search for books and compare prices
Tables of Contents for Alkaloids
Chapter/Section Title
Page #
Page Count
Chapter 1 Introduction
1
10
Margaret F. Roberts
Michael Wink
1. Introduction
1
1
2. Historical Importance of Alkaloids
1
1
3. Biochemistry
2
2
3.1. Classification of Alkaloids
2
1
3.2. Biogenetic Grouping of Alkaloids
3
1
3.3. Occurrence and Distribution
3
1
4. Ecology
4
1
5. Pharmacological Activities
5
1
References
6
5
Part I. Historical and Cultural Perspectives
11
76
Chapter 2 A Short History of Alkaloids
11
34
Michael Wink
1. Introduction
11
1
2. Alkaloids and Alkaloid-Producing Plants in Antiquity
12
5
2.1. Use of Alkaloid-Producing Plants in Early Medicine
12
2
2.2. Role of Alkaloids and Alkaloidal Plants for "Murder" and "Magic"
14
3
3. Alkaloidal Plants and Fungi Playing an Important Role in the History of Mankind
17
27
3.1. Aconitum napellus (Family Ranunculacaea)
17
1
3.2. Amanita muscaria (Family Amanitaceae)
18
1
3.3. Areca catechu (Family Arecaceae)
19
1
3.4. Aristolochia clematitis (Family Aristolochiaceae)
19
1
3.5. Atropa belladonna (Family Solanaceae)
20
2
3.6. Banisteriopsis caapa, B. inebrians (Family Malpighiaceae)
22
1
3.7. Buxus sempervirens (Family Buxaceae)
22
1
3.8. Camellia sinensis (Family Theaceae)
23
1
3.9. Chelidonium majus (Family Papaveraceae)
24
1
3.10. Claviceps purpurea (Family Hypocreaceae)
25
1
3.11. Colchicum autumnale (Family Liliaceae)
26
1
3.12. Conium maculatum (Family Umbelliferae)
27
1
3.13. Datura metel (Family Solanaceae)
28
1
3.14. Delphinium consolida (Family Ranunculaceae)
28
1
3.15. Dictamnus albus (Family Rutaceae)
29
1
3.16. Ephedra fragilis (Family Ephedraceae)
29
1
3.17. Erythroxylum coca (Family Erythroxylaceae)
30
1
3.18. Hyoscyamus niger, H. albus, H. muticus (Family Solanaceae)
31
1
3.19. Lophophora williamsii (Family Cactaceae)
32
1
3.20. Lupinus albus (Family Leguminosae)
32
1
3.21. Lycopodium clavatum, L. annotinum (Family Lycopodiaceae)
33
1
3.22. Mandragora officinarum, M. autumnalis (Family Solanaceae)
34
1
3.23. Nicotiana tabacum (Family Solanaceae)
35
1
3.24. Papaver somniferum (Family Papaveraceae)
35
2
3.25. Peganum harmala (Family Zygophyllaceae)
37
1
3.26. Physostigma venenosum (Family Leguminosae)
38
1
3.27. Psilocybe mexicana (Family Agaricaceae)
38
1
3.28. Punica granatum (Family Punicaceae)
39
1
3.29. Ruta graveolens (Family Rutaceae)
40
1
3.30. Solanum dulcamara (Family Solanaceae)
40
1
3.31. Taxus baccata (Family Taxaceae)
41
1
3.32. Turbina corymbosa (Family Convolvulaceae)
42
1
3.33. Veratrum album (Family Liliaceae)
42
2
References
44
1
Major Reviews
44
1
Key References
44
1
Chapter 3 Alkaloids in Arrow Poisons
45
42
H.D. Neuwinger
1. Introduction
45
1
2. African Arrow Poisons
46
25
2.1. Poisoned Weapons
47
2
2.2. Poison Preparation
49
1
2.3. Plant Sources and Their Active Principles
50
21
3. South American Arrow Poisons
71
6
3.1. Classification and Composition
72
1
3.2. Chemistry
73
1
3.3. Pharmacology, Toxicology
74
1
3.4. Medicinal Use
75
1
3.5. Other Plant Arrow Poisons
76
1
4. Asian Arrow Poisons
77
4
4.1. Indonesia, Borneo, Philippines, Hainan, Vietnam, Cambodia
78
1
4.2. Burma, Thailand, Malaysia
79
2
Appendix: Composition of African Arrow Poisons
81
1
References
82
1
General References
82
1
Specific References
83
4
Part II. Biochemistry
87
178
Chapter 4 Chemical Taxonomy of Alkaloids
87
22
Peter G. Waterman
1. Introduction
87
1
2. What Is an Alkaloid?
87
1
2.1. A Unifying Theme in the Biosynthesis of True Alkaloids
