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Triacylglycerol structure and interesterification of palmitic and stearic acid-rich fats: an overview and implications for cardiovascular disease

  • Sarah E. E. Berry (a1)
Abstract

The position of fatty acids in the TAG molecule (sn-1, sn-2 and sn-3) determines the physical properties of the fat, which affects its absorption, metabolism and distribution into tissues, which may have implications for the risk of CHD. The TAG structure of fats can be manipulated by the process of interesterification, which is of increasing commercial importance, as it can be used to change the physical characteristics of a fat without the generation of trans-fatty acids. Interesterified fats rich in long-chain SFA are commercially important, but few studies have investigated their health effects. Evidence from animal and human infant studies suggests that TAG structure and interesterification affect digestibility, atherogenicity and fasting lipid levels, with fats containing palmitic and stearic acid in the sn-2 position being better digested and considered to be more atherogenic. However, chronic studies in human adults suggest that TAG structure has no effect on digestibility or fasting lipids. The postprandial effects of fats with differing TAG structure are better characterised but the evidence is inconclusive; it is probable that differences in the physical characteristics of fats resulting from interesterification and changes in TAG structure are key determinants of the level of postprandial lipaemia, rather than the position of fatty acids in the TAG. The present review gives an overview of TAG structure and interesterified palmitic and stearic acid-rich fats, their physical properties and their acute and chronic effects in human adults in relation to CHD.

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Corresponding author
Corresponding author: Dr Sarah Berry, fax +44 20 7848 4185, email sarah.e.berry@kcl.ac.uk
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1M Lefevre , PM Kris-Etherton , G Zhao , . (2004) Dietary fatty acids, hemostasis, and cardiovascular disease risk. J Am Diet Assoc 104, 410419.

2FM Sacks & M Katan (2002) Randomized clinical trials on the effects of dietary fat and carbohydrate on plasma lipoproteins and cardiovascular disease. Am J Med 113, Suppl. 9B, 13S24S.

11AG Marangoni & D Rousseau (1995) Engineering triacylglycerols: the role of interesterification. Trends Food Sci Technol 6, 329335.

12H Lavery (1958) Differential thermal analysis of fats. II. Melting behavior of some pure glycerides. J Am Oil Chem Soc 35, 418422.

14D Mozaffarian , MB Katan , A Ascherio , . (2006) Trans fatty acids and cardiovascular disease. N Engl J Med 354, 16011613.

23SE Berry , R Woodward , C Yeoh , . (2007) Effect of interesterification of palmitic acid-rich triacylglycerol on postprandial lipid and factor VII response. Lipids 42, 315323.

24SM Innis , R Dyer & CM Nelson (1994) Evidence that palmitic acid is absorbed as sn-2 monoacylglycerol from human milk by breast-fed infants. Lipids 29, 541545.

27BC Mortimer , MA Kenrick , DJ Holthouse , . (1992) Plasma clearance of model lipoproteins containing saturated and polyunsaturated monoacylglycerols injected intravenously in the rat. Biochim Biophys Acta 1127, 6773.

28BC Mortimer , WJ Simmonds , CA Joll , . (1989) The effect of added monoacylglycerols on the removal from plasma of chylomicron-like emulsions injected intravenously in rats. Biochim Biophys Acta 1002, 359364.

29BC Mortimer , WJ Simmonds , SJ Cockman , . (1990) The effect of monostearoylglycerol on the metabolism of chylomicron-like lipid emulsions injected intravenously in rats. Biochim Biophys Acta 1046, 4656.

30KM Botham (2008) Oxidation of chylomicron remnants and vascular dysfunction. Atheroscler Suppl 9, 5761.

37W Smink , WJ Gerrits , R Hovenier , . (2008) Fatty acid digestion and deposition in broiler chickens fed diets containing either native or randomized palm oil. Poult Sci 87, 506513.

38A Lucas , P Quinlan , S Abrams , . (1997) Randomised controlled trial of a synthetic triglyceride milk formula for preterm infants. Arch Dis Child Fetal Neonatal Ed 77, F178F184.

39VP Carnielli , IH Luijendijk , JB van Goudoever , . (1996) Structural position and amount of palmitic acid in infant formulas: effects on fat, fatty acid, and mineral balance. J Pediatr Gastroenterol Nutr 23, 553560.

42RG Jensen (1999) Lipids in human milk. Lipids 34, 12431271.

43D Kritchevsky (1995) Fatty acids, triglyceride structure, and lipid metabolism. J Nutr Biochem 6, 172178.

44DM Small (1991) The effects of glyceride structure on absorption and metabolism. Annu Rev Nutr 11, 413434.

45EA Decker (1996) The role of stereospecific saturated fatty acid positions on lipid nutrition. Nutr Rev 54, 108110.

46A Bonanome & SM Grundy (1988) Effect of dietary stearic acid on plasma cholesterol and lipoprotein levels. N Engl J Med 318, 12441248.

