Lipids and lipid metabolism in eukaryotic algae

Progress in Lipid Research - Tập 45 Số 2 - Trang 160-186 - 2006
Irina A. Guschina1, John L. Harwood1
1School of Biosciences, Cardiff University, P.O. Box 911, Cardiff CF10 3US, UK

Tóm tắt

Từ khóa


Tài liệu tham khảo

Van den Hoek, 1995

Thompson, 1996, Lipids and membrane function in green algae, Biochim Biophys Acta, 1302, 17, 10.1016/0005-2760(96)00045-8

Hitchcock, 1971

Harwood, 1988, Lipid metabolism, 49

Harwood, 1989, Lipid metabolism in algae, Adv Bot Res, 16, 1, 10.1016/S0065-2296(08)60238-4

Harwood, 1998, Membrane lipids in algae, 53

Rontani, 2004, Long-chain alkenones and related compounds in the benthic haptophyte Chrysotila lamellose Anand HAP 17, Phytochemistry, 65, 117, 10.1016/j.phytochem.2003.09.021

Guella, 2003, A new solution for an old problem: the regiochemical distribution of the acyl chains in galactolipids can be established by electrospray ionization tandem mass spectrometry, Rapid Commun Mass Spectrom, 17, 1982, 10.1002/rcm.1142

Khotimchenko, 2004, An inositol-containing sphingolipid from the red alga Gracilaria verrucosa, Russ J Bioorg Chem, 30, 168, 10.1023/B:RUBI.0000023103.14189.27

Michaud, 2002, Double bond localization in minor homoallylic fatty acid methyl esters using acetonitrile chemical ionization tandem mass spectrometry, Anal Biochem, 307, 348, 10.1016/S0003-2697(02)00037-4

Dembitsky, 2003, Variability of the fatty acids of the marine green algae belonging to the genus Codium, Biochem Sys Ecol, 31, 1125, 10.1016/S0305-1978(03)00043-7

Achitouv, 2004, C31–C34 methylated squalene from a Bolivian strain of Botryococcus braunii, Phytochemistry, 65, 3159, 10.1016/j.phytochem.2004.09.015

Metzger, 2002, Lycopanerols H, two high molecular weight ether lipids fromBotryococcus braunii comprising an α-tocopherol unit, Tetrahedron Lett, 43, 2377, 10.1016/S0040-4039(02)00291-5

Metzger, 2005, Botryococcus braunii: a rich source for hydrocarbons and related ether lipids, Appl Microbiol Biotechnol, 66, 486, 10.1007/s00253-004-1779-z

Dembitsky, 2002, Natural halogenated fatty acids: their analogues and derivatives, Prog Lipid Res, 41, 315, 10.1016/S0163-7827(02)00003-6

Blokker, 1998, Cell wall-specific ω-hydroxy fatty acids in some freshwater green microalgae, Phytochemistry, 49, 691, 10.1016/S0031-9422(98)00229-5

Allard, 2001, High molecular weight lipids from the trilaminar outer wall (TLS)-containing microalgae Chlorella emersonii, Scenedesmus communis and Tetraedron minimum, Phytochemistry, 57, 459, 10.1016/S0031-9422(01)00071-1

Allard, 2000, Comparison of neutral lipid profile of various trilamelar outer cell wall (TLS)-containing microalgae with emphasis on algaenan occurrence, Phytochemistry, 54, 369, 10.1016/S0031-9422(00)00135-7

Eichenberger, 1995, Phosphatidyl-O-[N-(2-hydroxyethyl)glycine] (PHEG), a novel glycerophospholipid from brown algae (Phaeophyceae), J Plant Physiol, 146, 398, 10.1016/S0176-1617(11)81999-1

Eichenberger, 1997, Lipids of Pavlova lutheri: cellular site and metabolic role of DGCC, Phytochemistry, 45, 1561, 10.1016/S0031-9422(97)00201-X

Blee, 1998, Phytooxylipins and plant defense reactions, Prog Lipid Res, 37, 33, 10.1016/S0163-7827(98)00004-6

Gerwick, 1994, Structure and biosynthesis of marine algal oxylipins, Biochim Biophys Acta, 1211, 243, 10.1016/0005-2760(94)90147-3

