Skip to main content
SpringerLink
Log in

Modifying Vegetable Oils for Food and Non-food Purposes

  • Chapter
  • First Online:
Oil Crops

Part of the book series: Handbook of Plant Breeding ((HBPB,volume 4))

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  • Abbadi A, Domergue F, Bauer J, Napier JA, Welti R, Zahringer U, Cirpus P, Heinz E (2004) Biosynthesis of very-long-chain polyunsaturated fatty acids in transgenic oilseeds: constraints on their accumulation. Plant Cell 16: 2734–2748.

    Article  CAS  PubMed  Google Scholar 

  • Alt JL, Fehr WR, Welke GA, Sandu D (2005a) Phenotypic and molecular analysis of oleate content in the mutant soybean line M23. Crop Sci. 45: 1997–2000.

    Google Scholar 

  • Alt JL, Fehr WR, Welke GA, Shannon JG (2005b) Transgressive segregation for oleate content in three soybean populations. Crop Sci. 45: 2005–2007.

    Article  CAS  Google Scholar 

  • Ayorinde FO, Nana EY, Nicely PD, Woods AS, Price EO, Nwaonicha CP (1997) Syntheses of 12-aminododecanoic and 11-aminoundecanoic acids from vernolic acid. J. Am. Oil. Chem. Soc. 74: 531–538.

    Article  CAS  Google Scholar 

  • Barre DE (2001) Potential of evening primrose, borage, black currant, and fungal oils in human health. Ann. Nutr. Metab. 45: 47–57.

    Article  CAS  PubMed  Google Scholar 

  • Beaudoin F, Gable K, Sayanova O, Dunn T, Napier JA (2002) A Saccharomyces cerevisiae gene required for heterologous fatty acid elongase activity encodes a microsomal β-Keto-reductase. J. Biol. Chem. 277: 11481–11488.

    Article  CAS  PubMed  Google Scholar 

  • Beló A, Zheng P, Luck S, Shen B, Meyer DJ, Li B, Tingey S, Rafalski A (2008) Whole genome scan detects an allelic variant of fad2 associated with increased oleic acid levels in maize. Mol. Genet. Genomics 279: 1–10.

    Article  PubMed  CAS  Google Scholar 

  • Bentley R, Bennett JW (1999) Constructing polyketides: from collie to combinatorial biosynthesis. Annu. Rev. Microbiol. 53: 411–446.

    Article  CAS  PubMed  Google Scholar 

  • Bhardwaj HL, Hamama AA, Dierig DA (2007) Fatty acids in vernonia produced in the Mid-Atlantic region of the United States. J. Am. Oil. Chem. Soc. 84: 393–397.

    Article  CAS  Google Scholar 

  • Binkoski AE, Kris-Etherton PM, Wilson TA, Mountain ML, Nicolosi RJ (2005) Balance of unsaturated fatty acids is important to a cholesterol-lowering diet: comparison of mid-oleic sunflower oil and olive oil on cardiovascular disease risk factors. J. Am. Diet. Assoc. 105: 1080–1086.

    Article  CAS  PubMed  Google Scholar 

  • Booth JR, Broglie RM, Hitz WD, Kinney AJ, Knowlton S, Sebastian SA (2002) Gene combinations that alter the quality and functionality of soybean oil. United States Patent US 6426448.

    Google Scholar 

  • Booth JR, Cahoon RE, Hitz WD, Kinney AJ, Yadav NS (2006) Nucleotide sequences of a new class of diverged Δ9 stearoyl-ACP desaturase genes. European Patent Publication EP1311659.

    Google Scholar 

  • Boswell K, Koskelo EK, Carl L, Glaza S, Hensen DJ, Williams KD, Kyle DJ (1996) Preclinical evaluation of single-cell oils that are highly enriched with arachidonic acid and docosahexaenoic acid. Food Chem. Toxicol. 34: 585–593.

    Article  CAS  PubMed  Google Scholar 

  • Bourre JM, Piciotti M, Dumont O. (1990) Δ6 desaturase in brain and liver during development and aging. Lipids 25: 354–356.

    Article  CAS  PubMed  Google Scholar 

  • Breslow JL (2006) n-3 fatty acids and cardiovascular disease. Am. J. Clin. Nutr. 83: 1477–1482.

    Google Scholar 

  • Bubeck DM, Fehr WR, Hammond EG (1989) Inheritance of palmitic and stearic acid mutants of soybean. Crop Sci. 29: 652–656

    Article  Google Scholar 

  • Buhr T, Sato S, Ebrahim F, Xing A, Zhou Y, Mathiesen M, Schweiger B, Kinney AJ, Staswick P, Clemente T (2002) Ribozyme termination of RNA transcripts down-regulate seed fatty acid genes in transgenic soybean. Plant J. 30: 155–163.

    Article  CAS  PubMed  Google Scholar 

  • Burdge GC, Jones AE, Wootton SA. (2002) Eicosapentaenoic and docosapentaenoic acids are the principal products of α-linolenic acid metabolism in young men. Br. J. Nutr. 88: 355–363.

    Article  CAS  PubMed  Google Scholar 

  • Burton JW, Miller JF, Vick BA, Scarth R, Holbrook CC (2004) Altering fatty acid composition in oil seed crops. Adv. Agron. 84: 273–306.

