Anthocyanins

by Gould, Kevin; Davies, Kevin; Winefield, Chris

• ISBN13: 9780387773346
• ISBN10: 0387773347
• Format: Hardcover
• Copyright: 2008-10-10
• Publisher: Springer Verlag

Summary

In recent years there has been an unprecedented expansion of knowledge about anthocyanins pigments. Indeed, the molecular genetic control of anthocyanins biosynthesis is now one of the best understood of all secondary metabolic pathways. There have also been substantial improvements in analytical technology that have led to the discovery of novel anthocyanin compounds. Armed with this knowledge and the tools for genetic engineering, plant breeders are now introducing vibrant new colors into horticultural crops.The food industry has also benefited from the resurgence of interest in anthocyanins. A greater understanding of the chemistry of these pigments has led to improved methods for stabilizing the color of anthocyanins extracts, so that they are more useful as food colorings. Methods for the bulk production of anthocyanins from cell cultures have been optimized for this purpose.Possible benefits to human health from the ingestion of anthocyanin-rich foods have also been a major feature of the recent scientific literature. Anthocyanins are remarkably potent antioxidants, and their ingestion has been postulated to stave off the effects of oxidative stress. These pigments, especially in conjunction with other flavonoids, have been associated with reductions in the incidence and severity of many other non-infectious diseases, including diabetes, cardiovascular disease and certain cancers. An industry is developing around anthocyanins as nutritional supplements.Finally, there has been significant progress in our understanding of the benefits of anthocyanins to plants themselves. Originally considered an extravagance without a purpose, anthocyanins are now implicated in multifarious vital functions. These include the attraction of pollinators and frugivores, aposematic defense from herbivores, and protection from environmental stressors such as strong light, UVB, drought, and free radical attacks. Anthocyanins are evidently highly versatile, and enormously useful to plants.This book covers all aspects of the biosynthesis and function of anthocyanins (and related compounds such as proanthocyanidins) in plants, and their applications in agriculture, food products, and human health. Featured areas include their relevance to:* Plant stress* Flower and fruit color* Human health* Wine quality and health attributes* Food colorants and ingredients* Cell culture production systems* The pastoral sector

