Long-chain conversion of [13C]linoleic acid and α-linolenic acid in response to marked changes in their dietary intake in men

Journal of Lipid Research

Volumn 46, Issue 2, 2005, Pages 269-280

  Hussein, Nahed ^a   Ah Sing, Eric ^a   Wilkinson, Paul ^a   Leach, Clare ^a   Griffin, Bruce A ^a   Millward, D Joe ^a  

^a UNIVERSITY OF SURREY   (United Kingdom)

Author keywords

Flaxseed oil; Long chain polyunsaturated fatty acid; Stable isotopes

Indexed keywords

ARACHIDONIC ACID; CARBON 13; DOCOSAHEXAENOIC ACID; DOCOSAPENTAENOIC ACID; FISH OIL; ICOSAPENTAENOIC ACID; LINOLEIC ACID; LINOLENIC ACID; LINSEED OIL; PHOSPHOLIPID; SUNFLOWER OIL;

ADULT; ARACHIDONIC ACID METABOLISM; ARTICLE; CONTROLLED STUDY; DIET SUPPLEMENTATION; DIETARY INTAKE; ERYTHROCYTE; HUMAN; HUMAN EXPERIMENT; HYPERLIPIDEMIA; LIPID COMPOSITION; MALE; NORMAL HUMAN; PRIORITY JOURNAL;

ADULT; ALPHA-LINOLENIC ACID; ARACHIDONIC ACID; AREA UNDER CURVE; CHROMATOGRAPHY, GAS; DIET; DOCOSAHEXAENOIC ACIDS; EICOSAPENTAENOIC ACID; ERYTHROCYTES; FATTY ACIDS; FATTY ACIDS, UNSATURATED; HUMANS; LINOLEIC ACID; MALE; MIDDLE AGED; MODELS, BIOLOGICAL; PHOSPHOLIPIDS; RISK; TIME FACTORS;

EID: 13944270939     PISSN: 00222275     EISSN: None     Source Type: Journal    
DOI: 10.1194/jlr.M400225-JLR200     Document Type: Article

References (64)

