Recent Research Trends on the Enzymatic Synthesis of Structured Lipids

Journal of Food Science

Volumn 80, Issue 8, 2015, Pages C1713-C1724

  Kim, Byung Hee ^a   Akoh, Casimir C ^b  

^a Chung Ang University   (South Korea)

^b UNIVERSITY OF GEORGIA   (United States)

Author keywords

Enzymatic reaction; Lipase; Phospholipase; Structured lipids

Indexed keywords

THEOBROMA CACAO;

FAT INTAKE; FAT SUBSTITUTE; FATTY ACID; MARGARINE; PHOSPHOLIPASE; PHOSPHOLIPID; THEOBROMA OIL; TRIACYLGLYCEROL; TRIACYLGLYCEROL LIPASE;

BREAST MILK; CACAO; CHEMISTRY; FAT INTAKE; FAT SUBSTITUTE; PHYSICAL CHEMISTRY; SYNTHESIS;

CACAO; DIETARY FATS; FAT SUBSTITUTES; FATTY ACIDS; LIPASE; MARGARINE; MILK, HUMAN; PHOSPHOLIPASES; PHOSPHOLIPIDS; PHYSICOCHEMICAL PHENOMENA; TRIGLYCERIDES;

EID: 84938982271     PISSN: 00221147     EISSN: 17503841     Source Type: Journal    
DOI: 10.1111/1750-3841.12953     Document Type: Article

References (124)