    Article  CAS  Google Scholar 

  • Cahoon EB, Kinney AJ (2005) The production of vegetable oils with novel properties: using genomic tools to probe and manipulate plant fatty acid metabolism. Eur. J. Lipid Sci. Technol. 107: 239–243.

    Article  CAS  Google Scholar 

  • Cahoon EB, Carlson TJ, Ripp KG, Schweiger BJ, Cook GA, Hall SE, Kinney AJ (1999) Biosynthetic origin of conjugated double bonds: production of fatty acid components of high-value drying oils in transgenic soybean embryos. Proc. Natl. Acad. Sci. USA 96: 12935–12940.

    Article  CAS  PubMed  Google Scholar 

  • Cahoon EB, Ripp KG, Hall SE, Kinney AJ (2001) Formation of conjugated Δ8,Δ10-double bonds by Δ12-oleic-acid desaturase-related enzymes: biosynthetic origin of calendic acid. J. Biol. Chem. 276: 2637–2643.

    Article  CAS  PubMed  Google Scholar 

  • Cahoon EB, Ripp KG, Hall SE, McGonigle B (2002) Transgenic production of epoxy fatty acids by expression of a cytochrome P450 enzyme from Euphorbia lagascae seed. Plant Physiol. 128: 615–624.

    Article  CAS  PubMed  Google Scholar 

  • Cahoon EB, Dietrich CR, Meyer K, Damude HG, Dyer JM, Kinney AJ (2006) Conjugated fatty acids accumulate to high levels in phospholipids of metabolically engineered soybean and Arabidopsis seeds. Phytochemistry 67: 1166–1176.

    Article  CAS  PubMed  Google Scholar 

  • Cahoon EB, Carlson T, Hitz WD, Ripp KG (2007a) Genes for plant fatty acid modifying enzymes associated with conjugated double bond formation. United States Patent US 7,244,563.

    Google Scholar 

  • Cahoon EB, Shockey JM, Dietrich CR, Gidda SK, Mullen RT, Dyer JM (2007b) Engineering oilseeds for sustainable production of industrial and nutritional feedstocks: solving bottlenecks in fatty acid flux. Curr. Opin. Plant Biol. 10: 236–244.

    Article  CAS  PubMed  Google Scholar 

  • Calder PC (2003) N-3 polyunsaturated fatty acids and inflammation: from molecular biology to the clinic. Lipids 38: 343–352.

    Article  CAS  PubMed  Google Scholar 

  • Cardinal AJ, Burton JW (2007) Correlations between palmitate content and agronomic traits in soybean populations segregating for the fap1, fap nc , and fan alleles. Crop Sci. 47: 1804–1812.

    Article  CAS  Google Scholar 

  • Cardinal AJ, Burton JW, Camacho-Roger AM, Yang JH, Wilson RF, Dewey RE (2007) Molecular analysis of soybean lines with low palmitic acid content in the seed oil. Crop Sci. 47: 304–310.

    Article  CAS  Google Scholar 

  • Cerutti H (2003) RNA interference: traveling in the cell and gaining functions? Trends Genet. 19: 39–46.

    Article  CAS  PubMed  Google Scholar 

  • Cheesbrough TM (1990) Decreased growth temperature increases soybean stearoyl-acyl carrier protein desaursae activity. Plant Physiol. 93: 555–559.

    Article  CAS  PubMed  Google Scholar 

  • Chen R, Matsui K, Ogaw M, Oe M, Ochiai M, Kawashima H, Sakuradani E, Shimizu S, Ishimoto M, Hayashi M, Murooka Y, Tanaka Y (2006) Expression of Δ6, Δ5 desaturase and GLELO elongase genes from Mortierella alpina for production of arachidonic acid in soybean [Glycine max (L.) Merrill] seeds. Plant Sci. 170: 399–406.

    Article  CAS  Google Scholar 

  • Damude HG, Yadav NS (2005) Cloning and sequences of fungal Δ15 desaturases suitable for production of polyunsaturated fatty acids in oilseed plants for food or industrial uses. International Patent Publication WO 2005047479.

    Google Scholar 

  • Damude HG, Zhang H, Farrall L, Ripp, KG Tomb J-F, Hollerbach D, Yadav NS (2006) Identification of bifunctional Δ12/ω3 fatty acid desaturases for improving the ratio of ω3 to ω6 fatty acids in microbes and plants. Proc. Natl. Acad. Sci. USA 103: 9446–9451.

    Article  CAS  PubMed  Google Scholar 

  • Davis BC, Kris-Etherton PM (2003) Achieving optimal essential fatty acid status in vegetarians: current knowledge and practical implications. Am. J. Clin. Nutr. 78: 640–646.

    Google Scholar 

  • Denic V, Weissman JS (2007) A molecular caliper mechanism for determining very long-chain fatty acid length. Cell 130: 663–677.

    Article  CAS  PubMed  Google Scholar 

  • Dörmann P, Voelker TA, Ohlrogge JB (2000) Accumulation of palmitate in Arabidopsis mediated by the acyl-acyl carrier protein thioesterase FATB1. Plant Physiol. 123: 637–644.

