Plant Pigments And Their Manipulation

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ISBN: 9781405117371 | 1405117370
Cover: Hardcover
Copyright: 12/30/2005

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Annual Plant Reviews, Volume 14 It is difficult to over-state the importance of plant pigments in biology. Chlorophylls are arguably the most important organic compounds on earth, as they are required for photosynthesis. Carotenoids are also necessary for the survival of both plants and mammals, through their roles in photosynthesis and nutrition, respectively. The other plant pigment groups, such as flavonoids and betalains, have important roles in both the biology of plants and the organisms with which plants interact. This book provides an overview of pigment chemistry and biology, together with an up-to-date account of the biosynthesis of pigments and the modification of their production using biotechnology. The chapters cover a wide scope of pigmentation research - from the importance of structural diversity in generating the range of colours seen in plants, through to improving human health properties of crops by increasing pigment levels in transgenic plants. The volume is directed at researchers and professionals in plant biochemistry, molecular biology and genetics.

List of contributors	p. xii
Preface	p. xiv
An introduction to plant pigments in biology and commerce	p. 1
Introduction	p. 1
Plant pigmentation	p. 1
The physical basis of pigmentation	p. 1
Structural variation of plant pigments	p. 2
The history of plant pigment research	p. 4
The biosynthesis of plant pigments	p. 4
The functions of pigments in plants	p. 5
The function of pigments in vegetative tissues	p. 5
The function of pigments in reproductive tissues	p. 7
The roles of plant pigments in non-plant organisms	p. 10
Economic aspects of plant pigments	p. 12
Natural food colourants	p. 13
Modification of pigment biosynthesis in transgenic plants	p. 16
References	p. 18
Chlorophylls	p. 23
Introduction	p. 23
What are chlorophylls and where are they found in plants?	p. 23
Photochemical properties of chlorophylls	p. 25
Chlorophyll biosynthesis	p. 25
Overview of chlorophyll biosynthesis	p. 25
ALA biosynthesis	p. 26
ALA to protoporphyrin IX	p. 29
ALA-dehydratase	p. 29
Hydroxymethylbilane synthase	p. 30
Uroporphyrinogen III synthase	p. 30
Uroporphyrinogen III decarboxylase	p. 31
Coporphyrinogen III oxydase	p. 31
Protoporphyrinogen IX oxydase	p. 32
Protoporphyrin IX to chlorophyll	p. 32
Magnesium chelatase	p. 32
S-adenosylmethionine: magnesium protoporphyrin IX-O-methyltransferase (E.C. 2.1.1.11)	p. 36
Magnesium-protoporphyrin IX monomethylester oxidative cyclase	p. 36
Reduction of the 8-vinyl group	p. 38
Protochlorophyllide oxidoreductases	p. 38
Chlorophyll a synthase	p. 40
Interconversion of chlorophyll a and b	p. 41
Chlorophyll degradation	p. 41
Regulation	p. 42
Regulation of ALA synthesis	p. 42
Magnesium chelatase	p. 44
Protochlorophyllide reductase	p. 44
Chlorophyll and chemically modified chlorophylls as photodynamic agents	p. 45
References	p. 46
Carotenoids	p. 57
Introduction	p. 57
Structure, function and manipulation	p. 57
Nutrition	p. 60
Protein and membrane scaffolds	p. 65
Photoprotection and plant fitness	p. 67
Biosynthesis and regulation	p. 68
Carotenoid biosynthesis and the plastid	p. 68
Isoprenoids - carotenoid substrates	p. 70
Phytoene synthase	p. 72
Desaturases	p. 73
Isomerase	p. 74
Cyclases	p. 76
Hydroxylases	p. 78
Zeaxanthin epoxidase and violaxanthin de-epoxidase	p. 79
Neoxanthin synthase	p. 79
Cleavage products	p. 80
Conclusions and future directions	p. 81
Acknowledgements	p. 82
References	p. 82
Flavonoids	p. 92
Introduction	p. 92
Flavonoids as pigments	p. 92
Primary structures	p. 93
Anthocyanins	p. 95
Yellow flavonoid pigments	p. 98
Secondary structures	p. 99
Tertiary structures	p. 100
Metal complexation	p. 102
Localisation	p. 102