1. Adhikari P, Peng H, Zhang YF. 2012a. Oxidative stabilities of enzymatically interesterified fats containing conjugated linoleic acid. J Am Oil Chem Soc 89:1961-70.
2. Adhikari P, Shin JA, Lee JH, Hu JN, Zhu XM, Akoh CC, Lee KT. 2010a. Production of trans-free margarine stock by enzymatic interesterification of rice bran oil, palm stearin and coconut oil. J Sci Food Agric 90:703-11.
3. Adhikari P, Shin JA, Lee JH, Kim HR, Kim IH, Hong ST, Lee KT. 2012b. Crystallization, physicochemical properties, and oxidative stability of the interesterified hard fat from rice bran oil, fully hydrogenated soybean oil, and coconut oil through lipase-catalyzed reaction. Food Bioprocess Technol 5:2474-87.
4. Adhikari P, Zhu XM, Gautam A, Shin JA, Hu JN, Lee JH, Akoh CC, Lee KT. 2010b. Scaled-up production of zero-trans margarine fat using pine nut oil and palm stearin. Food Chem 119:1332-8.
5. Akoh CC, Kim BH. 2008. Structured lipids. In: Akoh CC, Min DB, editors. Food lipids-Chemistry, nutrition, and biotechnology. 3rd ed. Boca Raton: CRC Press. pp 841-64.
6. Baeza-Jimenez R, Miranda K, Garcia HS, Otero C. 2013. Lipase-catalyzed glycerolysis of fish oil to obtain diacylglycerols. Grasas Aceites 64:237-42.
7. Bai S, Aziz S, Khodadadi M, Mitri CB, St-Louis R, Kermasha S. 2013. Lipase-catalyzed synthesis of medium-long-medium type structured lipids using tricaprylin and trilinolenin as substrate models. J Am Oil Chem Soc 90:377-89.
8. Bang HO, Dyerberg J, Stofferson E. 1978. Eicosapentaenoic acid and prevention of thrombosis and atherosclerosis? Lancet 2:117-9.
9. Bebarta B, Jhansi M, Kotasthane P, Sunkireddy YR. 2013. Medium chain and behenic acid incorporated structured lipids from sal, mango and kokum fats by lipase acidolysis. Food Chem 136:889-94.
10. Bilgic S, Yesilcubuk NS. 2012. Lipase-catalyzed acidolysis of olive oil with echium oil stearidonic acid: optimization by response surface methodology. J Am Oil Chem Soc 89:1971-80.
11. Bispo P, Batista I, Bernardino RJ, Bandarra NM. 2014. Preparation of triacylglycerols rich in omega-3 fatty acids from sardine oil using a Rhizomucor miehei lipase: Focus in the EPA/DHA ratio. Appl Biochem Biotechnol 172:1866-81.
12. Brys J, Wirkowska M, Gorska A, Ostrowska-Ligeza E, Brys A. 2014. Application of the calorimetric and spectroscopic methods in analytical evaluation of the human milk fat substitutes. J Therm Anal Calorim 118:841-8.
13. Caballero E, Soto C, Olivares A, Altamirano C. 2014. Potential use of avocado oil on structured lipids MLM-type production catalysed by commercial immobilised lipases. PLoS One 9:e107749.
14. 2. J Am Oil Chem Soc 88:443-6.
15. Cao Y, Qi SJ, Zhang Y, Wang XN, Yang B, Wang YH. 2013. Synthesis of structured lipids by lipase-catalyzed interesterification of triacetin with camellia oil methyl esters and preliminary evaluation of their plasma lipid-lowering effect in mice. Molecules 18:3733-44.
16. Carlson SE, Rhodes PG, Ferguson MG. 1986. Docosahexaenoic acid status of preterm infants at birth and following feeding with human milk or formula. Am J Clin Nutr 44:798-804.
17. Casas-Godoy L, Marty A, Sandoval G, Ferreira-Dias S. 2013. Optimization of medium chain length fatty acid incorporation into olive oil catalyzed by immobilized Lip2 from Yarrowia lipolytica. Biochem Eng J 77:20-7.
18. Cervera MAR, Venegas EV, Bueno RR, Garcia IR, Guil-Guerrero JL. 2013. Acyl migration evaluation in monoacylglycerols from Echium plantagineum seed oil and Marinol. J Biosci Bioeng 115:518-22.