    Article  PubMed  Google Scholar 

  • Dirienzo MA, Lemke SL, Petersen BJ, Smith KM (2008) Effect of substitution of high stearic low linolenic acid soybean oil for hydrogenated soybean oil on fatty acid intake. Lipids 43: 451–456.

    Article  CAS  PubMed  Google Scholar 

  • Eckert H, LaVallee B, Schweiger BJ, Kinney AJ, Cahoon EB, Clemente T (2006) Co-expression of the borage Δ6 desaturase and the Arabidopsis Δ15 desaturase results in high accumulation of stearidonic acid in the seeds of transgenic soybean. Planta 224: 1050–1057.

    Article  CAS  PubMed  Google Scholar 

  • Erhan SZ, Bagby MO (1991) Lithographic and letterpress ink vehicles from vegetable oils. J. Am. Oil. Chem. Soc. 68: 635–638.

    Article  CAS  Google Scholar 

  • Erhan SZ, Sharma BK, Perez JM (2006) Oxidation and low temperature stability of vegetable oil-based lubricants. Ind. Crop. Prod. 24: 292–299.

    Article  CAS  Google Scholar 

  • Fleith M, Clandinin MT (2005) Dietery PUFA for preterm and term infants: review of clinical studies. Crit. Rev. Food Sci. Nutr. 45: 205–229.

    Article  CAS  PubMed  Google Scholar 

  • Funk CD (2001) Prostaglandins and leukotrienes: advances in eicosanoid biology. Science 294: 1871–1875.

    Article  CAS  PubMed  Google Scholar 

  • Gable K, Garton S, Napier JA, Dunn TM (2004) Functional characterization of the Arabidopsis thaliana orthologue of Tsc13p, the enoyl reductase of the yeast microsomal fatty acid elongating system. J. Exp. Bot. 55: 543–545.

    Article  CAS  PubMed  Google Scholar 

  • Han G, Gable K, Kohlwein SD, Beaudoin F, Napier JA, Dunn TM (2002) The Saccharomyces cerevisiae YBR159w gene encodes the 3-ketoreductase of the microsomal fatty acid elongase. J. Biol. Chem. 277: 35440–35449.

    Article  CAS  PubMed  Google Scholar 

  • Hawkins DJ, Kridl JC (1998) Characterization of acyl-ACP thioesterases of mangosteen (Garcinia mangostana) seed and high levels of stearate production in transgenic canola. Plant J. 13: 743–752.

    Article  CAS  PubMed  Google Scholar 

  • Heppard EP, Kinney AJ, Stecca KL, Miao GH (1996) Developmental and growth temperature regulation of two different microsomal ω-6 desaturase genes in soybeans. Plant Physiol. 110: 311–319

    Article  CAS  PubMed  Google Scholar 

  • Hibbeln JR, Nieminen LR, Lands WE (2004) Increasing homicide rates and linoleic acid consumption among five Western countries, 1961–2000. Lipids 39: 1207–1213.

    Article  CAS  PubMed  Google Scholar 

  • Hitz WD (1998) Fatty acid modifying enzymes from developing seeds of Vernonia galamenensis. United States Patent US 5846784.

    Google Scholar 

  • Hong H, Datla N, Reed DW, Covello PS, MacKenzie SL, Qiu X (2002) High-level production of γ-linolenic acid in Brassica juncea using a Δ6 desaturase from Pythium irregulare. Plant Physiol. 129: 354–362.

    Article  CAS  PubMed  Google Scholar 

  • Horrocks LA, Farooqui AA (2004) Docosahexaenoic acid in the diet: its importance in maintenance and restoration of neural membrane function. Prostaglandins Leukot. Essent. Fatty Acids 70: 361–372.

    Article  CAS  Google Scholar 

  • Hu X, Sullivan-Gilbert M, Gupta M, Thompson SA (2006) Mapping of the loci controlling oleic and linolenic acid contents and development of fad2 and fad3 allele-specific markers in canola (Brassica napus L.). Theor. Appl. Genet. 113, 497–507.

    Article  CAS  PubMed  Google Scholar 

  • Iribarren C, Markovitz JH, Jacobs Jr. DR, Schreiner PJ, Daviglus M, Hibbeln JR (2004) Dietary intake of n-3, n-6 fatty acids and fish: relationship with hostility in young adults – the CARDIA study. Eur. J. Clin. Nutr. 58: 24–31.

    Article  CAS  PubMed  Google Scholar 

  • James MJ, Ursin VM, Cleland LG (2003) Metabolism of stearidonic acid in human subjects: comparison with the metabolism of other n-3 fatty acids. Am. J. Clin. Nutr. 77: 1140–1145.

    CAS  PubMed  Google Scholar 

  • Kinney AJ (1996) Development of genetically engineered soybean oils for food applications. J Food Lipids 3: 273–292.

    Article  CAS  Google Scholar 

  • Kinney AJ (1997) Genetic engineering of oilseeds for desired traits. In JK Setlow (ed.), Genetic Engineering. Vol 19. Plenum Press, New York, NY, pp. 149–166.

    Google Scholar 

  • Kinney AJ, Knowlton S (1997) Designer oils: the high oleic soybean. In S Harander, S Roller, (eds.), Genetic Engineering for Food Industry: a Strategy for Food Quality Improvement. Blackie Academic, London, pp. 193–213.

