Enzymatic modification of lipids for functional foods and nutraceuticals

Handbook of Functional Lipids

Volumn , Issue , 2005, Pages 437-455

  Shimada, Yuji ^a  

^a Osaka Municipal Technical Institute   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85123446996     PISSN: None     EISSN: None     Source Type: Book    
DOI: None     Document Type: Chapter

References (73)

1. Brzozowski, A.M. et al., A model for interfacial activation in lipases from the structure of a fungal lipase-inhibitor complex, Nature, 351, 491, 1991.
2. Tilbeurgh, H. et al., Interfacial activation of the lipase-procolipase complex by mixed micelles revealed by x-ray crystallography, Nature, 362, 814, 1993.
3. Tanaka, Y. et al., Triglyceride specificity of Candida cylindracea lipase: effect of docosahexaenoic acid on resistance of triglyceride to lipase, J. Am. Oil Chem. Soc., 70, 1031, 1993.
4. Shimada, Y. et al., Selective hydrolysis of polyunsaturated fatty acid-containing oil with Geotrichum candidum lipase, J. Am. Oil Chem. Soc., 72, 1577, 1995.
5. Watanabe, Y. et al., Enzymatic conversion of waste edible oil to biodiesel fuel in a fixed-bed bioreactor, J. Am. Oil Chem. Soc., 78, 703, 2001.
6. Sugihara, A. et al., A novel Geotrichum candidum lipase with some preference for the 2-position on a triglyceride molecule, Appl. Microbiol. Biotechnol., 35, 738, 1991.
7. Sugihara, A. et al., Positional and fatty acid specificities of Geotrichum candidum lipases, Prot. Eng., 7, 585, 1994.
8. Hoshino, T., Yamane, T., and Shimizu, S., Selective hydrolysis of fish oil by lipase to concentrate n-3 polyunsaturated fatty acids, Agric. Biol. Chem., 54, 1459, 1990.
9. Shimada, Y., Sugihara, A., and Tominaga, Y., Production of functional lipids containing polyunsaturated fatty acids with lipase, in Enzymes in Lipid Modification, Bornscheuer, U.T., Ed., Wiley-VCH, Weinheim, Germany, 2000, p. 128.
10. Shimada, Y. et al., Selective hydrolysis of borage oil with Candida rugosa lipase: two factors affecting the reaction, J. Am. Oil Chem. Soc., 75, 1581, 1998.
11. Syed Rahmatullah, M.S.K., Shukla, V.K.S., and Mukherjee, K.D., Enrichment of γ-linolenic acid from evening primrose oil and borage oil via lipase-catalyzed hydrolysis, J. Am. Oil Chem. Soc., 71, 569, 1994.
12. Shimada, Y. et al., Enzymatic purification of n-6 polyunsaturated fatty acids, Kagaku to Kogyo, 73, 125, 1999 (in Japanese).
13. Okumura S., Iwai, M., and Tsujisaka, Y., Synthesis of various kinds of esters by four microbial lipases, Biochim. Biophys. Acta, 575, 156, 1979.
14. Makita, A., Nihira, T., and Yamada, Y., Lipase catalyzed synthesis of macrocyclic lactones in organic solvents, Tetrahedron Lett., 28, 805, 1987.
15. Okumura, S., Iwai, M., and Tsujisaka, Y., Synthesis of estolides during hydrolysis of castor oil by Geotrichum candidum lipase, J. Jpn. Oil Chem. Soc., 32, 271, 1983.
16. Yoshida, Y. et al., Synthesis of estolides with immobilized lipase, J. Jpn. Oil Chem. Soc., 44, 328, 1995.
17. Shimada, Y. et al., Enzymatic synthesis of L-methyl esters in organic solvent-free system, J. Am. Oil Chem. Soc., 76, 1139, 1999.
18. Shimada, Y. et al., Enzymatic synthesis of steryl esters of polyunsaturated fatty acids, J. Am. Oil Chem. Soc., 76, 713, 1999.
19. Zhang, X. et al., Lipase-catalyzed synthesis of monolauroyl maltose through condensation of maltose and lauric acid, Food Sci. Technol. Res., 9, 110, 2003.
20. Kobayashi, T., Adachi, S., and R. Matsuno, Kinetic analysis of the immobilized-lipase-catalyzed synthesis of octanoyl octyl glucoside in acetonitrile, Biochem. Eng. J., 16, 323, 2003.
21. Kuwabara, K. et al., Synthesis of 6-O-unsaturated acyl L-ascorbates by immobilized lipase in acetone in the presence of molecular sieve, Biochem. Eng. J., 16, 17, 2003.
22. Kuwabara, K. et al., Continuous production of acyl L-ascorbates using a packed-bed reactor with immobilized lipase, J. Am. Oil Chem. Soc., 80, 895, 2003.
23. Haraldsson, G.G., Gudmundsson, B.O., and Almarsson, O., The preparation of homogeneous triglycerides of eicosapentaenoic acid and docosahexaenoic acid by lipase, Tetrahedron Lett., 34, 5791, 1993.
