ω3 fatty acid desaturases from microorganisms: structure, function, evolution, and biotechnological use
Tóm tắt
Từ khóa
Tài liệu tham khảo
Aguilar PS, de Mendoza D (2006) Control of fatty acid desaturation: a mechanism conserved from bacteria to humans. Mol Microbiol 62(6):1507–1514. doi: 10.1111/j.1365-2958.2006.05484.x
Aitzetmüller K, Tsevegsüren N (1994) Seed fatty acids, «front-end»-desaturases and chemotaxonomy—a case study in the Ranunculaceae. J Plant Physiol 143(4–5):538–543. doi: 10.1007/BF00039536
Ando A, Sumida Y, Negoro H, Suroto DA, Ogawa J, Sakuradani E, Shimizu S (2009) Establishment of Agrobacterium tumefaciens-mediated transformation of an oleaginous fungus, Mortierella alpina 1S-4, and its application for eicosapentaenoic acid producer breeding. Appl Environ Microbiol 75(17):5529–5535. doi: 10.1128/AEM.00648-09
Berka RM, Grigoriev IV, Otillar R, Salamov A, Grimwood J, Reid I, Ishmael N, John T, Darmond C, Moisan MC, Henrissat B, Coutinho PM, Lombard V, Natvig DO, Lindquist E, Schmutz J, Lucas S, Harris P, Powlowski J, Bellemare A, Taylor D, Butler G, de Vries RP, Allijn IE, van den Brink J, Ushinsky S, Storms R, Powell AJ, Paulsen IT, Elbourne LD, Baker SE, Magnuson J, Laboissiere S, Clutterbuck AJ, Martinez D, Wogulis M, de Leon AL, Rey MW, Tsang A (2011) Comparative genomic analysis of the thermophilic biomass-degrading fungi Myceliophthora thermophila and Thielavia terrestris. Nat Biotechnol 29(10):922–927. doi: 10.1038/nbt.1976
Carlson SE, Werkman SH, Peeples JM, Cooke RJ, Tolley EA (1993) Arachidonic acid status correlates with first year growth in preterm infants. Proc Natl Acad Sci U S A 90(3):1073–1077. doi: 10.1073/pnas.90.3.1073
Chen YQ, Berquin IM, Daniel LW, Edwards IJ, O’Flaherty JT, Thomas MJ, Tooze JA, Wykle B (2006) Omega-3 fatty acids and cancer risk. JAMA: J Am Med Assoc 296(3):278–282. doi: 10.1001/jama.296.3.282-a
Chen H, Gu Z, Zhang H, Wang M, Chen W, Lowther WT, Chen YQ (2013) Expression and purification of integral membrane fatty acid desaturases. PLoS ONE 8(3):e58139. doi: 10.1371/journal.pone.0058139
Connor KM, SanGiovanni JP, Lofqvist C, Aderman CM, Chen J, Higuchi A, Hong S, Pravda EA, Majchrzak S, Carper D, Hellstrom A, Kang JX, Chew EY, Salem N, Serhan CN, Smith LEH (2007) Increased dietary intake of [omega]-3-polyunsaturated fatty acids reduces pathological retinal angiogenesis. Nat Med 13(7):868–873. doi: 10.1038/nm1591
Damude HG, Zhang H, Farrall L, Ripp KG, Tomb JF, Hollerbach D, Yadav NS (2006) Identification of bifunctional delta12/omega3 fatty acid desaturases for improving the ratio of omega3 to omega6 fatty acids in microbes and plants. Proc Natl Acad Sci U S A 103(25):9446–9451. doi: 10.1073/pnas.0511079103
Diaz AR, MaC M, Vila AJ, de Mendoza D (2002) Membrane topology of the acyl-lipid desaturase from Bacillus subtilis. J Biol Chem 277(50):48099–48106. doi: 10.1074/jbc.M208960200
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(4):2027–2038. doi: 10.1104/pp. 102.010835
Dyer DH, Lyle KS, Rayment I, Fox BG (2005) X-ray structure of putative acyl-ACP desaturase DesA2 from Mycobacterium tuberculosis H37Rv. Protein Sci 14(6):1508–1517. doi: 10.1110/ps.041288005
Gagne SJ, Reed DW, Gray GR, Covello PS (2009) Structural control of chemoselectivity, stereoselectivity, and substrate specificity in membrane-bound fatty acid acetylenases and desaturases. Biochemistry (Mosc) 48(51):12298–12304. doi: 10.1021/bi901605d
