Abstract
Four sources of long-chain polyunsaturated fatty acids (LCP) differing in their chemical structure (triglycerides or phospholipids) and in their origin (tuna triglycerides, fungal triglycerides, egg phospholipids, and pig brain phospholipids) were analyzed to determine the distribution of the component fatty acids within the molecule. Lipase and phospholipase A2 hydrolysis was performed to obtain 2-monoacylglycerols and lysophospholipids, respectively, which allowed us to determine the distribution of fatty acids between the sn-2 and sn-1,3 positions of triglycerides or between the sn-1 and sn-2 position of phospholipids. Fatty acids in the LCP sources analyzed were not randomly distributed. In tuna triglycerides, half of the total amount of 22∶6n−3 was located at the sn-2 position (49.52%). In fungal triglycerides, 16∶0 and 18∶0 were esterified to the sn-1,3 (92.22% and 91.91%, respectively) 18∶1 and 18∶2 to the sn-2 position (59.77% and 62.62%, respectively), and 45% of 20∶3n−6 and only 21.64% of 20∶4n−6 were found at the sn-2 position. In the lipid sources containing phospholipids, LCP were mainly esterified to the phosphatidylethanolamine fraction. In egg phospholipids, most of 20∶4n−6 (5.50%, sn-2 vs. 0.91%, sn-1) and 22∶6n−3 (2.89 vs. 0.28%) were located at the sn-2 position. In pig brain phospholipids, 22∶6n−3 was also esterified to the sn-2 (13.20 vs. 0.27%), whereas 20∶4n−6 was distributed between the two positions (12.35 vs. 5.86%). These results show a different fatty acid composition and distribution of dietary LCP sources, which may affect the absorption, distribution, and tissue uptake of LCP, and should be taken into account when supplementing infant formulas.
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Abbreviations
- EFA:
-
essential fatty acids
- FFA:
-
free fatty acids
- HPTLC:
-
high-performance thin-layer chromatography
- LCP:
-
long-chain polyunsaturated fatty acids
- LYsoPC:
-
lysophosphatidylcholine
- LysoPE:
-
lysophosphatidylethanolamine
- 2-MG:
-
2-monoacylglycerols
- MONO:
-
monounsaturated fatty acids
- PC:
-
phosphatidylcholine
- PE:
-
phosphatidylethanolamine
- PL:
-
phospholipids
- SAT:
-
saturated fatty acids
- TG:
-
triglycerides
- TLC:
-
thin-layer chromatography
References
Neuringer, M., Connor, W.E., Lin, D.S., Barstad, L., and Luck, S. (1986) Biochemical and Functional Effects of Prenatal and Postnatal ω-3 Fatty Acid Deficiency on Retina and Brain in Rhesus Monkeys, Proc. Natl. Acad. Sci. USA 83, 4021–4025.
Bourre, J.M., Francois, M., Youyou, A., Dumont, O., Piciott, M., Pascal, G., and Durand, G. (1989) The Effects of Dietary α-Linoleic Acid on the Composition of Nerve Membranes, Enzymatic Activity, Amplitude of Electrophysiological Parameters, Resistance to Poisons and Performance of Learning Tasks in Rats, J. Nutr. 119, 1880–1892.
Heird, W.C., Prager, T.C., and Anderson, R.E. (1997) Docosahexaenoic Acid and the Development and Function of the Infant Retina, Cur. Opin. Lipidology 8, 12–16.
Pufal, D.A., Quilan, P.T., and Salter, A.M. (1995) Effect of Dietary Triacylglycerol Structure on Lipoprotein Metabolism: A Comparison of the Effects of Dioleoylpalmitoylglycerol in Which Palmitate Is Esterified to the sn-2 or 1(3)-Position of the Glycerol, Biochim. Biophys. Acta 1258, 41–48.
Yang, L.Y., Kuksis, A., and Myher, J.J. (1989) Lumenal Hydrolysis of Menhaden and Rapeseed Oils and Their Fatty Acid Methyl and Ethyl Esters in the Rat, Biochem. Cell Biol. 67, 192–204.
Thomson, A.B.R., Keelan, M., Garg, M.L., and Clandinin, M.T. (1988) Intestinal Aspects of Lipid Absorption: In Review, Can. J. Physiol. Pharmacol. 67, 179–191.
Carnielli, V.P., Luijendijk, I.H.T., Van Gouder, J.B., Sulkers, E.J., Boerlage, A.A., Degenhart, H.J., and Sauer, P.J.J. (1995) Feeding Premature Newborn Infants Palmitic Acid in Amounts and Stereoisomeric Position Similar to That of Human Milk: Effect on Fat and Mineral Balance, Am. J. Clin. Nutr. 61, 1037–1042.
Jensen, M.M., Christensen, M.S., and Høy, C.-E. (1994) Intestinal Absorption of Octanoic, Decanoic and Linoleic Acids: Effect of Triglyceride Structure, Ann. Nutr. Metab. 38, 104–116.
Innis, S.M., Dyer, R., Wadsworth, L., Quilan, P., and Diersen-Schade, D. (1993) Dietary Saturated, Monounsaturated, n−6 and n−3 Fatty Acids, and Cholesterol Influence Platelet Fatty Acids in the Exclusively Formula-Fed Piglet, Lipids 28, 645–650.