    Google Scholar 

  • Kinney AJ, Cahoon EB, Damude HG, Hitz WD, Kolar CW, Liu Z-B (2004). Production of very long chain polyunsaturated fatty acids in oilseed plants. International Patent Publication WO 2004071467.

    Google Scholar 

  • Kinney AJ, Clemente TE (2005) Modifying soybean oil for enhanced performance in biodiesel blends. Food Process. Technol. 86: 1137–1147.

    Article  CAS  Google Scholar 

  • Knauf VC, Shewmaker C, Flider FJ, Emlay D, Ray E (2006) Safflower With Elevated γ-Linolenic Acid. International Patent Publication WO 2006127789.

    Google Scholar 

  • Knowlton S (1999) Soybean oil having high oxidative stability. United States Patent US 5981781.

    Google Scholar 

  • Korver O, Katan MB (2006) The elimination of trans fats from spreads: how science helped to turn an industry around. Nutr. Rev. 64: 275–279.

    PubMed  Google Scholar 

  • Kridl JC (2002) Methods for increasing stearate content in soybean oil. United States Patent US 6365802.

    Google Scholar 

  • Kris-Etherton PM (1999) AHA Science Advisory. Monounsaturated fatty acids and risk of cardiovascular disease. American Heart Association. Nutrition Committee. Circulation 100: 1253–1258.

    CAS  PubMed  Google Scholar 

  • Kris-Etherton, PM, Griel AE, Psota TL, Gebauer SK, Zhang J, Etherton TD (2005) Dietary stearic acid and risk of cardiovascular disease: intake, sources, digestion, and absorption. Lipids 40: 1193–200.

    Article  CAS  PubMed  Google Scholar 

  • Lai L, Kang JX, Li R, Wang X, Witt WT. Yong HY, Hao Y, Wax DM, Murphy CN, Rieke A, Samuel M, Linville ML, Korte SW, Evans RW, Starzl TE, Prather RS, Dai Y (2006) Generation of cloned transgenic pigs rich in ω-3 fatty acids. Nat. Biotechnol. 24: 435–436.

    Article  CAS  PubMed  Google Scholar 

  • Lee M, Lenman M, Banas A, Bafor M, Singh S, Schweizer M, Nilsson R, Liljenberg C, Dahlqvist A, Gummeson PO, Sjodahl S, Green A, Stymne S (1998) Identification of non-heme diiron proteins that catalyze triple bond and epoxy group formation. Science 280: 915–918.

    Article  CAS  PubMed  Google Scholar 

  • Lichtenstein AH, Matthan NR, Jalbert SM, Resteghini NA, Schaefer EJ, Ausman LM. (2006) Novel soybean oils with different fatty acid profiles alter cardiovascular disease risk factors in moderately hyperlipidemic subjects. Am J Clin Nutr. 84: 497–504.

    CAS  PubMed  Google Scholar 

  • Liu Q, Singh S, Green A (2002) High-oleic and high-stearic cottonseed oils: nutritionally improved cooking oils developed using gene silencing. J Am Coll Nutri 21: 205S–211S.

    CAS  Google Scholar 

  • Liu Z, Erhan SZ, Akin DE, Barton FE (2006) ; “Green” composites from renewable sources:preparation of epoxidized soyabean oil and flax fiber composites. J. Agric. Food Chem. 54:2134–2137.

    Google Scholar 

  • Lumor SE, Jones KC, Ashby R, Strahan GD, Kim BH, Lee GC, Shaw JF, Kays SE, Chang SW, Foglia TA, Akoh CC (2007) Synthesis and characterization of canola oil-stearic acid-based trans-free structured lipids for possible margarine application. J Agric. Food Chem. 55: 10692–10702.

    Article  CAS  PubMed  Google Scholar 

  • Mazur B, Krebbers E, Tingey S (1999) Gene discovery and product development for grain quality traits. Science 285: 372–375.

    Article  CAS  PubMed  Google Scholar 

  • Mensink RP (2005) Effects of stearic acid on plasma lipid and lipoproteins in humans. Lipids 40: 1201–1205.

    Article  CAS  PubMed  Google Scholar 

  • Mensink RP, Katan MB (1990) Effect of dietary trans fatty acids on high-density and low-desnity lipoprotein cholesterol levels in healthy subjects. N. Engl. J. Med. 323: 439–445.

    Article  CAS  PubMed  Google Scholar 

  • Metz JG, Weaver CA, Barclay WR, Flatt JH (2004) Polyunsaturated fatty acid polyketide synthase genes and enzyme systems from Thraustochytrium and Schizochytrium and their use for preparation of bioactive molecules. International Patent Publication WO 2004087879.

    Google Scholar 

  • Metz JG, Roessler P, Facciotti D, Levering C, Dittrich F, Lassner M, Valentine R, Lardizabal K, Domergue F, Yamada A, Yazawa K, Knauf V, Browse J (2001) Production of polyunsaturated fatty acids by polyketide synthases in both prokaryotes and eukaryotes. Science 293: 290–293.