Ge Y, Wang X, Chen Z, Landman N, Lo EH, Kang JX (2002) Gene transfer of the Caenorhabditis elegans n−3 fatty acid desaturase inhibits neuronal apoptosis. J Neurochem 82(6):1360–1366. doi: 10.1046/j.1471-4159.2002.01077.x
Gill I, Valivety R (1997) Polyunsaturated fatty acids, part 1: occurrence, biological activities and applications. Trends Biotechnol 15(10):401–409. doi: 10.1016/S0167-7799(97)01076-7
Guy JE, Whittle E, Kumaran D, Lindqvist Y, Shanklin J (2007) The crystal structure of the ivy Delta4-16:0-ACP desaturase reveals structural details of the oxidized active site and potential determinants of regioselectivity. J Biol Chem 282(27):19863–19871. doi: 10.1074/jbc.M702520200
Heilmann I, Mekhedov S, King B, Browse J, Shanklin J (2004) Identification of the Arabidopsis palmitoyl-monogalactosyldiacylglycerol delta7-desaturase gene FAD5, and effects of plastidial retargeting of Arabidopsis desaturases on the fad5 mutant phenotype. Plant Physiol 136(4):4237–4245. doi: 10.1104/pp. 104.052951
Hoffmann M, Hornung E, Busch S, Kassner N, Ternes P, Braus GH, Feussner I (2007) A small membrane-peripheral region close to the active center determines regioselectivity of membrane-bound fatty acid desaturases from Aspergillus nidulans. J Biol Chem 282(37):26666–26674. doi: 10.1074/jbc.M705068200
Hongsthong A, Subudhi S, Sirijuntarat M, Cheevadhanarak S (2004) Mutation study of conserved amino acid residues of Spirulina delta 6-acyl-lipid desaturase showing involvement of histidine 313 in the regioselectivity of the enzyme. Appl Microbiol Biotechnol 66(1):74–84. doi: 10.1007/s00253-004-1655-x
Jareonkitmongkol S, Kawashima H, Shirasaka N, Shimizu S, Yamada H (1992) Production of dihomo-γ-linolenic acid by a Δ5-desaturase-defective mutant of Mortierella alpina 1S-4. Appl Environ Microbiol 58(7):2196–2200
Jia Q, Lupton JR, Smith R, Weeks BR, Callaway E, Davidson LA, Kim W, Fan Y-Y, Yang P, Newman RA, Kang JX, McMurray DN, Chapkin RS (2008) Reduced colitis-associated colon cancer in fat-1 (n−3 fatty acid desaturase) transgenic mice. Cancer Res 68(10):3985–3991. doi: 10.1158/0008-5472.can-07-6251
Kang JX, Wang J, Wu L, Kang ZB (2004) Transgenic mice: Fat-1 mice convert n−6 to n−3 fatty acids. Nature 427(6974):504–504. doi: 10.1038/427504a
Lindqvist Y, Huang W, Schneider G, Shanklin J (1996) Crystal structure of delta9 stearoyl-acyl carrier protein desaturase from castor seed and its relationship to other di-iron proteins. EMBO J 15(16):4081–4092
Liu HL, Yin ZJ, Xiao L, Xu YN, Qu LQ (2012) Identification and evaluation of ω-3 fatty acid desaturase genes for hyperfortifying α-linolenic acid in transgenic rice seed. J Exp Bot 63(8):3279–3287. doi: 10.1093/jxb/ers051
López Alonso D, García-Maroto F, Rodríguez-Ruiz J, Garrido JA, Vilches MA (2003) Evolution of the membrane-bound fatty acid desaturases. Biochem Syst Ecol 31(10):1111–1124. doi: 10.1016/s0305-1978(03)00041-3
Los DA, Murata N (1998) Structure and expression of fatty acid desaturases. Biochim Biophys Acta 1394(1):3–15
Lu Y, Nie D, Witt WT, Chen Q, Shen M, Xie H, Lai L, Dai Y, Zhang J (2008) Expression of the fat-1 gene diminishes prostate cancer growth in vivo through enhancing apoptosis and inhibiting GSK-3β phosphorylation. Mol Cancer Ther 7(10):3203–3211. doi: 10.1158/1535-7163.mct-08-0494
Man WC, Miyazaki M, Chu K, Ntambi JM (2006) Membrane topology of mouse stearoyl-CoA desaturase 1. J Biol Chem 281(2):1251–1260. doi: 10.1074/jbc.M508733200
