Abstract
Structured lipids (SL) are broadly referred to as modified or synthetic oils and fats or lipids with functional or pharmaceutical applications. Some structured lipids, such as triglycerides that contain both long-chain (mainly essential) fatty acids and medium- or short-chain fatty acids and also artificial products that mimic the structure of natural materials, namely human milk fat substitutes and cocoa butter equivalents, have been discussed. Further, other modified or synthetic lipids, such as structured phospholipids and synthetic phenolic lipids are also included in this chapter. For all the products described in this chapter, enzymatic production in industry has been already conducted in one way or another. Cocoa butter equivalents, healthy oil containing medium-chain fatty acids, phosphatidyl serine, and phenol lipids from enzyme technology have been reported for commercial operation. As the demand for better quality functional lipids is increasing, the production of structured lipids becomes an interesting area. Thus, in this chapter we have discussed latest developments as well as present industrial situation of all commercially important structured lipids.
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- CAL B:
-
Candida antarctica lipase B
- CL:
-
Cardiolipin
- CB:
-
Cocoa butter
- CBEs:
-
Cocoa butter equivalents
- FA:
-
Fatty acid
- GRAS:
-
Generally recognized as safe
- LCFAs, C12-C24:
-
Long-chain fatty acids
- LCTs:
-
Long-chain triacylglycerols
- MLCTs:
-
Medium- and long-chain triacylglycerols
- MCTs:
-
Medium-chain triacylglycerols
- MCFAs, C6-C10:
-
Medium-chain fatty acids
- PC:
-
Phosphatidylcholine
- PE:
-
Phosphatidylethanolamine
- PG:
-
Phosphatidylglycerol
- PI:
-
Phosphatidylinositol
- PS:
-
Phosphatidylserine
- PLA1 :
-
Phospholipase A1
- PLA2 :
-
Phospholipase A2
- PL:
-
Phospholipid
- RSM:
-
Response surface methodology
- RBOSL:
-
Rice bran oil structured lipid
- SFC:
-
Solid fat content
- TAGS:
-
Triacylglycerol species
References
Bi Y (2005) Property and application of oil and fat. In: Bi Y, Guo Z, Yang T (eds) Fat and oil chemistry. Chemical Industrial Press, Beijing
Shukla VKS (1996) Confectionery fats. In: Hamilton R J (ed) Developments in oils and fats. Blackie Academic & Professional, Glasgow
Liu K, Chang H, Liu K (2007) Enzymatic synthesis of cocoa butter analog through interesterification of lard and tristearin in supercritical carbon dioxide by lipase. Food Chem 100:1303–1311
Rozendaal A, Macrae AR (1997) Interesteri-fication of oils and fats. In: Gunstone FD, Padley FB (eds) Lipid technologies and applications. Marcel Dekker Inc, New York
Yang T (2002) Enzymatic production of human milk fat substitutes: PhD Thesis. Beijing, Agricultural University of China
Xu X, Skands ARH, Høy CE, Mu H, Balchen S, Adler-Nissen J (1998) Production of specific-structured lipids by enzymatic interesterification: Elucidation of acyl migration by response surface design. J Am Oil Chem Soc 75:1179–1186
Eigtved P (1992) Enzymes and lipid modification. In: Padley FB (ed) Advances in applied lipid research. JAI Press Ltd, London
Brady RL, Brzozowski AM, Derewenda ZS et al (1990) A serine proteases triad forms the catalytic center of a triacylglycerol lipase. Nature 343:757–770
Derewenda ZS (1994) Structure and function of lipases. Adv Protein Chem 45:1–52
