Identification and ruminal outflow of long-chain fatty acid biohydrogenation intermediates in cows fed diets containing fish oil

Lipids

Volumn 46, Issue 7, 2011, Pages 587-606

  Kairenius, Piia ^a   Toivonen, Vesa ^a   Shingfield, Kevin J ^a  

^a ANIMAL PRODUCTION RESEARCH   (Finland)

Author keywords

Biohydrogenation; Fish oil; Gas chromatography mass spectrometry; Lactating cow; Silver ion thin layer chromatography

Indexed keywords

CARBOXYL GROUP; CIS FATTY ACID; FATTY ACID ESTER; FISH OIL; LONG CHAIN FATTY ACID; TRANS FATTY ACID;

ANIMAL FOOD; ANIMAL TISSUE; ARTICLE; BIOACCUMULATION; CHEMICAL BOND; CHEMICAL STRUCTURE; CONTROLLED STUDY; COW; DIET SUPPLEMENTATION; FAT INTAKE; FATTY ACID ANALYSIS; FATTY ACID SYNTHESIS; FLOW KINETICS; FOOD ANALYSIS; HYDROGENATION; ISOMERIZATION; LACTATION; LIPID COMPOSITION; MASS FRAGMENTOGRAPHY; NONHUMAN; NUTRIENT CONCENTRATION; RUMINANT STOMACH; THIN LAYER CHROMATOGRAPHY; TISSUE DISTRIBUTION;

ANIMAL FEED; ANIMALS; CATTLE; CHROMATOGRAPHY, THIN LAYER; DIET; DIETARY SUPPLEMENTS; FATTY ACIDS; FATTY ACIDS, ESSENTIAL; FATTY ACIDS, OMEGA-3; FATTY ACIDS, OMEGA-6; FEMALE; FISH OILS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HYDROGENATION; LACTATION; RUMEN;

EID: 79959894740     PISSN: 00244201     EISSN: 15589307     Source Type: Journal    
DOI: 10.1007/s11745-011-3561-1     Document Type: Article

References (60)

