas chromatography by application of different temperature and pressure programs on a single capillary column J. Chromatogr., A 2003, 1015, 151-161 (Pubitemid 37163514)
21. Mjøs, S. A. Two-dimensional fatty acid retention indices J. Chromatogr., A 2004, 1061, 201-209 (Pubitemid 39586748)
22. Thompson, R. H. Direct measurement of total trans-and cis -octadecenoic fatty acids based on a gas-liquid chromatographic class separation of trans -18:1 and cis -18:1 fatty acid methyl esters J. Chromatogr. Sci. 1997, 35, 536-544 (Pubitemid 127478582)
23. Martin, C. A.; de Oliveira, C. C.; Visentainer, J. V.; Matsushita, M.; de Souza, N. E. Optimization of the selectivity of a cyanopropyl stationary phase for the gas chromatographic analysis of trans fatty acids J. Chromatogr., A 2008, 1194, 111-117
24. Mjøs, S. A. Properties of trans isomers of eicosapentaenoic acid and eicosahexaenoic acid methyl esters on cyanopropyl stationary phases J. Chromatogr., A 2005, 1100, 185-192 (Pubitemid 41773357)
25. Wolff, R. L. Analysis of α-linolenic acid geometrical isomers in deodorized oils by capillary gas-liquid chromatography on cyanoalkyl polysiloxane stationary phases: a note of caution J. Am. Oil Chem. Soc. 1994, 71, 907-909
26. Miwa, T. K.; Mikolajczak, K. L.; Earle, F. R.; Wolff, I. A. Gas chromatographic characterization of fatty acids Anal. Chem. 1960, 32, 1739-1742
27. Mjøs, S. A.; Pettersen, J. Determination of trans double bonds in polyunsaturated fatty acid methyl esters from their electron impact mass spectra Eur. J. Lipid Sci. Technol. 2003, 105, 156-164 (Pubitemid 36589230)
28. Bligh, E. G.; Dyer, W. J. A rapid method of total lipid extraction and purification Can. J. Biochem. Physiol. 1959, 37, 911-917
29. Mjøs, S. A. The prediction of fatty acid structure from selected ions in electron impact mass spectra of fatty acid methyl esters Eur. J. Lipid. Sci. Technol. 2004, 106, 550-560 (Pubitemid 39220995)
30. Mjøs, S. A.; Grahl-Nielsen, O. Prediction of gas chromatographic retention of polyunsaturated fatty acid methyl esters J. Chromatogr., A 2006, 1110, 171-180 (Pubitemid 43375930)
31. Mjøs, S. A.; Solvang, M. Geometrical isomerisation of EPA and DHA at high temperatures Eur. J. Lipid Sci. Technol. 2006, 108, 589-597 (Pubitemid 44146212)
32. The nomenclature of lipids. J. Lipid Res. 1978, 19, 114 - 128.
33. Ettre, L. S. Nomenclature for chromatography Pure Appl. Chem. 1993, 65, 819-872
34. Mjøs, S. A. Retention behavior of trans isomers of eicosapentaenoic and docosahexaenoic acid methyl esters on a polyethylene glycol stationary phase Eur. J. Lipid Sci. Technol. 2008, 110, 547-553
35. 18 fatty acid positional isomers J. Am. Oil Chem. Soc. 1997, 74, 125-130 (Pubitemid 127553464)
36. 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
37. Ratnayake, W. M. N.; Pelletier, G. Positional and geometrical isomers of linoleic acid in partially hydrogenated oils J. Am. Oil Chem. Soc. 1992, 69, 95-105
38. Wolff, R. L. Cis-trans isomerization of octadecatrienoic acids during heating. Study of pinolenic (cis-5, cis-9, cis-12 18:3) acid geometrical isomers in heated pine seed oil J. Am. Oil Chem. Soc. 1994, 71, 1129-1134
39. Wolff, R. L.; Bayard, C. C. Improvement in the resoution of individual trans -18:1 isomers by capillary gas-liquid chromatography: use of a 100-m CP-Sil 88 column J. Am. Oil Chem. Soc. 1995, 72, 1197-1212
40. Wijesundera, R. C.; Ackman, R. G. Evaluation of calculation of ECL values for cis and trans isomers of some diethylenic C20 fatty acids: mono- and diethylenic capillary GLC data for the liquid phases SP-2340, Supelcowax-10, and SPB-1 J. Chromatogr. Sci. 1989, 27, 399-404
41. Molkentin, J.; Precht, D. Occurence of trans-C16:1 acids in bovine milkfats and partially hydrogenated edible oils Milchwissenshaft 1997, 52, 380-385 (Pubitemid 127099117)
42. Ratnayake, W. N.; Ackman, R. G. Fatty alcohols in capelin, herring and mackerel oils and muscle lipids: I. Fatty alcohol details linking dietary copepod fat with certain fish depot fats Lipids 1979, 14, 795-803
43. Ackman, R. G.; Hansen, R. P. The occurrence of diastereomers of phytanic and pristanic acids and their determination by gas-liquid chromatography Lipids 1967, 2, 357-362