Wong DWS (1995) Food enzymes: structure and mechanism. Chapman & Hall, New York
Fernandez P, Cabral JMS, Pinheiro HM (1998) Stability of free and immobilized mycobacterium sp. cells in aqueous and organic media. In: Ballesteros A, Plou FJ, Iborra JL, Halling PJ (eds) Stability and stabilization of biocatalysts. Elsevier Science, Amsterdam
Xu X, Høy CE, Adler-Nissen J (1998) Effects of lipid–borne compounds on the activity and stability of lipases in micro aqueous systems for lipase-catalyzed reaction. In: Ballesteros A, Plou FJ, Iborra JL, Halling PJ (eds) Stability and stabilization of biocatalysts. Elsevier Science, Amsterdam
Macrae AR, Hammond RC (1985) Present and future applications of lipases. Biotechnol Genet Eng Rev 3:193–217
Macrae AR (1989) Tailored triacylglycerols and esters. Biochem Soc Transact 17:1146–1148
Macrae AR (1992) Modifying oils-enzymatic methods. In: Shukla VKS, Gunstone FD (eds) Proceedings of oils and fats in the nineties. International Food Science Center A/S, Fredericia
Xu X, Hu X, Balchen S, Zhang G, Adler-Nissen J (1997) Pilot batch production of cocoa butter–like fats from Chinese vegetable tallow by enzymatic interesterification. In: Proceedings of international symposium on the approaches to functional cereals and oils. CCOA, Beijing
Xu X (1994) Several potential sources of edible oils and fats from tree plants in China. Malay. Oil Sci Technol 3:46–50
Xu X, Hu X, Zhang G (1994) Cocoa butter equivalents from tea seed oil by lipase-catalyzed modification. In: Proceedings of international symposium on new approaches in the production of food stuffs and intermediate products from cereal grains and oil seeds. CCOA, Beijing
Wang H, Wu H, Ho CT, Weng X (2006) Cocoa butter equivalent from enzymatic interesterification of tea seed oil and fatty acid methyl esters. Food Chem 97:661–665
Yokozeki K, Yamanada S, Takinami K et al (1982) Application of immobilized lipase to region-specific interesterification of triglyceride in organic solvent. Eur J Appl Microbiol Biotechnol 14:1–5
Gitlesen T, Svensson I, Adlercreutz P, Mattiasson B, Nilsson J (1995) High-oleic-acid rapeseed oil as starting material for the production of confectionery fats via lipase-catalyzed transesterification. Ind Crop Prods 4:167–171
Sridhar R, Lakshminarayana G, Kaimal TNB (1991) Modification of selected Indian vegetable fats into cocoa butter substitutes by lipase-catalyzed ester interchange. J Am Oil Chem Soc 68:726–730
Savamura N, Hashida W, Hashimoto Y, Matsuo T (1982) Methods for producing cacao butter substitute. CA 1134198 patent
Sawamura N, Matsuo T, Hashimoto Y (1991) Method for processing glyceride fats and oils. US 4985358 patent
Yamaguchi K, Fukazawa M, Shimoda T, Izumi T (2000) Enzymatic process for interesterification of fats and oils using distillation. US 6090598 patent
Okada T, Yamaguchi K (2004) Procede de production de matiere grasse glyceridique transformee. EP1400582 (A1) patent
Moore, Harry (1987) Edible fats. EP 0245076 (A2) patent
Matsuo T, Sawamura N, Hashimoto Y, Hashida W (1981) Method for producing cacao butter substitute. US 4268527 patent
Macrae, Alasdair, R (1991) Edible fats. EP0185524 patent
Halling PJ, Macrae AR (1982) Fat processing. EP0064855 patent
Macrae AR, How P (1988) Rearrangement Process. US4719178 patent
Coleman MH, Macrae AR (1980) Fat process and composition. UK patent 1577933.