Gerwick, 1999, Biogenesis and biological function of marine algal oxylipins, Adv Exp Med Biol, 447, 211, 10.1007/978-1-4615-4861-4_20

Sajiki, 1998, Identification of eicosanoids in the red algae, Gracilaria asiatica, using high-performance liquid chromatography and electrospray ionization mass spectrometry, J Chromatogr A, 795, 227, 10.1016/S0021-9673(97)00943-6

Jiang, 2000, 5-Lipoxygenase-derived oxylipins from the red alga Rhodymenia pertusa, Phytochemistry, 53, 129, 10.1016/S0031-9422(99)00445-8

Bouarab, 2004, The innate immunity of a marine red alga involves oxylipins from both eicosanoic and octadecanoic pathways, Plant Physiol, 135, 1838, 10.1104/pp.103.037622

Liu, 1994, Isolation of gametophyte-specific cDNA encoding a lipoxygenase from the red alga Porphyra purpurea, Mol Mar Biol Biotechnol, 3, 206

Zheng, 2002, Polyenoic fatty acid isomerase from the marine alga Ptilota filicina: protein characterization and functional expression of the cloned cDNA, Arch Biochem Biophys, 401, 11, 10.1016/S0003-9861(02)00002-4

D’Ippolito, 2004, The role of complex lipids in the synthesis of bioactive aldehydes of the marine diatom Skeletonema costatum, Biochim Biophys Acta, 1686, 100, 10.1016/j.bbalip.2004.09.002

Miralto, 1999, The insidious effect of diatoms on copepod reproduction, Nature, 402, 173, 10.1038/46023

Pohnert, 2000, Wound-activated chemical defense in unicellular planktonic algae, Angew Chem Int Ed, 39, 4352, 10.1002/1521-3773(20001201)39:23<4352::AID-ANIE4352>3.0.CO;2-U

Pohnert, 2002, Phospholipase A2 activity triggers the wound-activated chemical defense in the diatom Thalassiosira rotula, Plant Physiol, 129, 103, 10.1104/pp.010974

D’Ippolito, 2002, Detection of short-chain aldehydes in marine organisms: the diatom Thalassiosira rotula, Tetrahedron Lett, 43, 6137, 10.1016/S0040-4039(02)01283-2

D’Ippolito, 2002, New birth-control aldehydes from the marine diatom Skeletonema costatum: characterization and biogenesis, Tetrahedron Lett, 43, 6133, 10.1016/S0040-4039(02)01285-6

Romano, 2003, A marine diatom-derived aldehyde induces apoptosis in copepod and sea urchin embryos, J Exp Biol, 206, 3487, 10.1242/jeb.00580

Tosti, 2003, Bioactive aldehydes from diatoms block the fertilization current in ascidian oocytes, Mol Reprod Dev, 66, 72, 10.1002/mrd.10332

Adolph, 2004, Cytotoxicity of diatom-derived oxylipins in organisms belonging to different phyla, J Exp Biol, 207, 2935, 10.1242/jeb.01105

Casotti, 2005, Growth inhibition and toxicity of the diatom aldehyde 2-trans, 4-trans-decadienal on Thalassiosira weissflogii (Bacillariophyceae), J Phycol, 41, 7, 10.1111/j.1529-8817.2005.04052.x

Ianora, 2004, Aldehyde suppression of copepod recruitment in blooms of a ubiquitous planktonic diatoms, Nature, 429, 403, 10.1038/nature02526

Wendel, 1996, Lipoxygenase-mediated formation of hydrocarbons and unsaturated aldehydes in freshwater diatoms, Phytochemistry, 41, 1445, 10.1016/0031-9422(95)00828-4

Pohnert, 1996, Biosynthesis of the algal pheromone hormosirene by the freshwater diatom Gomphonema parvulum (Bacillariophyceae), Tetrahedron, 52, 10073, 10.1016/0040-4020(96)00548-0

Boonprab, 2003, Hydroperoxy-arachidonic acid mediated n-hexanal and (Z)-3- and (E)-2-nonenal formation in Laminaria angustata, Phytochemistry, 63, 669, 10.1016/S0031-9422(03)00026-8