19. Chae MH, Park HK, Kwon KI, Kim JW, Hong SI, Kim Y, Kim BH, Kim IH. 2011. Lipase-catalyzed interesterification in packed bed reactor using 2 different temperatures. J Food Sci 76:C555-9.
20. Chen BQ, Zhang H, Cheong LZ, Tan TW, Xu XB. 2012. Enzymatic production of ABA-type structured lipids containing omega-3 and medium-chain fatty acids: Effects of different acyl donors on the acyl migration rate. Food Bioprocess Technol 5:541-7.
21. Chnadhapuram M, Sunkireddy YR. 2012. Preparation of palm olein enriched with medium chain fatty acids by lipase acidolysis. Food Chem 132:216-21.
22. Choi JH, Kim BH, Hong SI, Kim Y, Kim IH. 2012. Synthesis of structured lipids containing pinolenic acid at the sn-2 position via lipase-catalyzed acidolysis. J Am Oil Chem Soc 89:1449-54.
23. Chopra R, Rastogi NK, Sambaiah K. 2011. Enrichment of rice bran oil with alpha-linolenic acid by enzymatic acidolysis: Optimization of parameters by response surface methodology. Food Bioprocess Technol 4:1153-63.
24. Compton DL, Laszlo JA, Appell M, Vermillion KE, Evans KO. 2014. Synthesis, purification, and acyl migration kinetics of 2-monoricinoleoylglycerol. J Am Oil Chem Soc 91:271-9.
25. Compton DL, Laszlo JA, Evans KO. 2013. Influence of solid supports on acyl migration in 2-monoacylglycerols: Purification of 2-MAG via flash chromatography. J Am Oil Chem Soc 90:1397-403.
26. da Silva RC, Soares FASD, Fernandes TG, Castells ALD, da Silva KCG, Goncalves MIA, Ming CC, Goncalves LAG, Gioielli LA. 2011. Interesterification of lard and soybean oil blends catalyzed by immobilized lipase in a continuous packed bed reactor. J Am Oil Chem Soc 88:1925-33.
27. deAraujo MEMB, Campos PRB, Noso TM, Alberici RM, Cunha IBD, Simas RC, Eberlin MN, Carvalho PD. 2011. Response surface modelling of the production of structured lipids from soybean oil using Rhizomucor miehei lipase. Food Chem 127:28-33.
28. Dhara R, Singhal RS. 2014. Process optimization of enzyme catalyzed production of dietary diacylglycerol (DAG) using TLIM as biocatalyst. J Oleo Sci 63:169-76.
29. Elibal B, Suzen HF, Aksoy HA, Ustun G, Tuter M. 2011. Production of structured lipids containing conjugated linolenic acid: Optimisation by response surface methodology. Int J Food Sci Technol 46:1422-7.
30. Farfan M, Villalon MJ, Ortiz ME, Nieto S, Bouchon P. 2013. The effect of interesterification on the bioavailability of fatty acids in structured lipids. Food Chem 139:571-7.
31. Foresti ML, Ferreira ML. 2010. Lipase-catalyzed acidolysis of tripalmitin with capric acid in organic solvent medium: Analysis of the effect of experimental conditions through factorial design and analysis of multiple responses. Enzyme Microb Technol 46:419-29.
32. Gokce J, Yesilcubuk NS, Ustun G. 2013. Enzymatic production of low-calorie structured lipid from Echium seed oil and lauric acid: Optimisation by response surface methodology. Int J Food Sci Technol 48:1383-9.
33. Hamam F, Budge SM. 2010. Structured and specialty lipids in continuous packed column reactors: Comparison of production using one and two enzyme beds. J Am Oil Chem Soc 87:385-94.
34. Hong SI, Kim Y, Kim CT, Kim IH. 2011. Enzymatic synthesis of lysophosphatidylcholine containing CLA from sn-glycero-3-phosphatidylcholine (GPC) under vacuum. Food Chem 129:1-6.
35. Ifeduba EA, Akoh CC. 2014. Modification of stearidonic acid soybean oil by immobilized Rhizomucor miehei lipase to incorporate caprylic acid. J Am Oil Chem Soc 91:953-65.