Matsuo T, Sawamura N, Hashimoto Y, Hashida W (1980) Producing a cocoa butter substitute by transesterification of fats and oils. UK 2035359A patent
Quinlan P, Moore S (1993) Modification of triglycerides by lipases: process technology and its application to the production of nutritionally improved fats. Inform 4:580–585
Owusu-Ansah Y J (1994) Enzymes in lipid technology and cocoa butter substitutes. In: Kamel BS, Kakuda Y (eds) Technological advances in improved and alternative sources of lipids, Blackie Academic & Professional, London
Hashimoto Y (1993) Production of cocoa butter-like fats by enzymatic transesterification. In: Tanaka A, Tosa T et al (eds) Industrial application of immobilized biocatalysts. Marcel Dekker, Inc., New York
Jensen R, Bitman J, Carlson S et al (1995) Hand book of milk composition. Academic, San Diego
Jensen R (1999) Lipids in human milk. Lipids 34:1243–1271
Chen Z, Kwan K, Tong K et al (1997) Breast milk fatty acid composition: a comparative study between Hong Kong and Chongching Chinese. Lipids 32:1061–1067
Jensen R (1998) Human milk lipids as a model for infant formula. Lipid Technol 3:34–38
Christie W (1995) Composition and structure of milk lipids. In: Fox P (ed) Advanced Dairy Chemistry-2: Lipids. 2nd ed, Chapman & Hall, London
Clark A, Hundrieser K (1993) A lack of correction among fatty acids associated with different lipid classes in human milk. Lipids 28:157–159
Jensen C, Chen H, Fraley J et al (1996) Biochemical effects of dietary linoleic/α–linolenic acid ratio in term infants. Lipids 31:107–113
Uauy R, Hoffman D, Peirano P et al (2001) Essential fatty acids in visual and brain development. Lipids 36:885–896
Brenna J, Varamini B, Jensen R et al (2007) Docosahexaenoic and arachidonic acid concentrations in human breast milk worldwide. Am J Clin Nutr 85:1457–1464
Lien E, Boyle F, Yuhas R, Tomarelli R, Quinlan P (1997) The effect of triglyceride positional distribution on fatty acid absorption in rats. J Pediatr Gastroenterol Nutr 25:167–174
Forsyth J (1998) Lipids and infant formulas. Nutr Res Rev 11:255–278
Zainal Z, Yusoff M (1999) Enzymatic interesterification of palm stearin and palm kernel olein. J Am Oil Chem Soc 76:1003–1008
Sharma R, Chisti Y, Banerjee UC (2001) Production, purification, characterization, and applications of lipases. Biotechnol Adv 19:627–662
Tecelao C, Silva J, Dubreucq E et al (2010) Production of human milk fat substitutes enriched in omega-3 polyunsaturated fatty acids using immobilized commercial lipases and Candida parapsilosis lipase/acyltransferase. J Mol Catal B Enzym 65:122–127
Mukherjee K, Kiewitt I (1998) Structured triacylglycerols resembling human milk fat by transesterification catalyzed by papaya latex. Biotechnol Lett 20:613–616
Yang T, Xu X, He C, Li L (2003) Lipase-catalyzed modification of lard to produce human milk fat substitutes. Food Chem 80:473–481
Soumanou M, Bornscheuer U, Schmid R (1998) Two-step enzymatic reaction for the synthesis of pure structured triacylglycerides. J Am Oil Chem Soc 75:703–710
Schmid U, Bornscheuer U, Soumanou M, McNeill G, Schmid R (1998) Optimization of the reaction conditions in the lipase-catalyzed synthesis of structured triglycerides. J Am Oil Chem Soc 75:1527–1531
Schmid U, Bornscheuer, U, Soumanou et al (1999) Highly selective synthesis of 1,3–oleoyl–2–palmitoylglycerol by lipase catalysis. Biotechnol Bioeng 64:678–684
Akimmoto K, Yaguchi T, Fujikawa S (1999) Novel triglyceride and composition comprising the same. EP 0965 578 A1
