• Alimuddin KV, Satou S, Takeuchi T, Yoshizaki G (2008) Cloning and over-expression of a masu salmon (Oncorhynchus masou) fatty acid elongase-like gene in zebrafish. Aquaculture 282:13–18

  Article CAS  Google Scholar 

• Ashton NW, Cove DC (1977) To isolation and preliminary characterization of auxotrophic and analogue resistance mutants in the mossPhyscomitrella patens. Mol Gen Genet 154:87–95

  Article  Google Scholar 

• Certik M, Shimizu S (1999) Biosynthesis and regulation of microbial polyunsaturated fatty acid production. J Biosci Bioeng 87:1–14

  Article CAS  Google Scholar 

• Chodok P, Kanjana-Opas A, Kaewsuwan S (2010) Plackett–Burman design for evaluating the production of polyunsaturated fatty acids byPhyscomitrella patens. J Am Oil Chem Soc 87:521–529

  Article CAS  Google Scholar 

• Chodok P, Cove DJ, Quatrano RS, Kanjana-Opas A, Kaewsuwan S (2012) Metabolic engineering and oil supplementation ofPhyscomitrella patens for activation of C₂₂ polyunsaturated fatty acid production. J Am Oil Chem Soc 89:465–476

  Article CAS  Google Scholar 

• Cove DJ, Perroud PF, Charron AJ, McDaniel SF, Khandelwal A, Quatrano RS (2009) The moss,Physcomitrella patens. A novel model system for plant development and genomic studies. In: Crotty DA, Gann A (eds) Emerging model organisms, a laboratory manual, vol 1. Cold Spring Harbor Laboratory Press, New York, pp 69–104

  Google Scholar 

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

  Article CAS  Google Scholar 

• Domergue F, Lerchl J, Zähringer U, Heinz E (2002) Cloning and functional characterization ofPhaeodactylum tricornutum front-end desaturases involved in eicosapentaenoic acid biosynthesis. Eur J Biochem 269:4105–4113

  Article CAS  Google Scholar 

• Domergue F, Abbadi A, Ott C, Zank TK, Zähringer U (2003) Acyl carriers as substrates by desaturases and elongases involved in very ling chain polyunsaturated fatty acids biosynthesis in yeast. J Biol Chem 278:35115–35126

  Article CAS  Google Scholar 

• Felsenstein J (2004) PHYLIP (phylogeny inference package), version 3.63. Distributed by the author. Department of Genome Sciences, University of Washington, Seattle, USA

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

  Article CAS  Google Scholar 

• Girke T, Schmidt H, Zähringer U, Reski R, Heinz E (1998) Identification of a novel Δ6-acyl-group desaturase by targeted gene disruption inPhyscomitrella patens. Plant J 15:39–48

  Article CAS  Google Scholar 

• Grimsley NH, Grimsley JM, Hartmann E (1981) Fatty acid composition of mutants of the mossPhyscomitrella patens. Phytochemistry 20:1519–1524

  Article CAS  Google Scholar 

• Hashimoto K, Yoshizawa AC, Okuda S, Kuma K, Goto S, Kanehisa M (2008) The repertoire of desaturases and elongases reveals fatty acid variations in 56 eukaryotic genomes. J Lipid Res 49:183–191

  Article CAS  Google Scholar 

• Horrocks LA, Yeo YK (1999) Health benefits of docosahexaenoic acid (DHA). Pharmacol Res 40:211–225

  Article CAS  Google Scholar 

• Huang YS, Pereira SL, Leonard AE (2004) Enzymes for transgenic biosynthesis of long-chain polyunsaturated fatty acids. Biochimie 86:793–798

  Article CAS  Google Scholar 

• Iskandarov U, Goldberg IK, Ofir R, Cohen Z (2009) Cloning and characterization of the Δ⁶ polyunsaturated fatty acid elongase from the green microalgaParietochloris incisa. Lipids 44:545–554

  Article CAS  Google Scholar 

• Iskandarov U, Goldberg IK, Cohen Z (2010) Identification and characterization of Δ12, Δ6, and Δ5 desaturases from the green microalgaParietochloris incisa. Lipids 45:519–530

  Article CAS  Google Scholar 

• Jackson MR, Nilsson T, Peterson PA (1990) Identification of a consensus motif for retention of transmembrane proteins in the endoplasmic reticulum. EMBO J 9:3153–3162

  CAS  Google Scholar 

• Jakobsson A, Westerberg R, Jacobsson A (2006) Fatty acid elongases in mammals: their regulation and roles in metabolism. Prog Lipid Res 45:237–249

  Article CAS  Google Scholar 

• Kaewsuwan S, Cahoon EB, Perroud RF, Wiwat C, Panvisavas N, Quatrano RS, Cove DJ, Bunyapraphatsara N (2006) Identification and functional characterization of the mossPhyscomitrella patens ∆⁵-desaturase gene involved in arachidonic and eicosapentaenoic acid biosynthesis. J Biol Chem 281:21988–21997