Boonprab, 2003, C6-aldehyde formation by fatty acid hydroperoxide lyase in the brown alga Laminaria angustata, Z Naturforsch C, 58, 207, 10.1515/znc-2003-3-412

Kamenarska, 2002, Comparative study of the volatile compounds from some Black Sea brown algae, Bot Mar, 45, 502, 10.1515/BOT.2002.053

Santiago-Vázquez, 2004, Identification of hydroxy fatty acids by liquid chromatography–atmospheric pressure chemical ionization mass spectrometry, J Chromatogr, 803, 233, 10.1016/j.jchromb.2003.12.021

Harris, 2001, Chlamydomonas as a model organism, Annu Rev Plant Physiol Plant Mol Biol, 52, 363, 10.1146/annurev.arplant.52.1.363

Hanikenne, 2003, Chlamydomonas reinhardtii as a eukaryotic photosynthetic model for studies of heavy metal homeostasis and tolerance, New Phytol, 159, 331, 10.1046/j.1469-8137.2003.00788.x

Fuhrmann, 2002, Expanding the molecular tool kits for Chlamydomonas reinhardtii – from history to new frontiers, Protist, 153, 357, 10.1078/14344610260450082

Riekhof, 2003, The sulfolipids 2′-O-acyl-sulfoquinovosyldiacylglycerol and sulfoquinovosyldiacylglycerol are absent from a Chlamydomonas reinhardtii mutant deleted in SQD1, Plant Physiol, 133, 864, 10.1104/pp.103.029249

Sato, 2003, Involvement of sulfoquinovosyl diacylglycerol in the structural integrity and heat-tolerance of photosystem II, Planta, 217, 245, 10.1007/s00425-003-0992-9

Dubertret, 2002, Importance of trans-Δ3-hexadecenoic acid containing phosphatidylglycerol in the formation of the trimeric light-harvesting complex in Chlamydomonas, Plant Physiol Biochem, 40, 829, 10.1016/S0981-9428(02)01442-0

Pineau, 2004, A single mutation that causes phosphatidylglycerol deficiency impairs synthesis of photosystem II cores in Chlamydomonas reinhardtii, Eur J Biochem, 271, 329, 10.1046/j.1432-1033.2003.03931.x

Sato, 1996, Contribution of lowered unsaturation levels of chloroplast lipids to high temperature tolerance of photosynthesis in Chlamydomonas reinhardtii, J Photochem Photobiol B: Biol, 36, 333, 10.1016/S1011-1344(96)07389-7

Giroud, 1988, Lipids of Chlamydomonas reinhardtii: analysis of molecular species and intracellular site(s) of biosynthesis, Plant Cell Physiol, 29, 587

Yang, 2004, Membrane lipid biosynthesis in Chlamydomonas reinhardtii: ethanolaminephosphotransferase is capable of synthesizing both phosphatidylcholine and phosphatidylethanolamine, Arch Biochem Biophys, 430, 198, 10.1016/j.abb.2004.07.016

Moore, 2001, Membrane lipid biosynthesis in Chlamydomonas reinhardtii. In vitro biosynthesis of diacylglyceryltrimethylhomoserine, Plant Physiol, 125, 423, 10.1104/pp.125.1.423

Riekhof, 2005, Annotation of genes involved in glycerolipid biosynthesis in Chlamydomonas reinhardtii: discovery of the betaine lipid synthase BTA1Cr, Eukaryotic Cell, 4, 242, 10.1128/EC.4.2.242-252.2005

Blouin, 2003, Membrane lipid biosynthesis in Chlamydomonas reinhardtii. Partial characterization of CDP-diacylglycerol:myo-inositol 3-phosphatidyltransferase, Plant Physiol Biochem, 41, 11, 10.1016/S0981-9428(02)00003-7

Arisz, 2000, Polar glycerolipids of Chlamydomonas moewusii, Phytochemistry, 53, 265, 10.1016/S0031-9422(99)00505-1

Meijer, 2003, Phospholipid-based signaling in plants, Annu Rev Plant Biol, 54, 265, 10.1146/annurev.arplant.54.031902.134748

Wang, 2004, Lipid signaling, Curr Opin Plant Biol, 7, 1, 10.1016/j.pbi.2004.03.012

