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Eicosapentaenoic and docosapentaenoic acids are the principal products of α-linolenic acid metabolism in young men*

  • Graham C. Burdge (a1), Amanda E. Jones (a1) and Stephen A. Wootton (a1)
Abstract

The capacity for conversion of α-linolenic acid (ALNA) to n−3 long-chain polyunsaturated fatty acids was investigated in young men. Emulsified [U13C]ALNA was administered orally with a mixed meal to six subjects consuming their habitual diet. Approximately 33 % of administered [13C]ALNA was recovered as 13CO2 on breath over the first 24 h. [13C]ALNA was mobilised from enterocytes primarily as chylomicron triacylglycerol (TAG), while [13C]ALNA incorporation into plasma phosphatidylcholine (PC) occurred later, probably by the liver. The time scale of conversion of [13C]ALNA to eicosapentaenoic acid (EPA) and docosapentaenoic acid (DPA) suggested that the liver was the principal site of ALNA desaturation and elongation, although there was some indication of EPA and DPA synthesis by enterocytes. [13C]EPA and [13C]DPA concentrations were greater in plasma PC than TAG, and were present in the circulation for up to 7 and 14 d, respectively. There was no apparent 13C enrichment of docosahexaenoic acid (DHA) in plasma PC, TAG or non-esterified fatty acids at any time point measured up to 21 d. This pattern of 13C n−3 fatty acid labelling suggests inhibition or restriction of DHA synthesis downstream of DPA. [13C]ALNA, [13C]EPA and [13C]DPA were incorporated into erythrocyte PC, but not phosphatidylethanolamine, suggesting uptake of intact plasma PC molecules from lipoproteins into erythrocyte membranes. Since the capacity of adult males to convert ALNA to DHA was either very low or absent, uptake of pre-formed DHA from the diet may be critical for maintaining adequate membrane DHA concentrations in these individuals.

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Corresponding author
Corresponding author:Dr G. C. Burdge, fax +44 23 80794945, email gcb@soton.ac.uk
References
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Allman, MA, Pena, MM & Peng, D (1995) Supplementation with flaxseed oil versus sunflower oil in healthy young men when consuming a low fat diet: effects on platelet composition and function. European Journal of Clinical Nutrition 49, 169178.
Beitz, J, Mest, HJ & Forster, W (1981) Influence of linseed oil diet on the pattern of serum phospholipids in man. Acta Biologica Medica Germany 40, K31K35.
Bennoson, J, Humayun, MA, Jones, AE, Hounslow, A & Wootton, SA (1999) Within-individual variability in the gastrointestinal handling and metabolism of [1,1,1-13C]tripalmitin. Proceedings of the Nutrition Society 58, 25A.
Burdge, GC, Wright, P, Jones, AE & Wootton, SA (2000) A method for separation of phosphatidylcholine, triacylglycerol, non-esterified fatty acids and cholesterol esters from plasma by solid phase extraction. British Journal of Nutrition 84, 781787.
Caesar, PA, Wilson, SJ, Normand, ICS & Postle, AD (1988) A comparison of the specificity of phosphatidylcholine synthesis by human fetal lung maintained in either organ or organotypic culture. Biochemical Journal 253, 451457.
Carnielli, CP, Wattimena, JDL, Luijendijk, IHT, Boerlage, A, Dagenhart, HJ & Sauer, PJJ (1996) The very-low-birth-weight premature infant is capable of synthesizing arachidonic and docosahexaenoic acid from linolenic and linolenic acid. Pediatric Research 40, 169174.
Chan, JK, McDonald, BE, Gerrard, JM, Bruce, VM, Weaver, BJ & Holub, BJ (1993) Effect of dietary α-linolenic acid and its ratio to linoleic acid on platelet and plasma fatty acids and thrombogenesis. Lipids 28, 811817.
