Long-chain polyunsaturated fatty acid sources and evaluation of their nutritional and functional properties

Elahe Abedi, Mohammad Ali Sahari, Elahe Abedi, Mohammad Ali Sahari

Abstract

Recent studies have clearly shown the importance of polyunsaturated fatty acids (as essential fatty acids) and their nutritional value for human health. In this review, various sources, nutritional properties, and metabolism routes of long-chain polyunsaturated fatty acids (LC-PUFA) are introduced. Since the conversion efficiency of linoleic acid (LA) to arachidonic acid (AA) and also α-linolenic acid (ALA) to docosahexaenoic acid (DHA) and eicosatetraenoic acid (EPA) is low in humans, looking for the numerous sources of AA, EPA and EPA fatty acids. The sources include aquatic (fish, crustaceans, and mollusks), animal sources (meat, egg, and milk), plant sources including 20 plants, most of which were weeds having a good amount of LC-PUFA, fruits, herbs, and seeds; cyanobacteria; and microorganisms (bacteria, fungi, microalgae, and diatoms).

Keywords: Docosahexaenoic acid; eicosapentaenoic acid; long-chain polyunsaturated fatty acids; nutritional and functional properties; sources; α-linolenic acid.

Figures

Figure 1
Figure 1
Long-chain polyunsaturated fatty acid structure.

References

    1. Ahn DH, Lutz S, Sim JS. Effects of dietary α-linolenic acid on the fatty acid composition, storage stability and sensory characteristics of pork loin. Meat Sci. 1996;43:291–299.
    1. Aki T, Shimada Y, Inagaki K, Higashimoto H, Kawamoto S, Shigeta S. Molecular cloning and functional characterization of rat delta-6 fatty acid desaturase. Biochem. Biophys. Res. Commun. 1999;255:575–579.
    1. Aleksandra A, Niveska P, Vesna V, Jasna T, Tamara P, Marija G. Milk in human nutrition: comparision of fatty acid profiles. Acta. Vet. 2009;59:569–578.
    1. Allen EE, Bartlett DH. Structure and regulation of the omega-3 polyunsaturated fatty acid synthase genes from the deep-sea bacterium Photobacterium profundum strain SS9. Microbiology. 2002;148:1903–1913.
    1. Andrew P, DeFilippis MD, Laurence S, Sperling MD, Atlanta GA. Understanding omega-3′s. Am. Heart J. 2006;151:564–570.
    1. Angers P, Morales MR. Progress in new crops. In: Janick J, Simon JE, editors. Basil seed oil. Arlington, VA: ASHS Press; 1996. pp. 598–601.
    1. Anonymous. 2005. EPA and DHA content of fish species (Data from NDB SR 16-1) (fish listed in bold indicate the form of the fish used in the analysis—usually the most commonly eaten, without added fat). Available at .
    1. Appel LJ, Miller ER, Seidler AJ, Whelton PK. Does supplementation of diet with “fish oil” reduce blood pressure? A meta-analysis of controlled clinical trials. Arch. Intern. Med. 1993;153:1429–1438.
    1. Appel LJ, Miller ER, Seidler AJ, Whelton PK. Diet supplementation with fish oils and blood pressure reduction: a meta-analysis. Ann. Intern. Med. 1994;120:9.
    1. Ayerza R, Coates W. Dietary levels of chia: influence on yolk cholesterol, lipid content and fatty acid composition, for two strains of hens. Poult. Sci. 2000;79:724–739.
    1. Bates D, Cartlidge N, French JM, Jackson MJ, Nightingale S, Shaw DA, et al. A double blind controlled trial of long chain n-3 polyunsaturated fatty acids in the treatment of multiple sclerosis. JNNP. 1989;52:18–22.
    1. Belluzzi A, Brignola C, Campieri M, Pera A, Boschi S, Miglioli M. Effect of an enteric-coated fish-oil preparation on relapses in Crohn's disease. N. Engl. J. Med. 1996;334:1557–1560.
    1. Berti M, Johnson BL, Dash S, Fischer S, Wilckens R. Issues in new crops and new uses. In: Janick J, Whipkey A, Hevia F, editors. Echium: a source of stearidonic acid adapted to the Northern great plains in the US. Alexandria, VA: ASHS Press; 2007. pp. 120–125.
    1. Beynen AC. Fatty acid composition of eggs produced by hens fed diets containing groundnut, soya bean or linseed. NJAS. 2002;52:1.
    1. Bhardwaj HL, Hamama AA, Santen EV. Fatty acids and oil content in white lupin seed as affected by production practices. J. Am. Oil Chem. Soc. 2004;81:1035–1038.
    1. Bigogno C, Khozin-Goldberga I, Boussibaa S, Vonshaka A, Cohena Z. Lipid and fatty acid composition of the green oleaginous alga Parietochloris incisa, the richest plant source of arachidonic acid. Phytochemistry. 2002;60:497–503.