Table of Contents

Preface	p. v
Contributors	p. xvii
Anthocyanin Function in Vegetative Organs	p. 1
Introduction	p. 1
Anthocyanins and Stress Responses	p. 2
Photoprotection	p. 3
Protection Against Ultraviolet Radiation	p. 6
Free Radical Scavenging	p. 7
Paradigm Shift	p. 10
Modulation of Signalling Cascades: A New Hypothesis	p. 10
References	p. 12
Role of Anthocyanins in Plant Defence	p. 21
Introduction	p. 21
Hypotheses	p. 23
Reluctance to Accept Hypotheses on Defensive Colouration	p. 23
Colour Vision in Animals	p. 24
Anthocyanins and Other Red Pigments	p. 25
Olfactory Signals	p. 25
Aposematic Colouration	p. 26
Poisonous Plants	p. 26
Thorny plants	p. 26
Defensive Mimicry	p. 29
Mimicry of Dead Leaves	p. 29
Defensive Thorn Automimicry	p. 30
Defensive Animal Mimicry by Plants	p. 31
Ant Mimicry	p. 31
Aphid Mimicry	p. 32
Mimicry of Aposematic Poisonous Caterpillars	p. 32
Camouflage	p. 33
Whole Plants and Seeds	p. 33
Variegation in Understory Herbs	p. 34
Undermining Crypsis of Invertebrate Herbivores	p. 34
Red Young Leaves Divert Herbivores from More Costly Old Ones	p. 35
Signalling by Red Autumn Leaves	p. 36
General	p. 36
Signalling of Defensive Potential	p. 36
The "Defence Indication Hypothesis"	p. 38
Aposematism of Red Autumn Leaves	p. 38
Conclusions and Suggestions for Further Research	p. 39
Leaf Colouration and the Level of Risk	p. 39
No Defence is Perfect	p. 40
Exceptions	p. 41
References	p. 41
Modifying Anthocyanin Production in Flowers	p. 49
Introduction	p. 49
Anthocyanin Biosynthesis in Flowers	p. 50
Anthocyanins as Flower Pigments	p. 57
Regulation of Anthocyanin Production in Flowers	p. 58
Genetic Modification of Anthocyanin Biosynthesis	p. 60
Preventing Anthocyanin Production	p. 62
Increasing Anthocyanin Production by Altering Biosynthetic Enzyme Activity	p. 64
Anthocyanins with Unusual Patterns of A- or C-Ring Hydroxylation	p. 65
Generating New Flower Colours by Altering Anthocyanin B-Ring Hydroxylation	p. 66
Changing Flower Colour by Altering Anthocyanin Secondary Modifications	p. 69
Black Flower Colours	p. 70
GM Application of Anthocyanin-related Transcription Factors	p. 71
Concluding Comments	p. 73
Acknowledgments	p. 73
References	p. 74
Prevalence and Functions of Anthocyanins in Fruits	p. 85
Introduction	p. 85
Prevalence of Fruit Colours	p. 86
Developmental Patterns	p. 88
Distribution of Anthocyanins in Fruit	p. 89
Environmental Regulation of Colour Development	p. 89
Light	p. 90
Temperature	p. 90
Other Factors	p. 91
Anthocyanins in Attraction	p. 92
Visual Systems	p. 92
Red Fruits	p. 93
Blue and Black Fruits	p. 94
Fruit Quality and Composition	p. 95
Health Benefits	p. 95
Nutritional Content and Defensive Strength	p. 96
Maturity	p. 97
Anthocyanin and Fruit Size	p. 98
Photoprotection	p. 98
Perspectives	p. 99
References	p. 100
Anthocyanin Biosynthesis in Plant Cell Cultures: A Potential Source of Natural Colourants	p. 107
Introduction	p. 107
The Anthocyanins	p. 107
Plant Cell Cultures	p. 109
Daucus carota (Carrot)	p. 111
Types of Anthocyanins	p. 111
Glucosyltransferases from Carrot Cell Cultures	p. 111
Phytohormones	p. 112
GA[subscript 3]	p. 113
Nutrients (Carbon, Nitrogen, Phosphate)	p. 114
Elicitation	p. 115
Light	p. 116
Aggregate Size	p. 117
Future Strategies for Enhanced Production of Anthocyanins	p. 117
Vitis vinifera (Grape)	p. 118
Types of Anthocyanins	p. 119
Modification of Anthocyanins in Grape Cell Cultures	p. 119
Phytohormones	p. 119
Nutrients (Carbon, Nitrogen, Phosphate)	p. 120
pH, Conditioned Media and Feeder Layers	p. 122
Elicitation and Light	p. 122
Localisation of Anthocyanins in the Plant Cell	p. 123
Physical Parameters	p. 125
Conclusions	p. 126
Fragaria ananassa (Strawberry)	p. 126
Types of Anthocyanins	p. 126
Phytohormones	p. 127
Nutrients (Carbon, Nitrogen, Phosphate)	p. 127
Conditioned Medium	p. 128
Elicitation	p. 129
Physical parameters	p. 130
Conclusions	p. 132
Ajuga Species	p. 132
Types of Anthocyanin	p. 132
Phytohomones	p. 133
Nutrients (Carbon, Nitrogen, Phosphate)	p. 133
Physical Parameters	p. 134
Conclusions	p. 134
Ipomea batatas (Sweet Potato)	p. 134
Types of Anthocyanin	p. 135
Phytohormones	p. 135