Extrinsic factors contributing to flower colour	p. 104
Flavonoid biosynthesis	p. 105
Overview	p. 105
Formation of flavonoid precursors	p. 106
Formation of chalcones	p. 106
Formation of anthocyanidin 3-O-glycosides	p. 107
Formation of flavanones	p. 107
Formation of dihydroflavonols	p. 108
Formation of leucoanthocyanidins	p. 108
Formation of anthocyanins	p. 108
Formation of 3-deoxyanthocyanins	p. 110
Hydroxylation	p. 111
Secondary modifications of flavonoids	p. 112
Glycosylation	p. 112
Methylation	p. 113
Acylation	p. 114
Formation of aurones	p. 115
Formation of flavones and flavonols	p. 117
Subcellular organisation of the enzymes	p. 118
Import into the vacuole	p. 118
Regulation of flavonoid biosynthesis in flowers	p. 120
Transcriptional regulation of flavonoid biosynthesis in flowers	p. 120
Biotechnology applications of transcription factors regulating flavonoid biosynthesis	p. 123
Genetic modification of flower colour	p. 125
Overview	p. 125
Preventing anthocyanin production	p. 126
Redirecting substrate in the flavonoid pathway	p. 128
Introducing novel flavonoid compounds	p. 129
Chalcones, aurones and flavonols	p. 129
3-deoxyanthocyanins	p. 131
Altering B-ring hydroxylation	p. 131
Secondary modifications	p. 133
Modifying the cellular environment of the flavonoid	p. 134
Prospects for new flavonoid gene technology	p. 135
Concluding comments	p. 135
Acknowledgements	p. 136
References	p. 136
Condensed tannins	p. 150
Introduction	p. 150
Economic importance	p. 154
Biosynthesis from coumaroyl-CoA to leucoanthocyanidin	p. 156
CHS	p. 156
CHI	p. 158
FHT (F3H)	p. 158
F3'H and F3',5'H	p. 159
DFR	p. 161
FLS	p. 162
Synthesis of catechin (2,3-trans-flavan-3-ol)	p. 162
LAR (LCR)	p. 162
Synthesis of epicatechin (2,3-cis-flavan-3-ol)	p. 164
ANS (LDOX)	p. 164
ANR (BANYULS)	p. 165
Intravacuolar transport and polymerisation	p. 166
Intravacuolar transport	p. 166
Polymerization (condensation)	p. 168
Evolution of biochemical pathways	p. 171
Regulation of biosynthesis	p. 171
Opportunities for manipulation of proanthocyanidins	p. 172
Manipulation of structural genes	p. 173
Manipulation of regulatory genes	p. 175
Conclusion	p. 175
Acknowledgments	p. 176
References	p. 176
Betalains	p. 185
Betalain pigments	p. 185
Chemistry	p. 185
Betacyanins	p. 186
Betaxanthins	p. 187
Physiology of betalains	p. 190
Light	p. 190
Cytokinins and other hormones	p. 191
Cell and hairy root cultures	p. 192
Genetics of betalains	p. 193
Portulaca grandiflora - large flowered purslane	p. 193
Beta vulgaris - table beet	p. 194
Enzymology and biotechnology	p. 195
Polyphenol - tyrosinase reactions	p. 196
The ring-opening reaction	p. 197
The fungal (Amanita muscaria) enzyme	p. 197
The plant (Portulaca grandiflora) enzyme	p. 198
Glycosylation and other modifications	p. 200
DOPA decarboxylation	p. 202
Degradation	p. 202
Evolution of betalains	p. 203
Social and economic value	p. 204
Prospectives	p. 206
Acknowledgements	p. 207
References	p. 208
Important rare plant pigments	p. 214
Introduction	p. 214
Quinones	p. 215
Naphthoquinones	p. 216
Anthraquinones	p. 221
Indigo	p. 225
Quinochalcones	p. 228
Apocarotenoids	p. 230
Phenylphenalenones and related pigments	p. 232
Miscellaneous plant pigments	p. 235
Concluding comments	p. 240
Acknowledgements	p. 241
References	p. 241
Plant pigments and human health	p. 248
Introduction/Overview	p. 248
Anthocyanins (and associated flavonoids)	p. 251
Diverse roles of anthocyanin pigments in human health maintenance	p. 251
Anthocyanins and treatment of vision disorders	p. 253
Anthocyanins and neuroprotection	p. 254
Anthocyanins and inhibition of cardiovascular disease	p. 254
Anthocyanins and cancer chemoprevention	p. 255
Potentiation of anthocyanin bioactivity	p. 255
Betalains	p. 256
Diverse roles of betalain pigments in human health maintenance	p. 256
Betalains and cancer chemoprevention	p. 256
Carotenoids	p. 257
Diverse roles of carotenoid pigments in human health maintenance	p. 257
