Incorporation of medium chain fatty acids into fish oil triglycerides by chemical and enzymatic interesterification

Grasas y Aceites

Volumn 60, Issue 2, 2009, Pages 168-176

  Feltes, Maria M C ^a   De Oliveira Pitol, L ^a   Correia, J F Gomes ^a   Grimaldi, R ^b   Blockc, J Mara ^a   Ninow, Jorge L ^a  

^a FEDERAL UNIVERSITY OF SANTA CATARINA   (Brazil)

^b UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

Fish oil; Interesterification; Mediumchain fatty acid; Structured triglycerides

Indexed keywords

EICOSAPENTAENOIC ACID; ENZYMATIC INTERESTERIFICATION; FATTY ACID COMPOSITION; FISH OIL; INTERESTERIFICATION; MEDIUM CHAIN TRIGLYCERIDES; MEDIUM-CHAIN FATTY ACIDS; STRUCTURED TRIGLYCERIDES;

CATALYSTS; CHAINS; DIFFERENTIAL SCANNING CALORIMETRY; NUTRITION; POLYUNSATURATED FATTY ACIDS;

FATTY ACIDS;

EID: 65349109740     PISSN: 00173495     EISSN: 19884214     Source Type: Journal    
DOI: 10.3989/gya.074708     Document Type: Article

References (70)

