Plant lipids : biology, utilisation, and manipulation

426 Pages·3.179 MB·English

by  Denis J Murphy

PlantLipids
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Biological Sciences Series
Aserieswhichprovidesanaccessiblesourceofinformationatresearchandprofessional
levelinchosensectorsofthebiologicalsciences.
SeriesEditor:
Professor J.A. Roberts, Plant Science Division, School of Biosciences, University of
Nottingham,UK
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PlantLipids-Biology,UtilisationandManipulation
EditedbyD.J.Murphy
SuniAllsebastian: “Deni:fm” — 2004/10/14 — 06:33 — page ii — #2
Plant Lipids
Biology,UtilisationandManipulation
Editedby
DENISJ.MURPHY
BiotechnologyUnit
SchoolofAppliedSciences
UniversityofGlamorgan
Cardiff,UK
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Contents
Contributors xiii
Preface xv
1 Thestudyandutilisationofplantlipids:frommargarineto
lipidrafts 1
DENISJ.MURPHY
1.1 Introduction 1
1.2 Earlystudiesofplantlipids 1
1.3 Thechemistryera–andthedefinitionoftheterm‘lipid’ 4
1.4 Thebiochemistryera 7
1.5 Themoleculargeneticsrevolution 14
1.6 Newfrontiers–cellbiologyandthe’omics 18
1.7 Conclusionsandfutureprospects 22
2 Fattyacidbiosynthesis 27
JOHNL.HARWOOD
2.1 Introduction 27
2.2 Carbonsupplyforfattyacidformation 27
2.3 Acetyl-CoAcarboxylase 29
2.3.1 StructureofACCase 30
2.3.2 PropertiesofdifferentisoformsofACCase 33
2.3.3 HerbicidesactingonACCase 33
2.3.4 GenescodingforACCase 36
2.3.5 RegulationofACCase 38
2.4 Fattyacidsynthase 39
2.4.1 Acylcarrierprotein 40
2.4.2 Condensingenzymes 42
2.4.3 TheothercomponentenzymesofFAS 47
2.4.4 TerminationofFAS 49
2.4.5 MitochondrialFAS 52
2.5 Regulationoffattyacidformation 52
2.6 Biotechnologicalaspects 56
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vi CONTENTS
3 Fattyacidmanipulation 67
DAVIDF.HILDEBRAND,KESHUNYU,CHARLESMCCRACKEN
andSURYADEVARAS.RAO
3.1 Introduction 67
3.2 Thesoluble∆9desaturases 69
3.2.1 Engineeringchainlengthspecificityofsoluble∆9
desaturases 71
3.2.2 Stearoyl-CoAdesaturases 74
3.3 Front-enddesaturases 76
3.4 ∆12Desaturase-likeenzymesandtheiruseinthemodificationof
fattyacidresidues 77
3.4.1 Structuresandfunctions 77
3.4.2 Substratesandproducts 78
3.4.3 Geneisolation,characterizationandtesting 79
3.4.4 Rationalgenedesign 81
3.5 Segregationofnovelfattyacidsfrommembranelipids 81
3.5.1 Compartmentationofstorageandmembranelipidsynthesis 82
3.6 Selectiveaccumulationofnovelfattyacidsinoilbodies 83
3.6.1 Medium-chainfattyacids 84
3.6.2 Very-long-chainfattyacids 85
3.6.3 Novelmonoenoicfattyacids 86
3.6.4 NovelfattyacidsproducedbydivergedFad2enzymes 86
3.6.5 Genespecificpromotersfortissuespecificnovelfattyacid
accumulation 87
3.7 Structuresandoccurrencesofhydroxy,conjugatedand
epoxyfattyacidsinplantseedoils 87
3.7.1 Hydroxyfattyacids 88
3.7.2 Conjugatedfattyacids 89
3.7.3 Epoxyfattyacids 90
4 Non-foodlipids 103
SEVIMZ.ERHANandATANUADHVARYU
4.1 Introduction 103
4.1.1 Structureandcompositionoflipids 103
4.1.1.1 Simplelipids 103
4.1.1.2 Triacylglycerols 105
4.2 Industrialapplications 110
4.2.1 Industrialcommodityseedoils 110
4.2.1.1 Soybeanoil 110
4.2.1.2 Canolaoil 112
