Gamma-linolenic and stearidonic acids: Purification and upgrading of C18-PUFA oils

European Journal of Lipid Science and Technology

Volumn 112, Issue 10, 2010, Pages 1068-1081

  Guil Guerrero, José Luis ^a   Rincón Cervera, Miguel Ángel ^a   Venegas Venegas, Elena ^a  

^a UNIVERSITY OF ALMERÍA   (Spain)

Author keywords

Linolenic acid; C18 PUFA; Essential fatty acid; Fatty acid purification; Stearidonic acid

Indexed keywords

EID: 79961037595     PISSN: 14387697     EISSN: 14389312     Source Type: Journal    
DOI: 10.1002/ejlt.200900294     Document Type: Review

References (100)

1. Guil-Guerrero, J. L., Occurrence of g-linolenic acid. in: Majundar, D. K. Govil, J. N. Singh,V. K. (Eds.), Recent Progress in Medicinal Plants, Vol. VIII, Scitech Publishing LLC, Texas, USA 2002, pp. 467-487.
2. WHO/FAO, Dietary fats and oils in human nutrition. Report of an Expert Consultation, Rome, Italy 1977, pp. 56-59.
3. Department of Health, Nutritional aspects of cardiovascular disease. Report on Health and Social Subjects N 46, HMSO, London 1997, p. 132.
4. Leaf, A., Weber, P. C., A new era for science in nutrition. Am. J. Clin. Nutr. 1987, 45, 1048-1053.
5. Eaton, S. B., Sinclair, E. J., Cordain, L., Mann, N. J., Dietary intake of long-chain polyunsaturated fatty acids during the paleolithic. in: Simopoulos, A. P. (Ed.), The Return of ω3 Fatty Acids into the Food Supply. I. Land-Based Animal Food Products and Their Health Effects, World Rev. Nutr. Diet. Basel, Switzerland 1988, pp. 12-23.
6. Pérez-Martínez, P., Pérez-Jiménez, F., López-Miranda, J., n-3 PUFA and lipotoxicity. Biochim. Biophys. Acta 2010, 1801, 362-366.
7. Harris, K. A., Hill, A. M., Kris-Etherton, P. M., Health benefits of marine-derived ω-3 fatty acids. ACSM's Health Fitness J. 2010, 14, 22-28.
8. James, M. J., Ursin, V. M., Cleland, L. G., Metabolism of stearidonic acid in human subjects: comparison with the metabolism of other n-3 fatty acids. Am. J. Clin. Nutr. 2003, 77, 1140-1145.
9. URL: http://www.cyberlipid.org.
10. McEntee, M. F., Whelan, J., Polyunsaturated fatty acids in biology and diseases. Dietary polyunsaturated fatty acids and colorectal neoplasia. Biomed. Pharmacother. 2002, 56, 380-387.
11. Guil Guerrero, J. L., Stearidonic acid (18:4n-3): metabolism, nutritional importance, medical uses and natural sources. Eur. J. Lipid Sci. Technol. 2007, 109, 1226-1236.
12. Gamma-linolenic acid. Monograph (2004) Alternative Medicine Review, Thorne Research Inc. 9, 70-78.
13. Seylers, H., Incidence of delta 6, 9, 12, 15-octadecatetraenoic acid in herring oil and its isolation. Z. Physiol. Chem. 1957, 307, 272-277.
14. Klenk, E., Brockerhoff, H., South African pilchard oil. 7. The isolation and structure of an octadecatetraenoic acid from South African pilchard oil. Biochem. J. 1958, 68, 692-695.
15. Matic, M., Isolation of delta-6,9,12,15-n-octadecatetraenoic acid from the fruit of Lithospermum officinale L. Biochem. Z. 1963, 3, 212-218.
16. Czaplicki, S., Zadernowski, R., Ogrodowska, D., Triacylglycerols from viper bugloss (Echium vulgare L.) seed bio-oil. Eur. J. Lipid Sci. Technol. 2009, 111, 1266-1269.
17. Harris, W. S., Lemke, S. L., Hansen, S. N., Goldstein, D. A. et al., Stearidonic acid-enriched soybean oil increased the v-3 index, an emerging cardiovascular risk marker. Lipids 2008, 43, 805-811.
18. Guil-Guerrero, J. L., Giménez-Giménez, A., Robles-Medina, A., Rebolloso-Fuentes, M. M. et al., Hexane reduces peroxidation of fatty acids during storage. Eur. J. Lipid Sci. Technol. 2002, 103 271-278.
19. Council directives 88/344/CEE, 92/115/CEE, 94/52/CEE and 97/60/CEE