36. Ilyasoglu H, Gultekin-Ozguven M, Ozcelik B. 2011. Production of human milk fat substitute with medium-chain fatty acids by lipase-catalyzed acidolysis: Optimization by response surface methodology. LWT-Food Sci Technol 44:999-1004.
37. Jandack RJ, Whiteside JA, Holcombe BN, Volpenhein RA, Taulbee JD. 1987. The rapid hydrolysis and efficient absorption of triglycerides with octanoic-acid in the 1 position and 3 position and long-chain fatty acid in the 2 position. Am J Clin Nutr 45:940-5.
38. Jennings BH, Shewfelt RL, Akoh CC. 2010. Food applications of a rice bran oil structured lipid in fried sweet potato chips and an energy bar. J Food Quality 33:679-92.
39. Jin J, Li D, Zhu XM, Adhikari P, Lee KT, Lee JH. 2011. Production of diacylglycerols from glycerol monooleate and ethyl oleate through free and immobilized lipase-catalyzed consecutive reactions. New Biotechnol 28:190-5.
40. Kadivar S, DeClercq N, Vande Walle D, Dewettinck K. 2014. Optimisation of enzymatic synthesis of cocoa butter equivalent from high oleic sunflower oil. J Sci Food Agric 94:1325-31.
41. Kanjilal S, Kaki SS, Rao BVSK, Sugasini D, Rao YP, Prasad RBN, Lokesh BR. 2013. Hypocholesterolemic effects of low calorie structured lipids on rats and rabbits fed on normal and atherogenic diet. Food Chem 136:259-65.
42. Kelley NS, Hubbard NE, Erickson KL. 2007. Conjugated linoleic acid isomers and cancer. J Nutr 137:2599-607.
43. Kennedy A, Martinez K, Schmidt S, Mandrup S, LaPoint K, McIntosh M. 2010. Antiobesity mechanisms of action of conjugated linoleic acid. J Nutr Biochem 21:171-9.
44. Khodadadi M, Aziz S, St-Louis R, Kermasha S. 2013. Lipase-catalyzed synthesis and characterization of flaxseed oil-based structured lipids. J Funct Foods 5:424-33.
45. Khodadadi M, Kermasha S. 2014a. Modeling lipase-catalyzed interesterification of flaxseed oil and tricaprylin for the synthesis of structured lipids. J Mol Catal B Enzym 102:33-40.
46. Khodadadi M, Kermasha S. 2014b. Optimization of lipase-catalyzed interesterification of flaxseed oil and tricaprylin using response surface methodology. J Am Oil Chem Soc 91:395-403.
47. Kim BH, Akoh CC. 2006. Characteristics of structured lipid prepared by lipase-catalyzed acidolysis of roasted sesame oil and caprylic acid in a bench-scale continuous packed bed reactor. J Agric Food Chem 54:5132-41.
48. Kim BH, Lumor SE, Akoh CC. 2008. Trans-free margarines prepared with canola oil/palm stearin/palm kernel oil-based structured lipids. J Agric Food Chem 56:8195-205.
49. Kim HR, Hou CT, Lee KT, Kim BH, Kim IH. 2010. Enzymatic synthesis of structured lipids using a novel cold-active lipase from Pichia lynferdii NRRL Y-7723. Food Chem 122:846-9.
50. 2 and lipase. Food Sci Biotechnol 23:1207-11.
51. Kim S, Kim IH, Akoh CC, Kim BH. 2014. Enzymatic production of cocoa butter equivalents high in 1-palmitoyl-2-oleoyl-3-stearin in continuous packed bed reactors. J Am Oil Chem Soc 91:747-57.
52. Kleiner L, Vazquez L, Akoh CC. 2012. Increasing stearidonic acid (SDA) in modified soybean oil by lipase-mediated acidolysis. J Am Oil Chem Soc 89:1267-75.
53. Kocak D, Keskin H, Fadiloglu S, Kowalski B, Gogus F. 2011. Characterization of terebinth fruit oil and optimization of acidolysis reaction with caprylic and stearic acids. J Am Oil Chem Soc 88:1531-8.
54. Lee JH, Son JM, Akoh CC, Kim MR, Lee KT. 2010. Optimized synthesis of 1, 3-dioleoyl-2-palmitoylglycerol-rich triacylglycerol via interesterification catalyzed by a lipase from Thermomyces lanuginosus. New Biotechnol 27:38-45.