Munnik, 1998, Phospholipid signaling in plants, Biochim Biophys Acta, 1389, 222, 10.1016/S0005-2760(97)00158-6

Munnik, 1998, Detailed analysis of turnover of polyphosphoinositides and phosphatidic acid upon activation of phospholipase C and D in Chlamydomonas cells treated with non-permeabilizing concentrations of mastoparan, Planta, 207, 133, 10.1007/s004250050465

Meijer, 2001, Identification of a new polyphosphoinositide in plants, phosphatidylinositol 5-monophosphate (PtdIns5P), and its accumulation upon osmotic stress, Biochem J, 360, 491, 10.1042/0264-6021:3600491

Arisz, 2003, Substrate preference of stress-activated phospholipase D in Chlamydomonas and its contribution to PA formation, Plant J, 34, 595, 10.1046/j.1365-313X.2003.01750.x

Meijer, 2001, Hyperosmotic stress rapidly generates lyso-phosphatidic acid in Chlamydomonas, Plant J, 25, 541, 10.1046/j.1365-313x.2001.00990.x

Wen, 2003, Heterotrophic production of eicosapentaenoic acid by microalgae, Biotech Adv, 21, 273, 10.1016/S0734-9750(03)00051-X

Sijtsma, 2004, Biotechnological production and application of the ω-3 polyunsaturated fatty acid docosahexaenoic acid, App Microbiol Biotechnol, 64, 146, 10.1007/s00253-003-1525-y

Shiran, 1996, Biosynthesis of eicosapentaenoic acid in the microalga Porphyridium cruentum. 1. The use of externally supplied fatty acids, Lipids, 31, 1277, 10.1007/BF02587913

Khozin, 1997, Elucidation of the biosynthesis of eicosapentaenoic acid in the microalga Porphyridium cruentum. 2. Studies with radiolabeled precursors, Plant Physiol, 114, 223, 10.1104/pp.114.1.223

Adlerstein, 1997, The effect of growth temperature and culture density on the molecular species composition of the galactolipids in the red microalga Porphyridium cruentum (Rhodophyta), J Phycol, 33, 975, 10.1111/j.0022-3646.1997.00975.x

Khozin-Goldberg, 1999, Salicylhydroxamic acid inhibits delta 6 desaturation in the microalga Porphyridium cruentum, Biol Lipids, 1439, 384, 10.1016/S1388-1981(99)00107-9

Khozin-Goldberg, 2002, Biosynthesis of eicosapentaenoic acid (EPA) in the freshwater eustigmatophyte Monodus subterraneus (Eustagmatophyceae), J Phycol, 38, 745, 10.1046/j.1529-8817.2002.02006.x

Schneider, 1994, Radiolabelling studies of lipids and fatty acids in Nannochloropsis (Eustigmatophyceae), an oleaginous alga, J Phycol, 30, 594, 10.1111/j.0022-3646.1994.00594.x

Schneider, 1995, A mutant of Nannochloropsis deficient in eicosapentaenoic acid production, Phytochemistry, 40, 807, 10.1016/0031-9422(95)00365-E

Haigh, 1996, The characterisation and cyclic production of a highly unsaturated homoserine lipid in Chlorella minutissima, Biochim Biophys Acta, 1299, 183, 10.1016/0005-2760(95)00205-7

Dembitsky, 1996, Betaine ether-linked glycerolipids: chemistry and biology, Prog Lipid Res, 35, 1, 10.1016/0163-7827(95)00009-7

Khozin-Goldberg, 2000, Triacylglycerols of the red microalga Porphyridium cruentum can contribute to the biosynthesis of eukaryotic galactolipids, Lipids, 35, 881, 10.1007/S11745-000-0597-8

Tonon, 2002, Long chain polyunsaturated fatty acid production and partitioning to triacylglycerols in four microalgae, Phytochemistry, 61, 15, 10.1016/S0031-9422(02)00201-7

Meireles, 2003, Lipid class composition of the microalga Pavlova lutheri: eicosapentaenoic and docosahexaenoic acids, J Agric Food Chem, 51, 2237, 10.1021/jf025952y