1. World Health Organization (2003) Diet, nutrition and the prevention of chronic diseases. World Health Organ Tech Rep Ser 916:1-148
2. Wang C, Harris WS, Chung M, Lichtenstein AH, Balk EM, Kupelnick B, Jordan HS, Lau J (2006) n-3 Fatty acids from fish or fish-oil supplements, but not a-linolenic acid, benefit cardiovascular disease outcomes in primary- and secondary-prevention studies: a systematic review. Am J Clin Nutr 84:5-17 (Pubitemid 44699166)
3. Harris WS, Mozaffarian D, Lefevre M, Toner CD, Colombo J, Cunnane SC, Holden JM, Klurfeld DM, Morris MC, Whelan J (2009) Towards establishing dietary reference intakes for eicosapentaenoic and docosahexaenoic acids. J Nutr 139:804S-819S
4. Givens DI, Shingfield KJ (2006) Optimising dairy milk fatty acid composition. In: Williams C, Buttriss J (eds) Improving the fat content of foods. Woodhead, Cambridge, pp 252-280
5. Scollan N, Hocquette J-F, Nuernberg K, Dannenberger D, Richardson I, Moloney A (2006) Innovations in beef production systems that enhance the nutritional and health value of beef lipids and their relationship with meat quality. Meat Sci 74:17-33
6. Chilliard Y, Glasser F, Ferlay A (2007) Diet, rumen biohydrogenation and nutritional quality of cow and goat milk fat. Eur J Lipid Sci Technol 109:828-855 (Pubitemid 47313000)
7. Shingfield KJ, Ahvenjärvi S, Toivonen V, A ̈ rölä A, Nurmela KVV, Huhtanen P, Griinari JM (2003) Effect of dietary fish oil on biohydrogenation of fatty acids and milk fatty acid content in cows. Anim Sci 77:165-179 (Pubitemid 36953201)
8. Lee MRF, Shingfield KJ, Tweed JKS, Toivonen V, Huws SA, Scollan ND (2008) Effect of fish oil on ruminal biohydrogenation of C18 unsaturated fatty acids in steers fed grass or red clover silages. Animal 2:1859-1869
9. Shingfield KJ, Lee MRF, Humphries DJ, Scollan ND, Toivonen V, Reynolds CK, Beever DE (2010) Effect of incremental amounts of fish oil in the diet on ruminal lipid metabolism in growing steers. Br J Nutr 104:56-66
10. Dohme F, Fievez K, Raes K, Demeyer DI (2003) Increasing levels of two different fish oils lower ruminal biohydrogenation of eicosapentaenoic and docosahexaenoic acid in vitro. Anim Res 52:309-320 (Pubitemid 37171742)
11. AbuGhazaleh AA, Jenkins TC (2004) Disappearance of docosahexaenoic and eicosapentaenoic acids from cultures of mixed ruminal microorganisms. J Dairy Sci 87:645-651 (Pubitemid 44151753)
12. Wa̧sowska I, Maia MRG, Niedźwiedzka KM, Czauderna M, Ribeiro JM, Ramalho C, Devillard E, Shingfield KJ, Wallace RJ (2006) Influence of fish oil on ruminal biohydrogenation of C18 unsaturated fatty acids. Br J Nutr 95:1199-1211
13. Kramer JKG, Fellner V, Dugan MER, Sauer FD, Mossoba MM, Yurawecz MP (1997) 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 32:1219-1228 (Pubitemid 27508115)
14. Cruz-Hernandez C, Deng Z, Zhou J, Hill AR, Yurawecz MP, Delmonte P, Mossoba MM, Dugan MER, Kramer JKG (2004) Methods for analysis of conjugated linoleic acids and trans-18:1 isomers in dairy fats by using a combination of gas chromatography, silver-ion thin-layer chromatography/gas chromatography, and silver-ion liquid chromatography. JAOAC Int 87:545-562
15. Ratnayake WMN (2004) Overview of methods for the determination of trans fatty acids by gas chromatography, silver-ion thinlayer chromatography, silver-ion liquid chromatography, and gas chromatography/mass spectrometry. JAOAC Int 87:523-539
16. Kramer JKG, Hernandez M, Cruz-Hernandez C, Kraft J, Dugan MER (2008) 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 Agion SPE fractionation. Lipids 43:259-273
17. Radin NS (1981) Extraction of tissue lipids with a solvent of low toxicity. Methods Enzymol 72:5-8
18. Christie WW (1982) A simple procedure for rapid transmethylation of glycerolipids and cholesteryl esters. J Lipid Res 23: 1072-1075
19. Precht D, Molkentin J (1996) Rapid analysis of the isomers of trans-octadecenoic acid in milk fat. Int Dairy J 6:791-809 (Pubitemid 27093530)