    Article  CAS  PubMed  Google Scholar 

  • Metz JG, Flatt JH, Kuner JM (2006) The genes for the enzymes of the polyunsaturated fatty acid polyketide synthase of Schizochytrium and their use in the manufacture of polyunsaturated fatty acids. International Patent Publication WO 2006135866.

    Google Scholar 

  • Metz JG, Kuner JM, Lippmeier JC (2007) Polyunsaturated fatty acid production in genetically modified organisms using PUFA polyketide synthase systems. International Patent Publication WO 2007106903.

    Google Scholar 

  • Mikkilineni V, Rocheford TR (2003) Sequence variation and genomic organization of fatty acid desaturase-2 (fad2) and fatty acid desaturase-6 (fad6) cDNAs in maize. Theor. Appl. Genet. 106: 1326–1332.

    CAS  PubMed  Google Scholar 

  • Miles EA, Banerjee T, Maaike MB, Dooper MM, M’Rabet L, Graus YMF, Calder PC (2004) The influence of different combinations of γ-linolenic acid, stearidonic acid and EPA on immune function in healthy young male subjects. Br. J. Nutr. 91: 893–903.

    Article  CAS  PubMed  Google Scholar 

  • Minihane AM, Harland JI (2007) Impact of oil used by the frying industry on population fat intake. Crit. Rev. Food Sci. Nutr. 47: 287–297.

    Article  CAS  PubMed  Google Scholar 

  • Mozaffarian D, Rimm EB (2006) Fish intake, contaminants, and human health. Evaluating the risks and the benefits. JAMA 296: 1885–1899.

    Article  CAS  PubMed  Google Scholar 

  • Mozaffarian D, Willett WC (2007) Trans fatty acids and cardiovascular risk: a unique cardiometabolic imprint? Curr. Atheroscler. Rep. 9: 486–493.

    Article  CAS  PubMed  Google Scholar 

  • Mukerji P, Huang V, Das T, Thurmond JM, Leonard AE, Pereira SL (2002) Protein and cDNA sequences of Δ4 desaturases isolated from fungi and therapeutical uses thereof. International Patent Publication WO 2002090493.

    Google Scholar 

  • Oksman M, Livonen H, Hogyes E, Amtul Z, Penke B, Leenders I, Broersen L, Lutjohann D, Hartmann T, Tanila H (2006) Impact of different saturated fatty acid, polyunsaturated fatty acid and cholesterol containing diets on beta-amyloid accumulation in APP/PS1 transgenic mice. Neurobiol. Dis. 32: 563–572.

    Article  CAS  Google Scholar 

  • Okuley J, Lightner J, Feldmann K, Yadav N, Lark E, Browse J (1994) Arabidopsis FAD2 gene encodes the enzyme that is essential for polyunsaturated lipid synthesis. Plant Cell 6: 147–158.

    Article  CAS  PubMed  Google Scholar 

  • Oura T, Kajiwara S (2004) Saccharomyces kluyveri FAD3 encodes an ω3 fatty acid desaturase. Microbiology 150: 1983–1990.

    CAS  Google Scholar 

  • Pantalone VR, Wilson RF, Novitzky WP, Burton JW (2002) Genetic regulation of elevated stearic acid concentration in soybean oil. J. Am. Oil Chem. Soc. 79: 549–553.

    Article  CAS  Google Scholar 

  • Parker-Barnes JM, Das T, Bobik E, Leonard AE, Thurmond, JM Chaung LT, Huang YS, Mukerji P (2000) Identification and characterization of an enzyme involved in the elongation of n-6 and n-3 polyunsaturated fatty acids. Proc. Natl. Acad. Sci. USA 97: 8284–8289.

    Article  CAS  PubMed  Google Scholar 

  • Patel M, Jung S, Moore K, Powell G, Ainsworth C, Abbott A (2004) High-oleate peanut mutants result from a MITE insertion into the FAD2 gene. Theor. Appl. Genet. 108: 1492–1502.

    Article  CAS  PubMed  Google Scholar 

  • Paul S, Gable K, Dunn TM (2007) A Six-membrane-spanning topology for yeast and Arabidopsis Tsc13p, the enoyl reductases of the microsomal fatty acid elongating system. J. Biol. Chem. 282: 19237–19246.

    Article  CAS  PubMed  Google Scholar 

  • Pauly D, Christensen V, Guenette S, Pitcher TJ, Sumaila UR, Walters CJ, Watson R, Zeller D (2002) Towards sustainability in world fisheries. Nature 418: 689–695.

    Article  CAS  PubMed  Google Scholar 

  • Pérez-Vich B, Fernández-Martínez JM, Grondona M, Knapp SJ, Berry ST (2002) Stearoyl-ACP and oleoyl-PC desaturase genes cosegregate with quantitative trait loci underlying high stearic and high oleic acid mutant phenotypes in sunflower. Theor. Appl. Genet. 104: 338–349.

    Article  PubMed  Google Scholar 

  • Pereira SL, Leonard AE, Huang YS, Chuang LT, Mukerji P (2004a) Identification of two novel microalgal enzymes involved in the conversion of the ω3-fatty acid, eicosapentaenoic acid, into docosahexaenoic acid. Biochem. J. 384: 357–366.