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CONTENTS vii
4.2.1.3 Sunfloweroil 112
4.2.1.4 Saffloweroil 113
4.2.1.5 Linseedoil 114
4.2.1.6 Tungoil 114
4.2.2 Newindustrialoilseedcrops 115
4.2.2.1 Meadowfoamoil 115
4.2.2.2 Lesquerellaoil 115
4.2.2.3 Cupheaoil 116
4.2.2.4 Crambeoil 116
4.2.2.5 Jojobawax 116
4.2.3 Useoftallowandyellowgreaseforindustrialapplications 117
4.3 Structuralmodifications 117
4.3.1 Interesterification 117
4.3.2 Fractionation 118
4.3.2.1 Solventfractionation 118
4.3.2.2 Columnchromatography 118
4.3.2.3 Thin-layerchromatography 119
4.3.3 Hydrogenation 119
4.4 Concludingremarks 119
5 Membranelipids 123
PETERDÖRMANN
5.1 Introduction 123
5.2 Structuresandlocalisationofglycerolipids 124
5.2.1 Phosphatidicacid 124
5.2.2 Galactolipids 124
5.2.3 Sulfolipid 126
5.2.4 Phosphatidylglycerolanddiphosphatidylglycerol 127
5.2.5 Phosphatidylcholine,phosphatidylethanolamine,
phosphatidylserineandN-acyl-phosphatidylethanolamine 127
5.2.6 Phosphatidylinositol 128
5.3 Biosynthesisofmembraneglycerolipids 128
5.3.1 Biosynthesisofphosphatidicacid 128
5.3.2 Synthesisofglycerolipidsfromdiacylglycerolor
CDP-diacylglycerol 130
5.3.3 Biosynthesisofgalactolipids 134
5.3.4 Biosynthesisofsulfolipid 136
5.3.5 BiosynthesisofPGandDPG 137
5.3.6 BiosynthesisofPS,PC,PEandNAPE 137
5.3.7 BiosynthesisofPI 139
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viii CONTENTS
5.4 Membranelipidturnover 139
5.4.1 Hydrolysisofphospholipidheadgroups:phospholipasesC
andD 140
5.4.1.1 PhospholipaseC 140
5.4.1.2 PhospholipaseD 140
5.4.2 Hydrolysisofacylgroupsfrommembranelipids 142
5.4.2.1 PhospholipaseA1 142
5.4.2.2 PhospholipaseA2 142
5.4.2.3 Lysophospholipase 143
5.4.2.4 Patatin-likeacylhydrolaseswithphospholipase
andglycolipaseactivities 143
5.4.2.5 DAD1-likeacylhydrolases 144
5.4.2.6 SAG101-likeacylhydrolasesandPDAT-like
acyltransferases 144
5.4.3 Glycolipases 145
5.4.4 Fattyacylturnoverandacyl-CoAsynthetases 145
5.5 Physiologicalrolesofmembranelipids 146
5.5.1 Growthathighandlowtemperatures 146
5.5.1.1 Unsaturatedfattyacids 147
5.5.2 TheroleofunsaturatedmolecularspeciesofPGinchilling
sensitivity 148
5.5.2.1 IncreaseofPCsynthesisduringcoldtreatment 149
5.5.3 Theroleofthylakoidlipidsinphotosynthesis 149
5.5.4 Growthduringphosphatedeprivation 151
5.6 Summaryandfutureperspectives 152
6 Storagelipids 162
RANDALLJ.WESELAKE
6.1 Introduction 162
6.2 Pathwaysleadingtotriacylglycerols 164
6.3 Propertiesandregulationofenzymesinvolvedintriacylglycerol
biosynthesisandassociatedphospholipidmetabolism 166
6.3.1 sn-Glycerol-3-phosphateacyltransferase 166
6.3.2 Lysophosphatidicacidacyltransferase 168
6.3.3 Phosphatidicacidphosphatase 170
6.3.4 Diacylglycerolacyltransferase 173
6.3.5 Enzymescatalyzingacyl-CoA-independentsynthesisof
triacylglycerol 179
6.3.6 CDP-choline:-1,2-diacylglycerolcholinephosphotransferase 180
6.3.7 Lysophosphatidylcholineacyltransferase 181
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CONTENTS ix
6.3.8 Phospholipases 182
6.3.9 Solublelysophosphatidicacidphosphataseand
monoacylglycerolacyltransferaseindevelopingpeanut 183
6.4 Complexmetabolicprocessescanaffectthefattyacidcomposition
