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Studies on effects of dietary fatty acids as related to their position on triglycerides

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Lipids

Abstract

This article reviews published literature on how the stereospecific structure of dietary triglycerides may affect lipid metabolism in humans. Animal studies have shown enhanced absorption of fatty acids in the sn-2 position of dietary triglycerides. Increasing the level of the saturated fatty acid palmitic acid in the sn-2 position (e.g., by interesterification of the fat to randomize the positions of the fatty acids along the glycerol backbone) has been shown in rabbits to increase the atherogenic potential of the fat without impacting levels of blood lipids and lipoproteins. In contrast, enhancing the level of stearic acid in the sn-2 position has not been found to affect either atherogenic potential or levels of blood lipids and lipoproteins in rabbit. Fatty acids other than palmitic and stearic have not been studied systematically with respect to possible positional effects. A limited number of human studies have shown no significant effects of interesterified fats on blood lipid parameters. However, it is unknown whether modifying the stereospecific structure of dietary triglycerides would affect atherogenicity or other long-term health conditions in humans. It is possible that incorporation of palmitic acid into the sn-2 position of milk fat is beneficial to the human infant (as a source of energy for growth and development) but not to human adults. Additional research is needed to determine whether processes like interesterification, which can be used to alter physical parameters of dietary fats (e.g., melting characteristics), may result in favorable or unfavorable long-term effects in humans.

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Abbreviations

AHA:

American Heart Association

apo:

apolipoprotein

CHO:

cholesterol

HDL:

high density lipoprotein

HOSO:

high-oleic sunflower oil

LDL:

low density lipoprotein

LMP:

lauric, myristic, and palmitic fatty acids

MCFA:

medium-chain fatty acid

MCT:

medium-chain triglycerides

NCEP:

National Cholesterol Education Program

O:

oleic acid

OL:

oleic acid diet

P:

palmitic acid

RBD:

refined bleached, deodorized

S:

stearic acid

SCFA:

short-chain fatty acid

STE:

stearic acid diet

TFA:

trans fatty acids

VOO:

virgin olive oil

References

  1. Hegsted, D.M., Ausman, L.M., Johnson, J.A., and Dallal, G.E. (1993) Dietary Fat and Serum Lipids: An Evaluation of the Experimental Data, Am. J. Clin. Nutr. 57, 875–883.

    PubMed  CAS  Google Scholar 

  2. Keys, A., Anderson, J.T., and Grande, F. (1957) Prediction of Serum-Cholesterol Responses in Man to Changes in Fats in the Diet, Lancet 2, 959–966.

    Article  Google Scholar 

  3. Hegsted, D.M., McGandy, R.B., Meyers, M.L., and Stare, F.J. (1965) Quantitative Effects of Dietary Fat on Serum Cholesterol in Man, Am. J. Clin. Nutr. 17, 281–295.

    PubMed  CAS  Google Scholar 

  4. Hegsted, D.M., and Kritchevsky, D. (1997) Diet and Serum Lipid Concentrations: Where Are We? Am. J. Clin. Nutr. 65, 1893–1896.

    PubMed  CAS  Google Scholar 

  5. Katan, M.B., Zock, P.L., and Mensink, R.P. (1994) Effects of Fats and Fatty Acids on Blood Lipids in Humans: An Overview, Am. J. Clin. Nutr. 60 (suppl.) 1017S-1022S.

    PubMed  CAS  Google Scholar 

  6. Bonanome, A., and Grundy, S.M. (1988) Effect of Dietary Stearic Acid on Plasma Cholesterol and Lipoprotein Levels, N. Engl. J. Med. 318, 1244–1248.

    Article  PubMed  CAS  Google Scholar 

  7. Mattson, F.H., and Grundy, S.M. (1985) Comparison of Effects of Dietary Saturated, Monounsaturated, and Polyunsaturated Fatty Acids on Plasma Lipids and Lipoproteins in Man, J. Lipid Res. 26, 194–202.

    PubMed  CAS  Google Scholar 

  8. Decker, E.A. (1996) The Role of Stereospecific Saturated Fatty Acid Positions on Lipid Metabolism, Nutr. Rev. 54, 108–110.