1. Akoh CC. 1995. Structured lipids - Enzymatic approach. Inform 6, 1055-1061.
2. Akoh CC, Lee K-T, Fomuso LB. 1998. Synthesis of positional isomers of structured lipids with lipases as biocatalysts, in Christophe A (Ed.) Structural Modified Food Fats: Synthesis, Biochemistry, and Use. AOCS Press, Champaign, pp. 46-72.
3. AOCS. 1990. Official Methods and Recommended Practices of the American Oil Chemists' Society. 4th ed, AOCS Press, Champaign.
4. AOCS. 1997. Official Methods and Recommended Practices of the American Oil Chemists' Society. 5th ed, AOCS Press, Champaign.
5. Aro T, Tahvonen R, Mattila T, Nurmi J, Sivonen T, Kallio H. 2000. Effects of season and processing on oil content and fatty acids of Baltic herring (Clupea harengus membras). J. Agr. Food Chem. 48, 6085-6093.
6. Bach A, Babayan VK. 1982. Medium-chain triglycerides: an update. Am. J. Clin. Res. 32, 950-962.
7. Bailey AE. 1979. Bailey's Industrial Oil and Fat Products. 4th ed, John Wiley & Sons, New York.
8. Bell SJ, Bradley D. 1997. The new dietary fats in health and disease. J. Am. Diet Assoc. 97, 280-286.
9. Bistrian BR. 1997. Novel lipid sources in parenteral and enteral nutrition. Proceed Nutr. Soc 56, 471-477.
10. Bockisch M. 1993.Fats and Oils Handbook. AOCS Press, Champaign.
11. Bourque C, St-Onge M-P, Papamandjaris AA, Cohn JS, Jones PJH. 2003. Consumption of an oil composed of medium chain triacylglycerols, phytosterols, and n-3 fatty acids improves cardiovascular risk profile in overweight women. Metabolism 52, 771-777.
12. Carpentier YA. 2008. Basic in clinical nutrition: substrates used in parenteral and enteral nutrition-lipids. e-SPEN, Eur e-J Clin. Nutr. Metab. doi:10.1016/ j.ecinm.2008.07.009.
13. Cater NB, Heller HJ, Denke MA. 1997. Comparison of the effects of medium-chain triacylglycerols, palm oil, and high oleic acid sunflower oil on plasma triacylglycerol fatty acids and lipid and lipoprotein concentrations in humans. Am. J. Clin. Nutr. 65, 41-45.
14. Christie WW. 1982. Lipid Analysis. 2nd ed, Pergamon Press, Oxford.
15. Christophe A. 1998. Metabolism and physiological effects of dietary fats in relation to their structure, in Christophe A (Ed.) Structural Modified Food Fats: Synthesis, Biochemistry, and Use. AOCS Press,
16. Champaign, pp. 139-148. Díaz Gamboa O, Gioielli LA. 2003a. Consistencia de lípidos estructurados a partir de aceite de pescado y grasa de palmiste. Grasas y Aceites 54,122-129.
17. Díaz Gamboa O, Gioielli LA. 2003b. Lípidos estructurados obtenidos por interesterificación química y enzimática a partir de aceite de pescado y grasa de palmiste. Grasas y Aceites 54, 161-168.
18. Dunford NT. 2004. Oil- and oilseed-based bioactive compounds and their health effects, in Dunford NT, Dunford HB. (Ed.) Nutritionally Enhanced Edible Oil and Oilseed Processing. AOCS Press, Champaign, pp. 1-24.
19. Férézou J, Gulik A, Domingo N, Milliat F, Dedieu J-C, Dunel-Erb S, Chevalier C, Bach AC. 2001. Intralipid 10%: physicochemical characterization. Nutrition 17, 930-933.
20. Food and Agriculture Organization/World Health Organization - FAO-WHO, CODEX ALIMENTARIUS. 1981, revision 1999. Codex Standard for Edible Fats and Oils not Covered by Individual Standards, CODEX-STAN 19.
21. Food and Drug Administration - FDA. 1995, revision 2003. Code of Federal Regulations: 21 CFR 184 - Direct Food Substances affirmed as Generally Recognized as Safe.
22. Galante JH, Tenore RR. 2006. Medium-chain triglycerides, in Akoh CC (Ed.) Handbook of Functional Lipids - Functional Foods and Nutraceuticals. CRC Press, Boca Ratón, pp. 177-184.
23. Goldberg I (Ed.). 1994. Functional Foods: Designer Foods, Pharmafoods, Nutraceuticals. Chapman & Hall, New York.
24. Grimaldi R, Gonçalves LAG, Gioielli LA, Simões IS. 2001. Interactions in interesterified palm and palm kernel oils mixtures. II - Microscopy and differential scanning calorimetry. Grasas y Aceites 52, 363-368.
