Enzymes for transgenic biosynthesis of long-chain polyunsaturated fatty acids

Biochimie

Volumn 86, Issue 11, 2004, Pages 793-798

  Huang, Yung Sheng ^a   Pereira, Suzette L ^a   Leonard, Amanda E ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

Biosynthesis; Enzyme; Long chain polyunsaturated fatty acid; Transgenic

Indexed keywords

ARACHIDONIC ACID; DELTA4 DESATURASE; DELTA5 DESATURASE; DELTA8 DESATURASE; DELTA9 SPECIFIC ELONGASE; DESATURASE; DOCOSAHEXAENOIC ACID; ENZYME; FATTY ACID SYNTHASE; FISH OIL; GAMMA LINOLENIC ACID; ICOSAPENTAENOIC ACID; LINOLEOYL COENZYME A DESATURASE; LONG CHAIN FATTY ACID; OMEGA 3 FATTY ACID; OMEGA 6 FATTY ACID; POLYUNSATURATED FATTY ACID; UNCLASSIFIED DRUG; VEGETABLE OIL;

ALGA; BIOSYNTHESIS; CAENORHABDITIS ELEGANS; CHRONIC DISEASE; DEVELOPMENT; DIATOM; DIET SUPPLEMENTATION; ECONOMICS; ENZYME ISOLATION; FATTY ACID DESATURATION; FATTY ACID METABOLISM; FATTY ACID SYNTHESIS; FISH; FOOD INDUSTRY; FOOD PROCESSING; FUNGUS; GENE EXPRESSION; GENE IDENTIFICATION; GENE ISOLATION; GENETIC ENGINEERING; GENETICALLY MODIFIED CROP; HEALTH; HUMAN; NONHUMAN; PATHOGENESIS; PHYTOPLANKTON; PLANT SEED; RAPESEED; REVIEW; SACCHAROMYCES CEREVISIAE; SHEWANELLA; SOYBEAN; SYMPTOM; TRANSGENIC PLANT; TRANSGENICS;

EID: 10044253311     PISSN: 03009084     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.biochi.2004.09.019     Document Type: Short Survey

References (85)