    Article  PubMed  CAS  Google Scholar 

  9. Kubow, S. (1996) The Influence of Positional Distribution of Fatty Acids in Native, Interesterified, and Structure-Specific Lipids on Lipoprotein Metabolism and Atherogenesis, J. Nutr. Biochem. 7, 530–541.

    Article  CAS  Google Scholar 

  10. Brockerhoff, H., and Yurkowski, M. (1966) Stereospecific Analyses of Several Vegetable Fats, J. Lipid Res. 7, 62–64.

    PubMed  CAS  Google Scholar 

  11. Brockerhoff, H., Hoyle, R.J., and Wolmark, N. (1966) Positional Distribution of Fatty Acids in Triglycerides of Animal Depot Fats, Biochim. Biophys. Acta 116, 67–72.

    PubMed  CAS  Google Scholar 

  12. Nawar, W.W. (1996) Lipids, in Food Chemistry (Fennema, O.R., ed.), 3rd edn., pp. 225–319, Marcel Dekker, Inc., New York.

    Google Scholar 

  13. Padley, F.B., Gunstone, F.D., and Harwood, J.L. (1994) Occurrence and Characteristics of Oils and Fats, in The Lipid Handbook (Gunstone, F.D., Harwood, J.L., and Padley, F.B., eds.), 2nd edn., pp. 47–223, Chapman & Hall, London.

    Google Scholar 

  14. Small, D.M. (1991) The Effects of Glyceride Structure on Absorption and Metabolism, Ann. Rev. Nutr. 11, 412–434.

    Google Scholar 

  15. Kritchevsky, D. (1988) Effects of Triglyceride Structure on Lipid Metabolism, Nutr. Revs. 46, 177–181.

    Article  CAS  Google Scholar 

  16. Bracco, U. (1999) Effect of Triglyceride Structure on Fat Absorption, Am. J. Clin. Nutr. 60 (suppl) 1002S-1009S.

    Google Scholar 

  17. Mattson, F.H., and Volpenhein, R.A. (1964) The Digestion and Absorption of Triglycerides, J. Biol. Chem. 239, 2772–2777.

    PubMed  CAS  Google Scholar 

  18. Breckenridge, W.C. (1978) Stereospecific Analysis of Triacylglycerols, in Handbook of Lipid Research. Fatty Acids and Glycerides, (Kuksis, A., ed.), Vol. 1, pp. 197–232, Plenum Press, New York.

    Google Scholar 

  19. Filer, L.J., Jr., Mattson, F.H., and Fomon, S.J. (1969) Triglyceride Configuration and Fat Absorption by the Human Infant, J. Nutr. 99, 293–298.

    PubMed  CAS  Google Scholar 

  20. Lien, E.L., Yuhas, R.J., Boyle, R.G., and Tomarelli, R.M. (1993) Corandomization of Fats Improves Absorption in Rats, J. Nutr. 123, 1859–1867.

    PubMed  CAS  Google Scholar 

  21. Renaud, S.C., Ruf, J.C., and Petithorny, D. (1995) The Positional Distribution of Fatty Acids in Palm Oil and Lard Influences Their Biologic Effects in Rats, J. Nutr. 125, 229–237.

    PubMed  CAS  Google Scholar 

  22. Tomarelli, R.M., Meyer, B.J., Weaber, J.R., and Bernhart, F.W. (1968) Effect of Positional Distribution on the Absorption of the Fatty Acids of Human Milk and Infant Formulas, J. Nutr. 95, 583–590.

    PubMed  CAS  Google Scholar 

  23. Carnielli, V.P., Luijendijk, I.H.T., van Goudoever, 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: Effects on Fat and Mineral Balance, Am. J. Clin. Nutr. 61, 1037–1042.

    PubMed  CAS  Google Scholar 

  24. Bernback, S., Blackberg, L., and Hernell, O. (1990) The Complete Digestion of Human Milk Triacylglycerol in vitro Requires Gastric Lipase, Pancreatic Colipase-Dependent Lipase, and Bile Salt-Stimulated Lipase, J. Clin. Invest. 85, 1221–1226.