20. Goncharova, S. N., Kostetsky, E. Y., Sanina, N. M., The effect of seasonal shifts in temperature on the lipid composition of marine macrophytes. Russ. J. Plant Physiol. 2004, 51, 169-175.
21. Zhukov, A. V., Vereshchagin, A. G., Current techniques of extraction, purification and preliminary fractionation of polar lipids of natural origin. in: Paoletti, R. Kritchevsky, D. (Eds.), Advances in Lipid Research, Academic Press, New York, USA 1981, pp. 247-282.
22. Hara, A., Radin, N. S., Lipid extraction of tissues with a low-toxicity solvent. Anal. Biochem. 1978, 90, 420-426.
23. MacKenzie, S. L., Giblin, E. M., Mazza, G., Stereospecific analysis of Onosmodium hispidissimum Mack. Seed oil triglycerides. J. Am. Oil Chem. Soc. 1993, 70, 629-631.
24. Vioque, J., Pastor, J. E., Vioque, E., Estudio de la composiciónenácidos grasos del aceite de las semillas en algunas plantas silvestres espan?olas. Grasas y Aceites 1994, 45, 161-163.
25. Sridhar, R., Lakshminarayana, G., Lipid classes, fatty acids, and tocopherols of leaves of six edible plant species. J. Agric. Food Chem. 1993, 41, 61-63.
26. Kates, M., Techniques of Lipidology: Isolation, Analysis and Identification of Lipids, 2nd Edn., Elsevier Science publishers, Amsterdam, Netherlands 1988.
27. Daun, J. K., Tkachuk, R., Fatty acid composition of oils extracted from Canadian Weed Seeds. J. Agric. Food. Chem. 1977, 53, 661-662.
28. Arffmann, E., Heated fats and allied compounds as carcinogens. Acta Pathol. Microbiol. Scand. 1964, 61, 161-180.
29. Traitler, H., Wille, H. J., Studer, A., Fractionation of blackcurrant seed oil. J. Am. Oil Chem. Soc. 1988, 65, 755-760.
30. Molina-Grima, E., Robles-Medina, A., Gimenez-Gimenez, A., Sanchez-Perez, J. A. et al., Comparison between extraction of lipids and fatty acids from microalgal biomass. J. Am. Oil Chem. Soc. 1994, 71, 955-959.
31. Guil Guerrero, J. L., López Martínez, J. C., Campra Madrid, P., Gamma-linolenic extraction from seeds by SFC and several solvent systems. Int. J. Food Sci. Technol. 2008, 43, 1176-1180.
32. Guil-Guerrero, J. L., López-Martínez, J. C., Campra-Madrid, P., Rincón-Cervera, M. A., GLA purification form Echium fastuosum seed oil in a two-step process: simultaneous PUFAs extraction/concentration and selective enzymatic esterification. J. Food Biochem. 2007, 31, 386-398.
33. López-Martínez, J. C., Campra-Madrid, P., Rincón-Cervera, M. A., Guil-Guerrero, J. L., Ecological and simultaneous seed oil/extraction/saponification/GLA concentration. Eur. J. Lipid Sci. Technol. 2005, 107, 180-186.
34. 2 extraction of γ-linolenic acid (GLA) from the cyanobacterium Arthrospira (Spirulina) maxima experiments and modeling. Chem. Eng. J. 2005, 105, 147-152.
35. Mishra, V. K., Temelli, F., Ooraikul, B., Extraction and purification of ω3-fatty acids with an emphasis on super-critical fluid extraction, a review. Food Res. Inter. 1993, 26, 217-226.
36. Eisenbach, W., Supercritical fluid extraction; a film demonstration. Ber. Bunsenges Phys. Chem. 1984, 88, 882-887.
37. Nilsson, W. B., Gauglitz, E. J., Hudson, L. K., Supercritical fluid extraction of fish oil esters using incremental pressure programming and temperature programming. J. Am. Oil Chem. Soc. 1989, 66, 1596-1600.
38. Catchpole, O. J., Tallon, S. J., Eltringham, W. E., Grey, J. B. et al., The extraction and fractionation of specialty lipids using near critical fluids. J. Supercrit. Fluids 2009, 47, 591-597.
39. Yamagouchi, K., Murakami, W., Nakano, H., Konosu, S. et al., Supercritical carbon dioxide extraction of oils from Antarctic Krill. J. Agric. Food Chem. 1986, 34, 904-907.
40. Choi, K. J., Nakhost, Z., Krukonis, V. J., Karel, M., Supercritical fluid extraction and characterization of lipid of an unusual polyunsaturated fatty acid in liver of rats fed with heated linseed oil. Competes Rendus de Acad. des Sci. Ser. 3, Sci. de la Vie 1987, 300, 353-358.