    1. Blanchemain A, Grizeau D. Increased production of eicosapentaenoic acid by Skeletonema costatum cells after decantation at low temperature. Biotechnol. Tech. 1999;13:497–501.
    1. Boersma ER, Offringa PJ, Muskiet FAJ, Chase WM, Simmons IJ. Vitamin E, lipid fractions and fatty acid composition of colostrum, transitional milk and mature milk: an international comparative study. Am. J. Clin. Nutr. 1991;53:1197–1204.
    1. Boyd Eaton S, Eaton SB, Sinclair AJ, Cordain L, Mann NJ. Dietary intake of long-chain polyunsaturated fatty acids during the paleolithic. World Rev. Nutr. Diet. 1998;83:12–23.
    1. Budin JT, Breene WM, Putnam DH. Some compositional properties of camelina (Camelina sativa L. Crantz) seeds and oils. J. Am. Oil Chem. Soc. 1995;72:309–315.
    1. Burr ML, Fehily AM, Gilbert JF. Effect of changes in fat, fish and fibre intakes on death and myocardial reinfarction: diet and reinfarction trial (DART) Lancet. 1989;2:757–761.
    1. Calder PC. n−3 Polyunsaturated fatty acid, inflammation, and inflammatory diseases. Am. J. Clin. Nutr. 2006;83:1505S–1519S.
    1. Callaway JC, Tennil T, Pate DW. Occurrence of “omega-3” stearidonic acid (cis-6,9,12,15-octadecatetraenoic acid) in hemp (Cannabis sativa L.) seed. J. Int. Hemp. Assoc. 1996;3:61–63.
    1. Certik M, Shimizu S. Biosynthesis and regulation of microbial polyunsaturated fatty acid production. J. Biosci. Bioeng. 1999;87:1–14.
    1. Certik M, Sakuradani E, Shimizu S. Desaturase defective fungal mutants: useful tools for the regulation and overproduction of polyunsaturated fatty acids. Trends Biotechnol. 1998;16:500–505.
    1. Cherian G, Sim JS. Dietary a-linolenic acid alters the fatty acid composition of lipid classes in swine tissues. J. Agric. Food Chem. 1995;43:2911–2916.
    1. Cho HP, Nakamura M, Clarke SD. Cloning, expression, and nutritional regulation of the mammalian Delta-6 desaturase. J. Biol. Chem. 1999;274:471–477.
    1. Chukwuemeka U, Ndukwe GI, Audu TO. Comparison of fatty acids profile of some freshwater and marine fishes. Int. J. Food. Safety. 2008;10:9–17.
    1. Clough P. Sources and production of specialty oils containing GLA and stearidonic acid. Lipid Technol. 1993;5:9–12.
    1. Coates W, Ayerza R. Commercial production of chia in Northwestern Argentina. J. Am. Oil Chem. Soc. 1998;75:1417–1420.
    1. Cobelas MA, Lechado JZ. Lipids in microalgae. A review. Biochemistry. 1989;40:118–145.
    1. Cohen Z. The production potential of eicosapentaenoic and arachidonic acids by the red alga Porphyridium cruentum. J. Am. Oil Chem. Soc. 1990;67:916–920.
    1. Cohen Z. Production of polyunsaturated fatty acids (EPA, ARA and GLA) by the microalgae Porphyridium and Spirulina. In: Kyle DJ, Ratledge C, Heimer YM, editors. Industrial applications of single cell oils. Champaign, IL: AOCS Press; 1992. pp. 243–273.
    1. Connor WE, Prince MJ, Ullman D. The hypotriglyceridemic effect of fish oil in adult-onset diabetes without adverse glucose control. Ann. N. Y. Acad. Sci. 1993;683:337–340.
    1. Crawford MA, Hassam AG, Stevens PA. Essential fatty acid requirements in pregnancy and lactation with special reference to brain development. Prog. Lipid Res. 1981;20:31–40.
    1. Cunnane SC, Stitt PA, Ganguli S, Armstrong JK. Raised omega-3 fatty acid levels in pigs fed flax. Can. J. Anim. Sci. 1990;70:251–254.
    1. De Caterina R, Caprioli R, Giannessi D. N-3 fatty acids reduce proteinuria inpatients with chronic glomerular disease. Kidney Int. 1993;44:843–850.
    1. De Lorgeril M, Renaud S, Mamelle N. Mediterranean α-linolenic acid-rich diet in secondary prevention of coronary heart disease. Lancet. 1994;343:1454–1459.
    1. De Lorgeril M, Salen P, Martin JL, Mamelle N, Monjaud I, Touboul P, et al. Effect of a mediterranean type of diet on the rate of cardiovascular complications in patients with coronary artery disease. Insights into the cardioprotective effect of certain nutriments. J. Am. Coll. Cardiol. 1996;28:1103–1108.