Meesapyodsuk D, Qiu X (2012) The front-end desaturase: structure, function, evolution and biotechnological use. Lipids 47(3):227–237. doi: 10.1007/s11745-011-3617-2
Meesapyodsuk D, Reed DW, Savile CK, Buist PH, Ambrose SJ, Covello PS (2000) Characterization of the regiochemistry and cryptoregiochemistry of a Caenorhabditis elegans fatty acid desaturase (FAT-1) expressed in Saccharomyces cerevisiae. Biochemistry (Mosc) 39(39):11948–11954. doi: 10.1021/bi000756a
Mitchell AG, Martin CE (1995) A novel cytochrome B(5)-like domain is linked to the carboxyl-terminus of the Saccharomyces cerevisiae delta-9 fatty-acid desaturase. J Biol Chem 270(50):29766–29772. doi: 10.1074/jbc.270.50.29766
Na-Ranong S, Laoteng K, Kittakoop P, Tanticharoen M, Cheevadhanarak S (2006) Targeted mutagenesis of a fatty acid Delta6-desaturase from Mucor rouxii: role of amino acid residues adjacent to histidine-rich motif II. Biochem Biophys Res Commun 339(4):1029–1034. doi: 10.1016/j.bbrc.2005.11.115
Oura T, Kajiwara S (2004) Saccharomyces kluyveri FAD3 encodes an omega3 fatty acid desaturase. Microbiology 150(Pt 6):1983–1990. doi: 10.1099/mic.0.27049-0
Oura T, Kajiwara S (2008) Substrate specificity and regioselectivity of Δ12 and ω3 fatty acid desaturases from Saccharomyces kluyveri. Biosci Biotechnol Biochem 72(12):3174–3179. doi: 10.1271/bbb.80361
Pereira SL, Leonard AE, Mukerji P (2003) Recent advances in the study of fatty acid desaturases from animals and lower eukaryotes. Prostaglandins Leukot Essent Fatty Acids 68(2):97–106. doi: 10.1016/S0952-3278(02)00259-4
Pereira SL, Huang YS, Bobik EG, Kinney AJ, Stecca KL, Packer JC, Mukerji P (2004) A novel omega3-fatty acid desaturase involved in the biosynthesis of eicosapentaenoic acid. Biochem J 378(Pt 2):665–671. doi: 10.1042/BJ20031319
Petrie JR, Shrestha P, Zhou X-R, Mansour MP, Liu Q, Belide S, Nichols PD, Singh SP (2012) Metabolic engineering plant seeds with fish oil-like levels of DHA. PLoS ONE 7(11):e49165. doi: 10.1371/journal.pone.0049165
Qiu X, 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(1):42–49. doi: 10.1139/b01-130
Racine RA, Deckelbaum RJ (2007) Sources of the very-long-chain unsaturated omega-3 fatty acids: eicosapentaenoic acid and docosahexaenoic acid. Curr Opin Clin Nutr Metab Care 10(2):123–128. doi: 10.1097/MCO.0b013e3280129652
Ratledge C, Wynn JP (2002) The biochemistry and molecular biology of lipid accumulation in oleaginous microorganisms. Adv Appl Microbiol 51:1–51. doi: 10.1016/S0065-2164(02)51000-5
Ruiz-Lopez N, Haslam RP, Usher SL, Napier JA, Sayanova O (2013) Reconstitution of EPA and DHA biosynthesis in Arabidopsis: Iterative metabolic engineering for the synthesis of n−3 LC-PUFAs in transgenic plants. Metab Eng 17:30–41. doi: 10.1016/j.ymben.2013.03.001
Sakamoto T, Los DA, Higashi S, Wada H, Nishida I, Ohmori M, Murata N (1994) Cloning of ω3 desaturase from cyanobacteria and its use in altering the degree of membrane-lipid unsaturation. Plant Mol Biol 26(1):249–263
Sakuradani E, Hirano Y, Kamada N, Nojiri M, Ogawa J, Shimizu S (2004a) Improvement of arachidonic acid production by mutants with lower n−3 desaturation activity derived from Mortierella alpina. Appl Microbiol Biotechnol 66(3):243–248. doi: 10.1007/s00253-004-1682-7
Sakuradani E, Hirano Y, Kamada N, Nojiri M, Ogawa J, Shimizu S (2004b) Improvement of arachidonic acid production by mutants with lower n−3 desaturation activity derived from Mortierella alpina 1S-4. Appl Microbiol Biotechnol 66(3):243–248. doi: 10.1007/s00253-004-1682-7