24. Kawashima, A. et al., Enzymatic synthesis of high-purity structured lipids with caprylic acid at 1,3-positions and polyunsaturated fatty acid at 2-position, J. Am. Oil Chem. Soc., 78, 611, 2001.
25. Matsuo, N. and Tokimitsu, I., Methabolic characteristics of diacylglycerol: an edible oil that is less likely to become body fat, INFORM, 12, 1098, 2001.
26. Sonntag, N.O.V., New developments in the fatty acid industry in America, J. Am. Oil Chem. Soc., 61, 229, 1984.
27. Lauridsen, J.B., Food emulsifiers: surface activity, edibility, manufacture, composition, and application, J. Am. Oil Chem. Soc., 53, 400, 1976.
28. Aha, B. et al., Lipase-catalyzed synthesis of regioisomerically pure mono- and dig-lycerides, in Enzymes in Lipid Modification, Bornscheuer, U.T., Ed., Wiley-VCH, Weinheim Germany, 2000, p. 100.
29. McNeil, G..P., Shimizu, S., and Yamane, T., High-yield enzymatic glycerolysis of fats and oils, J. Am. Oil Chem. Soc., 68, 1, 1991.
30. McNeil, G..P. and Yamane, T., Further improvements in the yield of monoglycerides during enzymatic glycerolysis of fats and oils, J. Am. Oil Chem. Soc., 68, 6, 1991.
31. Yamaguchi, S. and Mase, T., High-yield synthesis of monoglyceride by mono- and diacylglycerol lipase from Penicillium camembertii U-150, J. Ferment. Bioeng., 72, 162, 1991.
32. Watanabe, Y. et al., Production of MAG of CLA in a solvent-free system at low temperature with Candida rugosa lipase, J. Am. Oil Chem. Soc., 80, 909, 2003.
33. Pariza M.W., CLA, a new cancer inhibitor in dairy products, Bull. Int. Dairy Fed., 257, 29, 1991.
34. Ip, C. et al., Mammary cancer prevention by conjugated dienoic derivatives of linoleic acid, Cancer Res., 51, 6118, 1991.
35. Park, Y. et al., Effect of conjugated linoleic acid on body composition in mice, Lipids, 32, 853, 1997.
36. Ostrowska, E. et al., Dietary conjugated linoleic acids increase lean tissue and decrease fat deposition in growing pigs, J. Nutr., 129, 2037, 1999.
37. Lee, K.N., Kritchevsky, D., and Pariza M.W., Conjugated linoleic acid and atherosclerosis in rabbits, Atherosclerosis, 108, 19, 1994.
38. Nicolosi, R.J. et al., Dietary conjugated linoleic acid reduces plasma lipoproteins and early aortic atherosclerosis in hypercholesterolemic hamsters, Artery, 22, 266, 1997.
39. Sugano, M. et al., Conjugated linoleic acid modulates tissue levels of chemical mediators and immunoglobulins in rats, Lipids, 33, 521, 1998.
40. Watanabe, Y. et al., Synthesis of MAG of CLA with Penicillium camembertii lipase, J. Am. Oil Chem. Soc., 79, 891, 2002.
41. Watanabe, Y. et al., Production of monoacylglycerol of conjugated linoleic acid by esterification followed by dehydration at low temperature using Penicillium camem-bertii lipase, J. Mol. Catal. B: Enzymol., 27, 249, 2004.
42. Yokozeki, K. et al., Application of immobilized lipase to region-specific interesterification of triglyceride in organic solvent, Eur. J. Appl. Microbiol., 14, 1, 1982.
43. Breckenridge, W.C., Marai, L., and Kuksis, A., Triglyceride structure of human milk fat, Can. J. Biochem, 47, 761, 1969.
44. Martin, J.C. et al., Triacylglycerol structure of human colostrum and mature milk, Lipids, 28, 637, 1993.
45. Jensen, C., Buist, N.R., and Wilson, T., Absorption of individual fatty acids from long chain and medium chain triglycerides in very small infants, Am. J. Clin. Nutr., 43, 745, 1986.
46. Innis, S.M., Dyer, R., and Nelson, C.M., Evidence that palmitic acid is absorbed as sn-2-monoacylglycerol from human milk by breast-fed infants, Lipids, 29, 541, 1994.
47. Fomon, S.J. et al., Excretion of fat by normal full-term infants fed various milks and formulas, Am. J. Clin. Nutr., 23, 1299, 1970.
48. Akoh, C.C. and Xu, X., Enzymatic production of Betapol and other specialty fats, in Lipid Biotechnology, Kuo, T.M. and Gardner, H.W., Eds., Marcel Dekker, New York, 2002, 461.
49. Nagao, T. et al., Use of thermostable Fusarium heterosporum lipase for production of structured lipid containing oleic and palmitic acids in organic solvent-free system, J. Am. Oil Chem. Soc, 78,167, 2001.