    1. De Lorgeril M, Salen P, Martin JL, Monjaud I, Delaye J, Mamelle N. Mediterranean diet, traditional risk factors, and the rate of cardiovascular complications after myocardial infarction. Final report of the lyon diet heart study. Circulation. 1999;99:779–785.
    1. D'Ippolito G, Romano G, Iadicicco O, Miralto A, Ianora A, Cimino G. New birth control aldehydes from the marine diatom Skeletonema costatum: characterization and biogenesis. Tetrahedron Lett. 2002;43:6133–6136.
    1. D'Ippolito G, Tucci S, Cutignano A, Romano G, Cimino G, Miralto A. The role of complex lipids in the synthesis of bioactive aldehydes of the marine diatom Skeletonema costatum. Biochem. Biophys. 2004;1686:100–107.
    1. Donadio JV, Bergstralh JEJ, Offord KP, Spencer DC, Holley KE. A controlled trial of fish oil in IgA nephropathy. Mayo Nephrology Collaborative Group. N. Engl. J. Med. 1994;331:1194–1199.
    1. Enser M, Richardson RI, Wood JD, Gill BP, Sheard PR. Feeding linseed to increase the n-3 PUFA of pork: fatty acid composition of muscle, adipose tissue, liver and sausages. Meat Sci. 2000;55:201–212.
    1. Eroshin VK, Dedyukhina EG, Chistyakova TI, Zhelifonova VP, Botast RJ. Studies on arachidonic acid production by Mortierella fungi: a microbiological method for selecting arachidonic acid producers. Microbiologyia. 1996;65:31–36.
    1. Eskin NAM. Borage and evening primrose seed oil. Eur. J. Lipid Sci. Technol. 2008;110:655–661.
    1. Foran JA, Good DH, Carpenter DO, Hamilton MC, Knuyh BA, Schwager SJ. Quantitative analysis of the benefits and risks of consuming farmed and wild salmon. J. Nutr. 2005;135:2639–2643.
    1. Fredriksson S, Elwinger K, Pickova J. Fatty acid and carotenoids composition of egg yolk as an effect of microalgae addition to feed formula for laying hens. Food Chem. 2006;99:530–537.
    1. Gandemer G. Lipids and meat quality: lipolysis, oxidation, maillard reaction and flavour. Sci. Aliments. 1999;19:439–458.
    1. Gerster H. Can adults adequately convert alfa-linolenic acid to eicosapentaenoic acid and docosahexaenioc acid. Int. J. Vitam. Nutr. Res. 1998;68:159–173.
    1. Girke T, Schmidt H, Zahringer U, Reski R, Heinz E. Identification of a novel delta 6-acyl-group desaturase by targeted gene disruption in Physcomitrella patens. Plant J. 1998;15:39–48.
    1. Givens DI, Gibbs RA. Very long chain n-3 polyunsaturated fatty acids in the food chain in the UK and the potential of animal-derived foods to increase intake. Nutr. Bulletin. 2006;31:104–110.
    1. Gonzάlez-Félix ML, Gatliniii DM, Lawrence AL, Perez-Velazquez M. Nutritional evaluation of fatty acids for the open thelycum shrimp, Litopenaeus vannamei: II. Effect of dietary n-3 and n-6 polyunsaturated and highly unsaturated fatty acids on juvenile shrimp growth, survival, and fatty acid composition. Aquac. Nutr. 2003;9:115–122.
    1. Guedes AC, Amaro HM, Barbosa CR, Pereira RD, Malcata FX. Fatty acid composition of several wild microalgae and cyanobacteria, with a focus on eicosapentaenoic, docosahexaenoic and α-linolenic acids for eventual dietary uses. Food Res. Int. 2011;44:2721–2729.
    1. Guil JL, Torija ME, Giménez JJ, Rodriguez I. Identification of fatty acids in edible wild plants by gas chromatography. J. Chromatogr. A. 1996;719:229–235.
    1. Gunstone FD, Harwood J, Padley FB. The lipid handbook. 2nd ed. London, U.K: Chapman and Hall; 1994.
    1. Hassan-Zadeh A, Sahari MA, Barzegar M. Optimization of the ω-3 extraction as a functional food from flaxseed. Int. J. Food Sci. Nutr. 2008;59:526–534.
    1. Hino A, Adachi H, Toyomasu K, Yoshida N, Enomoto M, Hiratsuka A. Very long chain N-3 fatty acids intake and carotid atherosclerosis: an epidemiological study evaluated by ultrasonography. Atherosclerosis. 2004;176:145–149.
    1. Hofman M, Eichenberger W. Lipid and fatty acid composition of the marine brown alga Dictyopteris membranacea. Plant Cell Physiol. 1997;389:1046–1052.