oftriacylglycerol 184
6.5 Structure,compositionandbiogenesisoflipidbodies 185
6.6 Mobilizationofstoragelipids 191
6.6.1 Degradationoftriacylglycerolsintofattyacids 191
6.6.2 β-Oxidationoffattyacidsandconversionoflipidto
carbohydrate 194
6.6.3 β-Oxidationduringseedmaturation 198
6.7 Storagelipidsindevelopingpollengrains 199
6.8 Effectofenvironmentalconditionsandcarbonsourceon
triacylglycerolaccumulation 201
6.9 Theroleoflipid–proteinparticlesandplasmamembranevesicles
inmembraneturnover 204
6.10 Biosynthesisofliquidwaxesters 205
6.11 Doplantstransportstoragelipids? 206
6.12 Conclusionsandfuturedirections 206
7 Lipid-associatedproteins 226
DENISJ.MURPHY
7.1 Introduction 226
7.2 Plantlipid-associatedproteins 227
7.2.1 Oleosins 228
7.2.2 Oleo-pollenins(‘oleosin-likeproteins’) 232
7.2.3 Caleosins 235
7.2.4 Plastidlipid-associatedproteins 238
7.2.5 Minorlipid-associatedproteinsinplants 240
7.2.6 Lipid-associatedproteinsinnon-storagetissuesinplants 242
7.2.6.1 Phloem 242
7.2.6.2 Rootsandmeristems 243
7.2.6.3 Rubber 243
7.3 Comparisonswithnon-plantsystems 244
7.3.1 Animals 244
7.3.1.1 ThePATfamilyofcytosoliclipid-bodyproteins 245
7.3.1.2 Caveolins–theunexpectedlipid-associatedproteins249
7.3.1.3 Extracellularlipid-bodyproteins 250
7.3.2 Microorganisms 251
7.3.2.1 Fungi 252
7.3.2.2 Prokaryotes 255
7.3.2.3 Viruses 256
7.4 Conclusions 258
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x CONTENTS
8 Theplantcuticle:formationandstructureofepidermalsurfaces 270
LJERKAKUNST,A.L.SAMUELSandREINHARDJETTER
8.1 Introduction 270
8.2 Biosynthesisofcuticlecomponents 272
8.2.1 Denovofattyacidsynthesis 272
8.2.2 Cutinbiosynthesis 275
8.2.3 Synthesisofvery-long-chainfattyacidwaxprecursors 277
8.2.4 Synthesisofaliphaticcuticularwaxcomponents 279
8.2.4.1 Theacylreductionpathway 279
8.2.4.2 Thedecarbonylationpathway 280
8.2.5 Theβ-diketonepathway 280
8.3 Cuticlebiosynthesisinthecontextoftheepidermalcell 281
8.3.1 Saturatedlong-chainfattyacidsareexportedfromthe
plastidtotheERforelongation 281
8.3.2 VLCFAmodificationanddeliveryofwaxconstituentsto
theplasmamembrane 282
8.3.3 Exportofwaxcomponentsfromtheepidermalcelltothe
cuticle 284
8.4 Cuticlecompositionandstructure 285
8.4.1 Formationandcompositionofepicuticularcrystals 285
8.4.2 Physicalandchemicaldistinctionbetweenepicuticular
filmandintracuticularwax 290
8.4.3 Crystallinearrangementofepi-andintracuticularwax
molecules 291
8.5 Conclusions 294
9 Inositol-containinglipids:rolesincellularsignalling 303
BJØRNK.DRØBAK
9.1 Introduction 303
9.2 Phosphoinositides:synthesis,turnoverandfunction 304
9.2.1 Biosynthesisofphosphatidylinositol 304
9.3 Phosphorylationofphosphatidylinositolandotherphosphoinositides305
9.3.1 Phosphatidylinositol3-kinases 306
9.3.2 Phosphatidylinositol4-kinases 309
9.3.3 Phosphatidylinositol5-kinases 311
9.3.4 Phosphatidylinositol3-monophosphate5-kinases 312
9.3.5 Phosphatidylinositol4-monophosphate5-kinases 312
9.4 Phosphoinositide–proteininteractions 314
9.4.1 Profilin 315
9.4.2 ADF/cofilin 316
9.4.3 PARFandotherFYVE-fingerdomainproteins 317
9.4.4 ProteinscontainingPH-domains 319
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