Plant nucleotide metabolism biosynthesis, degradation and alkaloid formation

Cover......Page 1
Title Page......Page 5
Copyright......Page 6
Contents......Page 7
Preface......Page 17
Part I General Aspects of Nucleotide Metabolism......Page 19
  1.2 Nomenclature and Abbreviations of Nucleotide‐Related Compounds......Page 21
    1.3.1.1 Purine Bases......Page 23
    1.3.1.2 Purine Nucleosides......Page 24
    1.3.1.3 Purine Nucleotides......Page 25
   1.3.2 Pyrimidines......Page 26
    1.3.2.2 Pyrimidine Nucleosides......Page 27
    1.3.2.3 Pyrimidine Nucleotides......Page 28
  References......Page 29
  2.1 Purines and Pyrimidines......Page 31
   2.1.1 Concentration of Purine and Pyrimidine Nucleotides......Page 32
   2.1.2 Concentration of Purine and Pyrimidine Bases and Nucleosides......Page 34
   2.2.1 Concentration of Pyridine Nucleotides......Page 35
  2.4 Alkaloids Derived from Nucleotides......Page 36
  References......Page 37
  3.2 De Novo Biosynthesis of Ribonucleoside Monophosphates......Page 39
   3.3.1 Nucleoside‐Monophosphate Kinase......Page 41
  3.4 Conversion of Nucleoside Diphosphates to Nucleoside Triphosphates......Page 42
   3.4.1 ATP Synthesis by Electron Transfer Systems......Page 43
   3.4.3 Nucleoside‐Diphosphate Kinase......Page 44
  3.6 Nucleic Acid Biosynthesis......Page 47
  3.7 Supply of 5‐Phosphoribosyl‐1‐Pyrophosphate......Page 48
  3.9 Nitrogen Metabolism and Amino Acid Biosynthesis in Plants......Page 51
  3.10 Summary......Page 52
  References......Page 53
Part II Purine Nucleotide Metabolism......Page 57
  4.1 Introduction......Page 59
  4.2 Reactions and Enzymes......Page 61
   4.2.1 Synthesis of Phosphoribosylamine......Page 62
   4.2.3 Synthesis of Formylglycineamide Ribonucleotide......Page 64
   4.2.5 Synthesis of Aminoimidazole Ribonucleotide......Page 65
   4.2.7 Synthesis of Aminoimidazole Succinocarboxamide Ribonucleotide......Page 66
   4.2.9 Synthesis of IMP via Formamidoimidazole Carboxamide Ribonucleotide......Page 67
   4.2.10 Synthesis of AMP......Page 68
   4.2.11 Synthesis of GMP......Page 69
  References......Page 70
  5.1 Introduction......Page 73
  5.2 Characteristics of Purine Salvage in Plants......Page 74
   5.3.2 Hypoxanthine/Guanine Phosphoribosyltransferase......Page 77
   5.4.1 Adenosine Kinase......Page 80
   5.4.3 Deoxyribonucleoside Kinases......Page 82
  5.5 Properties of Nucleoside Phosphotransferase......Page 83
  References......Page 84
  6.2 Deamination Reactions......Page 89
   6.2.2 AMP Deaminase......Page 91
   6.2.3 Routes of Deamination of Guanine Ring......Page 92
  6.3 Dephosphorylation Reactions......Page 93
   6.4.1 Adenosine Nucleosidase......Page 94
   6.4.4 Recombinant Non‐Specific Nucleosidases......Page 96
   6.5.1 Metabolism of Adenine Nucleotides......Page 97
  6.6 In Situ Metabolism of Purine Nucleosides and Bases......Page 98
   6.6.1 Metabolism of Adenine and Adenosine......Page 100
   6.6.2 Metabolism of Guanine and Guanosine......Page 101
   6.6.4 Metabolism of Xanthine and Xanthosine......Page 102
   6.6.5 Metabolism of Deoxyadenosine and Deoxyguanosine......Page 103
  6.7 Summary......Page 106
  References......Page 107
  7.1 Introduction......Page 113
  7.2 (S)‐Allantoin Biosynthesis from Xanthine......Page 115
   7.2.1 Xanthine Dehydrogenase......Page 117
   7.2.2 Urate Oxidase......Page 118
  7.3 Catabolism of (S)‐Allantoin......Page 119
   7.3.1 Allantoinase......Page 121
   7.3.3 (S)‐Ureidoglycine Aminohydrolase......Page 122
   7.3.7 Urease......Page 123
  7.4 Purine Nucleotide Catabolism in Plants......Page 124
   7.5.1 Ureides in Plant Tissues and Xylem Sap......Page 125
   7.5.3 Role of Ureides in Germination and Development of Seeds......Page 127
   7.5.5 Other Role of Ureides in Plants......Page 128
  References......Page 129
Part III Pyrimidine Nucleotide Metabolism......Page 135
  8.1 Introduction......Page 137
   8.2.1 Synthesis of Carbamoyl‐phosphate......Page 139
