Abstract
The concentration of stearidonic acid (SDA, 18:4 ω-3) in free fatty acid (FFA) and fatty acid ethyl ester (FAEE) forms by low temperature crystallization (winterization) was studied. For this purpose, modified soybean oil (initial SDA content, ~23%) was transformed into its corresponding FFA and FAEE by chemical hydrolysis and ethanolysis, respectively. In the first study, the FFA and FAEE were used as starting material for winterization and variables such as winterization time, type of solvent, and the oil:solvent ratio were evaluated until optimization of the process was achieved. In the second study, changes in the winterization procedure were introduced to obtain a remarkable improvement on the SDA purity of the final products. Since winterization of FAEE was not efficient due to its low melting points, the second study focused on FFA. The best relationship between SDA purity (59.8%) and SDA yield (82.3%) was attained by performing winterization of FFA with hexane at 10% oil:solvent ratio for 24 h. Scaled-up processes were also performed to obtain 59 g of FFA (purity 59.6%; yield 82.6%) enriched in SDA. The products obtained can be used as starting materials for the production of functional lipids and for clinical trials.
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Kris-Etherton PM, Harris WS, Appel LJ (2002) Fish consumption, fish oil, omega-3 fatty acids, and cardiovascular disease. Circulation 106(21):2747–2757
Calder PC (2006) n-3 Polyunsaturated fatty acids, inflammation, and inflammatory diseases. Am J Clin Nutr 83(6):S1505–S1519
Fernandez E, Chatenoud L, La Vecchia C, Negri E, Franceschi S (1999) Fish consumption and cancer risk. Am J Clin Nutr 70(1):85–90
Lim GP, Calon F, Morihara T, Yang F, Teter B, Ubeda O, Salem NJ, Frautschy SA, Cole GM (2005) A diet enriched with the omega-3 fatty acid docosahexaenoic acid reduces amyloid burden in an aged Alzheimer mouse model. J Neurosci 25(12):3032–3040
Shahidi F, Wanasundara UN (1998) Omega-3 fatty acid concentrates: nutritional aspects and production technologies. Trends Food Sci Tech 9(6):230–240
Mendes A, Lopes da Silva T, Reis A (2007) DHA concentration and purification from the marine heterotrophic microalga Crypthecodinium cohnii CCMP 316 by winterization and urea complexation. Food Technol Biotech 45(1):38–44
Mantzioris E, James MJ, Gibson RA, Cleland LG (1994) Dietary substitution with an alpha-linolenic acid-rich vegetable oil increases eicosapentaenoic acid concentrations in tissues. Am J Clin Nutr 59(6):1304–1309
Whelan J (2009) Dietary stearidonic acid is a long chain (n-3) polyunsaturated fatty acid with potential health benefits. Am J Clin Nutr 139(1):5–10
Jacobsen C, Let MB, Nielsen NS, Meyer AS (2008) Antioxidant strategies for preventing oxidative flavour deterioration of foods enriched with n-3 polyunsaturated lipids: a comparative evaluation. Trends Food Sci Tech 19(2):76–93
Shimada Y, Sugihara A, Tominaga Y (2001) Enzymatic purification of polyunsaturated fatty acids. J Biosci Bioeng 91(6):529–538
Ratnayake WMN, Olsson B, Matthews D, Ackman RG (1988) Preparation of omega-3 PUFA concentrates from fish oils via urea complexation. Eur J Lipid Sci Tech 90(10):381–386
Senanayake SPJN, Shahidi F (2000) Concentration of docosahexaenoic acid (DHA) from algal oil via urea complexation. J Food Lipids 7(1):51–61
Guil-Guerrero J, López-Martínez J, Rincón-Cervera M, Campra-Madrid P (2007) One-step extraction and concentration of polyunsaturated fatty acids from fish liver. J Am Oil Chem Soc 84(4):357–361
Guil-Guerrero JL, Campra-Madrid P, Belarbi E-H (2000) γ-Linolenic acid purification from seed oil sources by argentated silica gel chromatography column. Process Biochem 36(4):341–354
López-Martínez JC, Campra-Madrid P, Guil-Guerrero JL (2004) γ-Linolenic acid enrichment from Borago officinalis and Echium fastuosum seed oils and fatty acids by low temperature crystallization. J Biosci Bioeng 97(5):294–298
Canas B, Yurawecz M (1999) Ethyl carbamate formation during urea complexation for fractionation of fatty acids. J Am Oil Chem Soc 76(4):537
Yokochi T, Usita M, Kamisaka Y, Nakahara T, Suzuki O (1990) Increase in the γ-linolenic acid content by solvent winterization of fungal oil extracted from Mortierella genus. J Am Oil Chem Soc 67(11):846–851
Chen T-C, Ju Y-H (2001) An improved fractional crystallization method for the enrichment of gamma-linolenic acid in borage oil fatty acid. Ind Eng Chem Res 40(17):3781–3784
Han D-S, Ahn B-H, Shin H-K (1987) Separation of EPA and DHA from fish oil by solubility differences of fatty acid salts in ethanol soaps. Korean J Food Sci Technol 19(5):430–434
Vázquez L, Akoh CC (2010) Fractionation of short and medium chain fatty acid ethyl esters from a blend of oils via ethanolysis and short-path distillation. J Am Oil Chem Soc 87(8):917–928
Torres CF, Vazquez L, Senorans FJ, Reglero G (2007) An efficient methodology for the preparation of alkoxyglycerols rich in conjugated linoleic acid and eicosapentaenoic acid. J Am Oil Chem Soc 84(5):443–448
Namal Senanayake S, Shahidi F (1999) Enzymatic incorporation of docosahexaenoic acid into borage oil. J Am Oil Chemists’ Soc 76(9):1009–1015
Luthria DL (2002) Process for making an enriched mixture of polyunsaturated fatty acid esters. Assigned to OmegaTech Inc. (Boulder, CO). US 6,395,778 B1 Patent (09/758,973)
Fabritius D (2009) Mixtures of triglycerides of natural polyunsaturated fatty acids with high polyunsaturated fatty acid content, method for producing same and use thereof. Assigned to Nutrinova Nutrition Specialities & Food Ingredients GmbH (Frankfurt,DE). US 7,588,791 B2 Patent (10/493,116)
AOAC International (1998) Official Methods of Analysis of AOAC International, 17th edn. Gaithersburg, MD, Method 996.01
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The authors would like to acknowledge the grant from Monsanto Company (St. Louis, MO) and the financial support from the Ministry of Science and Innovation and the Fulbright Commission in Spain, for the grant provided to Luis Vázquez to visit the University of Georgia.
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Vázquez, L., Akoh, C.C. Concentration of Stearidonic Acid in Free Fatty Acid and Fatty Acid Ethyl Ester Forms from Modified Soybean Oil by Winterization. J Am Oil Chem Soc 88, 1775–1785 (2011). https://doi.org/10.1007/s11746-011-1857-1
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DOI: https://doi.org/10.1007/s11746-011-1857-1