Abstract
In all living organisms lipids play several roles and, according to their structures, can be divided into two main groups: the non-polar lipids (acylglycerols, sterols, free fatty acids, wax and steryl esters) and polar lipids (phosphoglycerides, glycosylglycerides, and sphingolipids). Triacylglycerols act as compact, easily metabolised and non-hydrated energy stores. They are important storage products especially in plants producing oilseeds and in oily fruits such as avocado, olive and oil palm. Waxes are commonly extracellular components such as surface coverings, which function both to reduce water loss and to protect plants from noxious environmental conditions. They also act as an energy store in jojoba.
Access provided by Autonomous University of Puebla. Download to read the full chapter text
Chapter PDF
Similar content being viewed by others
Keywords
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.
References
Abbadi A, Domergue F, Bauer J, Napier JA, Welti R, Zähringer 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
Alonso DL, Maroto FG (2000) Plants as “chemical factories” for the production of polyunsaturated fatty acids. Biotechnol Adv 18: 481–497
Bafor M, Smith MA, Jonsson L, Stobart K, Stymne S (1993) Biosynthesis of vernoleate (cis-12-epoxyoctadeca-cis-9-enoate) in microsomal preparations from developing endosperm of Euphorbia lagascae. Arch Biochem Biophys 303: 145–151
Bouvier-Nave P, Benveniste P, Oelkers P, Sturley SL, Schaller H (2000) Expression in yeast and tobacco of plant cDNA encoding acyl-CoA:diacylglycerol acyltransferase. Eur J Biochem 267: 85–96
Broadwater JA, Whittle E, Shanklin J (2002) Desaturation and hydroxylation. Residues 148 and 324 of Arabidopsis FAD2, in addition to substrate chain length, exert a major influence in partitioning of catalytic specificity. J Biol Chem 277: 15613–15620
Brough CL, Coventry JM, Christie WW, Kroon JTM, Brown AP, Barsby TL, Slabas AR (1996) Towards genetic engineering of triacylglycerols of defined fatty acid composition: major changes in erucic acid content at the sn-2 position affected by the introduction of a 1-acyl-sn-glycerol-3-phosphate acyltransferase from Limnanthes douglasii into oil seed rape. Mol Breeding 2: 133–142
Broun P, Somerville C (1997) Accumulation of ricinoleic, lesquerolic, and densipolic acids in seeds of transgenic Arabidopsis plants that express a fatty acyl hydroxylase cDNA from castor bean. Plant Physiol 113: 933–942
Broun P, Boddupalli S, Somerville C (1998a) A bifunctional oleate 12- hydroxylase: desaturase from Lesquerella fendleri. Plant J 13: 201–210
Broun P, Shanklin J, Whittle E, Somerville C (1998b) Catalytic plasticity of fatty acid modification enzymes underlying chemical diversity of plant lipids. Science 282: 1315–1317
Cahoon EB, Shanklin J, Ohlrogge JB (1992) Expression of a coriander desaturase results in petroselinic acid production in transgenic tobacco. Proc Natl Acad Sci USA 89: 11184–11188
Cahoon EB, Ripp KG, Hall SE, Kinney AJ (2001) Formation of conjugated delta(8), delta(10)-double bonds by delta(12)-oleic-acid desaturase-related enzymes – biosynthetic origin of calendic acid. J Biol Chem 276: 2637–2643
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
Cahoon EB, Ohlrogge JB (1994) Metabolic evidence for the involvement of a delta(4)-palmitoyl-acyl carrier protein desaturase in petroselinic acid synthesis in coriander endosperm and transgenic tobacco cells. Plant Physiol 104: 827–837