Nutrients (Carbon, Nitrogen, Phosphate)	p. 135
Elicitation	p. 136
Conclusions	p. 137
Perilla frutescens	p. 137
Carbon Source and Elicitation	p. 137
Physical Parameters	p. 137
Conclusions	p. 139
Vaccinium Species	p. 139
Types of Anthocyanins	p. 139
Phytohormones	p. 140
Media Components and Elicitation	p. 140
Physical Parameters	p. 141
Conclusions	p. 142
Other plant Cell Lines	p. 142
Aralia Cordata	p. 142
Bupleurum falcatum	p. 143
Callistephus chinensis (China Aster)	p. 143
Campanula glomerata	p. 143
Camptotheca acuminata	p. 143
Catharanthus roseus	p. 144
Centaurea cyanus	p. 144
Euphorbia millii	p. 145
Fagopyrum esculentum (Buckwheat)	p. 145
Glehnia littoralis	p. 146
Haplopappus gracilis	p. 147
Hibiscus sabdariffa (Roselle)	p. 147
Hyoscyamus muticus	p. 147
Leontopodium alpinum (Edelweiss)	p. 147
Matthiola incana	p. 147
Oxalis sp.	p. 148
Penstemon serrulatus	p. 148
Petunia hybrida	p. 148
Plantanus acerifolia (Plane Tree)	p. 149
Populus (Poplar)	p. 149
Prunus cerasus (Sour Cherry)	p. 149
Rosa sp. (Paul's Scarlet Rose)	p. 150
Rudbeckia hirta	p. 150
Solanum tuberosum (Potato)	p. 151
Taraxacum officinale (Dandelion)	p. 151
Zea mays (Maize)	p. 151
Conclusions	p. 152
References	p. 154
Modification and Stabilization of Anthocyanins	p. 169
Introduction	p. 169
Glycosyltransferases	p. 170
Glycosylation of Anthocyanidins/Anthocyanins	p. 170
Stabilization of Anthocyanidins by Glycosylation	p. 170
Anthocyanidin/Anthocyanin Glycosyltransferases	p. 170
Enzymatic Characteristics of Anthocyanidin/Anthocyanin UGTs	p. 172
Structure of Anthocyanidin/Anthocyanin Glycosyltransferases	p. 174
Methyltransferases	p. 175
Anthocyanin Methyltransferases	p. 175
Acyltransferases	p. 177
Acylation of Anthocyanins	p. 177
Stabilization of Anthocyanins by Acylation	p. 178
Anthocyanin Acyltransferases	p. 179
Acyl-CoA-Dependent AATs	p. 179
Serine Carboxypeptidase-like (SCPL)-AATs	p. 184
Potential Application of AATs	p. 185
Conclusions and Perspectives	p. 185
References	p. 185
Flavonoid Biotransformations in Microorganisms	p. 191
Microbes as Flavonoid Production Platforms	p. 191
Stilbenes	p. 192
Flavanones	p. 194
Isoflavones	p. 195
Flavones	p. 196
Flavonols	p. 197
Leucoanthocyanidins and Flavan-4-ols	p. 198
Anthocyanin	p. 200
Hydroxylated Flavonoids from E. coli Expressing Plant P450s	p. 202
Microbial Metabolism of Flavonoids	p. 206
Chalcones	p. 207
Flavanones	p. 209
Isoflavones	p. 214
Flavones	p. 218
Flavonols	p. 221
Catechins	p. 223
Anthocyanins	p. 226
Pyranoanthocyanins	p. 229
Conclusions	p. 237
References	p. 238
Biosynthesis and Manipulation of Flavonoids in Forage Legumes	p. 257
Introduction	p. 257
Proanthocyanidins	p. 258
Isoflavonoids	p. 258
Flavonoids as Signaling Molecules	p. 259
Biosynthesis of Flavonoids in Legumes	p. 259
Biosynthesis of Flavonols in Legumes	p. 261
Biosynthesis of Anthocyanins	p. 261
Biosynthesis of Proanthocyanidins	p. 263
Biosynthesis of Isoflavonoids in Legumes	p. 264
Biosynthesis of O-methylated isoflavonoids	p. 266
Biosynthesis of Phytoalexins and Nod-Inducers in Legumes	p. 267
Manipulation of Flavonoids in Legumes	p. 268
Manipulation of Proanthocyanidins in Legumes	p. 268
Manipulation of Isoflavonoids in Legumes	p. 270
Conclusions	p. 271
References	p. 272
Anthocyanins as Food Colorants	p. 283
Introduction	p. 283
Anthocyanins as a Food Colorant	p. 284
Anthocyanins: Structure and Natural Sources	p. 285
Extraction and Analysis of Anthocyanins	p. 287
Anthocyanin Stability and Equilibrium Forms	p. 287
Anthocyanin Extracts and Applications	p. 290
Anthocyanins and Derived Pigments: New Colors	p. 291
Portisins: New Blue Anthocyanin-Derived Food Colorants?	p. 294
Future Perspectives for the Food Industry	p. 297
Acknowledgments	p. 298
References	p. 298
Interactions Between Flavonoids that Benefit Human Health	p. 305
Phytochemical Interactions	p. 305
Why Are Multiple Bioactive Phytochemicals Usually Involved?	p. 308
Flavonoid Interactions that Potentiate Biological Activity	p. 309
In Vitro Investigations of Flavonoid Interactions	p. 313
Conclusion/Opportunities for Future Research	p. 319
Acknowledgements	p. 320
References	p. 320
Index	p. 325
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