    Article  CAS  PubMed  Google Scholar 

  • Pereira SL, Huang YS, Bobik EG, Kinney AJ, Stecca, KL, Packer JCL, Mukerji P (2004b) A novel ω3-fatty acid desaturase involved in the biosynthesis of eicosapentaenoic acid. Biochem. J. 378: 665–671.

    Article  CAS  PubMed  Google Scholar 

  • Primomo VS, Falk DE, Ablett GR, Tanner JW, Rajcan I (2002) Genotype X environment interactions, stability, and agronomic performance of soybean with altered fatty acid profiles. Crop Sci. 42: 37–44.

    Article  CAS  PubMed  Google Scholar 

  • Qi B, Fraser T, Mugford S, Dobson G, Sayanova O, Butler J, Napier JA, Stobart AK, Lazarus CM (2004) Production of very long chain polyunsaturated ω-3 and ω-6 fatty acids in plants. Nat. Biotechnol. 22: 739–745.

    Article  CAS  PubMed  Google Scholar 

  • Qiu X, Hong H, MacKenzie SL (2001) Identification of a Δ4 fatty acid desaturase from Thraustochytrium sp. involved in the biosynthesis of docosahexanoic acid by heterologous expression in Saccharomyces cerevisiae and Brassica juncea. J. Biol. Chem. 276: 31561–31566.

    Article  CAS  PubMed  Google Scholar 

  • Qiu X, Reed DW, Hong H, MacKenzie SL, Covello PS (2001) Identification and analysis of a gene from Calendula officinalis encoding a fatty acid conjugase. Plant Physiol. 125: 847–855.

    Article  CAS  PubMed  Google Scholar 

  • Qiu XH, Hong H, Datla N, MacKenzie SL, Taylor DC, Thomas TL (2002) Expression of borage Δ6 desaturase in Saccharomyces cerevisiae and oilseed crops. Can. J. Bot. 80: 42–49.

    Article  CAS  Google Scholar 

  • Radwan SS (1991) Sources of C20-polyunsaturated fatty acids for biotechnological use. Appl. Microbiol. Biotechnol. 35: 421–430.

    Article  CAS  Google Scholar 

  • Rahman SM, Kinoshita T, Anai T, Takagi Y (2001) Combining ability in loci for high oleic and low linolenic acids in soybean. Crop Sci. 41: 26–29.

    Article  CAS  Google Scholar 

  • Rahman SM, Takagi Y, Miyamoto K, Kawakita T (1995) High stearic acid soybean mutant induced by X-ray irradiation. Biosci. Biotech. Biochem. 59: 922–923.

    Article  CAS  Google Scholar 

  • Ramakers JD, Mensink RP, Schaart G, Plat J (2007) Arachidonic acid but not eicosapentaenoic acid (EPA) and oleic acid activates NF-kB and elevates ICAM-1 expression in Caco-2 cells. Lipids 42: 687–698.

    Article  CAS  PubMed  Google Scholar 

  • Rebetzke GJ, Burton JW, Carter Jr. TE, Wilson RF (1998) Changes in agronomic and seed characteristics with selection for reduced palmitic acid content in soybean. Crop Sci. 38: 297–302.

    Article  CAS  Google Scholar 

  • Reddy AS, Thomas TL (1996) Expression of a cyanobacterial Δ6-desaturase gene results in γ-linolenic acid production in transgenic plants. Nat. Biotechnol. 14: 639–642.

    Article  CAS  PubMed  Google Scholar 

  • Robert S, Singh SP, Zhou X-R, Petrie JR, Blackburn SI, Mansour PM, Nichols PD, Liu Q, Green A (2005). Metabolic engineering of Arabidopsis to produce nutritionally important DHA in seed oil. Funct. Plant Biol. 32: 473–479.

    Article  CAS  Google Scholar 

  • Roberts CA, Ren C, Beuselinck PR, Benedict HR, Bilyeu K (2006) Fatty acid profiling of soybean cotyledons by near-infrared spectroscopy. Appl. Spectrosc. 60: 1328–1333.

    Article  CAS  PubMed  Google Scholar 

  • Ross AJ, Fehr, WR, Welke GA, Cianzio SR (2000) Agronomic and seed traits of 1%-linolenate soybean genotypes. Crop Sci. 40: 383–386.

    Article  CAS  Google Scholar 

  • Ruxton C, Reed SC, Simpson MJ, Millington KJ (2007) The health benefits of ω-3 polyunsaturated fatty acids: a review of the evidence. J. Hum. Nutr. Diet. 20: 275–285.

    Article  CAS  PubMed  Google Scholar 

  • Sakuradani E, Abe T, Iguchi K, Shimizu S (2005) A novel fungal ω3-desaturase with wide substrate specificity from arachidonic acid-producing Mortierella alpina 1S-4. Appl. Microbiol. Biotechnol. 66: 648–654.

    Article  CAS  PubMed  Google Scholar 

  • Sargent JR (1997) Fish oils and human diet. Br. J. Nutr. 78 Suppl 1: S5–S13.

    Article  CAS  PubMed  Google Scholar 

  • Sato S, Xing A, Ye X, Schweiger B, Kinney AJ, Graef G, Clemente TE (2004) Production of γ-linolenic acid and stearidonic acid in seeds of marker-free transgenic soybean. Crop Sci. 44: 646–652.