41. 2 extraction of fungal oil containing g-linolenic acid. Biotechnol. Technol. 1999, 13, 11-15.
42. Kotnik, P., Skerget, M., Knez, Z., Kinetics of supercritical carbon dioxide extraction of borage and evening primrose seed oil. Eur. J. Lipid Sci. Technol. 2006, 108, 569-576.
43. Soto, C., Conde, E., Moure, A., Zún?iga, M. E., Domínguez, H., Supercritical extraction of borage seed oil coupled to conventional solvent extraction of antioxidants. Eur. J. Lipid Sci. Technol. 2008, 110, 1035-1044.
44. Molero Gómez, A., Martinez de la Ossa, E., Quality of borage seed oil extracted by liquid and supercritical carbon dioxide. Chem. Eng. J. 2002, 88, 103-109.
45. Smith, A. E., Crystal structure of the urea-hydrogen complexes. Acta Cryst. 1952, 5, 224-235.
46. Schlenk, H., Urea inclusion compounds of fatty acids. in: Holman, R. T. Lundberg, W. O. Malki, T. (Eds.), Progress in the Chemistry of Fats and Other Lipids, Pergamon Press, New York, USA 1954, pp. 243-267.
47. Medina, A. R., Giménez, A. G., Camacho, F. G., Pérez, J. A. S. et al., Concentration and purification of stearidonic, eicosapentaenoic, and docosahexaenoic acids from codliver oil and the marine microalga Isochrysis-galbana. J. Am. Oil Chem. Soc. 1995, 72, 575-583.
48. Traifler, H., Wille, H. J., Studer, A., Fractionation of blackcurrant seed oil. J. Am. Oil. Chem. Soc. 1988, 65, 755-760.
49. Campra-Madrid, P., Guil-Guerrero, J. L., High-performance liquid chromatographic purification of g-linolenic acid (GLA) from the seed oil of two Boraginaceae species. Chromatographia 2002, 56, 673-679.
50. Spurvey, S. A., Shahidi, F., Concentration of gamma linolenic acid (GLA) from borage oil by urea complexation: Optimization of reaction conditions. J. Food Lip. 2000, 7, 163-174.
51. Cohe, Z., Reungjitchachawali, M., Siangdung, W., Tanticharoen, M., Production and partial purification of g-linolenic acid and some pigments from Spirulina platensis. J. Appl. Phycol. 1993, 5, 1573-1576.
52. Canas, B. I., Yurawecz, M. P., Ethyl carbamate formation during urea complexation for fractionation of fatty acids. J. Am. Oil Chem. Soc. 1999, 76, 537.
53. Erickson, D. R., Pryde, E. H., Brekke, O. L., Mounts, T. L., Falb, R. A., Handbook of Soy Oil Processing and Utilization, American Soybean Association and the American Oil Chemists Society, St. Louis, USA 1980.
54. Mounts, T. L., Pryde, E. H., Oilseeds. in: Wolff, I. E. (Ed.), Handbook of Processing and Utilization in Agriculture, Vol. II, part 2, CRC Press, Boca Raton, FL, USA 1983.
55. Ziller, S., Food Fats and Oils, 7th Edn., Institute of Shortening and Edible Oils, Washington, D.C., USA 1994.
56. López-Martinez, J. C., Campra-Madrid, P., Guil-Guerrero, J. L., γ-Linolenic acid enrichment from Borago officinalis and Echium fastuosum seed oils and fatty acids by low temperature crystallization. J. Biosci. Bioeng. 2004, 97, 294-298.
57. Chen, T. C., Ju, Y. H., An improved fractional crystallization method for the enrichment of gamma-linolenic acid in borage oil fatty acid. Ind. Eng. Chem. Res. 2001, 40, 3781-3784.
58. Chen, T. C., Ju, Y. H., High-purity gamma-linolenic acid from borage oil fatty acids. J. Am. Oil Chem. Soc. 2002, 79, 29-32.
59. http://www.inchem.org/documents/ehc/ehc/ehc154.htm.
60. Beebe, L. M., Brown, P. R., Turcotte, L. G., Preparative scale-high-performance Liquid Chromatography of ω-3 Polyunsaturated Fatty Acid Esters Derived from Fish Oil. J. Chromatogr. 1988, 495, 369-378.