    1. Hong H, Nagamani D, Darwin WR, Patrick SC, Samuel LM, Xiao Q. High-level production of γ-linolenic acid in Brassica juncea using a Δ6 desaturase from Pythium irregulare. Plant Physiol. 2002;129:354–362.
    1. Horrobin DF. Medical roles of metabolites of precursor EFA. Inform. 1995;6:428–435.
    1. Horrocks LA, Yeo YK. Health benefits of docosahexaenoic acid (DHA) Pharm. Res. 1999;40:211–225.
    1. Howe PH, Meyer B, Record S, Baghurst K. Dietary intake of long-chain ω3 polyunsaturated fatty acids: contribution of meat sources. Nutrition. 2006;22:47–53.
    1. Hu FB, Bronner J, Willett WC, Stampfer MJ, Rexrode KM, Albert CM, et al. Fish and omega-3 fatty acid intake and risk of coronary heart disease in women. JAMA. 2002;287:1815–1821.
    1. Huang Z, Leibovitz H, Lee CM, Millar R. Effect of dietary fish oil on omega-3 fatty acid levels in chicken eggs and thigh flesh. J. Agric. Food Chem. 1990;38:743–747.
    1. Huang YS, Chaudhary S, Thurmond JM, Bobik EG, Yuan L, Chan GM, et al. Cloning of Δ12- and Δ6-desaturases from Mortierella alpina and recombinant production of γ−linolenic acid in Saccharomyces cerevisiae. Lipids. 1999;34:649–659.
    1. Hudson BJF. Evening primrose (Oenothera spp.) oil and seed. J. Am. Oil Chem. Soc. 1984;61:540–543.
    1. Irie M, Sakimoto M. Fat characteristics of pigs fed fish oil containing eicosapentaenoic and docosahexaenoic acids. J. Anim. Sci. 1992;70:470–477.
    1. Ishida M, Konno Y, Suzuki K, Ogawa Y, Abe H. The effects of fish oil-enriched with n-3 polyunsaturated fatty acids on lipids and tasty compounds of pork loin. Nippon. Shokuhin. Kogaku. Kaishi. 1996;43:1219–1226.
    1. James JM, Gibson RA, Cleland LG. Dietary polyunsaturated fatty acids and inflammatory mediator production. Am. J. Clin. Nutr. 2000;71:343S–348S.
    1. Jiang Z, Ahn DU, Sim J. Effect of feeding flax and two types of sunflower seeds on fatty acid compositions of yolk lipid classes. Poult. Sci. 1991;41:2467–2475.
    1. Kelley VE, Ferritti A, Izni S, Strom TB. A fish oil diet rich in eicosapentaenoic acid reduses cyclooxygenase metabolites and suppresses lupus in MLR-lpr mice. J. Immunol. 1985;134:1914–1919.
    1. Kitano M, Matsukawa R, Karube I. Changes in eicosapentaenoic acid content of Navicula saprophilla Rhodomonas salina and Nitzschia sp. under mixotrophic conditions. J. Appl. Phycol. 1997;9:559–563.
    1. Kitessa SM, Peake D, Bencini R, Williams AJ. Fish oil metabolism in ruminants III. Transfer of n−3 polyunsaturated fatty acids (PUFA) from tuna oil into sheep's milk. Anim. Feed Sci. Technol. 2003;108:1–14.
    1. Kitessaa SM, Young P. Enriching milk fat with n-3 polyunsaturated fatty acids by supplementing grazing dairy cows with ruminally protected Echium oil. Anim. Feed Sci. Technol. 2011;170:35–44.
    1. Kneebone GM, Kneebone R, Gibson RA. Fatty acid composition of breast milk from three racial groups from Penang, Malaysia. Am. J. Clin. Nutr. 1985;41:765–769.
    1. Korn ED. The fatty acids of Euglena gracilis. J. Lipid Res. 1964;5:352–362.
    1. Krauss RM, Eckel RH, Howard B, Appel LJ, Daniels SR, Deckelbaum RJ, et al. AHA dietary guidelines: revision 2000: a statement for healthcare professionals from the Nutrition Committee of the American Heart Association. Circulation. 2000;102:2284–2299.
    1. Kremer JM. Effects of modulation of inflammatory and immune parameters in patients with rheumatic and inflammatory disease receiving dietary supplementation of n-3 and n-6 fatty acids. Lipids. 1996;31:S243–S247.
    1. Kremer JM, Lawrence D, Jubiz W. Different doses of fish oil fatty acid supplementation on rheumatoid arthritis. A prospective double-blinded randomized study. Arthritis Rheum. 1988;31:530–536.
    1. Kris-Etherton PM, Harris WS, Appel LJ. Fish consumption, fish oil, omega-3 fatty acids, and cardiovascular disease. Circulation. 2002;106:2747–2757.