88
1
3. The Impact of Alkaloids on Taxonomy
88
17
3.1. Alkaloids Originating from Tyrosine (and Phenylalanine), Usually through Dopa
90
6
3.2. Indole-seco-Loganin-Derived Alkaloids
96
2
3.3. Anthranilic Acid as an Alkaloid Substrate
98
2
3.4. Alkaloids from Ornithine and Lysine
100
4
3.5. Pseudoalkaloids
104
1
4. Concluding Comments
105
1
References
105
1
General Reviews
105
1
Key References
106
3
Chapter 5 Enzymology of Alkaloid Biosynthesis
109
38
Margaret F. Roberts
1. Introduction
109
1
2. Biosynthesis of Acetate-Derived Simple Piperidine Alkaloids
110
2
3. Biosynthesis of Quinolizidine Alkaloids
112
2
4. Biosynthesis of Benzylisoquinoline Alkaloids
114
7
4.1. The Formation of (S)-Norcoclaurine
114
2
4.2. Biosynthesis of the Tetrahydroberberine Alkaloids
116
2
4.3. The Route to the Protopine and Benzophenanthridine Alkaloids
118
2
4.4. Biosynthesis of the Morphinan Alkaloids
120
1
5. Indole Alkaloid Biosynthesis
121
11
5.1. Formation of (S)-Strictosidine
123
2
5.2. Deglucosylation of Strictosidine
125
1
5.3. Formation of Corynanthe-Type Alkaloids
125
1
5.4. The Formation of Sarpagan-Type Alkaloids
125
5
5.5. Formation of Aspidosperma-Type Alkaloids
130
2
5.6. Biosynthesis of Dimeric Indole Alkaloids
132
1
6. Ergot Alkaloid Biosynthesis
132
5
7. Cyclopenin-Viridicatin Alkaloid Biosynthesis
137
2
8. Acridone Alkaloid Biosynthesis
139
1
9. Conclusions
139
1
References
140
1
General Reviews
140
1
Key References
141
6
Chapter 6 Genes in Alkaloid Metabolism
147
12
Kazuki Saito
Isamu Murakoshi
1. Introduction
147
1
2. Isolation of Genes
147
2
3. Regulation
149
1
4. Expression of Recombinant Enzymes in Heterologous Systems
150
3
4.1. Expression in Microorganisms
150
3
4.2. Expression in Transgenic Plants and Other Higher Organisms
153
1
5. Molecular Evolution
153
1
6. Prospects
154
1
References
155
1
General Reviews
155
1
Key References
155
4
Chapter 7 Production of Alkaloids in Plant Cell Culture
159
40
Margaret F. Roberts
1. Introduction
159
2
2. Cell Technology
161
28
2.1. Cell Culture
161
3
2.2. Establishment of Specific Cell Lines
164
2
2.3. Growth and Product Accumulation
166
1
2.4. Development of Cultures with Improved Alkaloid Yield
167
2
2.5. Immobilization of Plant Cells and Enzymes
169
2
2.6. Organ Culture
171
1
2.7. Plant Propagation by Tissue Culture Techniques
172
1
2.8. Cell Cultures for the Production of Alkaloids
173
11
2.9. Lysine-Derived Quinolizidine Alkaloids
184
1
2.10. Ornithine-Derived Alkaloids
184
2
2.11. Nicotinic Acid-Derived and Purine Alkaloids
186
1
2.12. Anthranilic Acid-Derived Alkaloids
187
1
2.13. Acetate-Derived Alkaloids
188
1
3. Industrial Interest
189
3
3.1. The Problem of Cost-Effectiveness
189
1
3.2. The Problems Associated with Scaleup
190
1
3.3. Areas of Potential Industrial Interest
191
1
4. Summary
192
1
References
192
1
General Reviews
192
2
Key References
194
5
Chapter 8 The Biosynthesis of Alkaloids in Root Cultures
199
20
Richard J. Robins
1. Introduction
199
1
2. The Pyrrolidine Alkaloids
200
5
2.1. Regulation of the Pyrrolidine Alkaloid Pathway in Nicotiana
202
1
2.2. Studying the Pyrrolidine Alkaloid Pathway by Genetic Engineering
203
2
3. The Tropane Alkaloids
205
7
3.1. The Biosynthetic Route to the Tropane Alkaloids
206
1
3.2. Regulation of the Tropane Alkaloid Pathway in Datura, Hyoscyamus, and Atropa
206
5
3.3. Genetic Engineering of Tropane Alkaloid Biosynthesis
211
1
4. The Pyrrolizidine Alkaloids
212
3