61. Tokiwa, S., Kanazawa, A., Teshima, S., Preparation of eicosapentaenoic and docosahexaenoic acids by reversed phase high performance liquid chromatography. Bull. Jpn. Soc. Sci. Fish 1981, 47, 675.
62. Adlof, R. O., Emiken, E. A., The isolation of ω-3 polyunsaturated fatty acids and methyl esters of fish oils by silver resin chromatography. J. Am. Oil Chem. Soc. 1985, 62, 1592-1595.
63. Teshima, S., Kanazawa, A., Tokiwa, S., Separation of polyunsaturated fatty acids by column chromatography on silver nitrate-impregnated silica gel. Bull. Jpn. Soc. Sci. Fish 1978, 44, 927.
64. Hayashi, K., Kishimura, H., Preparation of n-3 PUFA ethyl ester concentrates from fish oil by column chromatography on silicic acid. Nippon Suisan Gakkaishi 1993, 59, 1429.
65. Arai, M., Fukuda, H., Morikawa, H., Selective separation of γ-linolenic acid ethyl ester using y-zeolite. J. Ferm. Technol. 1987, 65, 569-574.
66. Guil-Guerrero, J. L., Campra-Madrid, P., Belarbi, H., γ-Linolenic acid purification from seed oil sources by argentated silica gel chromatography column. Process Biochem. 2000, 36, 341-354.
67. Guil-Guerrero, J. L., Campra-Madrid, P., Navarro-Juárez, R., Isolation of some PUFA from edible oils by argentated silica gel chromatography. Grasas y Aceites 2003, 54, 116-121.
68. Rincón-Cervera, M. A., Rodríguez-García, I., Guil-Guerrero, J. L., GLA triglycerides purification from evening primrose oil by gravimetric chromatography column. J. Am. Oil Chem. Soc. 2009, 86, 605-609.
69. Rincón-Cervera, M. A., Guil-Guerrero, J. L., Preparation of stearidonic acid-enriched triacylglycerols from Echium plantagineum seed oil. Eur. J. Lipid Sci. Technol. 2010, 112, 227-232.
70. Ito, Y., Oka, H., Slemp, J. L., Improved high-speed countercurrent chromatography with three multilayer coils connected in series. I. Design of the apparatus and performance of semi-preparative columns in 2,4-dinitrophenyl amino acid separation. J. Chromatogr. 1989, 475, 219-227.
71. Craig, L. C., Post, O., Apparatus for countercurrent distribution. Anal. Chem. 1949, 21, 500-504.
72. Wanasundara, U., Centrifugal partition chromatography (CPC): Emerging separation and purification technique for lipid and related compounds. Food Technol. 2002, 13, 726-730.
73. Murayama, W., Kosuge, Y., Nakaya, N., Nunogaki, Y. et al., Preparative separation of unsaturated fatty acid esters by centrifugal partition chromatography. J. Liq. Chromatogr. 1988, 19, 283-300.
74. Bousquet, O., Sellier, N., Goffic, F. L., Characterization and purification of fatty acids from micro algae by GC-MS and countercurrent chromatography. Chromatographia 1994, 39, 40-44.
75. Berger, R., McPherson, W., Fractional distillation. J. Am. Oil Chem. Soc. 1979, 56, 743-746.
76. Shahidi, F., Wanasundara, U. N., v-3 Fatty acid concentrates: Nutritional aspects and production technologies. Trends Food Sci. Technol. 1998, 9, 230-240.
77. Stout, V. F., Niisson, W. B., Krzynowek, J., Schlenk, H., Fractionation of fish oil and their fatty acids. in: Stansby, M. E. (Ed.), Fish Oils In Nutrition, Van Nostrand Reinhold, New York, USA 1990, pp. 73-119.
78. Ackman, R. G., The year of fish oil. Chem. Ind. 1988, 3, 139-145.
79. Wijesundara, R. C., Ratnayake, W. M. N., Ackman, R. G., Eicosapentaenoic acid geometrical isomer artifacts in heated fish oil esters. J. Am. Oil Chem. Soc. 1989, 66, 1822-1830.
80. Fregolente, L. V., Moraes, E. B., Martins, P. F., Batistella, C. B. et al., Enrichment of natural products using an integrated solvent-free process: Molecular distillation. in: Distillation and Absorption Inst. of Chemical Engineers, London, UK 2006, pp. 648-656.
81. Houde, A., Kademi, A., Leblanc, D., Lipases and their industrial applications. An overview. Appl. Biochem. Biotechnol. 2004, 118, 155-171.