1. Burr, M. L., A. M. Fehily, J. F. Gilbert, S. Rogers, R. M. Holliday, P. M. Sweetnam, P. C. Elwood, and N. M. Deadman. 1989. Effects of changes in fat, fish, and fibre intakes on death and myocardial reinfarction: Diet And Re-infarction Trial (DART). Lancet, ii: 757-761.
2. GISSI Prevenzione Investigators. 1999. Dietary supplementation with n-3 polyunsaturated fatty acids and vitamin E after myocardial infarction: results of the GISSI-Prevenzione Trial. Lancet. 354: 447-455.
3. Dolecek, T. A., and G. Granits. 1991. Dietary polyunsaturated fatty acids and mortality in the Multiple Risk Factor Intervention Trial (MRFIT). World Rev. Nutr. Diet. 66: 205-216.
4. Hu, F. B., M. J. Stamfer, and J. E. Manson. 1999. Dietary intake of α-linolenic acid and risk of fatal ischemic heart disease among women. Am. J. Clin. Nutr. 69: 890-897.
5. de Longeril, M., P. Salen, J-L. Martin, I. Monjaud, J. Delaye, and N. Mamelle. 1999. Mediterranean diet, traditional risk factors, and the rate of cardiovascular complications after myocardial infarction Final report of the Lyon Heart Study. Circulation. 99: 779-785.
6. Oomen, C. M., M. C. Ocke, E. J. Peskens, F. J. Kok, and D. Kromhout. 2001. Alpha-linolenic acid intake is not beneficially associated with 10-year risk of coronary artery disease incidence: the Zupten Elderly Study. Am. J. Clin. Nutr. 74: 457-463.
7. Guallar, E., A. Aro, F. J. Jimenez, J. M. Martin-Moreno, I. Salminen, P. van't Veer, A. F. Kardinaal, J. Gomez-Aracena, B. C. Martin, L. Kohlmeier, J. D. Kark, V. P. Mazaev, J. Ringstad, J. Guillen, R. A. Riemersma, J. K. Huttunen, M. Thamm, and F. J. Kok. 1999. Omega-3 fatty acids in adipose tissue and risk of myocardial infraction: the EURAMIC Study. Arterioscler. Thromb. Vasc. Biol. 19: 1111-1118.
8. Pedersen, J. I., J. Ringstad, K. Almendingen, T. S. Haugen, I. Stensvold, and D. S. Thelle. 2000. Adipose tissue fatty acids and risk of myocardial infarction-a case-control study. Eur. J. Clin. Nutr. 54: 618-625.
9. Harris, W. S. 1997. n-3 fatty acid and serum lipoproteins: human studies. Am. J. Clin. Nutr. 65 (Suppl.): 1645-1654.
10. Brenner, R. R. 1989. Factors influencing fatty acid chain elongation and desaturation. In The Role of Fats in Human Nutrition. A. J. Vergrossen and M. Crawford, editors. Academic Press, San Diego, CA. 45-79.
11. Brenna, J. T. 2002. Efficiency of conversion of a-linolenic acid to long chain n-3 fatty acids in man. Curr. Opin. Clin. Nutr. Metab. Care. 5: 127-132.
12. Cho, H. P., M. T. Nakamura, and S. D. Clarke. 1999. Cloning, expression, and nutritional regulation of the mammalian delta-6 desaturase. J. Biol. Chem. 274: 471-477.
13. Cho, H. P., M. Nakamura, and S. D. Clarke. 1999. Cloning, expression, and fatty acid regulation of the human delta-5 desaturase. J. Biol. Chem. 274: 37335-37339.
14. Burdge, G. 2004. a-Linolenic acid metabolism in men and women: nutritional and biological implications. Curr. Opin. Clin. Nutr. Metab. Care. 7: 137-144.
15. Salem, N., Jr., B. Wegher, P. Mena, and R. Uauy. 1996. Arachidonic and docosahexaenoic acids are biosynthesized from their 18-carbon precursors in human infants. Proc. Natl. Acad. Sci. USA. 93: 49-54.
16. Carnielli, V. P., D. J. Wattimena, I. H. Luijendijk, A. Boerlage, H. J. Degenhart, and P. J. Sauer. 1996. The very low birth weight pre-mature infant is capable of synthesizing arachidonic and docosahexaenoic acids from linoleic and linolenic acids. Pediatr. Res. 40: 169-174.
17. Uauy, R., P. Mena, B. Wegher, and N. Salem, Jr. 2000. Long chain polyunsaturated fatty acid formation in neonates: effect of gestational age and intrauterine growth. Pediatr. Res. 47: 127-135.
18. Emken, E. A., R. O. Adlof, and R. M. Gulley. 1994. Dietary linoleic acid influences desaturation and acylation of deuterium-labeled linoleic and linolenic acids in young adult males. Biochim. Biophys. Acta. 1213: 277-288.
19. Emken, E. A., R. O. Adlof, S. M. Duval, and G. I. Nelson. 1998. Effect of dietary arachidonic acid on metabolism of deuterated linoleic acid by adult male subjects. Lipids. 33: 471-480.
20. Emken, E. A., R. O. Adlof, S. M. Duval, and G. I. Nelson. 1999. Effect of dietary docosahexaenoic acid on desaturation and uptake in vivo of isotope-labeled oleic, linoleic, and linolenic acids by male subjects. Lipids. 34: 785-791.
21. Salem, N., R. Powlosky, B. Wegher, and J. Hibbeln. 1999. In vivo conversion of linoleic acid to arachidonic acid in human adults. Prostaglandins Leukot. Essent. Fatty Acids. 60: 407-410.