4.1. The Biosynthetic Route to the Pyrrolizidine Alkaloids
212
1
4.2. Regulation of the Biosynthetic Pathway
213
2
5. Conclusions
215
1
References
215
1
General Reviews
215
1
Key References
216
3
Chapter 9 Induction of Alkaloid Biosynthesis and Accumulation in Plants and in Vitro Cultures in Response to Elicitation
219
20
U. Eilert
1. Introduction
219
1
2. Induction of Alkaloid Production by Climatic and Soil Conditions in Field-Grown Plants
220
2
2.1. Induction by Heat Stress
220
1
2.2. Induction by Light
221
1
3. Induction of Alkaloid Production in Vitro
222
1
4. Induction by Wounding
223
9
4.1. Effects of Mechanical Wounding
224
1
4.2. Elicitor Induction
225
7
5. Concluding Remarks
232
1
References
233
1
General Reviews
233
1
Key References
234
5
Chapter 10 Compartmentation of Alkaloid Synthesis, Transport, and Storage
239
26
Michael Wink
Margaret F. Roberts
1. Introduction
239
3
2.1. Sites and Compartmentation of Alkaloid Formation
239
2
2.2. Long-Distance Transport
241
1
3. Alkaloid Storage
242
6
3.1. Vacuolar Sequestration of Alkaloids
242
2
3.2. Mechanisms Underlying Vacuolar Sequestration
244
4
4. Turnover of Alkaloids
248
6
5. Sequestration as an Integral Part of the Defense Concept of Plants
254
2
References
256
1
General Reviews
256
2
Special References
258
7
Part III. Ecology
265
132
Chapter 11 Chemical Ecology of Alkaloids
265
36
Michael Wink
1. Introduction
265
3
2. Function of Alkaloids
268
1
3. Plant-Herbivore Interactions
269
15
3.1. Invertebrates
269
12
3.2. Vertebrate Herbivores
281
3
4. Plant-Microbe Interactions
284
2
5. Plant-Plant Interactions
286
1
6. Ecological Relevance of Alkaloids
286
10
6.1. Are Alkaloid Concentrations in Plants Sufficiently High?
287
2
6.2. Occurrence of Alkaloids at the Right Site and Right Time
289
3
6.3. Evidence for Alkaloid-Mediated Fitness
292
4
7. Conclusion
296
1
References
297
1
Major Reviews
297
1
Key References
298
3
Chapter 12 Modes of Action of Alkaloids
301
26
Michael Wink
1. Introduction
301
1
2. Molecular Targets of Alkaloids
301
19
2.1. Biomembranes
302
1
2.2. Signal Transduction at Biomembranes
302
7
2.3. Cytoskeleton
309
3
2.4. DNA/RNA
312
2
2.5. Protein Biosynthesis
314
2
2.6. Electron Chains
316
1
2.7. Modulation of Enzyme Activity through Alkaloids
316
1
2.8. Alkaloids Affecting More than One Target
316
4
3. Targets at the Organ Level
320
4
3.1. Central Nervous System and Neuromuscular Junction
320
2
3.2. Inhibition of the Digestive Process
322
1
3.3. Modulation of Liver and Kidney Function
323
1
3.4. Disturbance of Reproduction
323
1
3.5. Blood and Circulatory System
324
1
3.6. Allergenic Effects
324
1
4. Mechanisms of Allelochemical Activities in Antiviral, Antimicrobial, and Allelopathic Interactions
324
1
5. Conclusions
324
1
References
325
1
Major Reviews
325
1
Key References
325
2
Chapter 13 Plant Parasites
327
10
F.R. Stermitz
1. Introduction
327
1
2. Specificity
328
5
2.1. Host Plant Specificity
328
2
2.2. Specificity of Alkaloid Uptake: Root Parasites
330
1
2.3. Specificity of Alkaloid Uptake: Stem Parasites
330
3
3. Ecological Aspects of Alkaloid Transfer
333
2
References
335
1
General References
335
1
Specific References
335
2
Chapter 14 Allelopathy in Plants
337
12
J.V. Lovett
A.H.C. Hoult
1. Introduction
337
2
2. Allelopathic Activity of the Alkaloids
339
3
2.1. Against Microorganisms
339
1
2.2. Against Higher Plants
340
2
3. The Significance of Alkaloid-Mediated Allelopathy in Ecosystems
342
2