82. Marangoni, A., Rousseau, D., Engineering triacylglycerol: The role of interesterification. Trends Food Sci. Technol. 1995, 6, 329-335.
83. Shimada, Y., Sugihara, A., Tominaga, Y., Enzimatic purification of polyunsaturated fatty acids. J. Biosci. Bioeng. 2001, 91, 529-538.
84. Yadwad, V. B., Ward, O. P., Noronha, L. C., Application of lipase to concentrate the docosahexaenoic acid fraction of fish oil. Biotechnol. Bioeng. 1991, 38, 956-959.
85. Syed Rahmatullah, M. S. K., Shukla, V. K. S., Mukherjee, K. D., Enrichment of γ-linolenic acid from evening primrose oil and borage oil via lipase-catalyzed hydrolysis. J. Am. Oil Chem. Soc. 1994, 71, 569-573.
86. Murata, M., Kaneniwa, M., Saito, H., Komatsu, W., Shinohara, K., Purification of stearidonic acid (18:4n-3) and hexadecatetraenoic acid (16:4n-3) from algal fatty acid with lipase and medium pressure liquid chromatography. Biosci. Biotechnol. Biochem. 2000, 64, 2454-2457.
87. Shimada, Y., Murayama, K., Okazaki, S., Nakamura, M. et al., Enrichment of polyunsaturated fatty acids with Geotrichum candidum lipase. J. Am. Oil. Chem. Soc. 1994, 71, 951-954.
88. Shimada, Y., Sugihara, A., Tominaga, Y., Enzymatic purification of polyunsaturated fatty acids. J. Biosci. Bioeng. 2001, 91, 529-538.
89. Shimada, Y., Sakai, N., Sugihara, A., Fujita, H. et al., Large-scale purification of gamma-linolenic acid by selective esterification using Rhizopus delemar lipase. J. Am. Oil Chem. Soc. 1998, 75, 1539-1544.
90. Spurvey, S. A., Senanayake, S. P. J. N., Shahidi, F., Enzyme-assisted acidolysis of Menhaden and Seal Blubber oils with gamma-linolenic acid. J. Am. Oil Chem. Soc. 2001, 78, 1105-1112.
91. Huang, F. C., Ju, Y. H., Huang, C. W., Enrichment of γ-linolenic acid from borage oil via lipase-catalyzed reactions. J. Am. Oil Chem. Soc. 1997, 74, 977-981.
92. Mun?ío, M. M., Robles, A., Esteban, L., González, P. A., Molina, E., Synthesis of structured lipids by two enzymatic stops: Ethanolysis of fish oils and esterification of 2-monoacylglycerols. Proc. Biochem. 2009, 44, 723-730.
93. Zhang, H., Onal, G., Wijesundera, C., Xu, X., Practical synthesis of 1,3-oleoyl 2-docosahexaenoylglycerol by lipasecatalyzed reactions: An evaluation of different reaction routes. Proc. Biochem. 2009, 44, 534-539.
94. Pfeffer, J., Freund, A., Bel-Rhlid, R., Hansen, C. E. et al., Highly efficient enzymatic synthesis of 2-monoacylglycerides and structured lipids and their production on a technical scale. Lipids, 2007 42, 947-953.
95. Schmid, U., Bornscheuer, U. T., Soumanou, M. M., McNeill, G. P., Schmid, R. D., Highly selective synthesis of 1,3-oleoyl-2-palmitoylglycerol by lipase catalysis. Biotechnol. Bioeng. 1999, 64, 678-684.
96. Shimada, Y., Sugihara, A., Shibahiraki, M., Fujita, H. et al., Purification of g-linolenic acid from borage oil by a two-step enzymatic method. J. Am. Oil Chem. Soc. 1997, 47, 1465-1470.
97. Foglia, T. A., Sonnet, P. E., Fatty acid selectivity of lipases: γ-Linolenic acid from borage oil. J. Am. Oil Chem. Soc. 1995, 72, 417-420.
98. López-Martínez, J. C., Campra-Madrid, P., Ramírez- Fajardo, A., Esteban-Cerdán, L., Guil-Guerrero, J. L., Screening of lipases for enzymatic concentration of g-linolenic acid (GLA) from seed oils. J. Food Lipids 2006, 13, 362-374.
99. Syed Rahmatullah, M. S. K., Shukla, V. K. S., Mukherjee, K. D., g-Linolenic acid concentrates from borage oil and evening primrose oil fatty acids via lipase-catalyzed esterification. J. Am. Oil Chem. Soc. 1994, 71, 563-567.
100. Hills, M. J., Kiewitt, I., Mukherjee, K., Enzymatic fractionation of evening primrose oil by rape lipase: Enrichment of gamma-linolenic acid. Biotechnol. Lett. 1989, 2, 629-632.