Cahoon EB, Marillia EF, Stecca KL, Hall SE, Taylor DC, Kinney AJ (2000) Production of fatty acid components of meadowfoam oil in somatic soybean embryos. Plant Physiol 124: 243–251
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
Cahoon EB, Kinney AJ (2004) Dimorphecolic acid is synthesized by the coordinate activities of two divergent △12-oleic acid desaturases. J Biol Chem 279: 12495–12502
Chapman KD, Austin-Brown S, Sparace SA, Kinney AJ, Ripp KG, Pirtle IL, Pirtle RM (2001) Transgenic cotton plants with increased seed oleic acid content. J Amer Oil Chem Soc 78: 941–947
Davies HM (1996) Engineering new oilseed crops from rapeseed. In: Janick J (ed) Progress in new crops. ASHS Press, Alexandria, VA, pp 299–306
De Gyves EM, Sparks CA, Sayanova O, Lazzeri P, Napier JA, Jones HD (2004) Genetic manipulation of gamma-linolenic acid (GLA) synthesis in a commercial variety of evening primrose (Oenothera sp.). Plant Biotech J 2: 351–357
Dehesh K, Jones A, Knutzon DS, Voelker TA (1996) Production of high levels of 8:0 and 10:0 fatty acids in transgenic canola by overexpression of Ch FatB2, a thioesterase cDNA from Cuphea hookeriana. Plant J 9: 167–172
Dehesh K, Tai H, Edwards P, Byrne J, Jaworski JG (2001) Overexpression of 3- ketoacyl-acyl carrier protein synthase III in plants reduced the rate of lipid synthesis. Plant Physiol 125: 1103–1114
Dörmann P (2005) Membrane lipids. In: Murphy DJ (ed) Plant Lipids: Biology, utilisation and manipulation. Blackwell, Oxford, pp 123–161
Drexler H, Spiekermann P, Meyer A, Domergue F, Zank T, Sperling P, Abbadi A, Heinz E (2003) Metabolic engineering of fatty acids for breeding of new oilseed crops: strategies, problems and first results. J Plant Physiol 160: 779–802
Dyer JM, Chapital DC, Kuan JC, Mullen RT, Turner C, McKeon TA, Pepperman AB (2002) Molecular analysis of a bifunctional fatty acid conjugase/desaturase from tung. Implications for the evolution of plant fatty acid diversity. Plant Physiol 130: 2027–2038
Eccleston VS, Cranmer AM, Voelker TA, Ohlrogge JB (1996) Medium-chain fatty acid biosynthesis and utilization in Brassica napus plants expressing lauroyl-acyl carrier protein thioesterase. Planta 198: 46–53
Eccleston VS, Ohlrogge JB (1998) Expression of lauroyl-acyl carrier protein thioesterase in Brassica napus seeds induces pathway for both fatty acid oxidation and biosynthesis and implies a set point for triacylglycerol accumulation. Plant Cell 10: 613–622
Frentzen M, Wolter FP (1998) Molecular biology of acyltransferases involved in glycerolipid synthesis. In: Harwood JL (ed) Plant lipid biosynthesis: fundamentals and agricultural applications. Cambridge University Press, New York, pp 247–272
Gurr MI, Harwood JL, Frayn KN (2002) Lipid biochemistry. An introduction. 5th edt. Blackwell, Oxford
Harwood JL (1996) Recent advances in the biosynthesis of plant fatty acids. Biochim Biophys Acta 1301: 7–56
Harwood JL (2005) Fatty acid biosynthesis. In: Murphy DJ (ed) Plant lipids: biology, utilisation and manipulation. Blackwell, Oxford, pp 27–66
Hatanaka T, Shimizu R, Hildebrand D (2004) Expression of a Stokesia laevis epoxygenase gene. Phytochem 65: 2189–2196
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
Hildebrand DF, Yu K, McCracken C, Rao SS (2005) Fatty acid manipulation. In: Murphy DJ (ed) Plant lipids: biology, utilisation and manipulation. Blackwell, Oxford, pp 67–102
Hong H, Datla N, Reed DW, Covello PS, MacKenzie SL, Qiu X (2002) Highlevel production of γ-linolenic acid in Brassica juncea using a △6 desaturase from Pythium irregulare. Plant Physiol 129: 354–362