55. Lee K, Shin JA, Lee KT. 2012. Enzymatic synthesis of structured lipids containing conjugated linolenic acids extracted from pomegranate seed oil and their physicochemical characteristics. J Agric Sci 39:395-405.
56. Lei Q, Lee WL, Li TH. 2013. Design and synthesis of 1, 3-dicapryloyl-2-acetylglycerol as molecular probe for triacylglycerol metabolism study. Eur J Lipid Sci Technol 115:232-8.
57. 13C]DHA in phosphatidylcholine. J Lipid Res 40:1867-74.
58. Li D, Adhikari P, Shin JA, Lee JH, Kim YJ, Zhu XM, Hu JN, Jin J, Akoh CC, Lee KT. 2010. Lipase-catalyzed interesterification of high oleic sunflower oil and fully hydrogenated soybean oil comparison of batch and continuous reactor for production of zero trans shortening fats. LWT-Food Sci Technol 43:458-64.
59. Li RY, Pande G, Sabir JSM, Baeshen NA, Akoh CC. 2014. Enrichment of refined olive oil with palmitic and docosahexaenoic acids to produce a human milk fat analogue. J Am Oil Chem Soc 91:1377-85.
60. 1-catalyzed transesterification. Int J Mol Med Sci 15:15244-58.
61. Meng Z, Lu S, Geng WX, Huang JH, Wang XG, Liu YF. 2014. Preliminary study on acyl incorporation and migration in the production of 1, 3-diacylglycerol by immobilized Lipozyme RM IM-catalyzed esterification. Food Sci Technol Res 20:175-82.
62. Mensink RP, Katan MB. 1990. Effect of dietary trans fatty acids on high-density and low-density lipoprotein cholesterol levels in healthy subjects. N Engl J Med 323:439-45.
63. Mitra K, Kim SA, Lee JH, Choi SW, Lee KT. 2010. Production and characterization of alpha-linolenic acid enriched structured lipids from lipase-catalyzed interesterification. Food Sci Biotechnol 19:57-62.
64. Mohamed IO. 2012. Lipase-catalyzed synthesis of cocoa butter equivalent from palm olein and saturated fatty acid distillate from palm oil physical refinery. Appl Biochem Biotechnol 168:1405-15.
65. Mohamed IO. 2013. Lipase-catalyzed acidolysis of palm mid fraction oil with palmitic and stearic fatty acid mixture for production of cocoa butter equivalent. Appl Biochem Biotechnol 171:656-66.
66. Mounika C, Reddy SY. 2012. Specialty fats enriched with behenic and medium chain fatty acids from palm stearin by lipase acidolysis. J Am Oil Chem Soc 89:1691-7.
67. Mu H, Xu X, Hoy CE. 1998. Production of specific-structured triacylglycerols by lipase-catalyzed interesterification in a laboratory-scale continuous reactor. J Am Oil Chem Soc 75:1187-93.
68. Nagachinta S, Akoh CC. 2012. Enrichment of palm olein with long chain polyunsaturated fatty acids by enzymatic acidolysis. LWT-Food Sci Technol 46:29-35.
69. Nagao T, Watanabe Y, Maruyama K, Momokawa Y, Kishimoto N, Shimada Y. 2011. One-pot enzymatic synthesis of docosahexaenoic acid-rich triacylglycerols at the sn-1(3) position using by-product from selective hydrolysis of tuna oil. New Biotechnol 28:7-13.
70. Nunes PA, Pires-Cabral P, Guillen M, Valero F, Ferreira-Dias S. 2012. Batch operational stability of immobilized heterologous Rhizopus oryzae lipase during acidolysis of virgin olive oil with medium-chain fatty acids. Biochem Eng J 67:265-8.
71. 1-catalyzed acidolysis. Biotechnol Prog 29:230-6.
72. Otero C, Marquez P, Criado M, Hernandez-Martin E. 2013. Enzymatic interesterification between pine seed oil and a hydrogenated fat to prepare semi-solid fats rich in pinolenic acid and other polyunsaturated fatty acids. J Am Oil Chem Soc 90:81-90.