    Article  PubMed  CAS  Google Scholar 

  25. Carvajal, O., Nakayama, M., Kishi, T., Sato, M., Ikeda, I., Sugano, M., and Imaizumi, K. (2000) Effect of Medium-Chain Fatty Acid Positional Distribution in Dietary Triacylglycerol on Lymphatic Lipid Transport and Chylomicron Composition in Rats, Lipids 35, 1345–1351.

    Article  PubMed  CAS  Google Scholar 

  26. Summers, L.K.M., Fielding, B.A., Herd, S.L., Ilie, V., Clark, M.L., Quinlan, P.T., and Frayn, K.N. (1999) Use of Structured Triacylglycerols Containing Predominantly Stearic and Oleic Acids to Probe Early Events in Metabolic Processing of Dietary Fat, J. Lipid Res. 40, 1890–1898.

    PubMed  CAS  Google Scholar 

  27. Abia, R., Pacheco, Y.M., Perona, J.S., Montero, E., Muriana, F.J.G., and Ruiz-Gutierrez, V. (2001) The Metabolic Availability of Dietary Triacylglycerols from Two High Oleic Oils During the Postprandial Period Does Not Depend on the Amount of Oleic Acid Ingested by Healthy Men, J. Nutr. 131, 59–65.

    PubMed  CAS  Google Scholar 

  28. Kritchevsky, D., and Tepper, S.A. (1967) Cholesterol Vehicle in Experimental Atherosclerosis X. Influence of Specific Saturated Fatty Acids, Exp. Molec. Pathol. 6, 394–401.

    Article  CAS  Google Scholar 

  29. Kritchevsky, D., Tepper, S.A., Vesselinovitch, D., and Wissler, R.W. (1973) Cholesterol Vehicle in Experimental Atherosclerosis Part 13. Randomized Peanut Oil, Atherosclerosis 17, 225–243.

    Article  PubMed  CAS  Google Scholar 

  30. Kritchevsky, D., Tepper, S.A., and Klurfeld, D.M. (1998) Lectin May Contribute to the Atherogenicity of Peanut Oil, Lipids 33, 821–823.

    Article  PubMed  CAS  Google Scholar 

  31. Kritchevsky, D., Tepper, S.A., Kuksis, A., Eghtedary, K., and Klurfeld, D.M. (1998) Cholesterol Vehicle in Experimental Atherosclerosis. 21. Native and Randomized Lard and Tallow, J. Nutr. Biochem. 9, 582–585.

    Article  CAS  Google Scholar 

  32. Kritchevsky, D., Tepper, S.A., Wright, S., Kuksis, A., and Hughes, T.A. (1998) Cholesterol Vehicle in Experimental Atherosclerosis. 20. Cottonseed Oil and Randomized Cottonseed Oil, Nutr. Res. 18, 259–264.

    Article  CAS  Google Scholar 

  33. Kritchevsky, D., Tepper, S.A., Kuksis, A., Wright, S., and Czarnecki, S.K. (2000) Cholesterol Vehicle in Experimental Atherosclerosis. 22. Refined, Bleached, Deodorized (RBD) Palm Oil, Randomized Palm Oil and Red Palm Oil, Nutr. Res. 20, 887–892.

    Article  CAS  Google Scholar 

  34. Kritchevsky, D., Tepper, S.A., Chen, S.C., Meijer, G.W., and Krauss, R.M. (2000) Cholesterol Vehicle in Experimental Atherosclerosis. 23. Effects of Specific Synthetic Triglycerides, Lipids 35, 621–625.

    Article  PubMed  CAS  Google Scholar 

  35. Redgrave, T.G., Kodali, D.R., and Small, D.M. (1988) The Effect of Triacyl-sn-glycerol Structure on the Metabolism of Chylomicrons and Triglyceride-Rich Emulsions in the Rat, J. Biol. Chem. 263, 5118–5123.