Carnielli, V.P., Giovanna, V., Pederzini, F., Luijendijk, I., Boerlage, A., Pedrotti, D., and Sauer, P.J.J. (1998) Intestinal Absorption of Long-Chain Polyunsaturated Fatty Acids in Preterm Infants Fed Breast Milk or Formula, Am. J. Clin. Nutr. 67, 97–103.
Boehm, G., Muller, H., Kohn, G., Moro, G., Minoli, I., and Bohles, H.J. (1997) Docosahexaenoic and Arachidonic Acid Absorption in Preterm Infants Fed LCP-Free or LCP-Supplemented Formula in Comparison to Infants Fed Fortified Breast Milk, Ann. Nutr. Metab. 41, 235–241.
Myher, J.J., Kuksis, A., Geher, K., Park, P.W., and Diersen-Schade D. (1996) Stereospecific Analysis of Triacylglycerol Rich in Long-Chain Polyunsaturated Fatty Acids, Lipids 31, 207–215.
Martin, J.C., Bougnoux, P., Antoine, J.M., Lanson, M., and Couet, C. (1993) Triacylglycerol Structure of Human Colostrum and Mature Milk, Lipids 28, 637–643.
Leray, C., Raclot, T., and Groscolas, R. (1993) Positional Distribution of n−3 Fatty Acids in Triacylglycerols from Rat Adipose Tissue During Fish Oil Feeding, Lipids 28, 279–284.
Taylor, D.C., Mackenzie, S.L., McCirdy, A.R., McVetty, B.E., Giblin, E.M., Pass, E.W., Stone, S.J., Scarth, R., Rimmer, S.R., and Pickard, M.D. (1994) Stereospecific Analysis of Seed Triacylglycerols from High Erucic Acid Brassicaceae: Detection of Erucic Acid at the sn-2 Position in Brassica olearacea L. Genotypes, J. Am. Oil Chem. Soc. 71, 163–167.
Semporé, G., and Bezard, J. (1991) Determination of Molecular Species of Oil Triacylglycerols by Reversed-Phase and Chiral-Phase High Performance Liquid Chromatography, J. Am. Oil Chem. Soc. 68, 702–709.
Kendrick, A., and Ratledge, C. (1992) Phospholipid Fatty Acid Distribution of Three Fungi Indicates Positional Specificity for n−6 vs. n−3 Fatty Acids, Lipids 27, 505–508.
Henderson, R.J., Millar, R.-M., and Sargent, J.R. (1995) Effect of Growth Temperature on the Positional Distribution of Eicosapentaenoic Acid and Trans Hexadecenoic Acid in Phospholipids of a Vibrio Species of Bacterium, Lipids 30, 181–185.
Basilde, J., Diez, E., Schuller, A., and Mollinedo, F. (1987) Phospholipase A2 Activity in Resting and Activated Human Neutrophils, J. Biol. Chem. 263, 1929–1936.
Skipski, V.P., and Barclay, M. (1969) Thin-Layer Chromatography of Lipids, Methods Enzymol. 14, 530–598.
Lepage, G., and Roy, C.E. (1986) Direct Transesterification of All Classes of Lipids in a One-Step Reaction, J. Lipid Res. 27, 114–120.
Fischer, W.E., Heinz, E., and Zeus, M. (1973) The Suitability of Lipase from Rhizopus arrhizus delemar for the Analysis of Fatty Acid Distribution in Dihexosyl Diglycerides, Phospholipid and Plant Sulfolipids, Hoppe-Seyler's Z. Physiol. Chem. 354, 115–1123.
Griffiths, G., Stobart, A.K., and Stymne, S. (1985) The Acylation of sn-Glycerol 3-Phosphate and the Metabolism of Phosphatidate in Microsomal Preparation from the Developing Cotyledons of Safflower (Carthamus tinctotius L.) Seed, Biochem. J. 230, 379–388.
Bergmeyer, H.U., Grassi, M., and Walter, H.E. (1983) Methods of Enzymatic Analysis, 3rd edn., pp. 283–291, VCH, Deerfield Beach.
Sadou, H., Leger, C.L., Descomps, B., Barjon, J.N., Monnier, L., and Crastes de Paulet, A. (1995) Differential Incorporation of Fish-Oil Eicosapentaenoate and Docosahexaenoate into Lipids of Lipoprotein Fractions as Related to Their Glyceryl Esterification: A Short-Term (Postprandial) and Long-Term Study in Healthy Humans, Am. J. Clin. Nutr. 62, 1193–1200.
Carlier, H., Bernard, A., and Caselli, C. (1991) Digestion and Absorption of Polyunsaturated Fatty Acids, Reprod. Nutr. Dev. 31, 475–500.
Christensen, M.S., Høy, C.-E., Becker, C.C., and Redgrave, T.G. (1995) Intestinal Absorption and Lymphatic Transport of Eicosapentaenoic (EPA), Docosahexaenoic (DHA), and Decanoic Acids: Dependence on Intramolecular Triacylglycerol Structure, Am. J. Clin. Nutr. 61, 56–61.
Tso, P., Drake, D.S., Black, D.D., and Sabesin, S.M. (1984) Evidence for Separate Pathways of Chylomicron and Very Low-Density Lipoprotein Assembly and Transport by Rat Small Intestine, Am. J. Physiol. 247, G599-G610.
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Amate, L., Ramírez, M. & Gil, A. Positional analysis of triglycerides and phospholipids rich in long-chain polyunsaturated fatty acids. Lipids 34, 865–871 (1999). https://doi.org/10.1007/s11745-999-0434-0
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DOI: https://doi.org/10.1007/s11745-999-0434-0