Leblond, 2005, Lipid composition of chlorarachniophytes (Chlorarachniophyceae) from the genera Bigelowiella, Gymnochlora, and Lotharella, J Phycol, 41, 311, 10.1111/j.1529-8817.2005.04082.x

Jiang, 2004, Effects of lowering temperature during culture on the production of polyunsaturated fatty acids in the marine diatom Phaeodactylum tricornutum (Bacillariophyceae), J Phycol, 40, 651, 10.1111/j.1529-8817.2004.03112.x

Alonso, 2000, Acyl lipid composition variation related to culture age and nitrogen concentration in continuous culture of the microalga Phaeodactylum tricornutum, Phytochemistry, 54, 461, 10.1016/S0031-9422(00)00084-4

Arao, 1994, Biosynthesis of polyunsaturated fatty acids in the marine diatom, Phaeodactylum tricornutum, Phytochemistry, 35, 1177, 10.1016/S0031-9422(00)94817-9

Kitano, 1997, Changes in eicosapentaenoic acid content of Navicula saprophila, Rhodomonas salina and Nitzschia sp. under mixotrophic conditions, J Appl Phycol, 9, 559

De Swaaf, 1999, Optimisation of docosahexaenoic acid production in batch cultivation by Crypthecodinium cohnii, J Biotechnol, 70, 185, 10.1016/S0168-1656(99)00071-1

De Swaaf, 2003, Fed-batch cultivation of the docosahexaenoic-acid-producing marine alga Crypthecodinium cohnii on ethanol, Appl Microbiol Biotechnol, 61, 40, 10.1007/s00253-002-1118-1

De Swaaf, 2003, Analysis of docosahexaenoic acid biosynthesis in Crypthecodinium cohnii by 13C labelling and desaturase inhibitor experiments, J Biotechnol, 103, 21, 10.1016/S0168-1656(03)00070-1

Kyle, 1992, Bioproduction of docosahexaenoic acid (DHA) by microalgae, 287

Yokochi, 1998, Optimization of docosahexaenoic acid production by Schizochytrium limacinum SR21, Appl Microbiol Biotechnol, 49, 72, 10.1007/s002530051139

Singh, 1996, Docosahexaenoic acid production by Thraustochytrium sp. ATCC 20892, World J Microbiol Biotechnol, 12, 76, 10.1007/BF00327806

Jiang, 2004, Fatty acid composition and squalene content of the marine microalga Schizochytrium mangrovei, J Agric Food Chem, 52, 1196, 10.1021/jf035004c

Lewis, 1999, The biotechnological potential of thraustochytrids, Mar Biotechnol, 1, 580, 10.1007/PL00011813

Nakahara, 1996, Production of docosahexaenoic and docosapentaenoic acids by Schizochytrium sp. isolated from Yap islands, J Am Oil Chem Soc, 73, 1421, 10.1007/BF02523506

Yaguchi, 1997, Production of high yield of docosahexaenoic acid by Schizochytrium sp. strain SR21, J Am Oil Chem Soc, 74, 1431, 10.1007/s11746-997-0249-z

Iida, 1996, Improvement of docosahexaenoic acid production in a culture of Thraustochytrium aureum by medium optimization, J Ferment Bioeng, 81, 76, 10.1016/0922-338X(96)83125-4

Qiu, 2003, Biosynthesis of docosahexaenoic acid (DHA, 22:6-4, 7,10, 13, 16, 19): two distinct pathways, Prostaglandins Leukot Essent Fatty Acids, 68, 181, 10.1016/S0952-3278(02)00268-5

Qiu, 2001, Identification of a Δ4 fatty acid desaturase from Thraustochytrium sp. involved in the biosynthesis of docosahexaenoic acid by heterologous expression in Saccharomyces cerevisiae and Brassica juncea, J Biol Chem, 34, 31561, 10.1074/jbc.M102971200

Gurr, 2002

Metz, 2001, Production of polyunsaturated fatty acids by polyketide synthases in both prokaryotes and eukaryotes, Science, 293, 290, 10.1126/science.1059593

Bigogno, 2002, Lipid and fatty acid composition of the green oleaginous alga Parietochloris incisa, the richest plant source of arachidonic acid, Phytochemistry, 60, 497, 10.1016/S0031-9422(02)00100-0