    Article  CAS  Google Scholar 

  • Sayanova O, Haslam R, Venegas-Caleron M, Napier JA (2006) Identification of primula “front-end” desaturases with distinct n-6 or n-3 substrate preferences. Planta 224: 1269–1277.

    Article  CAS  PubMed  Google Scholar 

  • Sayanova O, Smith MA, Lapinskas P, Stobart AK, Dobson G, Christie WW, Shewry PR, Napier JA (1997) Expression of a borage desaturase cDNA containing an N-terminal cytochrome b5 domain results in the accumulation of high levels of Δ6-desaturated fatty acids in transgenic tobacco. Proc. Natl. Acad. Sci. USA 94: 4211–4216.

    Article  CAS  PubMed  Google Scholar 

  • Sayanova OV, Napier JA (2004) Eicosapentaenoic acid: biosynthetic routes and the potential for synthesis in transgenic plants. Phytochemistry 65: 147–158.

    Article  CAS  PubMed  Google Scholar 

  • Schaefer EJ (1997) Effects of dietary fatty acids on lipoproteins and cardiovascular disease risk: summary. Am. J. Clin. Nutr. 65: 1655S–1656S.

    CAS  PubMed  Google Scholar 

  • Shaw R (1966) Polyunsaturated fatty acids of microorganisms. Adv. Lipid Res. 4: 107–174.

    CAS  PubMed  Google Scholar 

  • Sharma BK, Adhvaryu A, Perez JM, Erhan SZ (2005) Soybean oil based greases: influence of composition on thermo-oxidative and tribochemical behavior. J. Agric. Food Chem. 53: 2961–2968.

    Article  CAS  PubMed  Google Scholar 

  • Simopoulos AP (1999) Essential fatty acids in health and chronic disease. Am. J. Clin. Nutr. 70: 560S–569S.

    CAS  PubMed  Google Scholar 

  • Simopoulos AP (2006) Evolutionary aspects of diet, the ω-6/ω-3 ratio and genetic variation: nutritional implications for chronic diseases. Biomed. Pharmacother. 60: 502–507.

    Article  CAS  PubMed  Google Scholar 

  • Smith WL (2005) Cyclooxygenases, peroxide tone and the allure of fish oil. Curr. Opin. Cell Biol. 17: 174–182.

    Article  CAS  PubMed  Google Scholar 

  • Sontrop J, Campbell MK (2006) ω-3 fatty acids and depression: a review of the evidence and a methodological critique. Prevent. Med. 42: 4–13.

    Article  CAS  Google Scholar 

  • SoyStats™ 2007 Reference Guide to Important Soybean Facts & Figures [Online]. http://www.soystats.com/2007/Default-frames.htm.

  • Sperling P, Ternes P, Zank TK, Heinz E (2003) The evolution of desaturases. Prostaglandins Leukot. Essent. Fatty Acids 68: 73–95.

    Article  CAS  Google Scholar 

  • Sprecher H (2000) Metabolism of highly unsaturated n-3 and n-6 fatty acids. Biochim. Biophys. Acta 1486: 219–231.

    CAS  PubMed  Google Scholar 

  • Sprecher H, Chen Q, Yin FQ (1999) Regulation of the biosynthesis of 22:5n-6 and 22:6n-3: a complex intracellular process. Lipids 34 Suppl: S153–S156.

    Article  CAS  PubMed  Google Scholar 

  • Spychalla JP, Kinney AJ, Browse J (1997) Identification of an animal ω-3 fatty acid desaturase by heterologous expression in Arabidopsis. Proc. Natl. Acad. Sci. USA 94: 1142–1147.

    Article  CAS  Google Scholar 

  • Stoll AL, Damico KE, Daly BP, Severus WE, Marangell LB (2001) Methodological considerations in clinical studies of ω-3 fatty acids in major depression and bipolar disorder. World Rev. Nutr. Diet. 88: 58–67.

    Article  CAS  PubMed  Google Scholar 

  • Takagi Y, Rahman SM (1996) Inheritance of high oleic acid content in the seed oil of soybean mutant M23. Theor. Appl. Genet. 92: 179–182.

    Article  CAS  Google Scholar 

  • Tang G-Q, Novitzky WP, Griffin HC, Huber SC, Dewey RE (2005) Oleate desaturase enzymes of soybean: evidence of regulation through differential stability and phosphorylation. Plant J 44: 433–446.

    Article  CAS  PubMed  Google Scholar 

  • Tat ME, Wang PS, Van Gerpen JH, Clemente TE (2007) Exhaust emissions from an engine fueled with biodiesel from high-oleic soybeans. J. Am. Oil. Chem. Soc. 84: 865–869.

    Article  CAS  Google Scholar 

  • van de Loo FJ, Broun P, Turner S, Somerville C (1995) An oleate 12-hydroxylase from Ricinus communis L. is a fatty acyl desaturase homolog. Proc. Natl. Acad. Sci. USA 92: 6743–6747.