   8.2.3 Formation of Dihydroorotase from Carbamoyl‐aspartate......Page 141
   8.2.4 Formation of Orotate from Dihydroorotate......Page 142
   8.2.5 Synthesis of UMP from Orotate......Page 143
   8.2.6 Synthesis of CTP from UTP......Page 144
   8.3.1 Fine Control of the De Novo Pathway......Page 145
   8.4.1 Formation of dUMP......Page 147
   8.4.3 Conversion of dUMP to dTMP......Page 148
  References......Page 149
  9.2 Characteristics of Pyrimidine Salvage in Plants......Page 155
  9.3 Enzymes of Pyrimidine Salvage......Page 157
   9.3.1 Uracil Phosphoribosyl Transferase......Page 158
   9.3.2 Uridine/Cytidine Kinase......Page 160
   9.3.3 Thymidine Kinase......Page 161
   9.3.5 Nucleoside Phosphotransferase......Page 162
  9.4 Role of Pyrimidine Salvage in Plants......Page 163
  References......Page 164
   10.2.1 Cytidine Deaminase......Page 167
   10.3.1 Uridine Nucleosidase......Page 170
  10.4 In Situ Metabolism of 14C‐Labelled Pyrimidines......Page 171
   10.4.2 Metabolic Fate of Uridine and Uracil......Page 172
   10.4.3 Metabolic Fate of Cytidine and Cytosine......Page 174
   10.4.4 Metabolic Fate of Deoxycytidine......Page 175
   10.4.5 Metabolic Fate of Thymidine......Page 176
  10.5 Summary......Page 177
  References......Page 178
  11.1 Introduction......Page 183
  11.2 Enzymes Involved in the Degradation Routes of Pyrimidines......Page 184
   11.2.2 Dihydropyrimidinase......Page 185
  11.3 The Metabolic Fate of Uracil and Thymine......Page 186
  11.4 Summary......Page 187
  References......Page 188
Part IV Physiological Aspects of Nucleotide Metabolism......Page 191
  12.2 Embryo Maturation......Page 193
   12.3.1 Purine Metabolism in Germination......Page 198
   12.3.2 Pyrimidine Metabolism in Germination......Page 201
  12.4 Organogenesis......Page 203
  12.7 Storage Organ Development and Sprouting......Page 204
   12.8.1 Nucleotide Pools......Page 205
   12.8.3 Nucleotide Availability......Page 206
  References......Page 207
  13.2 Effect of Phosphate on Nucleotide Metabolism......Page 213
  13.3 Effect of Salts on Nucleotide Metabolism......Page 217
  13.5 Effect of Wound Stress......Page 220
  13.6 Effect of Iron Deficiency......Page 223
  References......Page 224
Part V Purine Alkaloids......Page 229
  14.2 Chemical Structure of Purine Alkaloids......Page 231
   14.3.1 Purine Alkaloids in Tea and Related Species......Page 233
   14.3.2 Purine Alkaloids in Coffee and Related Species......Page 236
   14.3.3 Purine Alkaloids in Maté......Page 238
   14.3.4 Purine Alkaloids in Cacao and Related Species......Page 239
   14.3.6 Purine Alkaloids in Guaraná and Related Species......Page 241
   14.3.7 Purine Alkaloids in Citrus Species......Page 242
   14.3.8 Purine Alkaloids in Other Plants......Page 243
  References......Page 244
  15.2 A Brief History of Caffeine Biosynthesis Research......Page 249
  15.3 Caffeine Biosynthesis Pathway......Page 252
   15.3.2 Formation of 7‐Methylxanthine from Xanthosine......Page 254
   15.3.3 7‐Methylxanthosine Synthase......Page 255
   15.3.4 N‐Methylnucleosidase......Page 258
   15.3.6 Caffeine Synthase......Page 259
   15.3.7 Theobromine Synthase......Page 262
  15.4 Genes and Proteins of Caffeine Synthase Family......Page 263
  15.5 Xanthosine Biosynthesis from Purine Nucleotides......Page 267
   15.5.1 De Novo Purine Route......Page 268
   15.5.3 S‐Adenosyl‐l‐methionine Cycle Route......Page 269
   15.5.4 Nicotinamide Adenine Diphosphate Catabolism Route......Page 270
  References......Page 271
  16.2 Physiology of Caffeine Biosynthesis......Page 277
   16.2.2 Camellia......Page 279
   16.2.4 Theobroma......Page 282
   16.2.5 Maté......Page 284
   16.2.6 Guaraná......Page 285
   16.3.1 Caffeine Synthase......Page 286
   16.3.2 The De Novo Route Enzymes......Page 287
  16.4 Regulation of Caffeine Biosynthesis......Page 288
   16.5.1 Allelopathic Function Theory......Page 289
   16.5.2 Effect of Caffeine on Plant Growth......Page 290
   16.5.3 Allelopathy in Natural Ecosystems......Page 291