Shimada Y, Nagao T, Hamasaki Y et al (2000) Enzymatic synthesis of structured lipid containing arachidonic and palmitic acids. J Am Oil Chem Soc 77:89–93
Koji N, Teruyoshi Y (2010) Medium-chain fatty acids: Functional lipids for the prevention and treatment of the metabolic syndrome. Pharma Res 61(3):208–212
Aoyama T, Nosaka N, Kasai M (2007) Research on the nutritional characteristics of medium-chain fatty acids. J Med Invest 54:385–388
Babayan VK (1987) Medium chain triglycerides and structured lipids. Lipids 22: 417–420
Hashim SA, Tantibhedyangkul P (1987) Medium chain triglyceride in early life: Effects on growth of adipose tissue. Lipids 22:429–434
Papamandjaris AA, MacDougall DE, Jones PJH (1998) Medium chain fatty acid metabolism and energy expenditure: obesity treatment implications. Life Sci 62:1203–1215
Takeuchi H, Sekine S, Kojima K, Aoyama T (2008) The application of medium-chain fatty acids: edible oil with a suppressing effect on body fat accumulation. Asia Pac J Clin Nutr 17:320–323
Koh SP, Long K, Tan CP et al (2011) The use of enzymatically synthesized medium- and long-chain triacylglycerols (MLCT) oil blends in food application. Int Food Res J 18:355–366
Rubin M, Moser A, Vaserberg N et al (2000) Structured triacylglycerol emulsion, containing both medium- and long-chain fatty acids, in long-term home parenteral nutrition: a double-blind randomized cross-over study. Nutrition 16:5–100
Kim BH, Akoh CC (2005) Modelling of lipase catalyzed acidolysis of sesame oil and caprylic acid by response surface methodology: Optimization of reaction conditions by considering both acyl incorporation and migration. J Agric Food Chem 53:033–8037
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 Toxicol 44:530–1538
Bendixen H, Flint HA, Raben A et al (2002) Effect of modified fats and a conventional fat on appetite, energy intake, energy expenditure and substrate oxidation in healthy men. Am J Clin Nutr 75:47–56
Kasai M, Nosaka N, Maki H et al (2003) Effect of dietary medium- and long-chain triacylglycerols (MLCT) on accumulation of body fat in healthy humans. Asia Pacific J of Clin Nut 12:151–160
Matsuo T, Takeuchi H (2004) Effects of structured medium- and long-chain triacylglycerols in diets with various levels of fat on body fat accumulation in rats. British J Nut 91:219–125
Shinohara H, Shimada H, Noguchi O et al (2002) Effect of medium-chain fatty acids containing dietary oil on hepatic fatty acid oxidation enzyme activity in rats. J Oleo Sci 51:621–626
Shinohara H, Ogawa A, Kasai M, Aoyama T (2005) Effect of randomly interesterified triacylglycerols containing medium- and long-chain fatty acids on energy expenditure and hepatic fatty acid metabolism in rats. Biosci Biotechnol Biochem 69:1811–1818
Matsuo T, Matsuo M, Taguchi N, Takeuchi H (2001) The thermic effect is greater for structured medium- and long-chain triacylglycerols versus long-chain triacylglycerols in healthy young women. Metabolism 50:125–130
Negishi S, Itakura M, Arimoto S et al (2003) Measurement of foaming of frying oil and effect of the composition of TG on foaming. J Am Oil Chem Soc 80:471–474
Shieh CJS, Akoh CC, Koehler PE (1995) Four-factor response surface optimization of the enzymatic modification of triolein to structured lipids. J Am Oil Chem Soc 72:619–623
Shimada Y, Sugihara A, Maruyama K et al (1996) Production of structured lipid containing docosahexaenoicacid and caprylic acids using immobilized Rhizopus delemar lipase. J Ferment Bioeng 81:229–303