    1. Lands WEM. Fish and human health. Orlando, FL: Academic Press; 1986. p. 170.
    1. Lawson LD, Hughes BG. Triacylglycerol structure of plant and fungal oils containing γ-linolenic acid. Lipids. 1988;23:313–317.
    1. Leman J. Oleaginous microorganisms: an assessment of the potential. Adv. Appl. Microbiol. 1997;43:195–243.
    1. Leonarda AE, Pereira SL, Sprecher H, Huang YS. Elongation of long-chain fatty acids. Prog. Lipid Res. 2004;43:36–54.
    1. Leskanich CO, Matthews KR, Warkup CC, Noble RC, Hazzledine M. The effect of dietary oil containing (n-3) fatty acids on the fatty acid, physiochemical, and organoleptic characteristics of pig meat and fat. J. Anim. Sci. 1997;75:673–683.
    1. Li D, Hu X. Fish and its multiple human health effects in times of threat to sustainability and affordability: are there alternatives? APJCN. 2009;218:553–563.
    1. Lister CE, Wilson PE, Sutton KH, Morrison SC. Understanding the health benefits of blackcurrants. Acta Hort. 2002;585:443–449.
    1. Makewicz A, Gribi C, Eichenberger W. Lipids of Ectocarpus fasciculatus (Phaeophyceae). Incorporation of [1-14C] oleate and the role of TAG and MGDG in lipid metabolism. Plant Cell Physiol. 1997;38:952–960.
    1. Meyer A, Cirpus P, Ott C, Schlecker R, Zahringer U, Heinz E. Biosynthesis of docosahexaenoic acid in Euglena gracilis: Biochemical and molecular evidence for the involvement of a D4-fatty acyl group desaturase. Biochemistry. 2003;42:9779–9788.
    1. Molina Grima E, Sanchez Perez JA, Garcia Sanchez JL, Garcia Camacho F, Lopez Alonso D. EPA from Isochrysis galbana. Growth conditions and productivity. Process Biochem. 1992;27:299–305.
    1. Morgan CA, Noble RC, Cocchi M, McCartney R. Manipulation of the fatty acid composition of pig meat lipids by dietary means. J. Sci. Food Agric. 1992;58:357–368.
    1. Morita N, Ueno A, Tamaka M, Ohgiya S, Hoshino T, Kawasaki K, et al. Cloning and sequencing of clustered genes involved in fatty acid biosynthesis from the docosahexaenoic acid-producing bacterium, Vibrio marinus strain MP-1. Biotechnol. Lett. 1999;21:641–646.
    1. Mozaffarian D, Ascherio A, Hu FB, Stampfer MJ, Willett WC, Siscovick D, et al. Interplay between different polyunsaturated fatty acids and risk of coronary heart disease in men. Circulation. 2005;111:157–164.
    1. Nakamura MT, Nara TY. Structure, junction and dietary regulation of Δ6, Δ 5 and Δ 9 desaturases. Annu. Rev. Nut. 2004;24:345–376.
    1. Namazi L, Sahari MA, Zaringhalami S, Ghanati K. Possibility of the functional oil production from flax (ω-3) and safflower (ω-6) seeds and evaluation of its physico-chemical properties during 4 months storage. J. Med. Plants. 2011;4:144–159. (In Farsi)
    1. Napier JA, Hey SJ, Lacey DJ, Shewry PR. Identification of a Caenorhabditis elegans Delta6-fatty-acid-desaturase by heterologous expression in Saccharomyces cerevisiae. Biochem. J. 1998;330:611–614.
    1. Nazemroaya S, Sahari MA, Rezaei M. Identification of fatty acid in mackerel (Scomberomorus commersoni) and shark (Carcharhinus dussumieri) fillets and their changes during six month of frozen storage at -18˚Ϲ. J. Agr. Sci. Tech. 2011;13:553–566.
    1. Neuriger M, Connor WE, Van Petten C, Borstad C. Dietary omega-3 fatty acid deficiency and visual loss in infant rhesus monkeys. J. Clin. Invest. 1984;73:272–276.
    1. Park S, Johnson MA. Awareness of fish advisories and mercury exposure in women of childbearing age. Nutr. Rev. 2006;64:250–256.
    1. Parry JW, Yu L. Fatty acid content and antioxidant properties of cold-pressed black raspberry seed oil and meal. J. Food Sci. 2004;69:189–193.
    1. Perveen Z, Ando H, Ueno A, Ito Y, Yamamoto Y, Yamada Y, et al. Isolation and characterization of a novel thraustochytrid-like microorganism that efficiently produces docosahexaenoic acid. Biotechnol. Lett. 2006;28:197–202.
    1. Pirestani S, Sahari MA, Barzegar M, Nikoopour H. Lipid, cholesterol and fatty acid profile of some commercially important fish species from south Caspian Sea. J. Food Biochem. 2010;34:886–895.