Khozin-Goldberg, 2002, Nitrogen starvation induces the accumulation of arachidonic acid in the freshwater green alga Parietochloris incisa (Trebuxiophyceae), J Phycol, 38, 991, 10.1046/j.1529-8817.2002.01160.x

Bigogno, 2002, Accumulation of arachidonic acid-rich triacylglycerols in the microalga Parietochloris incisa (Trebuxiophyceae, Chlorophyta), Phytochemistry, 60, 135, 10.1016/S0031-9422(02)00037-7

Bigogno, 2002, Biosynthesis of arachidonic acid in the oleaginous microalga Parietochloris incisa (Chlorophyceae): radiolabeling studies, Lipids, 37, 209, 10.1007/s11745-002-0882-6

Berge, 1995, Reassessment of lipid composition of the diatom, Sceletonema costatum, Phytochemistry, 39, 1017, 10.1016/0031-9422(94)00156-N

Alonso, 1998, Acyl lipids of three microalgae, Phytochemistry, 47, 1473, 10.1016/S0031-9422(97)01080-7

Pernet, 2003, Variation of lipid class and fatty acid composition of Chaetoceros muelleri and Isochrysis sp. grown in a semicontinuous system, Aquaculture, 221, 393, 10.1016/S0044-8486(03)00030-9

Xu, 1998, Fatty acids of six Codium species from Southeast Australia, Phytochemistry, 48, 1335, 10.1016/S0031-9422(98)00115-0

Falk-Petersen, 1998, Lipids and fatty acids in ice algae and phytoplankton from the Marginal Ice Zone in the Barents Sea, Polar Biol, 20, 41, 10.1007/s003000050274

Henderson, 1998, Seasonal variation in fatty acid composition of ice algae from the Barents Sea, Polar Biol, 20, 48, 10.1007/s003000050275

Sato, 1997, Cloning of a gene for chloroplast omega-6 desaturase of a green algae, Chlamydomonas reinhardtii, J Biochem, 122, 1224, 10.1093/oxfordjournals.jbchem.a021885

Suga, 2002, Two low-temperature-inducible Chlorella genes for Δ12 and ω-3 fatty acid desaturase (FAD): isolation of Δ12 and ω-3 fad cDNA clones, expression of Δ12 fad in Saccharomyces cerevisiae, and expression of ω-3 fad in Nicotiana tabacum, Biosci Biotechnol Biochem, 66, 1314, 10.1271/bbb.66.1314

Domergue, 2002, Cloning and functional characterization of Phaeodactylum tricornutum front-end desaturases involved in eicosapentaenoic acid biosynthesis, Eur J Biochem, 269, 4105, 10.1046/j.1432-1033.2002.03104.x

Qi, 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, 10.1016/S0014-5793(01)03247-1

Qi, 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, 10.1016/S0014-5793(03)00676-8

Fraser, 2004, Expression of the Isochrysis C18-Δ9 polyunsaturated fatty acid elongase component alters Arabidopsis glycerolipid profile, Plant Physiol, 135, 859, 10.1104/pp.104.038984

Tonon, 2002, Identification of a very long chain polyunsaturated fatty acid Δ4-desaturase from the microalga Pavlova lutheri, FEBS Lett, 553, 440, 10.1016/S0014-5793(03)01078-0

Pereira, 2004, Identification of two novel microalgal enzymes involved in the conversion of the ω3-fatty acid, eicosapentaenoic acid, into docosahexaenoic acid, Biochem J, 384, 357, 10.1042/BJ20040970

Meyer, 2003, Biosynthesis of docosahexaenoic acid in Euglena gracilis: biochemical and molecular evidence for the involvement of a Δ4-fatty acyl group desaturation, Biochem, 42, 9779, 10.1021/bi034731y

Tonon, 2004, Identification of a fatty acid Δ11-desaturase from the microalga Thalassiosira pseudonana, FEBS Lett, 563, 28, 10.1016/S0014-5793(04)00241-8

Tonon, 2005, Fatty acid desaturases from the microalga Thalassiosira pseudonana, FEBS Lett, 272, 3401, 10.1111/j.1742-4658.2005.04755.x

Meyer, 2004, Novel fatty acid elongases and their use for the reconstitution of docosahexaenoic acid biosynthesis, J Lipid Res, 45, 1899, 10.1194/jlr.M400181-JLR200

