Trans isomers of EPA and DHA in omega-3 products on the European market

Lipids

Volumn 47, Issue 7, 2012, Pages 659-667

  Sciotto, Caterina ^a,b   Mjøs, Svein A ^a,c  

^a UNIVERSITY OF BERGEN   (Norway)

^b UNIVERSITY OF MESSINA   (Italy)

^c NOFIMA   (Norway)

Author keywords

DHA; EPA; Fish oil; Fish oil concentrates; Omega 3 supplements; Thermal isomerization; Trans fatty acids

Indexed keywords

CYANOPROPYL; DOCOSAHEXAENOIC ACID; FATTY ACID ESTER; ICOSAPENTAENOIC ACID; OIL; OMEGA 3 FATTY ACID; PROPANE; UNCLASSIFIED DRUG;

ARTICLE; DEODORIZATION; DIET SUPPLEMENTATION; EUROPE; FATTY ACID ANALYSIS; GAS CHROMATOGRAPHY; ISOMERIZATION; MARKET;

CHROMATOGRAPHY, GAS; DOCOSAHEXAENOIC ACIDS; EICOSAPENTAENOIC ACID; EUROPE; FATTY ACIDS, OMEGA-3; FISH OILS; FLAME IONIZATION;

EID: 84863987570     PISSN: 00244201     EISSN: 15589307     Source Type: Journal    
DOI: 10.1007/s11745-012-3672-3     Document Type: Article

References (38)