Lee KT, Akoh CC (1998) Solvent-free enzymatic synthesis of structured lipids from peanut oil and caprylic acid in a stirred tank batch reactor. J Am Oil Chem Soc 75: 1533–1537
Sharma V, Arora S, Wadhwa B (2001) Structured lipids and their applications. Indian Food Ind 20:52–55
Akoh CC (1998) Structured lipids. In: Akoh CC, Min DB (eds) Food lipids chemistry, nutrition, and biotechnology. Marcel Dekker, New York
Fomuso BL, Akoh CC (2002) Lipase-catalyzed acidolysis of olive oil and caprylic acid in a bench-scale packed bed bioreactor. Food Res Int 35:15–21
Huang KS, Akoh CC (1996) Enzymatic synthesis of structured lipids: transesterification of triolein and caprylic acid ethyl ester. J Am Oil Chem Soc 73:245–250
Lai OM, Low CT, Akoh CC (2005) Lipase-catalyzed acidolysis of palm olein and caprylic acid in a continuous bench-scale packed bed bioreactor. Food Chem 92:527–533
Lee KT, Akoh CC (1998) Structured lipids: synthesis and applications. Food Rev Int 14:17–34
Bektas I, Yucel S, Ustun G, Aksoy HA (2008) Production of reduced calorie structured lipid by acidolysis of tripalmitin with capric acid: optimization by response surface methodology. J Sci Food Agric 88:1927–1931
Ozturk T, Ustun G, Aksoy H (2010) Production of medium-chain triacylglycerols from corn oil: optimization by response surface methodology. Bioresour Technol 101:7456–7461
Jennings BH, Akoh CC (2000) Lipase-catalyzed modification of rice bran oil to incorporate capric acid. J Agric Food Chem 48:4439–4443
Jennings BH, Akoh CC (2009) Characte-rization of a rice bran oil structured lipid. J Agric Food Chem 57:3346–3350
Zhao H, Lu Z, Lu F et al (2006) Lipase-catalyzed acidolysis of lard with caprylic acid to produce structured lipids. Int J Food Sci Tech 41:1027–1032
Koh SP, Arifin N, Tan CP et al (2008) Rheological properties, oxidative stability and sensory evaluation of enzymatically synthesized medium- and long-chain triacylglycerol-based salad dressings. Eur J Lipid Sci Technol 110:1116–1126
Koh SP, Tan CP, Lai OM et al (2010) Enzymatic synthesis of medium-and long-chain triacylglycerols (MLCT): optimization of process parameters using response surface methodology. Food and Bioprocess Technol 3:288–299
Arifin N, Koh SP, Long K et al (2010) Modeling and optimization of Lipozyme RM IM-catalyzed esterification of medium-and long-chain triacylglycerols (MLCT) using response surface methodology. Food Bioprocess Technol. doi:10.1007/s11947-010-0325-5
Takeuchi H, Itakura M, Kubota F, Taguchi N (2004) Oil or Fat Composition. US 0191391 patent
Xue C, Liu Y, Wang J et al (2009) Consumption of medium- and long-chain triacylglycerols decreases body fat and blood triglyceride in chinese hypertriglyceridemic subjects. Eur J Clin Nutr 63:879–886
Hoy CE, Xu X (2001) Structured triacylglycerols. In: Gunstone FD (ed) Structured and modified lipids. Marcel Dekker Inc, New York
Guo Z, Vikbjerg AF, Xu X (2005) Enzymatic modification of phospholipids for functional applications and human nutrition. Biotech Adv 23:203–259
Hawthorne JN, Ansell GB (1982) Phospho-lipids new comprehensive biochemistry. Elsevier Biomedical Press, Amsterdam
Gabizon A, Goren D, Horowitz AT et al (1997) Long-circulating liposomes for drug delivery in cancer therapy: a review of biodistribution in tumor-bearing animals. Adv Drug Deliv Rev 24:337–344
New RRC (1993) Biological and biotechnological applications of phospholipids. In: Cevc G (ed) Phospholipid handbook. Marcel Dekker, New York