73. Ozturk T, Ustun G, Aksoy HA. 2010. Production of medium-chain triacylglycerols from corn oil: Optimization by response surface methodology. Bioresour Technol 101:7456-61.
74. Pacheco C, Crapiste GH, Carrin ME. 2010. Lipase-catalyzed acidolysis of sunflower oil: Kinetic behavior. J Food Eng 98:492-7.
75. Pacheco C, Palla C, Crapiste GH, Carrin ME. 2013. Optimization of reaction conditions in the enzymatic interesterification of soybean oil and fully hydrogenated soybean oil to produce plastic fats. J Am Oil Chem Soc 90:391-400.
76. Palla CA, Pacheco C, Carrin ME. 2012. Production of structured lipids by acidolysis with immobilized Rhizomucor miehei lipases: Selection of suitable reaction conditions. J Mol Catal B Enzym 76:106-15.
77. Pande G, Akoh CC. 2012. Enzymatic synthesis of trans-free structured margarine fat analogues using stearidonic acid soybean and high stearate soybean oils. J Am Oil Chem Soc 89:1473-84.
78. Pande G, Akoh CC. 2013. Enzymatic synthesis of trans-free structured margarine fat analogs with high stearate soybean oil and palm stearin and their characterization. LWT-Food Sci Technol 50:232-9.
79. Pande G, Sabir JSM, Baeshen NA, Akoh CC. 2013a. Enzymatic synthesis of extra virgin olive oil based infant formula fat analogue s containing ARA and DHA: One-stage and two-stage syntheses. J Agric Food Chem 61:10590-8.
80. Pande G, Sabir JSM, Baeshen NA, Akoh CC. 2013b. Synthesis of infant formula fat analogs enriched with DHA from extra virgin olive oil and tripalmitin. J Am Oil Chem Soc 90:1311-8.
81. Perignon M, Lecomte J, Pina M, Renault A, Simonneau-Deve C, Villeneuve P. 2013. Activity of immobilized Thermomyces lanuginosus and Candida antarctica B lipases in interesterification reactions: Effect of the aqueous microenvironment. J Am Oil Chem Soc 90:1151-6.
82. Qin XL, Huang HH, Lan DM, Wang YH, Yang B. 2014a. Typoselectivity of crude Geobacillus sp T1 lipase fused with a cellulose-binding domain and its use in the synthesis of structured lipids. J Am Oil Chem Soc 91:55-62.
83. Qin XL, Wang YM, Wang YH, Huang HH, Yang B. 2011. Preparation and characterization of 1, 3-dioleoyl-2-palmitoylglycerol. J Agric Food Chem 59:5714-9.
84. Qin XL, Zhong JF, Wang YH, Yang B, Lan DM, Wang FH. 2014b. 1, 3-Dioleoyl-2-palmitoylglycerol-rich human milk fat substitutes: Production, purification, characterization and modeling of the formulation. Eur J Lipid Sci Technol 116:282-90.
85. Ray J, Nagy ZK, Smith KW, Bhaggan K, Stapley AGF. 2013. Kinetic study of the acidolysis of high oleic sunflower oil with stearic-palmitic acid mixtures catalysed by immobilised Rhizopus oryzae lipase. Biochem Eng J 73:17-28.
86. Ruan X, Zhu XM, Xiong H, Wang SQ, Bai CQ, Zhao Q. 2014. Characterisation of zero-trans margarine fats produced from camellia seed oil, palm stearin and coconut oil using enzymatic interesterification strategy. Int J Food Sci Technol 49:91-7.
87. Sanchez DA, Tonetto GM, Ferreira ML. 2014. Enzymatic synthesis of 1, 3-dicaproyglycerol by esterification of glycerol with capric acid in an organic solvent system. J Mol Catal B Enzym 100:7-18.
88. Savaghebi D, Safari M, Rezaei K, Ashtari P, Farmani J. 2012. Structured lipids produced through lipase-catalyzed acidolysis of canola oil. J Agric Sci Technol 14:1297-310.
89. Segura N, da Silva RC, Soares FASD, Gioielli LA, Jachmanian I. 2011. Valorization of beef tallow by lipase-catalyzed interesterification with high oleic sunflower oil. J Am Oil Chem Soc 88:1945-54.