    1. Pohl P. Fatty acids and lipids of marine algae and the control of their biosynthesis by environmental factors. In: Tanaka Y, Zurheide F, editors; Hoppe HA, Levring T, editors. Marine algae in pharmaceutical science. Berlin: Walter de Gruyter; 1979. pp. 473–523.
    1. Przybylski R, Mag T, Eskin NAM. Canola oil. In: Shahidi F, McDonald BE, editors. Bailey industrial oil and fat products. New York, NY: John Wiley & Sons, Inc; 2005. pp. 135–195. Chapter 2, Vol. 6.
    1. Qi B, Fraser T, Mugford S, Dobson G, Sayanova O, Butlre J, et al. Production of very long chain polyunsaturated omega-3 and omega-6 fatty acids in plants. Nat. Biotechnol. 2004;22:739–745.
    1. Qiang H, Zhengyu H, Cohen Z, Richmond A. Enhancement of eicosapentaenoic acid (EPA) and γ-linolenic acid (GLA) production by manipulating algal density of outdoor cultures of Monodus subterraneus (Eustigmatophyta) and Spirulina platensis (Cyanobacteria) Eur. J. Phycol. 1997;32:81–86.
    1. Qiu X. Biosynthesis of docosahexaenoic acid (DHA, 22:6–4, 7, 10, 13, 16, 19): two distinct pathways. Prostaglandins Leukot. Essent. Fatty Acids. 2003;68:181–186.
    1. Qiu X, Hong H, Datla N, Mackenzie SL, Taylor DC, Thomas TL. Expression of borage Δ6 desaturase in Saccharomyces cerevisiae and oilseed crops. Can. J. Bot. 2002;80:42–49.
    1. Radwan SS. Sources of polyunsaturated fatty acids for biotechnological use. Appl. Microbiol. Biotechnol. 1991;35:421–430.
    1. Raes K, De Smet S, Demeyer D. Effect of dietary fatty acids on incorporation of long chain polyunsaturated fatty acids and conjugated linoleic acid in lamb, beef and pork meat: a review. Anim. Feed Sci. Technol. 2004;113:119–221.
    1. Raheja BS, Sadikot SM, Phatak RB, Rao MB. Significance of the n-6/n-3 ratio for insulin action in diabetes. Ann. N. Y. Acad. Sci. 1993;683:258–271.
    1. Ratledge C. Biotechnology of oils and fats. In: Ratledge C, Wilkinson SG, editors. Microbial lipids. London, U.K: Academic Press; 1989. pp. 567–668.
    1. Ratledge C. An overview of microbial lipids. In: Ratledge C, Wilkinson SG, Wilkinson SG, editors. Microbial lipids. London, U.K: Academic Press; 1988. pp. 3–22.
    1. Ratnayake WMN, Matthews DG, Ackman RGJ. Triacylglycerols of evening primrose Oenothera biennis seed oil. J. Am. Oil Chem. Soc. 1989;66:966–969.
    1. Reddy AS, Thomas TL. Expression of a cyanobacterial Δ6-desaturase gene results in γ−linolenic acid production in transgenic plants. Nat. Biotechnol. 1996;14:639–642.
    1. Reddy AS, Nuccio ML, Gross LM, Thomas TL. Isolation of a delta 6-desaturase gene from the cyanobacterium Synechocystis sp. strain PCC 6803 by gain-of-function expression in Anabaena sp. strain PCC 7120. Plant Mol. Biol. 1993;27:293–300.
    1. Renaud SM, Parry DL, Thinh LV. Microalgae for use in tropical aquaculture: I. Gross chemical and fatty acid composition of twelve species of microalgae from the North Territory, Australia. J. Appl. Phycol. 1994;6:337–345.
    1. Renaud SM, Thinh LV, Parry DL. The gross chemical composition and fatty acid composition of tropical Australia microalgae for possible use in mariculture. Aquaculture. 1999;170:147–159.
    1. Rhee KS, Ziprin YA, Ordonez G, Bohac CE. Fatty acid profiles of the total lipids and lipid oxidation in pork muscles as affected by canola oil in the animal diet and muscle location. Meat Sci. 1988;23:201–210.
    1. Rissanen T, Voutilainen S, Nyyssonen K, Lakka TA, Salonen JT. Fish oil-derived fatty acids, docosahexaenoic acid and docosapentaenoic acid, and the risk of acute coronary events: the Kuopio ischaemic heart disease risk factor study. Circulation. 2000;102:2677–2679.
    1. Romans JR, Johnson RC, Wulf DM, Libal GW, Costello WJ. Effects of ground flaxseed in swine diets on pig performance and on physical and sensory characteristics of ω3 fatty acid content of pork. I. Dietary level of flaxseed. J. Anim. Sci. 1995;73:1982–1986.
    1. Ruiz Del Castillo ML, Dobson G, Brennan R, Gordon S. Genotypic variation in fatty acid content of blackcurrant seeds. J. Agric. Food Chem. 2002;50:332–335.