1. R. Uauy, P. Peirano, D. Hoffman, P. Mena, D. Birch, and E. Birch Role of essential fatty acids in the function of the developing nervous system Lipids 31 Suppl. 1996 167S 176S
2. J.M. Bourre, O.S. Dumont, M.J. Piciotti, G.A. Pascal, and G.A. Durand Dietary alpha-linolenic acid deficiency in adult rats for 7:months does not alter brain docosahexaenoic acid content, in contrast to liver, heart and testes Biochim. Biophys. Acta 1124 1992 119 122
3. K. Retterstol, T.B. Haugen, and B.O. Christophersen The pathway from arachidonic to docosapentaenoic acid (20:4n-6 to 22:5n-6) and from eicosapentaenoic to docosahexaenoic acid (20:5n-3 to 22:6n-3) studied in testicular cells from immature rats Biochim. Biophys. Acta 1483 2000 119 131
4. D.B. Jump The biochemistry of n-3 polyunsaturated fatty acids J. Biol. Chem. 277 2002 8755 8758
5. A.P. Simopoulos Omega-3 fatty acids in inflammation and autoimmune diseases J. Am. Coll. Nutr. 21 2002 495 505
6. H. Sprecher Biochemistry of essential fatty acids Prog. Lipid Res. 20 1982 13 22
7. S.C. Cunnane, and M.J. Anderson The majority of dietary linoleate in growing rats is b-oxidized or stored in visceral fat J. Nutr. 127 1997 146 152
8. R.R. Brenner Endocrine control of fatty acid desaturation Biochem. Soc. Trans. 18 1990 773 775
9. T. Nakada, I.L. Kwee, and W.G. Ellis Membrane fatty acid composition shows Δ6-desaturae abnormalities in Alzheimer's disease Clin. Neurosci. Neuropathol. 1 1990 153 155
10. J.E. Brown, R.M. Lindsay, and R.A. Riemersma Linoleic acid metabolism in the spontaneously diabetic rat: delta6-desaturase activity vs. product/precursor ratios Lipids 35 2000 1319 1323
11. S. Abel, C.M. Smuts, C. de Villiers, and W.C. Gelderblom Changes in essential fatty acid patterns associated with normal liver regeneration and the progression of hepatocytes nodules in rat hepatocarcinogenesis Carcinogenesis 22 2001 795 804
12. G. Agatha, R. Hafer, and F. Zintl Fatty acid composition of lymphocyte membrane phospholipids in children with acute leukemia Cancer Lett. 173 2001 139 144
13. E. Demcakova, E. Sebokova, J. Ukropec, D. Gasperikova, and I. Klimes Delta-6 desaturase activity and gene expression, tissue fatty acid profile and glucose turnover rate in hereditary hypertriglyceridemic rats Endocr. Regul. 35 2001 179 186
14. D.R. Hoffman, J.C. DeMar, W.C. Heird, D.G. Birch, and R.E. Anderson Impaired synthesis of DHA in patients with X-linked retinitis pigmentosa J. Lipid Res. 42 2001 1395 1401
15. A.P. Simopoulos Essential fatty acids in health and chronic disease Am. J. Clin. Nutr. 70 1999 560S 569S
16. W.E. Connor Importance of n-3 fatty acids in health and disease Am. J. Clin. Nutr. 71 2000 171S 175S
17. G.A. Jamal, H.A. Carmichael, and A.I. Weir Gamma-linolenic acid in diabetic neuropathy Lancet I 1986 1098
18. J.M. Kremer, D.A. Lawrence, W. Jubiz, R. DiGiocomo, R. Rynes, and L.E. Bartholomew Dietary fish oil and olive oil supplementation in patients with rheumatoid arthritis. Clinical and immunologic effects Arthritis Rheum. 33 1990 810 820
19. J.S. Charnock, G.L. Crozier, and J. Woodhouse Gamma-linolenic acid, black currant seed and evening primrose oil in the prevention of cardiac arrhythmia in aged rats Nutr. Res. 14 1994 1089 1099
20. J.X. Kang, and A. Leaf Antiarrhythmic effects of polyunsaturated fatty acids Circulation 94 1996 1774 1780
21. R. Zurier, R.G. Rossetti, E.W. Jacobson, D.M. DeMarco, N.Y. Liu, and J.E. Temming Gamma-linolenic acid treatment of rheumatoid arthritis, A randomized, placebo-controlled trial Arthritis Rheum. 39 1996 1808 1817
22. T. Babcock, W.S. Helton, and N.J. Espat Eicosapentaenoic acid (EPA): an antiinflammatory ω-3 fat with potential clinical applications Nutrition 16 2000 1116 1118
23. S.E. Carlson, S.H. Werkman, J.M. Peeples, R.J. Cooke, and E.A. Tolley Arachidonic acid status correlates with first year growth in preterm infants Proc. Natl. Acad. Sci. USA 90 1993 1073 1077
24. M.A. Crawford, K. Costeloe, K. Ghebremeskel, A. Phylactos, L. Skirvin, and F. Stacey Are deficits of arachidonic and docosahexaenoic acids responsible for the neural and vascular complications of preterm babies? Am. J. Clin. Nutr. 66 1997 1032S 1041S