25. Grimaldi R, Nassu RT, Gonçalves LAG, Moreira RNC. 1998. Characterization of hydrogenated fats for margarine manufacturing purposes. Grasas y Aceites 49, 1-8.
26. Gunstone FD. 1999. Enzymes as biocatalysts in the modification of natural lipids. Review. J. Sci. Food Agr. 79, 1535-1549.
27. Gunstone FD, Harwood JL, Padley FB. 1994. Marine oils: fish and whale oils, in Gunstone FD, Harwood JL, Padley FB. (Ed.) The Lipid Handbook. Chapman & Hall, London, pp. 167-395.
28. Hartman L, Lago RCA. 1973. Rapid preparation of fatty acid methyl esters from lipids.Lab. Pract. 22, 475-477.
29. Hartvigsen MS, Mu H, Hoy C-E. 2003. Influence of maternal dietary n-3 fatty acids on breast milk and liver lipids of rat dams and offspring - a preliminary study. Nutr. Res. 23, 747-760.
30. Hasselmann M, Kummerlen C. 1998. Les lipides intraveineux: aspects qualitatifs. Nutr. Clin. Métab. 12, 117-126.
31. Institute of Shortening and Edible Oils - ISEO. 2006. Food Fats and Oils. Institute of Shortening and Edible Oils, New York.
32. Jandacek RJ, Whiteside JA, Holcombe BN, Volpenhein RA, Taulbee JD. 1987. The rapid hydrolysis and efficient absorption of triglycerides with octanoic acid in the 1 and 3 positions and long-chain fatty acid in the 2 position. Am. J. Clin. Nutr. 45, 940-945.
33. Jennings BH, Akoh CC. 1999. Enzymatic modification of triacylglycerols of high eicosapentaenoic and docosahexaenoic acids content to produce structured lipids. J. Am. Oil Chem. Soc. 76, 1133-1137.
34. Jennings BH, Akoh CC. 2001. Lipase catalyzed modification of fish oil to incorporate capric acid.Food Chem. 72, 273-278.
35. Jones PM, Butt Y, Messmer B, Boriak R, Bennett MJ. 2006. Medium-chain fatty acids undergo elongation before oxidation in fibroblasts. Biochem. Biophys. Res Commun. 346, 193-197.
36. Jores K. 2004. Lipid Nanodispersions as Drug Carrier Systems - A Physicochemical Characterization. Ph.D. Thesis. Martin-Luther- Universität Halle-Wittenberg, Germany. 111 p.
37. Klinkesorn U, H-Kittikun A, Chinachoti P, Sophanodora P. 2004. Chemical transesterification of tuna oil to enriched omega-3 polyunsaturated fatty acids. Food Chem. 87, 415-421.
38. Kris-Etherton PM, Harris WS, Appel LJ. 2002. Fish consumption, fish oil, omega-3 fatty acids, and cardiovascular disease. Circulation 106, 2747-2757.
39. Kubow S. 1996. The influence of positional distribution of fatty acids in native, interesterified and structurespecific lipids on lipoprotein metabolism and atherogenesis. J. Nutr. Biochem. 7, 530-541.
40. Lands WEM. 2002. Fish, Omega-3 and Human Health. 2nd ed, AOCS Press, Champaign.
41. Macrae AR. 1983. Lipase-catalyzed interesterification of oils and fats. J. Am. Oil Chem. Soc 60, 243-246.
42. Marangoni AG, Rousseau D. 1995. Engineering triacylglycerols: the role of interesterification. Trends Food Sci. Tech. 6, 329-335.
43. Matulka RA, Noguchi O, Nosaka N. 2006. Safety evaluation of a medium- and long-chain triacylglycerol oil produced from medium-chain triacylglycerols and edible vegetable oil. Food Chem. Toxic. 44, 1530-1538.
44. Moura JMLN de, Gonçalves LAG, Grimaldi R, Soares M da S, Ribeiro APB. 2006. Otimização das condições de produção de ésteres etílicos a partir de óleo de peixe com elevado teor de ácido graxos w-3. Quím. Nova 29, 956-959.
45. Mu H, Hoy C-E. 2000. Effects of different medium-chain fatty acids on intestinal absorption of structured triacylglycerols. Lipids 35, 83-89.
46. Mu H, Hoy C-E. 2001. Intestinal absorption of specific structured triacylglycerols. J. Lip Res. 42, 792-798.
47. Mu H, Porsgaard T. 2005. The metabolism of structured triacylglycerols. Progr. Lip. Res. 44, 430-448.
48. Nassu RT, Gonçalves LAG. 1999. Determination of melting point of vegetable oils and fats by differential scanning calorimetry (DSC) technique. Grasas y Aceites 50, 16-22.