  Article CAS  Google Scholar 

• Kaewsuwan S, Bunyapraphatsara N, Cove DJ, Quatrano RS, Chodok P (2010) High level production of adrenic acid inPhyscomitrella patens using the algaePavlova sp. ∆⁵-elongase gene. Bioresour Technol 101:4081–4088

  Article CAS  Google Scholar 

• Kajikawa M, Yamato KT, Kohzu Y, Nojiri M, Sakuradani E, Shimizu S, Sakai Y, Fukuzawa H, Ohyama K (2004) Isolation and characterization of ∆⁶-desaturase, an ELO-like enzyme and ∆⁵-desaturase from the liverwortMarchantia polymorpha and production of arachidonic and eicosapentaenoic acids in the methylotrophic yeastPichia pastoris. Plant Mol Biol 54:335–352

  Article CAS  Google Scholar 

• Kajikawa M, Yamato KT, Yasuyoshi S, Fukuzawa H, Ohyama K, Kohchi T (2006) Isolation and functional characterization of fatty acid ∆⁵-elongase gene from the liverwortMarchantia polymorpha L. FEBS Lett 580:149–154

  Article CAS  Google Scholar 

• Kang DH, Anbu P, Jeong YS, Chaulagain BP, Seo JW, Hur BK (2010) Identification and characterization of a novel enzyme related to the synthesis of PUFAs derived fromThraustochytrium aureum ATCC 34304. Biotechnol Bioprocess Eng 15:261–272

  Article CAS  Google Scholar 

• Kinsella JE, Lokesh B, Broughton S, Whelan J (1990) Dietary polyunsaturated fatty acids and eicosanoids: potential effects on the modulation of inflammatory and immune cells: an overview. Nutrition 1:24–44

  Google Scholar 

• Knight CD, Cove DJ, Cuming AC, Quatrano RS (2002) Moss gene technology. In: Gilmartin PM, Bowter C (eds) Molecular plant biology. Oxford University Press, Oxford, pp 285–301

  Google Scholar 

• Lassner MW, Lardizabal K, Metz JG (1996) A Jojoba β-ketoacyl-CoA synthase cDNA complements the canola fatty acid elongation mutation in transgenic plants. Plant Cell 8:281–292

  CAS  Google Scholar 

• Leonard AE, Bobik EG, Dorado J, Kroeger PE, Chuang LT, Thurmond JM, Parker-Barnes JM, Das T, Huang YS, Mukerji P (2000) Cloning of a human cDNA encoding a novel enzyme involved in the elongation of long-chain polyunsaturated fatty acids. Biochem J 350:765–770

  Article CAS  Google Scholar 

• Leonard AE, Pereira SL, Sprecher H, Huang YS (2004) Elongation of long-chain fatty acids. Prog Lipid Res 43:36–54

  Article CAS  Google Scholar 

• Los DA, Murata N (1998) Structure and expression of fatty acid desaturase. Biochem Biophys Acta 1394:3–15

  Article CAS  Google Scholar 

• Meyer A, Kirsch H, Domergue F, Abbadi A, Sperling P, Bauer J, Cirpus P, Zank TK, Moreau H, Roscoe TJ, Zähringer U, Heinz E (2004) Novel fatty acid elongases and their use for the reconstitution of docosahexaenoic acid biosynthesis. J Lipid Res 45:1899–1909

  Article CAS  Google Scholar 

• Millar AA, Kunst L (1997) Very-long-chain fatty acid biosynthesis is controlled through the expression and specificity of the condensing enzyme. Plant Cell 12:121–131

  CAS  Google Scholar 

• Niu Y, Kong J, Fu L, Yang J, Xu Y (2009) Identification of a novel C20-elongase gene from the marine microalgaePavlova viridis and its expression inEscherichia coli. Mar Biotechnol 11:17–23

  Article CAS  Google Scholar 

• Nugent AP (2004) The metabolic syndrome. Nutr Bull 29:36–43

  Article  Google Scholar 

• Page RDM (1996) TREEVIEW: an application to display phylogenetic trees on personal computers. Comput Applic Biosci 12:357–358

  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  Google Scholar 

• Pereira SL, Leonard AE, Mukeri P (2003) Recent advances in the study of fatty acid desaturases from animals and lower eukaryotes. Prostaglandins Leukot Essent 68:97–106

  Article CAS  Google Scholar 

• Petrie JR, Shresth P, Mansour MP, Nichols PD, Liu Q, Singh SP (2010) Metabolic engineering of omega-3 long-chain polyunsaturated fatty acids in plants using an acyl-CoA Δ6-desaturase with ω3-preference from the marine microalgaMicromonas pusilla. Metab Eng 12:233–240