Domergue, 2005, In vivo-characterization of the first acyl-CoA Δ6-desaturase from the plant kingdom, Biochem J, 389, 483, 10.1042/BJ20050111

Drexler, 2003, Metabolic engineering of fatty acids for breeding of new oilseed crops: strategies, problems and first results, J Plant Physiol, 160, 779, 10.1078/0176-1617-01025

Domergue, 2005, Relief for fish stocks: oceanic fatty acids in transgenic oilseeds, Trends Plant Sci, 10, 112, 10.1016/j.tplants.2005.01.003

Qi, 2004, Production of very long chain polyunsaturated omega-3 and omega-6 fatty acids in plants, Nat Biotechnol, 22, 739, 10.1038/nbt972

Wu, 2005, Stepwise engineering to produce high yields of very long-chain polyunsaturated fatty acids in plants, Nat Biotechnol, 23, 1013, 10.1038/nbt1107

Gurr, 1970, Biosynthesis of polyunsaturated fatty acids by photosynthetic tissue – composition of phosphatidylcholine species in Chlorella vulgaris during formation of linoleic acid, Eur J Biochem, 17, 19, 10.1111/j.1432-1033.1970.tb01126.x

Matucha, 1972, Gas-chromatographic analysis of higher fatty acids of alga Chlorella vulgaris (Pyrenoidosa), J Chromat, 65, 371, 10.1016/S0021-9673(00)92559-7

Khomova, 1986, Lipids of Chlorella vulgaris extracts, Khim Prir Soedin, 3, 284

Sato, 2003, Glycerolipid synthesis in Chlorella kessleri 11h I. Existence of a eukaryotic pathway, Biochim Biophys Acta, 1633, 27, 10.1016/S1388-1981(03)00069-6

Joh, 1993, Composition and positional distribution of fatty acids in polar lipids from Chlorella ellipsoidea differing in chilling susceptibility and frost hardiness, Physiol Plant, 89, 285, 10.1111/j.1399-3054.1993.tb00155.x

Murata, 1983, Molecular species composition of phosphatidylglycerols from chilling-sensitive and chilling resistant plants, Plant Cell Physiol, 24, 81, 10.1093/oxfordjournals.pcp.a076516

Guschina, 2003, Lipid metabolism in cultured lichen photobionts with different phosphorus status, Phytochemistry, 64, 209, 10.1016/S0031-9422(03)00279-6

Poerschmann, 2004, Fatty acid patterns in Chlamydomonas sp. as a marker for nutritional regimes and temperature under extremely acidic conditions, Microb Ecol, 48, 78, 10.1007/s00248-003-0144-6

Regnault, 1995, Lipid composition of Euglena gracilis in relation to carbon–nitrogen balance, Phytochemistry, 40, 725, 10.1016/0031-9422(95)00268-C

Lynn, 2000, Effect of nutrient availability on the biochemical and elemental stoichiometry in freshwater diatom Stephanodiscus minutulus (Bacillariophyceae), J Phycol, 36, 510, 10.1046/j.1529-8817.2000.98251.x

Floreto, 1996, Effects of nitrogen and phosphorus on the growth and fatty acid composition of Ulva pertusa Kjellman (Chlorophyta), Bot Mar, 39, 69, 10.1515/botm.1996.39.1-6.69

Reitan, 1994, Effect of nutrient limitation on fatty acid and lipid content of marine microalgae, J Phycol, 30, 972, 10.1111/j.0022-3646.1994.00972.x

El-Sheek, 1995, Effect of phosphorus starvation on growth, photosynthesis and some metabolic processes in the unicellular green alga Chlorella kessleri, Phyton, 35, 139

Sato, 2000, Environmental effects on acidic lipids of thylakoid membranes, 912

Benning, 1995, Accumulation of a novel glycolipid and a betaine lipid in the cells of Rhodobacter sphaeroides, Arch Biochem Biophys, 317, 103, 10.1006/abbi.1995.1141

Güler, 1996, A null mutant of Synechococcus sp. PCC7942 deficient in the sulfolipid sulfoquinovosyl diacylglycerol, J Biol Chem, 271, 7501, 10.1074/jbc.271.13.7501