49. Nicolosi RJ. 1997. Dietary fat saturation effects on lowdensity- lipoprotein concentrations and metabolism in various animal models. Am. J. Clin. Nutr. 65 (suppl), 1617S-1627S.
50. Nielsen NS, Göttsche JR, Holm J, Xu X, Mu H, Jacobsen C. 2005. Effect of structured lipids based on fish oil on growth and fatty acid composition in rainbow trout (Oncorhynchus mykiss). Aquaculture 250, 411-123.
51. Osborn HT, Akoh CC. 2002. Structured lipids - novel fats with medical, nutraceutical, and food applications. Compr. Rev. Food Sci. Food Saf. 1, 93-103.
52. Pacheco MTB, Barrera-Arellano D. 1994. Fraccionamiento del aceite de hígado de tiburón azul (Prionace glauca) y su estabilizació n con antioxidantes. Grasas y Aceites 45, 155-160.
53. Pigott GM, Tucker BW. 1990. Seafood: Effects of Technology on Nutrition. Marcel Dekker, Inc., New York.
54. Qi K, Seo T, Jiang Z, Carpentier YA, Deckelbaum RJ. 2006. Triglycerides in fish oil affect the blood clearance of lipid emulsions containing long- and medium-chain triglycerides in mice. J. Nutr. 136, 2766-2772.
55. Rao R, Sambaiah K, Lokesh BR. 2003. Cholesterol lowering structured lipids containing omega-3 polyunsaturated fatty acids and their process thereof. Patent no US 6.608.223 B2.
56. Reyes HR, Hill Jr CG. 1994. Kinetic modeling of interesterification reactions catalyzed by immobilized lipase. Biotechnol Bioeng. 43, 171-182.
57. Rousseau D, Forestière K, Hill AR, Marangoni AG. 1996. Restructuring butterfat through blending and chemical interesterification. 1. Melting behavior and triacylglycerol modifications. J. Am. Oil Chem. Soc. 73, 963-972.
58. Rousseau D, Marangoni AG. 2002. The effects of interesterification on the physical properties of fats, in Marangoni, AG, Narine SS. (Ed.) Physical Properties of Lipids. Marcel Dekker, Inc., New York, pp. 479-527.
59. Sathivel S. 2005. Thermal and flow properties of oils from salmon heads. J. Am. Oil Chem. Soc. 82, 147-152.
60. Shimada Y. 2006. Enzymatic modification of lipids for functional foods and nutraceuticals, in Akoh CC (Ed.) Handbook of Functional Lipids - Functional Foods and Nutraceuticals. CRC Press, Boca Ratón, pp. 437-456.
61. Simoens CM, Deckelbaum RJ, Massaut JJ, Carpentier YA. 2008. Inclusion of 10% fish oil in mixed mediumchain triacylglycerol-long-chain triacylglycerol emulsions increases plasma triacylglycerol clearance and induces rapid eicosapentaenoic acid (20:5n-3) incorporation into blood cell phospholipids. Am. J. Clin. Nutr. 88, 282-288.
62. Soccol MCH, Oetterer M. 2003. Seafood as functional food. Braz. Arch. Biol Techn. 46, 443-454.
63. Stein J. 1999. Chemically defined structured lipids - current status and future directions in gastrointestinal diseases. Int. J. Colorectal Dis. 14, 79-85.
64. St-Onge M-P. 2005. Dietary fats, teas, dairy, and nuts: potential functional foods for weight control? Am. J. Clin. Nutr. 81, 7-15.
65. St-Onge M-P, Bosarge A. 2008. Weight-loss diet that includes consumption of medium-chain triacylglycerol oil leads to a greater rate of weight and fat mass loss than does olive oil. Am. J. Clin. Nutr. 87, 621-626.
66. Straarup EM, Hoy C-E. 2000. Structured lipids improve fat absorption in normal and malabsorbing rats. J. Nutr. 130, 2802-2808.
67. Versleijen M, Roelofs H, Preijers F, Roos D, Wanten G. 2005. Parenteral lipids modulate leukocyte phenotypes in whole blood, depending on their fatty acid composition. Clin. Nutr. 24, 822-829.
68. Wanasundara UN, Shahidi F. 1998. Antioxidant and prooxidant activity of green tea extracts in marine oils. Food Chem. 63, 335-342.
69. Willis W, Lencki RW, Marangoni AG. 1998. Lipid modification strategies in the production of nutritionally functional fats and oils. Critical Reviews Food Sci. Nutr. 38, 639-674.
70. Xu X. 2004. Biocatalysis for lipid modifications, in Dunford NT, Dunford HB. (Ed.) Nutritionally Enhanced Edible Oil and Oilseed Processing. AOCS Press, Champaign, pp. 239-263.