Cunnane, SC, Hamadeh, MJ, Leide, AC, Thompson, LU, Wolver, TMS & Jenkins, DJA (1995 a) Nutritional attributes of tradition flaxseed in healthy young adults. American Journal of Clinical Nutrition 61, 6268.
Cunnane, SC, Ryan, MA, Craig, KS, Brookes, S, Koletzko, B, Demmelmair, H, Singer, J & Kyle, DJ (1995 b) Synthesis of linoleate and (-linolenate by chain elongation in the rat. Lipids 30, 781783.
Emken, EA, Adolf, RO, Duval, SM & Nelson, GJ (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, 785798.
Emken, EA, Adolf, RO & Gully, RM (1994) Dietary linoleic acid influences desaturation and acylation of deuterium-labeled linoleic and linolenic acids in young adult males. Biochimica Biophysica Acta 1213, 277288.
Ezaki, O, Takahashi, M, Shigematsu, T, Shimamura, K, Kimura, J, Ezaki, H & Gotoh, T (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. Journal of Nutritional Science and Vitaminology (Tokyo) 45, 759772.
Folch, JL, Lees, M & Sloane-Stanley, GH (1957) A simple method for the isolation and purification of total lipides from animal tissues. Journal of Biological Chemistry 226, 497509.
Freese, R, Mutanen, M, Valsta, LM & Salminen, I (1994) Comparison of the effects of two diets rich in monounsaturated fatty acids differing in their linoleic/α-linolenic acid ratio on platelet aggregation. Thrombosis and Haemostasis 71, 7377.
Galli, C, Sirtori, CR, Mosconi, C, Medini, L, Giafranceschi, G, Vaccarino, V & Scolastico, C (1992) Prolonged retention of doubly labelled phosphatidylcholine in human plasma and erythrocytes after oral administration. Lipids 27, 1051012.
Garg, ML, Keelan, M, Thomson, ABR & Clandinin, MT (1992) Desaturation of linoleic acid in the small bowel is increased by short-term fasting and by dietary content of linoleic acid. Biochimica Biophysica Acta 1126, 1725.
Gerster, H (1998) Can adults convert α-linolenic acid (18:3n-3) to eicosapentaenoic acid (20:5n-3) and docosahexaenoic acid (22:5n-3)? International Journal of Vitamin and Nutrition Research 68, 159173.
Irving, CS, Wong, WW, Schulman, RJ, Smith, EO & Klein, PD (1983) [13C]Bicarbonate kinetics in humans: intra- vs. inter-individual variations. American Journal of Physiology 245, R190R202.
Jones, AE, Stolinski, M, Smith, RD, Murphy, JL & Wootton, SA (1999) Effect of fatty acid chain length and saturation on the gastrointestinal handling and metabolic disposal of dietary fatty acids in women. British Journal of Nutrition 81, 3743.
Leyton, J, Drury, PJ & Crawford, MA (1987) Differential oxidation of saturated and unsaturated fatty acids in vivo in the rat. British Journal of Nutrition 57, 383393.
Li, D, Sinclair, A, Wilson, A, Nakkote, S, Kelly, F, Abedin, L, Mann, N & Turner, A (1999) Effect of dietary α-linolenic acid on thrombotic risk factors in vegetarian men. American Journal of Clinical Nutrition 69, 872882.
Luthria, DL, Mohammed, S & Sprecher, H (1996) Regulation of the biosynthesis of 4,7,10,13,16,19-docosahexaenoic acid. Journal of Biological Chemistry 271, 1602016025.
Ministry of Agriculture, Fisheries and Food (1997) Dietary Intake of Iodine and Fatty Acids. Food Information Surveillance Sheet 127. London: Ministry of Agriculture, Fisheries and Food.
Pawlosky, RJ, Hibbeln, JR, Novotny, JA & Salem, N (2001) Physiological compartmental analysis of α-linolenic acid metabolism in adult humans. Journal of Lipid Research 42, 12571265.