90. Sengupta A, Ghosh M. 2011. Hypolipidemic effect of mustard oil enriched with medium chain fatty acid and polyunsaturated fatty acid. Nutr 27:1183-93.
91. Shin JA, Akoh CC, Lee KT. 2010. Enzymatic interesterification of anhydrous butterfat with flaxseed oil and palm stearin to produce low-trans spreadable fat. Food Chem 120:1-9.
92. Silroy S, Ghosh M. 2011. Enzymatic synthesis of capric acid-rich structured lipids (MUM type) using Candida antarctica lipase. J Oleo Sci 60:275-80.
93. Silroy S, Sengupta A, Bhattacharyya DK, Ghosh M. 2014. Optimization of reaction parameters of acidolysis reaction between mustard oil and capric acid by using Thermomyces lanuginosus lipase. J Food Sci Technol 51:715-21.
94. Simoes T, Valero F, Tecelao C, Ferreira-Dias S. 2014. Production of human milk fat substitutes catalyzed by a heterologous Rhizopus oryzae lipase and commercial lipases. J Am Oil Chem Soc 91:411-9.
95. Soares FASD, Osorio NM, da Silva RC, Gioielli LA, Ferreira-Dias S. 2013. Batch and continuous lipase-catalyzed interesterification of blends containing olive oil for trans-free margarines. Eur J Lipid Sci Technol 115:413-28.
96. Sorensen ADM, Xu XB, Zhang L, Kristensen JB, Jacobsen C. 2010. Human milk fat substitute from butterfat: Production by enzymatic interesterification and evaluation of oxidative stability. J Am Oil Chem Soc 87:185-94.
97. Stewart IM, Kristott J. 2004. European union chocolate directive defines vegetable fats for chocolate. Lipid Technol 16:11-4.
98. Takeuchi H. 2010. Application of biotechnology in the development of a healthy oil capable of suppressing fat accumulation in the body. In: Bagchi D, Lau FC, Ghosh DK, editors. Biotechnology in functional foods and nutraceuticals. Boca Raton: CRC Press. p 104-12.
99. Tang L, Hu JN, Zhu XM, Luo LP, Lei L, Deng ZY, Lee KT. 2012. Enzymatic interesterification of palm stearin with Cinnamomum camphora seed oil to produce zero-trans medium-chain triacylglycerols-enriched plastic fat. J Food Sci 77:C454-60.
100. Tecelao C, Silva J, Dubreucq E, Ribeiro MH, Ferreira-Dias S. 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 65:122-7.
101. Teichert SA, Akoh CC. 2012. Modifications of stearidonic acid soybean oil by enzymatic acidolysis for the production of human milk fat analogues. J Agric Food Chem 59:13300-10.
102. Tomarelli RM, Meyer BJ, Weaber JR, Bernhart FW. 1968. Effect of positional distribution on the absorption of the fatty acids of human milk and infant formulas. J Nutr 95:583-90.
103. Turan D, Yesilcubuk NS, Akoh CC. 2012. Production of human milk fat analogue containing docosahexaenoic and arachidonic acids. J Agric Food Chem 60:4402-7.
104. Turan D, Yesilcubuk NS, Akoh CC. 2013. Enrichment of sn-2 position of hazelnut oil with palmitic acid: Optimization by response surface methodology. LWT-Food Sci Technol 50:766-72.
105. Wang XS, Li M, Wang T, Jin QZ, Wang XG. 2014a. An improved method for the synthesis of 2-arachidonoylglycerol. Process Biochem 49:1415-21.
106. Wang XS, Liang L, Yu ZZ, Rui LL, Jin QZ, Wang XG. 2014b. Scalable synthesis of highly pure 2-monoolein by enzymatic ethanolysis. Eur J Lipid Sci Technol 116:627-34.
107. Wang XS, Wang XG, Jin QZ, Wang T. 2013. Improved synthesis of monopalmitin on a large scale by two enzymatic methods. J Am Oil Chem Soc 90:1455-63.
108. Wang YY, Xia L, Xu XB, Xie L, Duan ZQ. 2012. Lipase-catalyzed acidolysis of canola oil with caprylic acid to produce medium-, long- and medium-chain-type structured lipids. Food Bioprod Process 90:707-12.