Sato, 2003, Glycerolipid synthesis in Chlorella kessleri 11h II. Effect of CO2 concentration during growth, Biochim Biophys Acta, 1633, 35, 10.1016/S1388-1981(03)00070-2

Pronina, 1998, Effect of CO2 concentration on the fatty acid composition of lipids in Chlamydomonas reinhardtii cia-3, a mutant deficient in CO2-concentrating mechanism, Russ J Plant Physiol, 45, 447

Muradyan, 2004, Changes in lipid metabolism during adaptation of the Dunaliella salina photosynthetic apparatus to high CO2 concentration, Russ J Plant Physiol, 51, 53, 10.1023/B:RUPP.0000011303.11957.48

Sushchik, 2003, A temperature dependence of the intra- and extracellular fatty acid composition of green algae and cyanobacterium, Russ J Plant Physiol, 50, 374, 10.1023/A:1023830405898

McLarnon-Riches, 1998, Effects of environmental factors and metals on Selenastrum capricornutum, Phytochemistry, 49, 1241, 10.1016/S0031-9422(98)00095-8

Zhu, 1997, Effects of temperature and growth phase on lipid and biochemical composition of Isochrysis galbana TK1, J Appl Phycol, 9, 451, 10.1023/A:1007973319348

Renaud, 2002, Effect of temperature on growth, chemical composition and fatty acid composition of tropical Australian microalgae grown in batch cultures, Aquaculture, 211, 195, 10.1016/S0044-8486(01)00875-4

Floreto, 1998, The fatty acid composition of seaweeds exposed to different levels of light intensity and salinity, Bot Mar, 41, 467, 10.1515/botm.1998.41.1-6.467

Fabregas, 2004, The cell composition of Nannochloropsis sp. changes under different irradiances in semicontinuous culture, World J Microbiol Biotechnol, 20, 31, 10.1023/B:WIBI.0000013288.67536.ed

Napolitano, 1994, The relationship of lipids with light and chlorophyll measurement in freshwater algae and periphyton, J Phycol, 30, 943, 10.1111/j.0022-3646.1994.00943.x

Brown, 1996, Effects of harvest stage and light on the biochemical composition of the diatom Thalassiosira pseudonana, J Phycol, 32, 64, 10.1111/j.0022-3646.1996.00064.x

Manoharan, 1999, Acclimation of Prorocentrum minimum (Dinophyceae) to prolonged darkness by use of an alternative carbon source from triacylglycerides and galactolipids, J Phycol, 35, 287, 10.1046/j.1529-8817.1999.3520287.x

Khotimchenko, 2005, Lipid composition of the red alga Tichocarpus crinitus exposed to different levels of photon irradiance, Phytochemistry, 66, 73, 10.1016/j.phytochem.2004.10.024

Khotimchenko, 2004, Effect of solar irradiance on lipids of the green alga Ulva fenestrata Postels et Ruprecht, Bot Mar, 47, 395, 10.1515/BOT.2004.050

Guckert, 1990, Triglyceride accumulation and fatty acid profile changes in Chlorella (Chlorophyta) during high pH-induced cell cycle inhibition, J Phycol, 26, 72, 10.1111/j.0022-3646.1990.00072.x

Tatsuzawa, 1996, Fatty acid and lipid composition of the acidophilic green alga Chlamydomonas sp, J Phycol, 32, 598, 10.1111/j.0022-3646.1996.00598.x

Azachi, 2002, Salt induction of fatty acid elongase and membrane lipid modifications in the extreme halotolerant alga Dunaliella salina, Plant Physiol, 129, 1320, 10.1104/pp.001909

Einicker-Lamas, 1996, Effects of cadmium on Euglena gracilis membrane lipids, Braz J Med Biol Research, 29, 941

Einicker-Lamas, 2002, Euglena gracilis as a model for the study of Cu2+ and Zn2+ toxicity and accumulation in eukaryotic cells, Environ Pollut, 120, 779, 10.1016/S0269-7491(02)00170-7

Guschina IA, Harwood JL. Lead and copper effects on lipid metabolism in cultured lichen photobionts with different phosphorus status. Phytochemistry 2006;67 [in press].