20. Cruz-Hernandez C, Kramer JKG, Kraft J, Santercole V, Or-Rashid M, Deng Z, Dugan MER, Delmonte P, Yurawecz M (2006) Systematic analysis of trans and conjugated linoleic acids in the milk and meat of ruminants. In: Yurawecz MP, Kramer JKG, Gudmundsen O, Pariza MW, Banni S (eds) Advances in conjugated linoleic acid research, 3rd edn. AOAC, Urbana, pp 45-93
21. Kawashima H, Ohnishi M (2004) Identification of minor fatty acids and various non-methylene-interrupted diene isomers in mantle, muscle, and viscera of the marine bivalve Megangulus zyonoensis. Lipids 39:265-271 (Pubitemid 38738138)
22. Fay L, Richli U (1991) Location of double bonds in polyunsaturated fatty acids by gas chromatography-mass spectrometry after 4,4-dimethyloxazoline derivatization. J Chromatogr 541:89-98
23. Spitzer V (1997) Structure analysis of fatty acids by gas chromatography-low resolution electron impact spectrometry of their 4,4-dimethyloxazoline derivatives-a review. Prog Lipid Res 35:387-408
24. Christie WW (1998) Gas chromatography-mass spectrometry methods for structural analysis of fatty acids. Lipids 33:343-353
25. Zhang JY, Yu QT, Liu BN, Huang ZH (1988) Chemical modification in mass spectrometry IV: 2-alkenyl-4, 4-dimethyloxazolines as derivatives for the double bond location of long-chain olefinic acids. Biomed Environ Mass Spectrom 15:33-44
26. Yu QT, Liu BN, Zhang JY, Huang ZH (1989) Location of double bonds in fatty acids of fish oil and rat testis lipids. Gas chromatography-mass spectrometry of the oxazoline derivatives. Lipids 24:79-83
27. Luthria DL, Sprecher H (1993) 2-Alkenyl-4, 4-dimethyloxazolines as derivatives for the structural elucidation of isomeric unsaturated fatty acids. Lipids 28:561-564 (Pubitemid 23177655)
28. Kramer JKG, Blackadar CB, Zhou J (2002) Evaluation of two GC columns (60-m SUPELCOWAX 10 and 100-m CP Sil 88) for analysis of milk fat with emphasis on CLA, 18:1, 18:2 and 18:3 isomers, and short- and long-chain FA. Lipids 37:823-835
29. Alves SP, Bessa RJB (2009) Comparison of two gas-liquid chromatograph columns for the analysis of fatty acids in ruminant meat. J Chromatogr A 1216:5130-5139
30. Destaillats F, Wolff RL, Angers P (2001) A new D7-polyunsaturated fatty acid in Taxus spp. Seed lipids, dihomotaxoleic (7, 11-20:2) acid. Lipids 36:319-321
31. Ryhage R, Stenhagen E (1960) Mass spectrometric studies. VI. Methyl esters of normal chain oxo-, hydroxy-, methoxy- and epoxy-acids. Arkiv Kemi 15:545-574
32. Zhang JY, Yu QT, Yang YM, Huang ZH (1988) Chemical modification in mass spectrometry. 11. A study on the mass spectra of 4,4-dimethyloxazoline derivatives of hydroxy fatty acids. Chem Scripta 28:357-363
33. Classen E, Marx F, Fabricius H (1994) Mass spectra of 4,4- dimethyloxazoline derivatives of oxooctadecanoic acids. Fat Sci Technol 96:331-332
34. Hou CT (1994) Production of 10-ketostearic acid from oleic acid by Flavobacterium sp. strain DS5 (NRRL B-14859). Appl Environ Microbiol 60:3760-3763
35. Kramer JKG, Cruz-Hernandez C, Deng Z, Zhou J, Jahreis G, Dugan MER (2004) Analysis of conjugated linoleic acid and trans 18:1 isomers in synthetic and animal products. Am J Clin Nutr 79:1137S-1145S
36. Lamberto M, Ackman RG (1995) Positional isomerisation of trans-3-hexadecenoic acid employing 2-amino-2-methyl-propanol as a derivatizing agent for ethylenic bond location by gas chromatography/mass spectrometry. Anal Biochem 230:224-228
37. Christie WW (1998) Mass spectrometry of fatty acids with methylene-interrupted ene-yne systems. Chem Phys Lipids 94:35-41
38. Garrido JL, Medina I (2002) Identification of minor fatty acids in mussels (Mytilus galloprovincialis) by GC-MS of their 2-alkenyl- 4,4-dimethyloxazoline derivatives. Anal Chim Acta 465: 409-416 (Pubitemid 34876435)
39. Wilson R, Lyall K, Payne JA, Riemersma RA (2000) Quantitative analysis of long-chain trans-monoenes originating from hydrogenated marine oil. Lipids 35:681-687 (Pubitemid 30451151)
40. Fournier V, Destaillats F, Juanéda P, Dionisi F, Lambelet P, Sébédio J-L, Berdeaux O (2006) Thermal degradation of longchain polyunsaturated fatty acids during deodorization of fish oil. Eur J Lipid Sci Technol 108:33-42 (Pubitemid 43198333)