Hornung E, Pernstich C, Feussner I (2002) Formation of conjugated delta11, delta13-double bonds by delta12-linoleic acid (1, 4)-acyl-lipiddesaturase in pomegranate seeds. Eur J Biochem 269: 4852–4859
Hornung E, Krueger C, Pernstich C, Gipmans M, Porzel A, Feussner I (2005) Production of (10E, 12Z)-conjugated linoleic acid in yeast and tobacco seeds. Biochim Biophys Acta 30: 105–114
Iwabuchi M, Kohno-Murase J, Imamura J (2003) Delta 12-oleate desaturaserelated enzymes associated with formation of conjugated trans-delta 11, cisdelta 13 double bonds. J Biol Chem 278: 4603–4610
Jadhav A, Marillia EF, Babic V, Giblin EM, Cahoon EB, Kinney AJ, Mietkiewska E, Brost JM, Taylor DC (2005) Production of 22:2(delta 5, delta 13) and 20:1 (delta 5) in Brassica carinata and soybean breeding lines via introduction of Limnanthes genes. Mol Breed 15: 157–167
Jain RK, Coffey M, Lai K, Kumar A, MacKenzie SL (2000) Enhancement of seed oil content by expression of glycerol-3-phosphate acyltransferase genes. Biochem Soc Trans 28: 958–961
Jako C, Kumar A, Wei Y, Zou J, Barton DL, Giblin EM, Covello PS, Taylor DC (2001) Seed-specific over-expression of an Arabidopsis cDNA encoding a diacylglycerol acyltransferase enhances seed oil content and seed weight. Plant Physiol 126: 861–874
Jaworski J, Cahoon EB (2003) Industrial oils from transgenic plants. Curr Opin Plant Biol 6: 178–184
Kinney AJ (1996) Development of genetically engineered soybean oils for food application. J Food Lipids 3: 273–292
Kinney AJ (1998a) Plants as industrial chemical factories – new oils from genetically engineered soybeans. Fett Lipid 100: 173–179
Kinney AJ (1998b) Manipulating flux through plant metabolic pathways. Curr Opin Plant Biol 1: 173–178
Kinney AJ, Clemente TE (2005) Modifying soybean oil for enhanced performance in biodiesel blends. Fuel Process Technol 86: 1137–1147
Knutzon DS, Thompson GA, Radke SE, Johnson WB, Knauf VC, Kridl JC (1992) Modification of Brassica seed oil by antisense expression of a stearoyl-acyl carrier protein desaturase gene. Proc Natl Acad Sci USA 89: 2624–2628
Knutzon DS, Thurmond JM, Huang YS, Chaudhary S, Bobik EG, Chan GM, Kirchnert SJ, Mukerji P (1998) Identification of △5-desaturase from Mortierella alpina by heterologous expression in bakers’ yeast and canola. J Biol Chem 273: 29360–29366
Knutzon DS, Hayes TR, Wyrick A, Xiong H, Davies HM, Voelker TA (1999) Lysophosphatidic acid acyltransferase from coconut endosperm mediates the insertion of laurate at the sn-2 position of triacylglycerols in lauric rapeseed oil and can increase total laurate levels. Plant Physiol 120: 739–746
Kohno-Murase J, Iwabuchi M, Endo-Kasahara S, Sugita K, Ebinuma H, Imamura J (2006) Production of trans-10, cis-12 conjugated linoleic acid in rice. Transgenic Res 15: 95–100
Kridl JC (1998) Engineering canola vegetable oil for food and industrial uses. In: Shewry PR, Napier JA, Davis PJ (eds) Engineering crop plants for industrial end uses. Portland, London, pp 159–169
Lardizabal KD, Metz JG, Sakamoto T, Hutton WC, Pollard MR, Lassner MW (2000) Purification of a jojoba embryo wax synthase, cloning of its cDNA, and production of high levels of wax in seeds of transgenic Arabidopsis. Plant Physiol 122: 645–655
Lassner MW, Levering CK, Davies HM, Knutzon DS (1995) Lysophosphatidic acid acyltransferase from meadowfoam mediates insertion of erucic acid at the sn-2 position of triacylglycerol in transgenic rapeseed oil. Plant Physiol 109: 1389–1394