    1. Ruiz Del Castillo ML, Dobson G, Brennan R, Gordon S. Fatty acid content and juice characteristics in blackcurrant (Ribes nigrum L.) genotypes. J. Agric. Food Chem. 2004;52:948–952.
    1. Sahari MA, Farahani F, Soleimanian Y, Mokhlesi A. n-3 fatty acid distribution of commercial fish species components. J. Am. Oil Chem. Soc. 2013;90:1167–1178.
    1. Sakuradani E, Kobayashi M, Shimizu S. Δ6-fatty acid desaturase from an arachidonic acid-producing Mortierella fungus. Gene cloning and its heterologous expression in a fungus, Aspergillus. Gene. 1999;238:445–453.
    1. Salimon J, Abdullah BM. A study on the thermal properties and solid fat content of Malaysian rubber seed oil. Malays. J. Anal. Sci. 2009;13:1–7.
    1. Sardi L, Martelli G, Lambertini L, Parisini P, Mordenti A. Effects of a dietary supplement of DHA-rich marine algae on Italian heavy pig production parameters. Livest. Sci. 2006;103:95–103.
    1. Sato M, Adan Y, Shibata K, Shoji Y, Sato H, Imaizumi K. Cloning of rat delta 6-desaturase and its regulation by dietary eicosapentaenoic or docosahexaenoic acid. World Rev. Nutr. Diet. 2001;88:196–199.
    1. Sato S, Xing A, Ye X, Schweiger B, Kinney A, Graef G, et al. Production of γ-linolenic acid and stearidonic acid in seeds of marker-free transgenic soybean. Crop Sci. 2004;44:646–652.
    1. Sayanova O, Haslam R, Guschina I, Lloyd D, Christie WW, Harwood JL, et al. A bifunctional 12, 15-desaturase from Acanthamoeba castellanii directs the synthesis of highly unusual n-1 series unsaturated fatty acids. J. Biol. Chem. 2006;281:36533–36541.
    1. Sessler AM, Ntambi JM. Polyunsaturated fatty acid regulation of gene expression. J. Nutr. 1998;128:923–926.
    1. Seto A, Wang HL, Hesseltine CW. Culture conditions affect eicosapentaenoic acid content of Chlorella minutissima. J. Am. Oil Chem. Soc. 1984;61:892–894.
    1. Shahar E, Folsom AR, Melnick SL. Dietary n-3 polyunsaturated fatty acids and smoking-related chronic obstructive pulmonary disease. Atherosclerosis risk in com munities study investigators. N. Engl. J. Med. 1994;331:228–233.
    1. Sharma B, Singh B, Dhyani D, Verma PK, Karthigeyan S. Fatty acid composition of wild growing rose species. J. Med. Plants Res. 2012;6:1046–1049.
    1. Shimizu S. Mortierella species (fungi): production of C20 polyunsaturated fatty acids. In: Bajaj YPS, Jareonkitmongkol S, editors. Biotechnology in agriculture and forestry. Berlin: Springer-Verlag; 1995. pp. 308–325.
    1. Sidhu KS. Health benefits and potential risks related to consumption of fish or fish oil. Regul. Toxicol. Pharmacol. 2003;38:336–344.
    1. Simopoulos AP, Salem N., Jr Egg yolk as a source of long-chain polyunsaturated fatty acids in infant feeding. Am. J. Clin. Nutr. 1992;55:411–414.
    1. Simpson MJA. Comparison of swathing and desiccation of borage (Borago officinalis) and estimation of optimum harvest stage. Ann. Appl. Biol. 1993a;123:105–108.
    1. Simpson MJA. A description and code of development of borage (Borago officinalis. Ann. Appl. Biol. 1993b;123:187–192.
    1. Siriamornpun S, Li D, Yang L, Suttajit S, Suttajit M. Variation of lipid and fatty acid compositions in Thai Perilla seeds grown at different locations. J. Sci. Technol. 2006;28:17–21.
    1. Sprecher H, Chen Q, Yin FQ. Regulation of the biosynthesis of 22:5 n-6 and 22:6 n-3: a complex intracellular process. Lipids. 1999;34:153–156.
    1. Steele EA. 2006. Letter regarding eggs with enhanced omega-3 fatty acid content and a balanced 1:1 ratio of omega-3/omega-6 fatty acids and reduced risk of heart disease and sudden fatal heart attack. Docket No. 2004Q-0072. Available at C:\Users\PITA\Desktop\pHd2\boraage\mohemaaaa\Belovo.htm (accessed 9 May 2006)
    1. Steffens W. Effects of variation feeds on nutritive in essential fatty acids in fish value of freshwater fish for humans. Aquaculture. 1997;151:97–119.