Redgrave, TG, Roberts, DCK & West, CE (1975) Separation of plasma lipoproteins by density gradient ultracentrifugation. Analytical Biochemistry 65, 4249.
Salem, N, Powlosky, R, Wegher, B & Hibbeln, J (1999) In vivo conversion of linoleic acid to arachidonic acid in human adults. Prostaglandins, Leukotrienes and Essential Fatty Acids 60, 407410.
Salem, N, Wegher, B, Mena, P & Uauy, R (1996) Arachidonic and docosahexaenoic acids are biosynthesized from their 18-carbon precursors in human infants. Proceedings of the National Academy of Sciences USA 93, 4954.
Sauerwald, TU, Hachey, DL, Jensen, CL, Chen, H, Anderson, RE & Heird, WC (1997) Intermediates in endogenous synthesis of C22:6ω3 and C20:4ω6 by term and preterm infants. Pediatric Research 41, 183187.
Sheaff, RC, Zhang, Q, Goodman, KJ, Giussani, DA, Nathanielsz, PW & Brenna, JT (1996) Linoleate, α-linolenate and docosahexaenoate recycling into saturated and monounsaturated fatty acids is a major pathway in pregnant or lactating adults and fetal or infant Rhesus monkeys. Journal of Lipid Research 37, 26752686.
Sniderman, AD, Cianflone, K, Arner, P, Summers, LKM & Frayn, KN (1998) The adipocyte, fatty acid trapping and atherogenesis. Atheriosclerosis, Thrombosis and Vascular Biology 18, 147151.
Sprecher, H (2000) Metabolism of highly unsaturated n-3 and n-6 fatty acids. Biochimica et Biophysica Acta 1486, 219231.
Stolinski, M, Murphy, JL, Jones, AE, Jackson, AA & Wootton, SA (1997) Stable-isotope method for determining the gastrointestinal handling of [1-13C]palmitic acid. Lipids 32, 337340.
Su, HM, Bernardo, L, Mirmiran, M, Ma, XH, Corso, TN, Nathanielsz, PW & Brenna, JT (1999 a) Bioequivalence of dietary alpha-linolenic and docosahexaenoic acids as sources of docosahexaenoate accretion in brain and associated organs of neonatal baboons. Pediatric Research 45, 8793.
Su, HM, Bernardo, L, Mirmiran, M, Ma, XH, Nathanielsz, PW & Brenna, JT (1999 b) Dietary 18:3n-3 and 22:6n-3 as sources of 22:6n-3 accretion in neonatal baboon brain and associated organs. Lipids 34, S347S350.
Valsta, LM, Salminen, I, Aro, A & Mutanen, M (1996) Alpha-linolenic acid in rapeseed oil partly compensates for the effect of fish restriction on plasma long chain n-3 fatty acids. European Journal of Clinical Nutrition 50, 229235.
Vermunt, SHF, Mensink, RP, Simonis, AMG & Hornstra, G (1999) Effects of age and dietary n-3 fatty acids on the metabolism of [13C]-α-linolenic acid. Lipids 34, S127 abstr.
Vermunt, SHF, Mensink, RP, Simonis, AMG & Hornstra, G (2000) Effects of dietary (-linolenic acid on the conversion and oxidation of [13C]-α-linolenic acid. Lipids 35, 137142.
Voss, A, Reinhart, M, Sankarappa, S & Sprecher, H (1991) The metabolism of 7,10,13,16,19-docosapentaenoic acid to 4,7,10,13,16,19-docosahexaenoic acid in rat liver is independent of a 4-desaturase. Journal of Biological Chemistry 266, 1999520000.
Watkins, JB, Klein, PD, Schoeller, DA, Kirschner, BS, Park, R & Perman, JA (1982) Diagnosis and differentiation of fat malabsorption in children using [13C]-labelled lipids: trioctanoin, triolein and palmitic acid breath tests. Gastroenterology 82, 911917.
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British Journal of Nutrition
  • ISSN: 0007-1145
  • EISSN: 1475-2662
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