    PubMed  CAS  Google Scholar 

  36. Innis, S.M., Dyer, R., Quinlan, P., and Diersen-Schade, D. (1995) Palmitic Acid Is Absorbed as sn-2 Monopalmitin from Milk and Formula with Rearranged Triacylglycerols and Results in Increased Plasma Triglyceride sn-2 and Cholesteryl Ester Palmitate in Piglets, J. Nutr. 125, 73–81.

    PubMed  CAS  Google Scholar 

  37. Innis, S.M., and Dyer, R. (1997) Dietary Triacylglycerols with Palmitic Acid (16∶0) in the 2-Position Increase 16∶0 in the 2-Position of Plasma and Chylomicron Triacylglycerols, but Reduce Phospholipid Arachidonic and Docosahexaenoic Acids, and Alter Cholesteryl Ester Metabolism in Formula-Fed Piglets, J. Nutr. 127, 1311–1319.

    PubMed  CAS  Google Scholar 

  38. Innis, S.M., Dyer, R.A., and Lien, E.L. (1997) Formula Containing Randomized Fats with Palmitic Acid (16∶0) in the 2-Position Increases 16∶0 in the 2-Position of Plasma and Chylomicron Triglycerides in Formula-Fed Piglets to Levels Approaching Those of Piglets Fed Sow's Milk, J. Nutr. 127, 1362–1370.

    PubMed  CAS  Google Scholar 

  39. Zock, P.L., de Vries, J.H.M., de Fouw, N.J., and Katan, M.B. (1995) Positional Distribution of Fatty Acids in Dietary Triglycerides: Effects on Fasting Blood Lipoprotein Concentrations in Humans, Am. J. Clin. Nutr. 61, 48–55.

    PubMed  CAS  Google Scholar 

  40. Nestel, P.J., Noakes, M., Belling, G.B., McArthur, R., and Clifton, P.M. (1995) Effect on Plasma Lipids of Interesterifying a Mix of Edible Oils, Am. J. Clin. Nutr. 62, 950–955.

    PubMed  CAS  Google Scholar 

  41. Nestel, P.J., Pomeroy, S., Kay, S., Sasahara, T., and Yamashita, T. (1998) Effect of a Stearic Acid-Rich, Structured Triacylglycerol on Plasma Lipid Concentrations, Am. J. Clin. Nutr. 68, 1196–1201.

    PubMed  CAS  Google Scholar 

  42. Meijer, G.W., and Weststrate, J.A. (1997) Interesterification of Fats in Margarine: Effect on Blood Lipids, Blood Enzymes, and Hemostasis Parameters, Eur. J. Clin. Nutr. 51, 527–534.

    Article  PubMed  CAS  Google Scholar 

  43. Nelson, C.M., and Innis, S.M. (1999) Plasma Lipoprotein Fatty Acids Are Altered by the Positional Distribution of Fatty Acids in Infant Formula Triacylglycerols and Human Milk, Am. J. Clin. Nutr. 70, 62–69.

    PubMed  CAS  Google Scholar 

  44. McGandy, R.B., Hegsted, D.M., and Meyers, M.L. (1970) Use of Semisynthetic Fats in Determining Effects of Specific Dietary Fatty Acids on Serum Lipids in Man, Am. J. Clin. Nutr. 23, 1288–1298.

    PubMed  CAS  Google Scholar 

  45. Grande, F., Anderson, J.T., and Keys, A. (1970) Comparison of Effects of Palmitic and Stearic Acids in the Diet on Serum Cholesterol in Man, Am. J. Clin. Nutr. 23, 1184–1193.

    PubMed  CAS  Google Scholar 

  46. Judd, J.T., Baer, D.J., Clevidence, B.A., Kris-Etherton, P., Muesing, R.A., and Iwane, M. (1998) Blood Lipid and Lipoprotein Modifying Effects of trans Monounsaturated Fatty Acids Compared to Carbohydrate, Oleic Acid, Stearic Acid, and C12∶0–16∶0 Saturated Fatty Acids in Men Fed Controlled Diets, FASEB J. 12, A229.