  16.6 Summary......Page 292
  References......Page 293
   17.2.1 Methylurate Biosynthesis......Page 299
   17.2.2 The Major Pathway of Caffeine Degradation......Page 300
   17.2.3 Purine Catabolic Pathways in Alkaloid Plants......Page 302
   17.3.1 Coffea Species......Page 303
   17.3.2 Camellia Species......Page 304
   17.3.5 Other Plant Species......Page 308
   17.3.6 Bacteria......Page 309
   17.4.1 Decaffeinated Coffee Plants......Page 311
   17.4.2 Decaffeinated Tea Plants......Page 312
   17.5.1 Antiherbivore Activity......Page 313
   17.5.2 Antipathogen Activity......Page 314
  References......Page 316
Part VI Pyridine Nucleotide Metabolism......Page 319
  18.2 Two Distinct Pathways of De Novo Nicotinate Mononucleotide Biosynthesis......Page 321
  18.3 The Outline of the De Novo Pathway of NAD Biosynthesis in Plants......Page 322
  18.4 Enzymes Involved in De Novo NAD Synthesis in Plants......Page 325
   18.4.1 l‐Aspartate Oxidase and Quinolinate Synthase......Page 326
   18.4.3 Nicotinate Mononucleotide Adenylyltransferase......Page 327
  References......Page 328
  19.2 Pyridine Nucleotide Cycle......Page 333
   19.2.1 Major Pyridine Nucleotide Cycles in Plants......Page 335
   19.2.2 Alternative Pyridine Nucleotide Cycles in Plants......Page 336
   19.2.3 Rate‐Limiting Step of the Pyridine Cycle......Page 337
   19.3.2 Degradation of Pyrimidine Ring......Page 338
   19.4.2 NAD Pyrophosphatase......Page 339
   19.4.4 Nicotinamidase and Nicotinamide Riboside Deaminase......Page 340
   19.5.1 Nicotinate Phosphoribosyltransferase......Page 341
   19.5.2 Nicotinate Riboside Kinase......Page 342
  References......Page 343
Part VII Pyridine Alkaloids......Page 347
  20.1 Introduction......Page 349
   20.2.1 Trigonelline in Plants......Page 351
   20.2.2 Other Pyridine Alkaloids in Plants......Page 352
   20.3.1 Trigonelline Biosynthesis......Page 353
   20.3.2 Nicotinate N‐Glucoside Biosynthesis......Page 354
   20.3.3 The Diversity of Biosynthetic Reactions......Page 355
    20.3.3.2 Gymnosperms......Page 356
    20.3.3.3 Angiosperms......Page 357
    20.3.3.4 Nicotinate Conjugate Formation......Page 358
   20.3.4 Biosynthesis of Ricinine......Page 359
   20.3.5 Biosynthesis of Nicotine (Pyridine Ring)......Page 361
  References......Page 363
   21.2.1 Coffee......Page 369
   21.2.2 Leguminous Plants......Page 372
  21.4 The Role of Trigonelline in Plants......Page 374
   21.4.2 Role of Trigonelline as a Compatible Solute......Page 375
   21.4.4 Cell Cycle Regulation......Page 376
   21.4.5 Detoxification of Nicotinate......Page 377
  21.5 Biotechnology of Trigonelline......Page 378
  21.6 Summary......Page 380
  References......Page 381
Part VIII Other Nucleotide‐Related Metabolites......Page 385
  22.1 Introduction......Page 387
  22.2 The Sugar Nucleotide Moiety......Page 388
   22.3.1 UDP‐Glucose Pyrophosphorylase......Page 389
   22.3.2 UDP‐Sugar Pyrophosphorylase......Page 392
   22.3.3 Sucrose Synthase......Page 394
  22.5 UDP‐Glucose‐Interconversion......Page 395
   22.6.1 Cyclic Nucleotides......Page 397
   22.6.2 Diadenosine Tetraphosphate......Page 399
  References......Page 400
  23.1 Introduction......Page 405
  23.2 Adenosine Phosphate‐Isopentenyl Formation......Page 406
  23.4 Formation of Cytokinin Bases......Page 407
   23.5.1 Cytokinin Inactivation by Adenine Phosphoribosyltransferase......Page 408
  23.6 New Purine‐Related Plant Growth Regulators......Page 410
  23.7 Summary......Page 411
  References......Page 412
Part IX Dietary Plant Alkaloids, Their Bioavailability, and Potential Impact on Human Health......Page 415
   24.1.1 Dietary Caffeine......Page 417
   24.1.2 Bioavailability and Bioactivity of Caffeine......Page 418
   24.2.1 Interactions with Flavan‐3‐ols......Page 422
   24.3.1 Dietary Trigonelline......Page 424
   24.3.2 Bioavailability and Bioactivity of Trigonelline......Page 425
  References......Page 427
Index......Page 433
EULA......Page 455