Lassner MW, Lardizabal K, Metz JC (1996) A jojoba beta-ketoacyl-CoA synthase cDNA complements the canola fatty acid elongation mutation in transgenic plants. Plant Cell 8: 281–292
Lee M, Lenman M, Banas A, Bafor M, Singh S, Schweizer M, Nilsson R, Liljenberg C, Dahlqvist A, Gummeson PO, Sjödahl S, Green A, Stymne S (1998) Identification of non-heme diiron proteins that catalyze triple bond and epoxy group formation. Science 280: 915–918
Leonard JM, Knapp SJ, Slabaugh MB (1998) A Cuphea beta-ketoacyl-ACP synthase shifts the synthesis of fatty acids towards shorter chains in Arabidopsis seeds expressing Cuphea FatB thioesterases. Plant J 13: 621–628
Liu Q, Singh S, Green A (2000) Genetic modification of cotton seed oil using inverted- repeat gene-silencing technique. Biochem Soc Trans 28: 927–929
Mekhedov S, de Ilarduya OM, Ohlrogge JB (2000) Toward a functional catalog of the plant genome. A survey of genes for lipid biosynthesis. Plant Physiol 122: 389–401
Metz JG, Pollard MR, Anderson L, Hayes TR, Lassner MW (2000) Purification of a jojoba embryo fatty acyl-coenzyme A reductase and expression of its cDNA in high erucic acid rapeseed. Plant Physiol 122: 635–644
Mietkiewska E, Giblin EM, Wang S, Barton DL, Dirpaul J, Brost JM, Katavic V, Taylor DC (2004) Seed-specific heterologous expression of a nasturtium FAE gene in Arabidopsis results in a dramatic increase in the proportion of erucic acid. Plant Physiol 136: 2665–2675
Moon H, Smith MA, Kunst L (2001) A condensing enzyme from the seeds of Lesquerella fendleri that specifically elongates hydroxyl fatty acids. Plant Physiol 127: 1635–1643
Murphy DJ (2005) The study and utilisation of plant lipids: from margarine to lipid rafts. In: Murphy DJ (ed) Plant lipids: biology, utilisation and manipulation. Blackwell, Oxford, pp 1–26
O’Hara P, Slabas AR, Fawcett T (2000) Modulation of fatty acid biosynthesis by β-keto reductase expression. Biochem Soc Trans 28: 613–615
Ohlrogge JB, Jaworski JG (1997) Regulation of fatty acid synthesis. Annu Rev Plant Physiol Plant Mol Biol 48: 109–136
Qi BX, Fraser T, Mugford S, Dobson G, Sayanova O, Butler J, Napier JA, Stobart AK, Lazarus CM (2004) Production of very long chain polyunsaturated omega-3 and omega-6 fatty acids in plants. Nat Biotechnol 22: 739–745
Qiu X, Hong HP, Datla N, MacKenzie SL, Taylor DC, Thomas TL (2002) Expression of borage delta 6 desaturase in Saccharomyces cerevisiae and oilseed crops. Can J Bot 80: 42–49
Ramli US, Baker DS, Quant PA, Harwood JL (2002) Control analysis of lipid biosynthesis in tissue cultures from oil crops shows that flux control is shared between fatty acid synthesis and lipid assembly. Biochem J 364: 393–401
Ramli US, Salas JJ, Quant PA, Harwood JL (2005) Metabolic control analysis reveals an important role for diacylglycerol acytransferase in olive but not in oil palm lipid accumulation. FEBS J 272: 5764–5770
Sayanova O, Davies GM, Smith MA, Griffiths G, Stobart AK, Shewry PR, Napier JA (1999) Accumulation of delta(6)-unsaturated fatty acids in transgenic tobacco plants expressing a delta(6)-desaturase from Borago officinalis. J Exptl Bot 50: 1647–1652
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 b 5 domain results in the accumulation of high levels of Δ6 –desaturated fatty acids in transgenic tobacco. Proc Natl Acad Sci USA 94: 4211–4216
Singh S, Thomaeus S, Lee M, Stymne S, Green A (2001) Transgenic expression of a delta 12-epoxygenase gene in Arabidopsis seeds inhibits accumulation of linoleic acid. Planta 212: 872–879