48Y Shahkhalili , E Duruz & K Acheson (2000) Digestibility of cocoa butter from chocolate in humans: a comparison with corn-oil. Eur J Clin Nutr 54, 120125.

51JT Snook , S Park , G Williams , . (1999) Effect of synthetic triglycerides of myristic, palmitic, and stearic acid on serum lipoprotein metabolism. Eur J Clin Nutr 53, 597605.

52SS Tuomasjukka , MH Viitanen & HP Kallio (2009) Regio-distribution of stearic acid is not conserved in chylomicrons after ingestion of randomised, stearic acid-rich fat in a single meal. J Nutr Biochem (epublication ahead of print version 4 February 2009).

57HR Jung , SM Turner , RA Neese , . (1999) Metabolic adaptations to dietary fat malabsorption in chylomicron-deficient mice. Biochem J 343, 473478.

58D Kritchevsky , SA Tepper , SC Chen , . (2000) Cholesterol vehicle in experimental atherosclerosis. 23. Effects of specific synthetic triglycerides. Lipids 35, 621625.

59D Kritchevsky , SA Tepper , A Kuksis , . (2000) Cholesterol vehicle in experimental atherosclerosis. 22. Refined, bleached, deodorized (RBD) palm oil, randomized palm oil and red palm oil. Nutr Res 20, 887892.

60D Kritchevsky , SA Tepper , G Bises , . (1982) Experimental atherosclerosis in rabbits fed cholesterol-free diets. Atherosclerosis 41, 279284.

61D Kritchevsky & SA Tepper (1977) Cholesterol vehicle in experimental atherosclerosis. Part 15. Randomized butter and randomized lard. Atherosclerosis 27, 339345.

62PJ van Jaarsveld , CM Smuts & AS Benadé (2002) Effect of palm olein oil in a moderate-fat diet on plasma lipoprotein profile and aortic atherosclerosis in non-human primates. Asia Pac J Clin Nutr 11, Suppl. 7, S424S432.

63JB Keogh , JA Grieger , M Noakes , . (2005) Flow-mediated dilatation is impaired by a high-saturated fat diet but not by a high-carbohydrate diet. Arterioscler Thromb Vasc Biol 25, 12741279.

64M Sarabi , B Vessby , J Millgard , . (2001) Endothelium-dependent vasodilation is related to the fatty acid composition of serum lipids in healthy subjects. Atherosclerosis 156, 349355.

65NJ de Fouw , GA Kivits , PT Quinlan , . (1994) Absorption of isomeric, palmitic acid-containing triacylglycerols resembling human milk fat in the adult rat. Lipids 29, 765770.

67MB Reena & BR Lokesh (2007) Hypolipidemic effect of oils with balanced amounts of fatty acids obtained by blending and interesterification of coconut oil with rice bran oil or sesame oil. J Agric Food Chem 55, 1046110469.

69PM Kris-Etherton , J Derr , DC Mitchell , . (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, 121129.

70WE Connor , DT Witiak , DB Stone , . (1969) Cholesterol balance and fecal neutral steroid and bile acid excretion in normal men fed dietary fats of different fatty acid composition. J Clin Invest 48, 13631375.

77AB Christophe , WF De Greyt , JR Delanghe , . (2000) Substituting enzymatically interesterified butter for native butter has no effect on lipemia or lipoproteinemia in man. Ann Nutr Metab 44, 6167.

78DB Zilversmit (1979) Atherogenesis: a postprandial phenomenon. Circulation 60, 473485.

79RA Vogel , MC Corretti & GD Plotnick (1997) Effect of a single high-fat meal on endothelial function in healthy subjects. Am J Cardiol 79, 350354.

80GJ Miller (1998) Postprandial lipaemia and haemostatic factors. Atherosclerosis 141, Suppl. 1, S47S51.

81SH Gianturco & WA Bradley (1999) Pathophysiology of triglyceride-rich lipoproteins in atherothrombosis: cellular aspects. Clin Cardiol 22, Suppl. 6, II7II14.

82JR Patsch , G Miesenbock , T Hopferwieser , . (1992) Relation of triglyceride metabolism and coronary artery disease. Studies in the postprandial state. Arterioscler Thromb 12, 13361345.

86KM Yli-Jokipii , US Schwab , RL Tahvonen , . (2003) Chylomicron and VLDL TAG structures and postprandial lipid response induced by lard and modified lard. Lipids 38, 693703.

91DM Robinson , NC Martin , LE Robinson , . (2009) Influence of interesterification of a stearic acid-rich spreadable fat on acute metabolic risk factors. Lipids 44, 1726.

94DT Stein , BE Stevenson , MW Chester , . (1997) The insulinotropic potency of fatty acids is influenced profoundly by their chain length and degree of saturation. J Clin Invest 100, 398403.

96M Kjalke , A Silveira , A Hamsten , . (2000) Plasma lipoproteins enhance tissue factor-independent factor VII activation. Arterioscler Thromb Vasc Biol 20, 18351841.

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Nutrition Research Reviews
  • ISSN: 0954-4224
  • EISSN: 1475-2700
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