25. S.M. Innis, H. Sprecher, D. Hachey, J. Edmond, and R.E. Anderson Neonatal polyunsaturated fatty acid metabolism Lipids 34 1999 139 149
26. L. Lauritzen, H.S. Hansen, M.H. Jorgensen, and K.F. Michaelsen The essentiality of long chain n-3 fatty acids in relation to development and function of the brain and retina Prog. Lipid Res. 40 2001 1 94
27. E.A. Trautwein n-3 Fatty acids--physiological and technical aspects for their role in food Eur. J. Lipid Sci. Technol. 103 2001 45 55
28. W.R. Barclay, K.M. Meager, and J.R. Abril Heterotrophic production of long-chain omega-3 fatty acids utilizing algae and algae-like microorganisms J. Appl. Phycol. 6 1994 123 129
29. P.K. Bajpai, P. Bajpai, and O.P. Ward Optimization of production of docosahexaenoic acid (DHA) by Thraustochytrium aureum ATCC 34304 J. Am. Oil Chem. Soc. 68 1991 509 514
30. D.E. Barre Potential of evening primrose, borage, black currant, and fungal oils in human health Ann. Nutr. Metab. 45 2001 47 57
31. A. Kendrick, and C. Ratledge Lipids of selected molds grown for production of n-3 and n-6 polyunsaturated fatty acids Lipids 27 1992 15 20
32. H. Streekstra On the safety of Mortierella alpina for the production of food ingredients, such as arachidonic acid J. Biotechnol. 56 1997 153 165
33. J.R. Sargent, and A.G.J. Tacon Development of farmed fish: a nutritionally necessary alternative to meat Proc. Nutr. Soc. 58 1999 377 383
34. E. Guallar, M.I. Sanz-Gallardo, P. Van't Veer, A. Aro, J. Gomez-Aracena, and J.D. Kark Mercury, fish oils, and the risk of myocardial infarction New Engl. J. Med. 347 2002 1747 1754
35. F.B. Padley, F.D. Gunstone, and J.L. Harwood Occurrence and characteristics of oils and fats F.D. Gunstone J.L. Harwood F.B. Padley The Lipid Handbook, second ed 1994 Chapman and Hall London 47 223
36. Y.-S. Huang, S. Chaudhary, J.M. Thurmond, E.G. Bobik Jr., L. Yuan, and G.M. Chan Cloning of Δ12- and Δ6-desaturases from Mortierella alpina and recombinant production of gamma-linolenic acid in Saccharomyces cerevisiae Lipids 34 1999 649 659
37. K. Laoten, R. Mannontarat, M. Tanticharoen, and S. Cheevadhanarak Δ6-desaturase of Mucor rouxii with high similarity to plant D6-desaturase and its heterologous expression in Saccharomyces cerevisiae Biochem. Biophys. Res. Commun. 279 2000 17 22
38. H. Hong, N. Datla, D.W. Reed, P.S. Covello, S.L. MacKenzie, and X. Qiu High-level production of gamma-linolenic acid in Brassica juncea using a delta6 desaturase from Pythium irregulare Plant Physiol. 129 2002 354 362
39. T. Girke, H. Schmidt, U. Zähringer, R. Reski, and E. Heinz Identification of a novel Δ6-acyl-group desaturase by targeted gene disruption in Physcomitrella patens Plant J. 15 1998 39 48
40. A.S. Reddy, M.L. Nuccio, L.M. Gross, and T.L. Thomas Isolation of a delta 6-desaturase from the cyanobacterium Synechocystics sp. strain PCC 6803 by gain-of-function expression in Anabaena sp. strain PCC7120 Plant Mol. Biol. 27 1993 293 300
41. F. Garcia-Maroto, J.A. Garrido-Cardenas, J. Rodriguez-Ruiz, M. Vilches-Ferron, A.C. Adam, and J. Polaina Cloning and molecular characterization of the delta6-desaturase from two Echium plant species: production of GLA by heterologous expression in yeast and tobacco Lipids 37 2002 417 426
42. O.V. Sayanova, F. Beaudoin, L.V. Michaelson, P.R. Shewry, and J.A. Napier Identification of primula fatty acid delta 6-desaturases with n-3 substrate preferences FEBS Lett. 542 2003 100 104
43. O. Sayanova, M.A. Smith, P. Lapinskas, A.K. Stobart, G. Dobson, and W.W. Christie Expression of a borage desaturase cDNA containing an N-terminal cytochrome b5 domain results in the accumulation of high levels of delta 6-desaturated fatty acids in transgenic tobacco Proc. Natl. Acad. Sci. USA 94 1997 4211 4216
44. F. Domergue, A. Abbadi, C. Ott, T.K. Zank, U. Zahringer, and E. Heinz Acyl carriers used as substrates by the desaturases and elongases involved in very long-chain polyunsaturated fatty acids biosynthesis reconstituted in yeast J. Biol. Chem. 278 2003 35115 35126