109. Xu X. 2000. Production of structured lipids: process reaction and acyl migration. INFORM 11:1121-31.
110. Yamada K, Ibuki M, McBrayer T. 2005. Cocoa butter, cocoa butter equivalents, and cocoa butter replacers. In: Lai OM, Akoh CC, editors. Healthful lipids. Champaign: AOCS Press. p 642-64.
111. Yang B, Wang WF, Zeng FK, Li T, Wang YH, Li L. 2012. Production and oxidative stability of a soybean oil containing conjugated linoleic acid produced by lipase catalysis. J Food Biochem 35:1612-8.
112. Yang D, Gan LJ, Shin JA, Kim S, Hong ST, Park SH, Lee JH, Lee KT. 2013. Antioxidative activities of Ginkgo biloba extract on oil/water emulsion system prepared from an enzymatically modified lipid containing alpha-linolenic acid. J Food Sci 78:C43-9.
113. Yang HL, Mu Y, Chen HT, Su CY, Yang TK, Xiu ZL. 2014a. Sn-1, 3-specific interesterification of soybean oil with medium-chain triacylglycerol catalyzed by Lipozyme TL IM. Chin J Chem Eng 22:1016-20.
114. Yang KZ, Bi YL, Sun SD, Yang GL, Ma SM, Liu W. 2014b. Optimisation of Novozym-435-catalysed esterification of fatty acid mixture for the preparation of medium- and long-chain triglycerides (MLCT) in solvent-free medium. Int J Food Sci Technol 49:1001-11.
115. Yeoh CM, Phuah ET, Tang TK, Siew WL, Abdullah LC, Choong TSY. 2014. Molecular distillation and characterization of diacylglycerol-enriched palm olein. Eur J Lipid Sci Technol 12:1654-63.
116. Yuksel A, Yesilcubuk NS. 2012. Enzymatic production of human milk fat analogues containing stearidonic acid and optimization of reactions by response surface methodology. LWT-Food Sci Technol 46:210-6.
117. Zhang JH, Jiang YY, Lin Y, Sun YF, Zheng SP, Han SY. 2013. Structure-guided modification of Rhizomucor miehei lipase for production of structured lipids. PLoS One 8:e67892.
118. Zhao SQ, Hu JN, Zhu XM, Bai CQ, Peng HL, Xiong H, Hu JW, Zhao Q. 2014. Characteristics and feasibility of trans-free plastic fats through Lipozyme TL IM-catalyzed interesterification of palm stearin and Akebia trifoliata variety Australis seed oil. J Agric Food Chem 62:3293-300.
119. Zhao TT, No DS, Kim BH, Garcia HS, Kim Y, Kim IH. 2014. Immobilized phospholipase A1-catalyzed modification of phosphatidylcholine with n-3 polyunsaturated fatty acid. Food Chem 157:132-40.
120. Zhu XM, Hu JN, Lee JH, Dan Y, Lee KT. 2014. Oxidation and antioxidative effects of rosemary extract and catechin on enzymatically modified lipids containing different total and positional fatty acid compositions. Food Sci Biotechnol 23:1389-96.
121. Zou XG, Hu JN, Zhao ML, Zhu XM, Li HY, Liu XR, Liu R, Deng ZY. 2014a. Lipozyme RM IM-catalyzed acidolysis of Cinnamomum camphora seed oil with oleic acid to produce human milk fat substitutes enriched in medium-chain fatty acids. J Agric Food Chem 62: 10594-603.
122. Zou XQ, Huang JH, Jin QZ, Guo Z, Cheong LZ, Xu XB, Wang XG. 2014b. Preparation of human milk fat substitutes from lard by lipase-catalyzed interesterification based on triacylglycerol profiles. J Am Oil Chem Soc 91:1987-98.
123. Zou XQ, Huang JH, Jin QZ, Liu YF, Song ZH, Wang XG. 2011. Lipase-catalyzed preparation of human milk fat substitutes from palm stearin in a solvent-free system. J Agric Food Chem 59:6055-63.
124. Zou XQ, Huang JH, Jin QZ, Liu YF, Song ZH, Wang XG. 2012. Lipase-catalyzed synthesis of human milk fat substitutes from palm stearin in a continuous packed bed reactor. J Am Oil Chem Soc 89:1463-72.