41. Fournier V, Juanéda P, Destaillats F, Dionisi F, Lambelet P, Sébédio J-L, Berdeaux O (2006) Analysis of eicosapentaenoic and docosahexaenoic acid geometrical isomers formed during fish oil deodorization. J Chromatogr A 1129:21-28 (Pubitemid 44348898)
42. Kitessa SM, Gulati SK, Ashes JR, Fleck E, Scott TW, Nichols PD (2001) Utilisation of fish oil in ruminants-I. Fish oil metabolism in sheep. Anim Feed Sci Technol 89:189-199
43. Toral PG, Shingfield KJ, Hervás G, Toivonen V, Frutos P (2010) 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 93:4804-4817
44. Hudson JA, MacKenzie CA, Joblin KN (1995) Conversion of oleic acid to 10-hydroxystearic acid by two species of ruminal bacteria. Appl Microbiol Biotechnol 44:1-6
45. Jenkins TC, AbuGhazaleh AA, Freeman S, Thies EJ (2006) The production of 10-hydroxystearic and 10-ketostearic acids is an alternative route of oleic acid transformation by the ruminal microbiota in cattle. J Nutr 136:926-931
46. McKain N, Shingfield KJ, Wallace RJ (2010) Metabolism of conjugated linoleic acids and 18:1 fatty acids by ruminal bacteria: products and mechanisms. Microbiology 156:579-588
47. Hudson JA, Morvan B, Joblin KN (1998) Hydration of linoleic acid by bacteria isolated from ruminants. FEMS Microbiol Lett 169:277-282 (Pubitemid 29050790)
48. Maia MRG, Chaudhary LC, Figueres L, Wallace RJ (2007) Metabolism of polyunsaturated fatty acids and their toxicity to the microflora of the rumen. Antonie van Leeuwenhoek 91:303-314 (Pubitemid 46681584)
49. Maia MRG, Chaudhary LC, Bestwick CS, Richardson AJ, McKain N, Larson TR, Graham IA, Wallace RJ (2010) Toxicity of unsaturated fatty acids to the biohydrogenating ruminal bacterium, Butyrivibrio fibrisolvens. BMC Microbiol 10:52
50. Harfoot CG, Hazlewood GP (1988) Lipid metabolism in the rumen. In: Hobson PN (ed) The rumen microbial ecosystem. Elsevier, London, pp 285-322
51. Jenkins TC, Wallace RJ, Moate PJ, Mosley EE (2008) BOARDINVITED REVIEW: recent advances in biohydrogenation of unsaturated fatty acids within the rumen microbial ecosystem. J Anim Sci 86:397-412 (Pubitemid 351229762)
52. Shingfield KJ, Ahvenjärvi S, Toivonen V, Vanhatalo A, Huhtanen P, Griinari JM (2008) Effect of incremental levels of sunflower-seed oil in the diet on ruminal lipid metabolism in lactating cows. Br J Nutr 99:971-983
53. Jouany J-P, Lassalas B, Doreau M, Glasser F (2007) Dynamic features of the rumen metabolism of linoleic acid, linolenic acid and linseed oil measured in vitro. Lipids 42:351-360 (Pubitemid 46668931)
54. Wallace RJ, McKain N, Shingfield KJ, Devillard E (2007) Isomers of conjugated linoleic acids are synthesized via different mechanisms in ruminal digesta and bacteria. J Lipid Res 48:2247-2254 (Pubitemid 47529566)
55. Banni S, Carta G, Contini MS, Angioni E, Deiana M, Dessi MA, Melis MP, Corongiu FP (1996) Characterization of conjugated diene fatty acids in milk, dairy products, and lamb tissues. J Nutr Biochem 7:150-155 (Pubitemid 26128276)
56. Michaud AL, Yurawecz MP, Delmonte P, Corl BA, Bauman DE, Brenna T (2003) Identification and characterization of conjugated fatty acid methyl esters of mixed double bond geometry by acetonitrile chemical ionization tandem mass spectrometry. Anal Chem 75:4925-4930 (Pubitemid 37139796)
57. Gómez-Córtes P, Tyburczy C, Brenna JT, Juárez M, Angel de la Fuente M (2009) Characterization of cis-9 trans-11 trans-15 C18:3 in milk fat by GC and covalent adduct chemical ionization tandem MS. J Lipid Res 50:2412-2420
58. Vlaeminck B, Harynuk J, Fievez V, Marriott P (2007) Comprehensive two-dimensional gas chromatography for the separation of fatty acids in milk. Eur J Lipid Sci Technol 109:757-766 (Pubitemid 47312994)
59. Wahl HG, Habel S-Y, Schmieder N, Liebich HM (1994) Identification of cis/trans isomers of methyl ester and oxazoline derivatives of unsaturated fatty acids using GC-FTIR-MS. J High Resolut Chromatogr 17:543-548
60. Lemaitre RN, King IB, Mozaffarian D, Sotoodehnia N, Rea TD, Kuller LH, Tracy RP, Siscovick DS (2006) Plasma phospholipid trans fatty acids, fatal ischemic heart disease, and sudden cardiac death in older adults. Circulation 114:209-215 (Pubitemid 44297114)