Slabas AR, Sanda SL (1998) Complex lipid biosynthesis and its manipulation in plants. In: Shewry PR, Napier JA, Davis PJ (eds) Engineering crop plants for industrial end uses. Portland, London, pp 171–179
Slabas AR, Chase D, Nishida I, Murata N, Sidebottom C, Safford R, Sheldon PS, Kekwick RGO, Hardie DG, MacKintosh RW (1992) Molecular-cloning of higher-plant 3-oxoacyl-(acyl carrier protein) reductase – sequence identities with the nodG-gene product of the nitrogen-fixing soil bacterium Rhizobium meliloti. Biochem J 283: 321–326
Smith M, Moon H, Kunst L (2000) Production of hydroxyl fatty acids in the seeds of Arabidopsis thaliana. Biochem Soc Trans 28: 947–950
Stobart K, Mancha M, Lenman M, Dahlqvist A, Stymne S (1997) Triacylglycerols are synthesized and utilized by transacylation reactions in microsomal preparations of developing safflower (Carthamus tinctorius L.) seeds. Planta 203: 58–66
Stoutjesdijk PA, Hurlestone C, Singh SP, Green AG (2000) High-oleic acid Australian Brassica napus and B. juncea varieties produced by co-supression of endogenous △ 12-desaturase. Biochem Soc Trans 28: 938–940
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: 6743–6447
Verwoert IIGS, van der Linden KH, Walsh MC, Nijkamp HJJ, Stuitje AR (1995) Modification of Brassica napus seed oil by expression of the Escherichia coli fab H gene, encoding 3-ketoacyl-acyl carrier protein synthase III. Plant Mol Biol 27: 875–886
Voelker TA, Worrell AC, Anderson L, Bleibaum J, Fan C, Hawkins DJ, Radke SE, Davies HM (1992) Fatty acid biosynthesis redirected to medium chains in transgenic oilseed plants. Science 257: 72–74
Voelker T, Kinney AJ (2001) Variations in the biosynthesis of seed-storage lipids. Annu Rev Plant Physiol Plant Mol Biol 52: 335–361
Weselake RJ (2005) Storage lipids. In: Murphy DJ (ed) Plant lipids: biology, utilisation and manipulation. Blackwell, Oxford, pp 162–225
Whittle E, Cahoon EB, Subrahmanyam S, Shanklin J (2005) A multifunctional acyl-acyl carrier protein desaturase from Hedera helix L. (English ivy) can synthesize 16- and 18-carbon monoene and diene products. J Biol Chem 280: 28169–28176
Yuan L, Voelker TA, Hawkins DJ (1995) Modification of the substrate specificity of an acyl-acyl carrier protein thioesterase by protein engineering. Proc Natl Acad Sci USA 92: 10639–10643
Zhang M, Barg R, Yin M, Gueta-Dahan Y, Leikin-Frenkel A, Salts Y, Shabtai S, Ben-Hayyim G (2005) Modulation of fatty acid desaturation via overexpression of two distinct omega-3 desaturases differentially alters tolerance to various abiotic stresses in transgenic tobacco cells and plants. Plant J 44: 361–371
Zou J, Katavic V, Giblin EM, Barton DL, MacKenzie SL, Keller WA, Hu X, Taylor DC (1997) Modification of seed oil content and acyl composition in the
Brassicaceae by expression of a yeast sn-2 acyltransferase gene. Plant Cell 9: 909–923
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2007 Springer
About this chapter
Cite this chapter
A. Guschina, I., Harwood, J. (2007). Complex lipid biosynthesis and its manipulation in plants. In: RANALLI, P. (eds) Improvement of Crop Plants for Industrial End Uses. Springer, Dordrecht. https://doi.org/10.1007/978-1-4020-5486-0_9
Download citation
DOI: https://doi.org/10.1007/978-1-4020-5486-0_9
Publisher Name: Springer, Dordrecht
Print ISBN: 978-1-4020-5485-3
Online ISBN: 978-1-4020-5486-0
eBook Packages: Biomedical and Life SciencesBiomedical and Life Sciences (R0)