50. Carlson, S.E. et al., Arachidonic acid status correlates with first year growth in preterm infants, Proc. Natl. Acad. Sci. USA, 90, 1073, 1993.
51. Lanting, C.I. et al., Neurological differences between 9-year-oil children fed breast-milk as babies, Lancet, 344, 1319, 1994.
52. Shimada, Y. et al., Enzymatic synthesis of structured lipid containing arachidonic and palmitic acids, J. Am. Oil Chem. Soc., 77, 89, 2000.
53. Shimada, Y. et al., Immobilization of Rhizopus delemar lipase, Kagaku to Kogyo, 74, 117, 2000 (in Japanese).
54. Nagao, T. et al., C-Terminal peptide of Fusarium heterosporum lipase is necessary for its increasing thermostability, J. Biochem., 124, 1124, 1998.
55. Nagao, T. et al., Amino acid residues contributing to stabilization of Fusarium het-erosporum lipase, J. Biosci. Bioeng., 89, 446, 2000.
56. Nagao, T. et al., Increase in stability of Fusarium heterosporum lipase, J. Mol. Catal. B: Enzymol., 17, 125, 2002.
57. Beer H.D. et al., The folding and activity of the extracellular lipase of Rhizopus oryzae are modulated by a prosequence, Biochem. J., 319, 351, 1996.
58. Negishi, S. et al., Activation of powdered lipase by cluster water and the use of lipase powders for commercial esterification of food oils, Enzmol. Microb. Technol., 32, 66, 2003.
59. Ikeda, I. et al., Lymphatic absorption of structured glycerolipids containing medium-chain fatty acids and linoleic acid, and their effect on cholesterol absorption in rats, Lipids, 26, 369, 1991.
60. Christensen, M.S. et al., Intestinal absorption and lymphatic transport of eicosapen-taenoic (EPA), docosahexaenoic (DHA), and decanoic acids: dependence on intramolecular triacylglycerols structure, Am. J. Clin. Nutr., 61, 56, 1995.
61. Xu, X, Enzymatic production of structured lipids: process reactions and acyl migration, Inform, 11, 1121, 2000.
62. Iwasaki, Y. and Yamane T., Lipase-catalyzed synthesis of structured triacylglycerols containing polyunsaturated fatty acids: monitoring the reaction and increasing the yield, in Enzymes in Lipid Modification, Bornscheuer, U.T., Ed., Wiley-VCH, Weinheim, Germany, 2000, p. 148.
63. Akoh, C.C. et al., Enzymatic synthesis of structured lipids, in Lipid Biotechnology, Kuo, T.M. and Gardner, H.W., Eds., Marcel Dekker, New York, 2002, p. 433.
64. Shimada, Y. et al., Production of structured lipid containing docosahexaenoic and caprylic acids using immobilized Rhizopus delemar lipase, J. Ferment. Bioeng., 81, 299, 1996.
65. Shimada, Y. et al., Continuous production of structured lipid containing γ-linolenic and caprylic acids by immobilized Rhizopus delemar lipase, J. Am. Oil Chem. Soc., 76, 189, 1999.
66. Shimada, Y. et al., Fatty acid specificity of Rhizopus delemar lipase in acidolysis, J. Ferment. Bioeng., 83, 321, 1997.
67. Shimada, Y. et al., Production of structured lipids containing essential fatty acids by immobilized Rhizopus delemar lipase, J. Am. Oil Chem. Soc., 73, 1415, 1996.
68. Soumanou, M.M., Bornscheuer, U.T., and Schmid, R.D., Two-step enzymatic reaction for synthesis of pure structured triacylglycerides, J. Am. Oil Chem. Soc., 75, 703, 1998.
69. Irimescu, R. et al., Two-step enzymatic synthesis of docosahexaenoic acid-rich symmetrically structured triacylglycerols via 2-monoacylglycerols, J. Am. Oil Chem. Soc., 78, 743, 2001.
70. Kawashima, A. et al., Production of structured TAG rich in 1,3-dicapryloyl-2-γ-linolenoyl glycerol from borage oil, J. Am. Oil Chem. Soc., 79, 871, 2002.
71. Nagao, T. et al., Production of structured TAG rich in 1,3-capryloyl-2-arachidonoyl glycerol from Mortierella single-cell oil, J. Am. Oil Chem. Soc., 80, 867, 2003.
72. Irimescu, R. et al., Enzymatic synthesis of 1,3-dicapryloyl-2-eicosapentaenoyl glycerol, J. Am. Oil Chem. Soc., 77, 501, 2000.
73. Irimescu, R. et al., Utilization of reaction medium-dependent regiospecificity of Candida antarctica lipase (Novozym 435) for the synthesis of 1,3-dicapryloyl-2- docosa-hexaenoyl (or eicosapentaenoyl) glycerol, J. Am. Oil Chem. Soc., 78, 285, 2001.