45. T. Okayasu, M. Nagao, T. Ishibashi, and Y. Imai Purification and partial characterization of linoleoyl-CoA desaturase from rat liver microsomes Arch. Biochem. Biophys. 206 1981 21 28
46. X. Qiu, H. Hong, N. Datla, S.L. MacKinzie, D.C. Taylor, and T.L. Thomas Expression of borage Δ6 desaturase in Saccharomyces cerevisiae and oilseed crops Can. J. Bot. 80 2002 42 49
47. D.S. Knutzon, G. Chan, P. Mukerji, J.M. Thurmond, S. Chaudhary, Y.-S. Huang, Genetic engineering of seed oil fatty acid composition. IX International Congress on Plant Tissue and Cell Culture, Jerusalem, Israel, 1998a.
48. J.-W. Liu, Y.-S. Huang, S. DeMichele, M. Bergana, E. Bobik, and C. Hastilow Evaluation of the seed oils from a canola plant genetically transformed to produce high levels of γ-linolenic acid Y.-S. Huang V.A. Ziboh γ-Linolenic Acid--Recent Advances in Biotechnology and Clinical Applications 2001 AOCS Press Champaign, IL 61 71
49. J.M. Parker-Barnes, T. Das, E. Bobik, A.E. Leonard, J.M. Thurmond, and L.-T. Chuang 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 2000 8284 8289
50. T. Das, Y.-S. Huang, and P. Mukerji Delta 6-desaturase and GLA biosynthesis: a biotechnology perspective Y.-S. Huang V.A. Ziboh Gamma-Linolenic Acid: Recent advances in Biotechnology and Clinical Applications 2000 AOCS Press Champaign, IL 6 23
51. T. Das, J.M. Thurmond, E. Bobik, A.E. Leonard, J.M. Parker-Barnes, and Y.-S. Huang Polyunsaturated fatty acid-specific elongation enzymes Biochem. Soc. Trans. 28 2000 658 660
52. T. Das, J.M. Thurmond, A.E. Leonard, J.M. Parker-Barnes, E. Bobik, and L.-T. Chuang Y.-S. Huang V.A. Ziboh γ-Linolenic Acid--Recent Advances in Biotechnology and Clinical Applications 2002 AOCS Press Champaign, IL 40 44
53. F. Beaudoin, L.V. Michaelson, S.J. Hey, M.J. Lewis, P.R. Shewry, and O. Sayanova heterologous reconstitution in yeast of the polyunsaturated fatty acid biosynthetic pathway Proc. Natl. Acad. Sci. USA 97 2000 6421 6426
54. T.K. Zank, U. Zahringer, J. Lerchl, and E. Heinz Cloning and functional expression of the first plant fatty acid elongase specific for delta(6)-polyunsaturated fatty acids Biochem. Soc. Trans. 28 2000 654 658
55. E. Heinz, T. Zank, U. Zaehringer, J. Lerchl, A. Renz, Patent: WO 0159128-A 16-Aug-2001.
56. A. Meyer, H. Kirsch, F. Domergue, A. Abbadi, P. Sperling, and J. Bauer Novel fatty acid elongases and their use for the reconstitution of docosahexaenoic acid biosynthesis J. Lipid Res. 45 2004 1899 1909
57. A.E. Leonard, E.G. Bobik, J. Dorado, P.E. Kroeger, L.-T. Chuang, and J.M. Thurmond Cloning of a human cDNA encoding a novel enzyme involved in the elongation of long-chain polyunsaturated fatty acids Biochem. J. 350 2000 765 770
58. M. Agaba, D.R. Tocher, C.A. Dickson, J.R. Dick, and A.J. Teale Zebrafish cDNA encoding multifunctional fatty acid elongase involved in production of eicosapentaenoic (20:5n-3) and docosahexaenoic (22:6n-3) acids Mar. Biotechnol 6 2004 251 261
59. C. Cassagne, R. Lessire, J.J. Bessoule, P. Moreau, A. Creach, and F. Schneider Biosynthesis of very long chain fatty acids in higher plants Prog. Lipid Res. 33 1994 55 69
60. P. Von Wettstein-Knowles, J.G. Olsen, K. Arnvig, and S. Larsen J.L. Harwood P.J. Quinn Recent Advances in the Biochemistry of Plant Lipids, Portland Press 2001 601 607
61. D. Hulanicka, J. Erwin, and K. Block Lipid metabolism of Euglena gracilis J. Biol. Chem. 239 1964 2778 2787
62. A.M. Lees, and E.D. Korn Metabolism of unsaturated fatty acids in protozoa Biochemistry 5 1966 1475 1481
63. A.G. Ulsamer, F.R. Smith, and E.D. Korn Lipids of Acanthamoeba castellanii. Composition and effects of phagocytosis on incorporation of radioactive precursors J. Cell. Biol. 43 1969 105 114
64. J.G. Wallis, and J. Browse The Δ8-desaturase of Euglena gracilis: an alternate pathway for synthesis of 20-carbon polyunsaturated fatty acids Arch. Biochem. Biophys. 365 1999 307 316
65. B. Qi, F. Beaudoin, T. Fraser, A.K. Stobart, J.A. Napier, and C.M. Lazarus Identification of a cDNA encoding a novel C18-Δ9 polyunsaturated fatty acid-specific elongating activity from the docosahexaenoic acid (DHA)-producing microalga, Isochrysis galbana FEBS Lett. 510 2002 159 165