22. Pawlosky, R. J., J. R. Hibbeln, J. A. Novotny, and N. Salem, Jr. 2001. Physiological compartmental analysis of alpha-linolenic acid metabolism in adult humans. J. Lipid Res. 42: 1257-1265.
23. Pawlosky, R. J., J. R. Hibbeln, Y. Lin, S. Goodson, P. Riggs, N. Sebring, G. Brown, and N. Salem, Jr. 2003. Effect of beef- and fish-based diets on the kinetics of n-3 fatty acid metabolism in human subjects. Am. J. Clin. Nutr. 77: 565-572.
24. Sauerwald, T. U., D. L. Hachey, C. L. Jensen, H. Chen, R. E. Anderson, and W. C. Heird. 1997. Intermediates in endogenous synthesis of C22:6 omega 3 and 20:4 omega 6 by term and preterm infants. Pediatr. Res. 41: 183-187.
25. Burdge, G. C., A. E. Jones, and S. A. Wootton. 2002. Eicosapentaenoic and docosapentaenoic acids are the principal products of α-linolenic acid metabolism in young men. Br. J. Nutr. 88: 355-363.
26. Burdge, G. C., and S. A. Wootton. 2002. Conversion of α-linolenic acid to eicosapentaenoic, docosapentaenoic and docosahexaenoic acids in young women. Br. J. Nutr. 88: 411-420.
27. 13C]a-linolenic acid to longer-chain fatty acids and partitioning towards b-oxidation in older men. Br. J. Nutr. 90: 311-321.
28. 13C]-α-linolenic acid (Abstract). Lipids. 34 (Suppl.): 127.
29. 13C-α-linolenic acid. Lipids. 35: 137-142.
30. Griffin, B. A., and A. Zampelas. 1995. Influence of dietary fatty acids on an atherogenic lipoprotein phenotype. Nutr. Res. Rev. 8:1-26.
31. Wilkinson, P. A., C. Leach, N. Hussein, G. J. Miller, D. J. Millward, and B. A. Griffin. 2004. Influence of α linolenic acid and fish-oil on markers of cardiovascular risk in subjects with an atherogenic lipoprotein phenotype. Atherosclerosis. In press.
32. Wilkinson, P. A., E. Ah-Sing, C. Emery, A. Fereday, D. J. Millward, S. Richards, J. Sheppard, and B. A. Griffin. 2000. The importance of alpha-linolenic acid as a source of long chain n-3 polyunsaturated fatty acids and its influence on risk factors of cardiovascular disease (Abstract). Proc. Nutr. Soc. 59: 16.
33. nd edition. B. M. Margetts and M. Nelson, editors. Oxford University Press, Oxford, UK. 241-272.
34. Podda, M., C. Weber, M. G. Traber, and L. Packer. 1996. Simultaneous determination of tissue tocopherol, tocotrienols, ubiquinols, and ubiquinones. J. Lipid Res. 37: 893-901.
35. Folch, J., M. Lees, and G. H. Sloane-Stanley. 1957. A simple method for the isolation and purification of total lipids from animal tissues. J. Biol. Chem. 226: 497-509.
36. Christie, W. W. 1990. Preparation of methyl esters. Part 2. Lipid Technol. 2: 79-80.
37. Burdge, G. C., P. Wright, A. E. Jones, and S. A. Wootton. 2000. A method for separation of phosphatidylcholine, triacylglycerol, non-esterified fatty acids and cholesterol esters from plasma by solid-phase extraction. Br. J. Nutr. 84: 781-787.
38. 13C]-labeled precursors. Anal. Chem. 64: 1088-1095.
39. Demmelmair, H., B. Iser, A. Rauh-Pfeiffer, and B. Koletzko. 1999. Comparison of bolus versus fractionated oral applications of linoleic acid in humans. Eur. J. Clin. Invest. 29: 603-609.
40. Katan, M. B., J. P. Deslypere, A. P. J. M. van Birgelen, M. Penders, and M. Zegwaard. 1997. Kinetics of the incorporation of dietary fatty acids into serum cholesteryl esters, erythrocyte membranes, and adipose tissue: an 18-month controlled study. J. Lipid Res. 38: 2012-2022.
41. Adam, O., G. Wolfram, and N. Zollner. 1986. Effect of alpha-linolenic acid in the human diet on linoleic acid metabolism and prostaglandin biosynthesis. J. Lipid Res. 27: 421-426.
42. Mantzioris, E., M. J. James, R. A. Gibson, and L. G. Cleland. 1995. Differences exist in the relationships between dietary linoleic and alpha-linolenic acids and their respective long-chain metabolites. Am. J. Clin. Nutr. 61: 320-324.
43. Chen, Z-Y., and S. C. Cunnane. 1993. Refeeding after fasting increases apparent oxidation of n-3 and n-6 fatty acids in pregnant rats. Metabolism. 42: 1206-1211.
44. Wood, D., R. Riemersma, S. Butler, M. Thomson, E. Macintyre, and M. Oliver. 1987. Linoleic and eicosapentaenoic acids in adipose tissue and platelets and risk of coronary heart disease. Lancet. 1: 177-183.
45. Hodgeson, J. M., M. L. Wahlqvist, J. A. Boxall, and N. D. Balazs. 1993. Can linoleic acid contribute to coronary artery disease? Am. J. Clin. Nutr. 58: 228-234.
46. Allman, M. A., M. M. Pena, and D. Pang. 1995. Supplementation with flaxseed oil versus sunflowerseed oil in healthy young men consuming a low fat diet: effects on platelet composition and function. Eur. J. Clin. Nutr. 49: 169-178.