    Google Scholar 

  47. Kris-Etherton, P.M., Derr, J.A., Mustad, V.A., Seligson, F.H., and Pearson, T.A. (1994) Effects of a Milk Chocolate Bar Per Day Substituted for a High-Carbohydrate Snack in Young Men on an NCEP/AHA Step 1 Diet, Am. J. Clin. Nutr. 60 (suppl.), 1037S-1042S.

    PubMed  CAS  Google Scholar 

  48. Snook, J.T., Park, S., Williams, G., Tsai, Y-H., and Lee, N. (1999) Effect of Synthetic Triglycerides of Myristic, Palmitic, and Stearic Acids on Serum Lipoprotein Metabolism, Eur. J. Clin. Nutr. 53, 597–605.

    Article  PubMed  CAS  Google Scholar 

  49. Tholstrup, T., Marckmann, P., Jespersen, J., and Sandstrom, B. (1994) Fat High in Stearic Acid Favorably Affects Blood Lipids and Factor VII Coagulant Activity in Comparison with Fats High in Palmitic Acid or High in Myristic Acid and Lauric Acid, Am. J. Clin. Nutr. 59, 371–377.

    PubMed  CAS  Google Scholar 

  50. Kris-Etherton, P., Daniels, S.R., Eckel, R.H., Engler, M., Howard, B.V., Krauss, R.M., Lichtenstein, A.H., Sacks, F., St. Jeor, S., and Stampfer, M. (2001) Summary of the Scientific Conference on Dietary Fatty Acids and Cardiovascular Health, Circulation 103, 1034–1039.

    PubMed  CAS  Google Scholar 

  51. Aro, A., Jauhiainen, M., Partanen, R., Salminen, I., and Mutanen, M. (1997) Stearic Acid, Trans Fatty Acids, and Dairy Fat: Effects on Serum and Lipoprotein Lipids, Apolipoproteins, Lipoprotein(a), and Lipid Transfer Proteins in Healthy Subjects, Am. J. Clin. Nutr. 65, 1419–1426.

    PubMed  CAS  Google Scholar 

  52. Mascioli, E.A., McLennan, C.E., Schaefer, E.J., Lichtenstein, A.H., Høy, C-E., Christensen, M.S., and Bistrian, B.R. (1999) Lipidemic Effects of an Interesterified Mixture of Butter, Medium-Chain Triacylglycerol and Safflower Oils, Lipids 34 889–894.

    Article  PubMed  CAS  Google Scholar 

  53. Schwab, U.S., Maliranta, H.M., Sarkkinen, E.S., Savolainen, M.J., Kesaniemi, Y.A., and Uusitupa, M.I.J. (1996) Different Effects of Palmitic and Stearic Acid-Enriched Diets on Serum Lipids and Lipoproteins and Plasma Cholesteryl Ester Transfer Protein Activity in Healthy Young Women, Metabolism 45, 143–149.

    Article  PubMed  CAS  Google Scholar 

  54. Kris-Etherton, P.M., Derr, J., Mitchell, D.C., Mustad, V.A., Russell, M.E., McDonnell, E.T., Salabsky, D., and Pearson, T.A. (1993) The Role of Fatty Acid Saturation on Plasma Lipids, Lipoproteins, and Apolipoproteins: I. Effects of Whole Food Diets High in Cocoa Butter, Olive Oil, Soybean Oil, Dairy Butter, and Milk Chocolate on the Plasma Lipids of Young Men, Metabolism 42, 121–129.

    Article  PubMed  CAS  Google Scholar 

  55. Dougherty, R.M., Allman, M.A., and Iacono, J.M. (1995) Effects of Diets Containing High or Low Amounts of Stearic Acid on Plasma Lipoprotein Fractions and Fecal Fatty Acid Excretion of Men, Am. J. Clin. Nutr. 61, 1120–1128.

    PubMed  CAS  Google Scholar 

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  1. Department of Chemistry, University of Cincinnati, P.O. Box 210172, 45221-0172, Cincinnati, OH

    J. Edward Hunter

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Hunter, J.E. Studies on effects of dietary fatty acids as related to their position on triglycerides. Lipids 36, 655–668 (2001). https://doi.org/10.1007/s11745-001-0770-0

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  • DOI: https://doi.org/10.1007/s11745-001-0770-0

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