Sakuradani E, Abe T, Iguchi K, Shimizu S (2005) A novel fungal omega3-desaturase with wide substrate specificity from arachidonic acid-producing Mortierella alpina 1S-4. Appl Microbiol Biotechnol 66(6):648–654. doi: 10.1007/s00253-004-1760-x
Sakuradani E, Abe T, Shimizu S (2009) Identification of mutation sites on omega3 desaturase genes from Mortierella alpina 1S-4 mutants. J Biosci Bioeng 107(1):7–9. doi: 10.1016/j.jbiosc.2008.08.001
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. Biochemistry (Mosc) 33(43):12787–12794. doi: 10.1021/bi00209a009
Shanklin J, Guy JE, Mishra G, Lindqvist Y (2009) Desaturases: emerging models for understanding functional diversification of diiron-containing enzymes. J Biol Chem 284(28):18559–18563. doi: 10.1074/jbc.R900009200
Shimiziu S, Kawashima H, Shinmen Y, Akimoto K, Yamada H (1988) Production of eicosapentaenoic acid by Mortierella fungi. J Am Oil Chem Soc 65(9):1455–1459. doi: 10.1007/bf02898307
Shinmen Y, Shimizu S, Akimoto K, Kawashima H, Yamada H (1989) Production of arachidonic-acid by Mortierella fungi—selection of a potent producer and optimization of culture conditions for large-scale production. Appl Microbiol Biotechnol 31(1):11–16. doi: 10.1007/BF00252518
Stukey JE, McDonough VM, Martin CE (1990) The OLE1 gene of Saccharomyces cerevisiae encodes the delta 9 fatty acid desaturase and can be functionally replaced by the rat stearoyl-CoA desaturase gene. J Biol Chem 265(33):20144–20149
Tocher DR, Leaver MJ, Hodgson PA (1998) Recent advances in the biochemistry and molecular biology of fatty acyl desaturases. Prog Lipid Res 37(2–3):73–117. doi: 10.1016/S0163-7827(98)00005-8
van Beilen JB, Penninga D, Witholt B (1992) Topology of the membrane-bound alkane hydroxylase of Pseudomonas oleovorans. J Biol Chem 267(13):9194–9201
Vanden Heuvel JP (2012) Nutrigenomics and Nutrigenetics of ω3 Polyunsaturated Fatty Acids. In: Bouchard C, Ordovas JM (eds) Progress in molecular biology and translational science. vol Volume 108. Academic, pp 75–112
Vanhercke T, Shrestha P, Green AG, Singh SP (2011) Mechanistic and structural insights into the regioselectivity of an Acyl-CoA fatty acid desaturase via directed molecular evolution. J Biol Chem 286(15):12860–12869. doi: 10.1074/jbc.M110.191098
Vrinten P, Hu Z, Munchinsky MA, Rowland G, Qiu X (2005) Two FAD3 desaturase genes control the level of linolenic acid in flax seed. Plant Physiol 139(1):79–87. doi: 10.1104/pp. 105.064451
Wada H, Gombos Z, Murata N (1990) Enhancement of chilling tolerance of a cyanobacterium by genetic manipulation of fatty acid desaturation. Nature 347(6289):200–203. doi: 10.1038/347200a0
Wang L, Chen W, Feng Y, Ren Y, Gu Z, Chen H, Wang H, Thomas MJ, Zhang B, Berquin IM, Li Y, Wu J, Zhang H, Song Y, Liu X, Norris JS, Wang S, Du P, Shen J, Wang N, Yang Y, Wang W, Feng L, Ratledge C, Zhang H, Chen YQ (2011) Genome characterization of the oleaginous fungus Mortierella alpina. PLoS ONE 6(12):e28319. doi: 10.1371/journal.pone.0028319
Xia S-H, Wang J, Kang JX (2005) Decreased n−6/n−3 fatty acid ratio reduces the invasive potential of human lung cancer cells by downregulation of cell adhesion/invasion-related genes. Carcinogenesis 26(4):779–784. doi: 10.1093/carcin/bgi019
Zhang X, Li M, Wei D, Xing L (2008) Identification and characterization of a novel yeast omega3-fatty acid desaturase acting on long-chain n−6 fatty acid substrates from Pichia pastoris. Yeast 25(1):21–27. doi: 10.1002/yea.1546