44. 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 and 18:3 except CLA isomers of milk fat as demonstrated using Ag-ion SPE fractionation Lipids 2008, 43, 259-273
45. 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, 475-487
46. Buchgrabner, M.; Ulberth, F. Determination of low level trans unsaturation in physically refined vegetable oils by capillary GLC - results of 3 intercomparison studies Eur. J. Lipid Sci. Technol. 2002, 104, 792-799 (Pubitemid 36098926)
47. Duchateau, G. S. M. J. E.; van Oosten, H. J.; Vasconcellos, M. A. Analysis of cis- and trans-fatty acid isomers in hydrogenated and refined vegetable oils by capillary gas-liquid chromatography J. Am. Oil Chem. Soc. 1996, 73, 275-282 (Pubitemid 126525469)
48. Fritsche, J.; Steinhart, H. Trans fatty acid content in German margarines Fett/Lipid 1997, 99, 214-217
49. Ratnayake, W. M. N.; Plouffe, L. J.; Pasquier, E.; Ganon, 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 (Pubitemid 135694537)
50. Kemény, Z.; Recseg, K.; Hénon, G.; Kóvari, K.; Zwobada, F. Deodorization of vegetable oils: prediction of trans polyunsaturated fatty acid content J. Am. Oil Chem. Soc. 2001, 78, 973-979 (Pubitemid 33113991)
51. León-Camacho, M.; Ruiz-Méndez, M. V.; Graciani-Constante, M.; Graciani-Constante, E. Kinetics of the cis-trans isomerization of linoleic acid in the deodorization and/or physical refining of edible fats Eur. J. Lipid Sci. Technol. 2001, 103, 85-92
52. OKeefe, S. F.; Wiley, V. A.; Wright, D. Effect of temperature on linolenic acid loss and 18:3 d9-cis d12-cis, d15 trans formation in soybean oil J. Am. Oil Chem. Soc. 1993, 70, 915-916
53. Wolff, R. L. Resolution of linolenic acid geometrical isomers by gas-liquid chromatography on a capillary column coated with a 100% cyanopropyl polysiloxane film (CP Sil-88) J. Chromatogr. Sci. 1992, 30, 17-22
54. Christie, W. W. Gas chromatography-mass spectrometry methods for structural analysis of fatty acids Lipids 1998, 33, 343-353 (Pubitemid 28217379)
55. Brakstad, F. Accurate determination of double bond position in mono-unsaturated straight-chain fatty acid ethyl esters from conventional electron impact mass spectra by quantitative spectrum-structure modelling Chem. Int. Lab. Syst. 1993, 19, 87-100 (Pubitemid 23174098)
56. Ledoux, M.; Laloux, L.; Wolff, R. L. Analytical methods for determination of trans-C18 fatty acid isomers in milk fat. A review Analusis 2000, 28, 402-412
57. Molkentin, J.; Precht, D. Optimized analysis of trans -octadecenoic acids in edible fats Chromatographia 1995, 41, 267-272
58. Mossoba, M. M.; McDonald, R. E.; Prosser, A. R. Gas chromatographic/ matrix isolation/fourier transform infrared spectroscopic determination of trans-monounsaturated and saturated fatty acid methyl esters in partially hydrogenated menhaden oil J. Agric. Food Chem. 1993, 41, 1998-2002
59. Mjøs, S. A.; Pettersen, J. A rapid method for the analysis of hydrogenated fats by GC with IR detection J. Am. Oil Chem. Soc. 2003, 80, 839-846
60. Hyötyläinen, T.; Kallio, M.; Lehtonen, M.; Lintonen, S.; Peräjoki, P.; ussila, M.; Riekkola, M. L. Comprehensive two-dimensional gas chromatography in the analysis of dietary fatty acids J. Sep. Sci. 2004, 27, 459-467 (Pubitemid 38559801)
61. Western, R. J.; Lau, S. S. G.; Marriott, P. J.; Nichols, P. D. Positional and geometrical isomer separation of FAME by comprehensive 2-D GC Lipids 2002, 37, 715-724
62. Bergé, J. P.; Barnathan, G. Fatty acids from lipids of marine organisms: molecular biodiversity, roles as biomarkers, biologically active compounds, and economical aspects Adv. Biochem. Eng./Biotechnol. 2005, 96, 49-125 (Pubitemid 44617132)
63. Hanuš, L. O.; Levitsky, D. O.; Shkrob, I.; Dembitsky, V. M. Plasmalogens, fatty acids and alkyl glyceryl ethers of marine and freshwater clams and mussels Food Chem. 2009, 116, 491-498
64. Brosche, T.; Platt, D.; Vostrowsky, O. Methyl enol ethers as artefacts in capillary gas chromatographic profiles of aldehyde dimethyl acetals J. Chromatogr. 1985, 345, 219-227 (Pubitemid 16182518)
65. Nichols, P. D.; Mooney, B. D.; Elliott, N. G. Unusually high levels of non-saponifiable lipids in the fishes escolar and rudderfish. Identification by gas and thin-layer chromatography J. Chromatogr., A 2001, 936, 183-191 (Pubitemid 33044631)