Carotenoids and photooxidative damage	p. 260
Carotenoids and modulation of the immune system response	p. 261
Carotenoids and inhibition of cardiovascular disease	p. 261
Carotenoids and cancer chemoprevention	p. 261
Potentiation of carotenoid bioactivity	p. 262
Chlorophylls	p. 263
Diverse roles of chlorophyll pigments in human health maintenance	p. 263
Chlorophylls and cancer chemoprevention	p. 264
Potentiation of chlorophyll bioactivity	p. 265
Other pigments and human health intervention	p. 265
Conclusions and prospects for future research on pigments and human health	p. 265
References	p. 267
Plant pigments and protection against UV-B Radiation	p. 275
Introduction	p. 275
The role of plant pigments	p. 276
Biosynthesis of UV-B protective pigments	p. 282
Signal transduction involved in the biosynthesis of protective pigments	p. 285
The cost and consequences of protection	p. 287
References	p. 287
Techniques of pigment identification	p. 293
Introduction	p. 293
Sample preparation and extraction	p. 294
Purification and separation	p. 295
Characterisation and identification	p. 296
Quantification	p. 297
Flavonoids	p. 297
Introduction	p. 297
Sample preparation and extraction	p. 298
Purification and separation	p. 298
Column chromatography	p. 298
Countercurrent chromatography	p. 298
Characterisation and identification	p. 299
Thin-layer chromatography	p. 299
High-performance liquid chromatography	p. 299
Capillary electrophoresis	p. 301
Hydrolysis	p. 302
UV spectroscopy	p. 302
Mass spectrometry	p. 303
Nuclear magnetic resonance spectroscopy	p. 303
Circular dichroism spectroscopy	p. 304
Quantification	p. 304
Anthocyanins	p. 305
Introduction	p. 305
Sample preparation and extraction	p. 306
Purification and separation	p. 308
Chromatography	p. 308
Characterisation, identification and quantification	p. 309
Chemical degradation	p. 310
Thin-layer chromatography	p. 310
Electrophoresis	p. 311
UV-visible absorption spectroscopy and CIELAB colours	p. 311
Mass spectrometry	p. 311
Nuclear magnetic resonance spectroscopy	p. 312
Miscellaneous in vivo techniques	p. 313
Chlorophylls	p. 314
Introduction	p. 314
Sample preparation and extraction	p. 314
Purification and separation	p. 315
Dioxane complexes	p. 315
Thin-layer and high-performance liquid chromatography	p. 316
Characterisation and identification	p. 317
Visible absorption spectroscopy	p. 317
Preparation of chlorophyll derivatives	p. 317
Nuclear magnetic resonance spectroscopy and mass spectrometry	p. 318
Quantification	p. 318
Carotenoids	p. 318
Introduction	p. 318
Sample preparation, extraction and saponification	p. 319
Saponification	p. 320
Purification and separation	p. 321
Column chromatography	p. 321
Thin-layer chromatography	p. 321
High-performance liquid chromatography	p. 323
Characterisation and identification	p. 323
Visible and infrared spectroscopy	p. 323
Nuclear magnetic resonance spectroscopy	p. 324
Mass spectrometry	p. 324
Stereochemical investigations	p. 325
Microchemistry	p. 325
Quantitative aspects	p. 326
Betalains	p. 326
Introduction	p. 326
Sample preparation and extraction	p. 326
Purification and separation	p. 327
Column chromatography	p. 328
High-speed countercurrent chromatography	p. 328
Characterisation, identification and quantification	p. 328
Thin-layer chromatography	p. 328
High-performance liquid chromatography	p. 329
Capillary electrophoresis	p. 329
UV and infrared spectroscopy and quantification	p. 329
Mass spectrometry	p. 329
Nuclear magnetic resonance spectroscopy	p. 330
Differentiation between betalains and anthocyanins	p. 331
Quinones	p. 331
Introduction	p. 331
Extraction and hydrolysis	p. 331
Purification and separation	p. 332
Thin-layer chromatography	p. 333
Characterisation and identification	p. 333
Visible spectrometry and mass spectrometry	p. 334
Nuclear magnetic resonance spectroscopy	p. 334
References	p. 335
Index	p. 342
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