    Article  PubMed  Google Scholar 

  • Venegas-Caleron M, Beaudoin F,Sayanova O, Napier JA (2007) Co-transcribed genes for long chain polyunsaturated fatty acid biosynthesis in the protozoon Perkinsus marinus include a plant-like FAE1 3-ketoacyl coenzyme A synthase. J. Biol. Chem. 282: 2996–3003.

    Article  CAS  PubMed  Google Scholar 

  • Vlcek T, Petrovic ZS (2006) Optimization of the chemoenzymatic epoxidation of soybean oil. J. Am. Oil Chem. Soc. 83: 247–252.

    Article  CAS  Google Scholar 

  • Voelker T, Kinney AJ (2001) Variations in the biosynthesis of seed-storage lipids. Annu. Rev. Plant Physiol. Plant Mol. Biol. 52: 335–361.

    Article  CAS  PubMed  Google Scholar 

  • Von Schacky C, Harris WS (2007) Cardiovascular benefits of ω-3 fatty acids. Cardiovasc. Res. 73: 310–315.

    Article  CAS  Google Scholar 

  • Wada M, DeLong CJ, Hong YH, Rieke CJ, Song I, Sidhu RS, Yuan C, Warnock M, Schmaier AH, Yokoyama C, Smyth EM, Wilson SJ, FitzGerald GA, Garavito RM, Sui DX, Regan JW, Smith WL (2007) Enzymes and receptors of prostaglandin pathways with Arachidonic acid-derived versus eicosapentaenoic acid-derived substrates and products. J. Biol. Chem. 282: 22254–22266.

    Article  CAS  PubMed  Google Scholar 

  • Wallis JG, Watts JL, Browse J (2002) Polyunsaturated fatty acid synthesis: what will they think of next? Trends Biochem. Sci. 27: 467.

    Article  CAS  PubMed  Google Scholar 

  • Wilkes R (2007) Stearidonic acid enriched soybean oil as a source of ω 3 in foods. 86th AOCS Annual Meeting & Expo, Quebec City, QC, Canada.

    Google Scholar 

  • Willatts P, Forsyth JS (2000) The role of long-chain polyunsaturated fatty acids in infant cognitive development. Prostaglandins Leukot. Essent. Fatty Acids 63: 95–100.

    Article  CAS  PubMed  Google Scholar 

  • Wolff RL, Pedrono F, Pasquier E, Marpeau AM (2000) General characteristics of Pinus spp. seed fatty acid compositions, and importance of Δ5-olefinic acids in the taxonomy and phylogeny of the genus. Lipids 35: 1–22.

    Article  CAS  PubMed  Google Scholar 

  • Wu G, Truksa M, Datla N, Vrinten P, Bauer J, Zank T, Cirpus P, Heinz E, Qiu X (2005) Stepwise engineering to produce high yields of very long-chain polyunsaturated fatty acids in plants. Nat. Biotechnol. 23: 1013–1017.

    Article  CAS  PubMed  Google Scholar 

  • Yadav NS, Wierzbicki A, Aegerter M, Caster CS, Perez-Grau L, Kinney AJ, Hitz WD, Booth, Jr. R, Schweiger B, Allen SM, Blackwell M, Reiter RS, Carlson TJ, Russell SH, Feldman KA, Pierce J, Browse J (1993) Cloning of higher plant ω-3 fatty acid desaturases. Plant Physiol. 103: 467–476.

    Article  CAS  PubMed  Google Scholar 

  • Yaqoob P (2003) Fatty acids as gatekeepers of immune cell regulation. Trends Immunol. 24: 639–645.

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgments

Research on unusual fatty acid metabolism in the Cahoon lab is supported by the National Science Foundation (DBI- 0701919).

Author information

Authors and Affiliations

  1. Center for Plant Science Innovation and Department of Biochemistry, University of Nebraska, Lincoln, NE, USA

    Edgar B. Cahoon

  2. Department of Horticulture and Agronomy, Center for Plant Science Innovation, University of Nebraska, 68588-0660, Lincoln, NE, USA

    Thomas E. Clemente

  3. DuPont Experimental Station, Crop Genetics Research and Development, 19880-0353, Wilmington, DE, USA

    Howard G. Damude & Anthony J. Kinney

Authors
  1. Edgar B. Cahoon
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Thomas E. Clemente
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Howard G. Damude
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Anthony J. Kinney
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Edgar B. Cahoon .

Editor information

Editors and Affiliations

  1. Inst. Pflanzenbau und Pflanzenzüchtung, Universität für Bodenkultur Wien, Gregor Mendel Str. 33A, Wien, 1180, Austria

    Johann Vollmann

  2. Dept. Plant Agriculture, University of Guelph, Stone Road W. 50, Guelph, N1G 2W1, Canada

    Istvan Rajcan

Rights and permissions

Reprints and permissions

Copyright information

© 2009 Springer Science+Business Media, LLC

About this chapter

Cite this chapter

Cahoon, E.B., Clemente, T.E., Damude, H.G., Kinney, A.J. (2009). Modifying Vegetable Oils for Food and Non-food Purposes. In: Vollmann, J., Rajcan, I. (eds) Oil Crops. Handbook of Plant Breeding, vol 4. Springer, New York, NY. https://doi.org/10.1007/978-0-387-77594-4_2

Download citation

Publish with us

Policies and ethics

Search

Navigation