1. von Schacky C (2003) The role of omega-3 fatty acids in cardiovascular disease. Curr Atheroscler Rep 5:139-145
2. Mozaffarian D, Rimm EB (2006) Fish intake contaminants and human health-evaluating the risks and the benefits. J Am Med Assoc 296:1885-1899
3. Fontani G, Corradeschi F, Felici A, Alfatti F, Migliorini S, Lodi L (2005) Cognitive and physiological effects of omega-3 polyunsaturated fatty acid supplementation in healthy subjects. Eur J Clin Invest 35:691-699
4. Morris MC, Evans DA, Bienias JL, Tangney CC, Bennett DA, Wilson RS, Aggarwal N, Schneider J (2003) Consumption of fish and n-3 fatty acids and risk of incident Alzheimer disease. Arch Neur 60:940-946
5. Lands W E M (1992) Biochemistry and physiology of n-3 fatty acids. FASEB J 6:2530-2536
6. Wall R, Ross RP, Fitzgerald GF, Stanton C (2010) Fatty acids from fish: the anti-inflammatory potential of long-chain omega-3 fatty acids. Nutr Rev 68:280-290
7. Patterson AC, Stark KD (2008) Direct determinations of the fatty acid composition of daily dietary intakes-incorporating nutraceuticals and functional food strategies to increase n-3 highly unsaturated fatty acids. J Am Coll Nutr 27:538-546
8. Simopoulos AP, Leaf A, Salem N (2000) Workshop statement on the essentiality of and recommended dietary Intakes for omega-6 and omega-3 fatty acids. Prostag Leukotr Ess 63:119-121
9. Kris-Etherton PM, Taylor DS, Yu-Poth S, Huth P, Moriarty KM, Fishell V, Hargrove RL, Zhao G, Etherton TD (2000) Polyunsaturated fatty acids in the food chain in the United States. Am J Clin Nutr 71:179S-188S
10. Wijesundera RC, Ratnayake W M N, Ackman RG (1989) Eicosapentaenoic acid geometrical isomer artifacts in heated fish oil esters. J Am Oil Chem Soc 66:1822-1830
11. Fournier V, Destaillats F, Juanéda P, Dionisi F, Lambelet P, Sébédio JL, Berdeux O (2006) Thermal degradation of longchain polyunsaturated fatty acids during deodorization of fish oils. Eur J Lipi Sci Technol 108:33-42
12. Fournier V, Juanéda P, Destaillats F, Dionisi F, Lambelet P, Sébédio JL, Berdeux O (2006) Analysis of eicosapentaenoic acid and docosahexaenoic acid geometrical isomers formed during fish oil deodorization. J Chromatogr A 1129:21-28
13. Mjøs SA, Solvang M (2006) Geometrical isomerisation of EPA and DHA at high temperatures. Eur J Lipid Sci Technol 108:589-597
14. Fournier V, Destaillats F, Hug B, Golay PA, Joffre F, Juanéda P, Sémon E, Dionisi F, Lambelet P, Sébédio JL, Berdeaux O (2007) Quantification of eicosapentaenoic and docosahexaenoic acid geometrical isomers formed during fish oil deodorization by gas-liquid chromatography. J Chromatogr A 1154:353-359
15. Official methods and recommended practices of the American Oil Chemists' Society (1998) 5th edn. AOCS Press, Champaign, IL (USA)
16. Mjøs SA (2005) Properties of trans isomers of eicosapentaenoic acid and eicosahexaenoic acid methyl esters on cyanopropyl stationary phases. J Chromatogr A 1100:185-192
17. Mjøs SA (2004) Two-dimensional fatty acid retention indices. J Chromatogr A 1061:201-209
18. http://www.chrombox.org/data (Accessed 01. Feb.2012)
19. Mjøs SA (2004) The prediction of fatty acid structure from selected ions in electron impact mass spectra of fatty acid methyl esters. Eur J Lipid Sci Technol 106:550-560
20. Mjøs SA (2003) Identification of fatty acids in gas chromatography by application of different temperature and pressure programs on a single capillary column. J Chromatogr A 1015:151-161
21. Mjøs SA, Grahl-Nielsen O (2006) Prediction of gas chromatographic retention of polyunsaturated fatty acid methyl esters. J Chromatogr A 1110:171-180
22. Castello G, Vezzani S, D'Amato G (1997) Effect of temperature on the polarity of some stationary phases for gas chromatography. J Chromatogr A 779:275-286
23. Mjøs SA (2008) Retention behavior of trans isomers of eicosapentaenoic and docosahexaenoic acid methyl esters on a polyethylene glycol stationary phase. Eur J Lipid Sci Technol 110:547-553
24. Hénon G, Kemény Z, Recseg K, Zwobada F, Kovari K (1999) Deodorization of vegetable oils-part I: modelling the geometrical isomerization of polyunsaturated fatty acids. J Am Oil Chem Soc 75:73-81
25. Wolff RL (1993) Further studies on artificial geometrical isomers of alpha-linolenic acid in edible linolenic acid-containing oils. J Am Oil Chem Soc 70:219-224
26. Wolff RL (1993) Heat-induced geometrical isomerization of alpha-linolenic acid: effect of temperature and heating time on the appearance of individual isomers. J Am Oil Chem Soc 70:425-430
27. Kemény Z, Recseg K, Hénon G, Kóvari K, Zwobada F (2001) Deodorization of vegetable oils: prediction of trans polyunsaturated fatty acid content. J Am Oil Chem Soc 78:973-979
28. Wolff RL, Nour M, Bayard CC (1996) Participation of the cis-12 ethylenic bond to cis-trans isomerization of the cis-9 and cis-15 ethylenic bonds in heated alpha-linolenic acid. J Am Oil Chem Soc 73:327-332
29. Wolff RL 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 71:1129-1134
30. Wolff RL (1992) Trans-polyunsaturated fatty acids in French edible rapeseed and soybean oils. J Am Oil Chem Soc 69:106-110
31. Martin CA, Visentainer JV, de Oliveira AN, de Oliveira CC, Matsushita M, de Souza NE (2008) Fatty acid contents of Brazilian soybean oils with emphasis on trans fatty acids. J Braz Chem Soc 19:117-122
32. Loï C, Chardigny JM, Cordelet C, Leclere L, Genty M, Ginies C, Noël JP, Sébédio JL (2000) Incorporation and metabolism of trans 20:5 in endothelial cells-effect on prostacyclin synthesis. Lipids 35:911-918
33. Loï C, Chardigny JM, Berdeaux O, Vatèle JM, Poullain D, Noël JP, Sébédio JL (1998) Effects of three trans isomers of eicosapentaenoic acid on rat platelet aggregation and arachidonic acid metabolism. Thromb Haemost 80:656-661
34. O'Keefe SF, Lagarde M, Grandgirard A, Sebedio JL (1990) Trans n-3 eicosapentaenoic and docosahexaenoic acid isomers exhibit different inhibitory effects on arachidonic acid metabolism in human platelets compared to the respective cis fatty acids. J Lipid Res 31:1241-1246
35. Chardigny JM, Sébédio JL, Juanéda P, Vatèle JM, Grandgirard A (1993) Occurrence of N-3 trans polyunsaturated fatty acids in human platelets. Nutr Res 13:1105-1111
36. Chardigny JM, Sebedio JL, Grandgirard A, Martine L, Berdeaux O, Vatele JM (1996) Identification of novel trans isomers of 20:5n-3 in liver lipids of rats fed a heated oil. Lipids 31:165-168
37. Chardigny JM, Bron A, Sébédio JL, Juaneda P, Grandgirard A (1994) Kinetics of incorporation of N-3 trans fatty acid in rat retina. Nutr Res 14:909-917
38. Acar N, Bonhomme B, Joffre C, Bron AM, Creuzot-Garcher C, Bretillon L, Doly M, Chardigny JM (2006) The retina is more susceptible than the brain and the liver to the incorporation of trans isomers of DHA in rats consuming trans isomers of alphalinolenic acid. Reprod Nutr Dev 5:515-525