Contributors .................................................... x
Preface ...................................................... xiii
1. Introduction: biochemistry, physiology and ecological
functions of secondary metabolites ........................... 1
Michael Wink
1.1. Introduction ............................................ 1
1.2. Biosynthesis ............................................ 2
1.3. Transport, storage and turnover ......................... 9
1.4. Costs of secondary metabolism .......................... 13
1.5. Ecological role of secondary metabolites ............... 14
References .................................................. 17
2. Biosynthesis of alkaloids and betalains ..................... 20
Margaret F. Roberts, Dieter Strack and Michael Wink
2.1. Introduction ........................................... 20
2.2. Nicotine and tropane alkaloids ......................... 23
2.3. Pyrrolizidine alkaloids (PAs) .......................... 33
2.4. Benzylisoquinoline alkaloids ........................... 35
2.5. Monoterpene indole alkaloids (MIA) ..................... 46
2.6. Ergot alkaloids ........................................ 56
2.7. Acridone alkaloid biosynthesis ......................... 60
2.8. Purine alkaloids ....................................... 61
2.9. Taxol .................................................. 62
2.10.Betalains .............................................. 66
2.11.Conclusions ............................................ 75
References .................................................. 75
3. Biosynthesis of cyanogenic glycosides, glucosinolates and
non-protein amino acids ..................................... 92
Dirk Selmar
3.1. Introduction ........................................... 93
3.2. Cyanogenic glycosides .................................. 94
3.3. Glucosinolates ........................................ 128
3.4. Non-protein amino acids ............................... 146
Acknowledgements ........................................... 157
References ................................................. 157
4. Biosynthesis of phenylpropanoids and related
compounds .................................................. 182
Maike Petersen, Joachim Hans and Ulrich Matern
4.1. Introduction .......................................... 182
4.2. General phenylpropanoid pathway and formation of
hydroxycinnamate conjugates ........................... 183
4.3. Coumarins ............................................. 197
4.4. Lignans ............................................... 209
4.5. Gallotannins and ellagitannins ........................ 223
4.6. Conclusion ............................................ 229
References ................................................. 230
5. Biochemistry of terpenoids: monoterpenes, sesquiterpenes
and diterpenes ............................................. 258
Mohamed Ashour, Michael Wink and Jonathan Gershenzon
5.1. Introduction .......................................... 259
5.2. Function .............................................. 260
5.3. Biosynthesis .......................................... 263
5.4. Conclusions ........................................... 285
References ................................................. 286
6. Biochemistry of sterols, cardiac glycosides,
brassinosteroids, phytoecdysteroids and steroid
saponins ................................................... 304
Wolfgang Kreis and Frieder Müller-Uri
6.1. Introduction .......................................... 305
6.2. Sterols ............................................... 308
6.3. Cardiac glycosides .................................... 319
6.4. Brassinosteroids ...................................... 336
6.5. Phytoecdysteroids ..................................... 341
6.6. Steroid saponins and steroid alkaloids ................ 343
6.7. Conclusions ........................................... 347
References ................................................. 348
7. Chemotaxonomy seen from a phylogenetic perspective and
evolution of secondary metabolism .......................... 364
Michael Wink, Flavia Botschen, Christina Gosmann,
Holger Schäfer and Peter G. Waterman
7.1. Introduction .......................................... 365
7.2. Establishment of chemotaxonomy as a research
discipline ............................................ 365
7.3. Developments in small molecule chemotaxonomy over
the past 35 years ..................................... 380
7.4. Molecular biology and plant taxonomy .................. 382
7.5. Comparison between patterns of secondary metabolites
and molecular phylogeny ............................... 383
7.6. Evolution of plant secondary metabolism ............... 406
Acknowledgements ........................................... 426
References ................................................. 426
Index ......................................................... 434
Color plate can be found between pages 368 and 369.
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