  Article CAS  Google Scholar 

• Pollak DW, Bostick MW, Yoon H, Wang J, Hollerbach DH, He H, Damude HG, Zhang H, Yadav NS, Hong SP, Sharpe P, Xue Z, Zhu Q (2012) Isolation of a Δ5 desaturase gene fromEuglena gracilis and functional dissection of its HPGG and HDASH motifs. Lipids 47:913–926

  Article CAS  Google Scholar 

• Qi B, Beaudoin F, Fraser T, Stobart AK, Napier JA, Lazarus CM (2002) 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 510:159–165

  Article CAS  Google Scholar 

• Qi B, Fraser TC, Bleakley CL, Shaw EM, Stobart AK, Lazarus CM (2003) The variant ‘his-box’ of the C18-Δ9-PUFA-specific elongase IgASE1 fromIsochrysis galbana is essential for optimum enzyme activity. FEBS Lett 547:137–139

  Article CAS  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 omega-3 and omega-6 fatty acids in plant. Nat Biotechnol 22:739–745

  Article CAS  Google Scholar 

• Ratledge C (2004) Fatty acid biosynthesis in microorganisms being used for single cell oil production. Biochimie 86:807–815

  Article CAS  Google Scholar 

• Robert SS, Petrie JR, Zhou XR, Mansour MP, Blackburn SI, Green AG, Singh SP, Nichols PD (2009) Isolation and characterisation of a Δ⁵-fatty acid elongase from the marine microalgaPavlova salina. Mar Biotechnol 11:410–418

  Article CAS  Google Scholar 

• Sayanova O, Haslam R, Qi B, Lazarus CM, Napier JA (2006) The alternative pathway C₂₀ ∆⁸-desaturase from the non-photosynthetic organismAcanthamoeba castellanii is an atypical cytochromeb₅-fusion desaturase. FEBS Lett 580:1946–1952

  Article CAS  Google Scholar 

• Shanklin J, Whittle E, Fox BG (1994) Eight histidine residues are catalytically essential in a membrane-associated iron enzyme, stearoyl-CoA desaturase, and are conserved in alkane hydroxylase and xylene monooxygenase. Biochem 33:12787–12794

  Article CAS  Google Scholar 

• Tan L, Meesapyodsuk D, Qiu X (2011) Molecular analysis of Δ6 desaturase and Δ6 elongase fromConidiobolus obscurus in the biosynthesis of eicosatetraenoic acid, a ω3 fatty acid with nutraceutical potential. Appl Microbiol Biotechnol 90:591–601

  Article CAS  Google Scholar 

• Tonon T, Sayanova O, Michaelson LV, Qing R, Harvey D, Larson TR, Li Y, Napier JA, Graham IA (2005) Fatty acid desaturases from the microalgaThalassiosira pseudonana. FEBS J 272:3401–3412

  Article CAS  Google Scholar 

• Trotter PJ (2001) The genetics of fatty acid metabolism inSaccharomyces cerevisiae. Annu Rev Nutr 21:97–119

  Article CAS  Google Scholar 

• Uauy R, Peirano P, Hoffman D, Mena P, Birch D, Birch E (1996) Role of essential fatty acids in the function of the developing nervous system. Lipids (Suppl) 31:167S–176S

  Article  Google Scholar 

• Vrinten PL, Hoffman T, Bauer J, Qiu X (2010) Specific protein regions influence substrate specificity and product length in polyunsaturated fatty acid condensing enzymes. Biochem 49:3879–3886

  Article CAS  Google Scholar 

• Wallis JG, Browse J (1999) The ∆⁸-desaturase ofEuglena gracilis: an alternative pathway for synthesis of 20-carbon polyunsaturated fatty acids. Arch Biochem Biophys 365:307–316

  Article CAS  Google Scholar 

• Yongmanitchai W, Ward OP (1989) Omega-3 fatty acids: alternative sources of production. Process Biochem 24:117–125

  CAS  Google Scholar 

• Zank TK, Zähringer U, Beckmann C, Pohnert G, Boland W, Holtorf H, Reski R, Lerchl J, Heinz E (2002) Cloning and functional characterization of an enzyme involved in the elongation of Δ⁶-polyunsaturated fatty acids from the mossPhyscomitrella patens. Plant J 31:255–268

  Article CAS  Google Scholar 

• Zhou XR, Robert S, Singh S, Green A (2006) Heterologous production of GLA and SDA by expression of anEchium plantagineum ∆6-desaturase gene. Plant Sci 170:665–673

  Article CAS  Google Scholar 

• Zhou XR, Robert SS, Petrie JR, Frampton DMF, Mansour MP, Blackburn SI, Nichols PD, Green AG, Singh SP (2007) Isolation and characterization of genes from the marine microalgaPavlova salina encoding three front-end desaturases involved in docosahexaenoic acid biosynthesis. Phytochemistry 68:785–796

  Article CAS  Google Scholar 

Download references