47. Bemelmans, W. J. E., J. Broer, E. J. M. Feskens, A. J. Smit, F. A. J. Muskiet, J. D. Lefrandt, V. J. J. Bom, J. F. May, and B. Meyboom-de Jong. 2002. Effect of an increased intake of α-linolenic acid and group nutritional education on cardiovascular risk factors: the Mediterranean Alpha-Linolenic Enriched Groningen Dietary Intervention (MARGARIN) Study. Am. J. Clin. Nutr. 75: 221-227.
48. Gerster, H. 1998. Can adults adequately convert α-linolenic acid (18:3n-3) to eicosapentaenoic acid (20:5n-3) and docosahexaenoic acid (22:6n-3)? Int. J. Vit. Nutr. Res. 68: 159-173.
49. Kew, S., T. Banerjee, A. M. Minihane, Y. E. Finnegan, R. Muggli, R. Albers, C. M. Williams, P. C. Calder. 2003. Lack of effect of foods enriched with plant- or marine-derived n-3 fatty acids on human immune function. Am. J. Clin. Nutr. 77: 1287-1295.
50. Valsta, L. M., I. Salminen, A. Aro, and M. Mutanen. 1996. Alpha-linolenic acid in rapeseed oil partly compensates for the effect of fish restriction on plasma long chain n-3 fatty acids. Eur. J. Clin. Nutr. 50: 229-235.
51. Ezaki, O., M. Takahashi, T. Shigematsu, K. Shimamura, J. Kimura, H. Ezaki, and T. Gotoh. 1999. Long-term effects of dietary alpha-linolenic acid from perilla oil on serum fatty acid composition and on the risk factors of coronary heart disease in Japanese elderly subjects. J. Nutr. Sci. Vitaminol. (Tokyo). 45: 759-772.
52. Hwang, D. H., M. Boudreau, and P. Chanmugam. 1988. Dietary linolenic acid and longer-chain n-3 fatty acids: comparison of effects on arachidonic acid metabolism in rats. J. Nutr. 118: 427-437.
53. Brenner, R. R., and R. O. Peluffo. 1969. Regulation of unsaturated fatty acid biosynthesis. Effect of unsaturated fatty acids of 18 carbons on the microsomal desaturation of linoleic acid into γ-linolenic acid. Biochim. Biophys. Acta. 176: 471-479.
54. Garg, M. L., E. Sebokova, A. B. R. Thomson, and M. T. Clandinin. 1988. A6-desaturase activity in liver microsomes of rats fed diets enriched with cholesterol and/or ω-3 fatty acids. Biochem. J. 249: 351-356.
55. Finnegan, Y. E., A. M. Minihane, E. C. Leigh-Firbank, S. Kew, G. W. Meijer, R. Muggli, P. C. Calder, and C. W. Williams. 2003. Plant- and marine-derived n-3 polyunsaturated fatty acids have differential effects on fasting and postprandial blood lipid concentrations and on the susceptibility of LDL to oxidative modification in moderately hyperlipidemic subjects. Am. J. Clin. Nutr. 77: 783-795.
56. Cunnane, S. C., P. W. N. Keeling, R. P. N. Thompson, and M. A. Crawford. 1984. Linoleic acid and arachidonic acid metabolism in human peripheral blood leucocytes: comparison with the rat. Br. J. Nutr. 51: 209-217.
57. Emken, E. A., R. O. Adlof, D. L. Hachey, C. Garza, M. R. Thomas, and L. Brown-Booth. 1989. Incorporation of deuterium-labeled fatty acids into human milk, plasma, and lipoprotein phospholipids and cholesteryl esters. J. Lipid Res. 30: 395-402.
58. Ackman, R. G., and S. C. Cunnane. 1991. Long chain polyunsaturated fatty acids: sources, biochemistry and nutritional/clinical implications. Adv. Appl. Lipid Res. 1: 161-215.
59. Diboune, M., G. Ferard, Y. Ingenbleek, P. A. Tulasne, B. Calon, M. Hasselman, P. Sauder, D. Speilmann, and P. Metais. 1992. Composition of phospholipid fatty acids in red blood cell membranes of patients in intensive care units: effects of different intakes of soy-bean oil, medium-chain triglycerides, and black-currant seed oil. J. Parenter. Enteral Nutr. 16: 136-141.
60. Sprecher, H., D. L. Luthria, B. S. Mohammed, and S. P. Baykousheva. 1995. Reevaluation of the pathways for the biosynthesis of polyunsaturated fatty acids. J. Lipid Res. 36: 2471-2477.
61. Sprecher, H., Q. Chen, and F. Q. Yin. 1999. Regulation of the biosynthesis of 22:5n-6 and 22:6n-3 complex intracellular process. Lipids. 34 (Suppl.): 153-156.
62. Tang, C., H. P. Cho, M. T. Nakamura, and S. D. Clarke. 2003. Regulation of human D-6 desaturase gene transcription: identification of a functional direct repeat-1 element. J. Lipid Res. 44: 686-695.
63. Dewailly, E., C. Blanchet, S. Lemieux, L. Sauvé, S. Gingras, P. Ayotte, and B. J. Holub. 2001. n 3 fatty acids and cardiovascular disease risk factors among the Inuit of Nunavik. Am. J. Clin. Nutr. 74: 464-473.
64. Fokkema, M. R., D. A. J. Brouwer, M. B. Hasperhoven, I. A. Martini, and F. A. J. Muskiet. 2000. Short-term supplementation of low-dose g-linolenic acid (GLA), a-linolenic acid (ALA), or GLA plus ALA does not augment LCPo3 status of Dutch vegans to an appreciable extent. Prostaglandins Leukot. Essent. Fatty Acids. 63: 287-292.