    1. Steffens W, Wirth M. Fresh water fish-an important source of n-3 polyunsaturated fatty acids: a review. Arch. Pol. Fish. 2005;13:5–16.
    1. Stenson WF, Cort D, Rodgers J. Dietary supplementation with fish oil in ulcerative colitis. Ann. Intern. Med. 1992;116:609–614.
    1. Sukenik A. Ecophysiological considerations in the optimization of eicosapentaenoic acid production by Nannochloropsis sp. (Eustigmatophyceae) Bioresour. Technol. 1991;35:263–269.
    1. Tan CK, Johns MR. Screening of diatoms for heterotrophic eicosapentaenoic acid production. J. Appl. Phycol. 1996;8:59–64.
    1. Thais F. Effect of dietary fish oil on renal function in immune mediated glomerular injury. In: Lands WEM, Stahl RA, editors. AOAC short course on polyunsaturated fatty acid and eicosanoids. Champaign, IL: AOCS Press; 1987. pp. 123–126.
    1. Tonon T, Harvey D, Qing R, Li Y, Larson TR, Graham IA. Identication of a fatty acid ▵11 desaturase from the microalga Thalassiosira pseudonana. FEBS Lett. 2004;563:28–34.
    1. Uzun B, Arslan C, Karhan M, Toker C. Fat and fatty acids of white lupin (Lupinus albus L.) in comparison to sesame (Sesamum indicum L.) Food Chem. 2007;102:45–49.
    1. Venegas-Calerón M, Sayanova O, Napier JA. An alternative to fish oils: metabolic engineering of oil-seed crops to produce omega-3 long chain polyunsaturated fatty acids. Prog. Lipid Res. 2010;49:108–119.
    1. Venkatachalam M, Sathe SK. Chemical composition of selected edible nut seeds. J. Agric. Food Chem. 2006;4:4705–4714.
    1. Vogel G, Eichenberger W. Betaine lipids in lower plants, biosynthesis of DGTS and DGTA in Ochromonas danica and the possible role of DGTS in lipid metabolism. Plant Cell Physiol. 1992;33:427–436.
    1. Vrinten P, Wu G, Truksa M, Qiu X. Production of polyunsaturated fatty acids in transgenic plants. Biotechnol. Genet. Eng. Rev. 2007;24:263–280.
    1. Wallis JG, Browse J. The 8-desaturase of Euglena gracilis: an alternate pathway for synthesis of 20-carbon polyunsaturated fatty acids. Arch. Biochem. Biophys. 1999;365:307–116.
    1. Wen ZY, Chen F. Production potential of eicosapentaenoic acid by the diatom Nitzschia laevis. Biotechnol. Lett. 2000;22:727–733.
    1. Williams CM, Burdge G. Long-chain n-3 PUFA: plant versus marine sources. Proc. Nutr. Soc. 2006;65:42–50.
    1. Wood JD, Enser H. Factors influencing fatty acids in meat and the role of antioxidants in improving meat quality. Br. J. Nutr. 1997;78:549–560.
    1. Wood JD, Enser M, Fisher AV, Nute GR, Richardson RI, Sheard PR. Manipulating meat quality and composition. Proc. Nutr. Soc. 1999;58:1–8.
    1. Wood JD, Richardson RI, Nute GR, Fisher AV, Campo MM, Kasapidou E, et al. Effects of fatty acids on meat quality: a review. Meat Sci. 2003;66:21–32.
    1. Woods VB, Fearon AM. Dietary sources of unsaturated fatty acids for animals and their transfer into meat, milk and eggs: a review. Livest. Sci. 2009;126:1–20.
    1. Wu ST, Yu ST, Lin LP. Effect of culture conditions on docosahexaenoic acid production by Schizochytrium sp. S31. Process Biochem. 2005;40:3103–3108.
    1. Yaniv Z, Ranen C, Levy A, Palevitch D. Effect of temperature on the fatty acid composition and yield of evening primrose (Oenothera lamarckiana) seeds. J. Exp. Bot. 1989;40:609–613.
    1. Yongmanitchai W, Ward OP. Omega-3 fatty acids: alternative sources of production. Process Biochem. 1989;24:117–125.
    1. Yongmanitchai W, Ward OP. Growth of and omega-3 fatty acid production by Phaeodactylum tricornutum under different culture conditions. Appl. Environ. Microbiol. 1991;57:419–425.
    1. Yu L, Parry J. Oils from fruit, spice, and herb seeds. In: Shahidi F, Zhou K, editors. Bailey's industrial oil and fat products. Hoboken, NJ: John Wiley and Sons Inc; 2005. pp. 233–258.
    1. Zhou XR, Robert SS, Petrie JR, Frampton DM, Mansour MP, Blackburn SI. Isolation and characterization of genes from the marine microalga Pavlova salina encoding three front-end desaturases involved in docosahexaenoic acid biosynthesis. Phytochemistry. 2007;68:785–796.

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