3.1. Criteria for Establishing Allelopathic Activity in Ecosystems
342
1
3.2. Soil Mediation
342
1
3.3. Other Interactions
343
1
4. Conclusion
344
1
References
345
1
General Reviews
345
1
Specific References
346
3
Chapter 15 Alkaloids in Animals
349
30
J.C. Braekman
D. Daloze
J.M. Pasteels
1. Introduction
349
1
2. Arthropods
350
14
2.1. Insecta
361
2
2.2. Arachnida
361
2
2.3. Myriapoda-Diplopoda
363
1
3. Vertebrates
364
3
3.1. Amphibia
364
3
3.2. Other Vertebrates
367
1
4. Marine Animals
367
5
4.1. Bryozoa (Ectoprocta or Moss Animals)
369
1
4.2. Tunicates (Ascidians)
369
3
4.3. Porifera
372
1
5. Biosynthesis
372
1
References
373
1
General Reviews
373
1
Specialist References
374
5
Chapter 16 Ecological Significance of Alkaloids from Marine Invertebrates
379
18
Peter Proksch
Rainer Ebel
1. Introduction
379
1
2. Chemical Defense against Fouling and Spatial Competition
380
3
3. Chemical Defense against Fish
383
2
4. Induced Chemical Defense of the Sponge Verongia aerophoba
385
3
5. Marine Alkaloids as Waterborne Signals in Inter- and Intraspecific Communication
388
1
6. Origin of Alkaloids from Marine Invertebrates
389
1
7. Chemical Defense in the Marine versus the Terrestrial Environment
390
1
References
391
1
General Reviews
391
1
Specific References
392
5
Part IV. Alkaloids in Medicine
397
64
Chapter 17 Antimicrobially Active Alkaloids
397
38
R. Verpoorte
1. Introduction
397
1
2. Indole Alkaloids
398
7
2.1. Terpenoid Indole Alkaloids
398
6
2.2. Other Indole Alkaloids
404
1
3. Isoquinoline Alkaloids
405
11
3.1. Bisbenzylisoquinoline Alkaloids
410
1
3.2. Aporphine Alkaloids
411
2
3.3. Benzophenanthridine Alkaloids
413
1
3.4. Protoberberine Alkaloids
414
2
3.5. Protopines
416
1
3.6. Miscellaneous Isoquinoline Alkaloids
416
1
4. Steroidal Alkaloids
416
5
5. Quinoline Alkaloids
421
1
6. Acridone Alkaloids
421
1
7. Terpenoid Alkaloids
422
1
8. Piperidine Alkaloids
422
1
9. Quinolizidine Alkaloids
423
1
10. Pyrrolizidine Alkaloids
423
1
11. Miscellaneous
423
1
12. Conclusion
424
1
References
425
1
General Reviews
425
1
Key References
426
9
Chapter 18 Utilization of Alkaloids in Modern Medicine
435
26
T. Schmeller
Michael Wink
1. Introduction
435
1
2. Alkaloids Used in Modern Medicine
436
22
2.1. Aconitine
436
1
2.2. Ajmaline
436
1
2.3. Atropine
437
1
2.4. Berberine
438
1
2.5. Boldine
438
1
2.6. Caffeine
439
1
2.7. Cathine
439
1
2.8. Cocaine
440
1
2.9. Codeine
440
1
2.10. Colchicine
441
1
2.11. Emetine
441
1
2.12. Ephedrine
442
1
2.13. Ergometrine
443
1
2.14. Ergotamine
443
1
2.15. Eserine (= Physostigmine)
444
1
2.16. Galanthamine
444
1
2.17. Hydrastine
445
1
2.18. Hyoscine (= Scopolamine)
445
1
2.19. Hyoscyamine
446
1
2.20. Lobeline
446
1
2.21. Morphine
446
1
2.22. Narceine
447
1
2.23. Nicotine
447
1
2.24. Noscapine (= Narcotine)
448
1
2.25. Papaverine
448
1
2.26. Physostigmine (see Eserine)
449
1
2.27. Pilocarpine
449
1
2.28. Quinidine
449
1
2.29. Quinine
450
1
2.30. Raubasine (= Ajmalicine)
450
1
2.31. Rescinnamine
451
1
2.32. Reserpine
451
1
2.33. Sanguinarine
452
1
2.34. Scopolamine (see Hyoscine)
453
1
2.35. Sparteine
453
1
2.36. Strychnine
453
1
2.37. Taxol
454
1
2.38. Theobromine
454
1
2.39. Theophylline
455
1
2.40. Tubocurarine
455
1
2.41. Vinblastine
456
1
2.42. Vincamine
457
1
2.43. Vincristine
457
1
2.44. Yohimbine
457
1
3. Conclusions
458
1
References
458
3
Subject Index Including Orders, Families, and Common Names
461
8
Index of Alkaloids, Amines, and Other Molecules
469
10
Organism Index
479