Nieuwenhuyzen WV, Thomas MC (2008) Update on vegetable lecithin and phospholipid technologies. Eur J Lipid Sci Technol 110:472–486
Gunston FD (1999) Lipid synthesis and manufacture. Sheffield Academic Press, Sheffield
Xu X, Guo Z, Zhang H et al (2006) Chemical and enzymatic interesterification of lipids for use in foods; b. Production separation and modification of phospholipids for use in food. In: Gunstone FD (ed) Modifying lipids for use in food. Woodhead Publising Limited, Cambridge
Xu X, Vikbjerg AF, Guo Z et al (2008) Enzymatic modification of phospholipids and related polar lipids; b. Uses of phospholipids as functional ingredients. In: Gunstone FD (ed) Phospholipid technology and processing. The oily press, Bridgwater
Vikbjerg AF, Mu H, Xu X (2005) Parameters affecting incorporation and by-product formation during the production of structured phospholipids by lipase-catalyzed acidolysis in solvent free system. J Mol Cat B Enzym 36:14–21
Vikbjerg AF, Peng L, Mu H, Xu X (2005) Continuous production of structured phospholipids in a packed bed reactor with lipase from Thermomyces lanuginosa. J Am Oil Chem Soc 82:237–242
Vikbjerg AF, Jonsson G, Mu H, Xu X (2006) Application of ultrafiltration membranes for purification of structured phospholipids produced by lipase-catalyzed acidolysis. Sep Pur Tech 50:184–191
Vikbjerg AF, Rusig JY, Jonsson G et al (2006) Strategies for lipase-catalyzed production and the purification of structured phospholipids. Eur J Lipid Sci Technol 108:802–811
Vikbjerg AF, Mu H, Xu X (2006) Elucidation of acyl migration during lipase-catalyzed production of structured phospholipids. J Am Oil Chem Soc 83:609–614
Vikbjerg AF, Mu H, Xu X (2007) Synthesis of structured phospholipids by immobilized phospholipase A2 catalyzed acidolysis. J Biotech 128:545–554
Reddy JRC, Vijeeta T, Karuna MSL et al (2005) Lipase-catalyzed preparation of palmitic and stearic acid-rich phosphatidyl choline. J Am Oil Chem Soc 82:727–730
Reddy JRC, Rao BVSK, Karuna MSL et al (2008) Lipase-catalyzed preparation of stearic acid-rich phospholipids. J Lipid Sci Technol 40:124–128
Totani Y, Hara S (1991) Preparation of polyunsaturated phospholipids by lipase-catalyzed transesterification. J Am Oil Chem Soc 68:848–851
Mutua LN, Akoh CC (1993) Lipase-catalyzed modification of phospholipids: Incorporation of n-3 fatty acids into biosurfactants. J Am Oil Chem Soc 70:125–128
Hosokawa M, Takahashi K, Miyazaki N et al (1995) Preparation of therapeutic phospholipids through porcine pancreatic phospholipase A2-mediated esterification and lipozyme–mediated acidolysis. J Am Oil Chem Soc 72:1287–1291
Haraldsson GG, Thorarensen A (1999) Preparation of phospholipids highly enriched with n-3 polyunsaturated fatty acids by lipase. J Am Oil Chem Soc 76:1143–1149
Park CW, Kwon SJ, Han JJ, Rhee JS (2000) Transesterification of phosphatidylcholine with eicosapentaenoic acid ethyl ester using phospholipase A2 in organic solvent. Biotechnol Lett 22:147–150
Monjur Hossen M (2005) Enzyme-catalyzed synthesis of structured phospholipids with conjugated linoleic acid and plant sterols, PhD thesis, Texas A & M University
Yazawa K, Watanabe K, Ishikawa C et al (1992) In: Kyle DJ, Ratledge C (eds) Industrial applications of single cell oils. Champaign, AOCS Press
Suzuki M, Asahi K, Isono K et al (1992) Differentiation inducing phosphatidyl choline(s) from the embryos of rainbow trout (Salmo gairdneri): Isolation and structural elucidation. Devel Growth Diff 34:301–307
Kohono H, Ota T, Maeda M et al (1992) Proc Jpn Cancer Assoc 51:398