66. D.S. Knutzon, J.M. Thurmond, Y.-S. Huang, S. Chaudhary, E.G. Bobik Jr., and G.M. Chan Identification of Δ5-desaturase from Mortierella alpina by heterologous expression in bakers' yeast and canola J. Biol. Chem. 273 1998 29360 29366
67. L.V. Michaelson, C.M. Lauzarus, G. Griffiths, J.A. Napier, and A.K. Stobart Isolation of a Δ5-fatty acid desaturase gene from Mortierella alpina J. Biol. Chem. 273 1998 19055 19059
68. F. Domergue, J. Lerchl, U. Zahringer, and E. Heinz Cloning and functional characterization of Phaeodactylum tricornutum front-end desaturases involved in eicosapentaenoic acid biosynthesis Eur. J. Biochem. 269 2002 4105 4113
69. J.L. Watts, and J. Browse Isolation and characterization of a Δ5-fatty acid desaturase from Caenorhabditis elegans Arch. Biochem. Biophys. 362 1999 175 182
70. A.E. Leonard, B. Kelder, E.G. Bobik, L.-T. Chuang, J.M. Parker-Barnes, J.M. Thurmond, P.E. Kroeger, J.J. Kopchick, Y.-S. Huang, and P. Mukerji cDNA cloning and characterization of human Δ5-desaturase involved in the biosynthesis of arachidonic acid Biochem. J. 347 2000 719 724
71. R. Zolfaghari, C.J. Cifelli, M.D. Banta, and A.C. Ross Fatty acid delta(5)-desaturase mRNA is regulated by dietary vitamin A and exogenous retinoic acid in liver of adult rats Arch. Biochem. Biophys. 391 2001 8 15
72. B. Qi, T. Fraser, S. Mugford, G. Dobson, O. Sayanova, and J. Butler Production of very long chain polyunsaturated omega-3 and omega-6 fatty acids in plants Nat. Biotechnol. 22 2004 739 745
73. D.R. Tocher, M.J. Leaver, and P.A. Hodgson Recent advances in the biochemistry and molecular biology of fatty acyl desaturases Prog. Lipid Res. 37 1998 73 117
74. J.P. Spychalla, A.J. Kinney, and J. Browse Identification of an animal omega-3 fatty acid desaturase by heterologous expression in Arabidopsis Proc. Natl. Acad. Sci. USA 94 1997 1142 1147
75. D. Meesapyodsuk, D.W. Reed, C.K. Savile, P.H. Buist, S.J. Ambrose, and P.S. Covello Characterization of the regiochemistry and cryptoregiochemistry of a Caenorhabditis elegans fatty acid desaturase (FAT-1) expressed in Saccharomyces cerevisiae Biochemistry 39 2000 11948 11954
76. S.L. Pereira, Y.-S. Huang, E.G. Bobik, A.J. Kinney, K.L. Stecca, and P. Mukerji A novel omega 3- (ω3-) fatty acid desaturase involved in the biosynthesis of eicosapentaenoic acid Biochem. J. 378 2003 665 671
77. A.E. Leonard, S.L. Pereira, and Y.-S. Huang Elongation of long-chain fatty acids Prog. Lipid Res. 43 2004 36 54
78. S.L. Pereira, A.E. Leonard, Y.-S. Huang, L.-T. Chuang, and P. Mukerji Identification of two novel microalgal enzymes involved in the conversion of the omega 3-fatty acid, eicosapentaenoic acid (EPA), to docosahexaenoic acid (DHA) Biochem. J. 384 2004 357 366
79. X. Qiu, H. Hong, and S.L. MacKenzie 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 2001 31561 31566
80. A. Meyer, P. Cirpus, C. Ott, R. Schlecker, U. Zahringer, and E. Heinz Biosynthesis of docosahexaenoic acid in Euglena gracilis: biochemical and molecular evidence for the involvement of a delta 4-fatty acyl group desaturase Biochemistry 42 2003 9779 9788
81. T. Tonon, D. Harvey, T.R. Larson, and I.R. Graham Identification of a very long chain polyunsaturated fatty acid delta4-desaturase from the microalga Pavlova lutheri FEBS Lett. 553 3 2003 440 444 (PMID: 14572666 [PubMed--indexed for MEDLINE)
82. K. Yazawa Production of eicospentaenoic acid from marine bacteria Lipids 31 1996 S297 S300
83. H. Takeyama, D. Takeda, K. Yazawa, A. Yamada, and T. Matsunaga Expression of the eicosapentaenoic acid synthesis gene cluster from Shewanella sp. in a transgenic marine Cyanobacterium, Synechococcus sp Microbiol. 143 1997 2725 2731
84. N. Morita, A. Ueno, M. Tanaka, S. Ohgiya, T. Hoshino, and K. Kawasaki Cloning and sequencing of clustered genes involved in fatty acid biosynthesis from the docosahexaenoic acid-producing bacterium, Vibrio marinus strain MP-1 Biotechnol. Lett. 21 1999 641 646
85. J.G. Metz, P. Roessler, D. Facciotti, C. Levering, F. Dittrich, and M. Lassner Production of polyunsaturated fatty acids by polyketide synthases in both prokaryotes and eukaryotes Science 293 2001 290 293