Matsumoto K, Morita I, Hibino H, Murota S (1993) Inhibitory effect of docosahexaenoic acid-containing phospholipids on 5-lipoxygenase in rat basophilic leukemia cells. Prostaglandins, Leucotriens Essential Fatty acids 49:861–866
Ekstrand B, Erickson C, Holmberg K, Osterberg E (1988) Sweedish patent application. 88-02095-3
Schneider M (2001) Phospholipids for functional food. Eur J Lipid Sci Technol 103:98–101
Hosokawa M, Minami K, Kohno H et al (1999) Differentiation-and apotosis-inducing activities of phospholipids containing docosahexaenoicacid for mouse myeloid leukemia M1 cells. Fish Sci 65:798–799
Eibl H, Unger C (1988) Phospholipids-selective drugs in cancer therapy. Proc Soc Exp Biol Med 29:358
Sakai K, Okuyama H, Yura J et al (1992) Composition and turnover of phospholipids and neutral lipids in human breast cancer and reference tissues. Carcinogenesis 13: 578–584
Song JK, Han JJ, Rhee JS (2005) Phospholipases: Occurrence and production in microorganisms, assay for high throughput screening, and gene discovery from natural and manmade diversity. J Am Oil Chem Soc 82:691–705
Xu X (2000) Enzyme bioreactors for lipid modification. Inform 11:1104–1112
Malcata FX, Reyes HR, Garcia HS et al (1990) Immobilized lipase reactors for modification of fats and oils – a review. J Am Oil Chem Soc 67:890–910
Härröd M, Elfman I (1995) Enzymatic synthesis of phosphatidylcholine with fatty acids, isooctane, carbon dioxide, and propane as solvents. J Am Oil Chem Soc 72: 641–646
Svensson I, Adlercreutz P, Mattiasson B (1992) Lipase-catalyzed transesterification of phosphatidylcholine at controlled water activity. J Am Oil Chem Soc 69:986–991
Mustranta A, Suorti T, Poutanen K (1994) a) Transesterification of phospholipids in different reaction conditions. J Am Oil Chem Soc 71:1415–1419
Mustranta A, Forsell P, Aura AM, Suortti T, Poutanen K (1994) Modification of phospholipids with lipases and phospholipases. Biocatal 9:181–194
Aura AM, Forssell P, Mustranta A, Poutanen K (1995) Transesterification of soy lecithin by lipase and phospholipase. J Am Oil Chem Soc 72:1375–1379
Hara F, Nakashima T (1996) Transesterification of phospholipids by acetone-dried cells of a Rhizopus species immobilized on biomass support particles. J Am Oil Chem Soc 73:657–659
Peng L, Xu X, Mu H et al (2002) Production of structured phospholipids by lipase-catalyzed acidolysis: optimization using response surface methodology. Enzyme Microb Technol 31:523–532
Hara S, Hasuo H, Nakasato M et al (2002) Modification of soybean phospholipids by enzymatic transacylation. J Oleo Sci 51:417–421
Doig SD, Diks RMM (2003) Toolbox for exchanging constituent fatty acids in lecithins. Eur J Lipid Sci Technol 105:359–367
Na A, Eriksson C, Erikson S et al (1990) Synthesis of phosphatidylcholine with (n-3) fatty acids by phospholipase A2 in micro emulsion. J Am Oil Chem Soc 67:766–770
Vijeeta T, Reddy JRC, Rao BVSK et al (2004) Phospholipase-mediated preparation of 1-ricinoleoyl-2-acyl-sn-glycero-3-Phosphocholine from soya and egg phosphatidylcholine. Biotechnology Lett 26:1077–1080
Pernas P, Olivier JL, Legoy MD, Bereziat G (1990) Phospholipid synthesis by extracellular phospholipase A2 in organic solvents. Biochem Biophys Res Commun 168:644–650
Kim IH, Garcia HS, Hills CG Jr (2007) Phospholipase A1-catalyzed synthesis of phospholipids enriched in n-3 polyunsaturated fatty acid residues. Enzyme Microb Technol 40:1130–1135
Rice Evans CA, Miller NJ, Paganga G (1996) Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Bio Med 26:1231–1237
Murakami A, Nakamura Y, Koshimizu K et al (2002) H. FA15, a hydrophobic derivative of ferulic acid, suppresses inflammatory responses and skin tumor promotion: comparison with ferulic acid. Cancer Lett 180:121–129
Figueroa-Espinoza MC, Villeneuve P (2005) Phenolic acids enzymatic lipophilization. J Agric Food Chem 53:2779–2787
Liu HL, Kong LY, Takaya Y, Niwa M (2005) Biotransformation of ferulic acid into two new dihydrotrimers by Momordica charantia peroxidase. Chem Pharm Bull 53:816–819
Lin FH, Lin JY, Gupta RD, Tournas JA, Burch JA, Selim MA, Monteiro–Riviere NA, Grichnik JM, Zielinski J, Pinnell SR (2005) Ferulic acid stabilizes a solution of vitamins C and E and doubles its photo protection of skin. J Invest Dermato 125: 826–832
Condo AMJ, Baker DC, Moreau RA, Hicks KB (2001) Improved method for the synthesis of trans-feruloyl-β-sitostanol. J Agric Food Chem 49:4961–4964
Compton DL, Laszlo JA, Berhow MA (2000) Lipase-catalyzed synthesis of ferulate esters. J Am Oil Chem Soc 77:513–519
Giuliani S, Piana S, Setti L, Hochkoeppler A, Pifferi PG, Williamson G, Faulds CB (2001) Synthesis of pentylferulate by a feruloyl esterase from Aspergillus niger using water-in-oil micro emulsions. Biotechnol Lett 23:325–330
Vosmann L, Weitkamp P, Weber N (2006) Solvent-free lipase-catalyzed preparation of long-chain alkyl phenyl propanoates and phenylpropyl alkanoates. J Agric Food Chem 54:2969–2976
Sabally K, Karboune S, St–Louis R, Kermasha S (2006) Lipase-catalyzed transesterification of trilinolein or trilinolenin with selected phenolic acids. J Am Oil Chem Soc 83:101–107
Zheng Y, Wu Xiao M, Branford–White C et al (2009) Enzymatic synthesis and characterization of novel feruloylated lipids in selected organic media. J Mol Catal B Enzym 58:65–71
Zheng Y, Quan J, Zhu LM et al (2008) Optimization of selective lipase-catalyzed feruloylated monoacylglycerols by response surface methodology. J Am Oil Chem Soc 85:635–639
Laszlo JA, Compton DL, Eller FJ et al (2003) Packed-bed bioreactor synthesis of feruloylated monoacyl- and diacylglycerols: clean production of a “green” sunscreen. Green Chem 5:382–386
Xin JY, Zhang L, Chen LL et al (2009) Lipase-catalyzed synthesis of ferulyl oleins in solvent-free medium. Food Chem 112:640–645
Sun SD, Shan L, Liu YF et al (2007) A novel, two consecutive enzyme syntheses of feruloylated monoacyl- and diacylglycerols in a solvent-free system. Biotechnol Lett 29:1947–1950
Compton D, Laszlo JA, Berhow MA (2006) Identification and quantification of feruloylated mono-, di-, and triacylglycerols from vegetable oils. J Am Oil Chem Soc 83:753–758
Compton DL, King JW (2001) Lipase-catalyzed synthesis of triolein-based sunscreens in supercritical CO2. J Am Oil Chem Soc 78:43–47
Sun SD, Shan L, Liu YF (2008) Solvent-free enzymatic preparation of feruloylated monoacylglycerols optimized of feruloylated monoacylglycerols optimized by response surface methodology. J Agric Food Chem 56:442–447
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Jala, R.C.R., Hu, P., Yang, T., Jiang, Y., Zheng, Y., Xu, X. (2012). Lipases as Biocatalysts for the Synthesis of Structured Lipids. In: Sandoval, G. (eds) Lipases and Phospholipases. Methods in Molecular Biology, vol 861. Humana Press. https://doi.org/10.1007/978-1-61779-600-5_23
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DOI: https://doi.org/10.1007/978-1-61779-600-5_23
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