Alkaloids - Secrets of Life: (eBook)

Cover 1
Copyright Page 5
Table of Contents 8
List of Figures 12
List of Tables 16
Preface 18
Chapter 1 Definition, Typology and Occurrence of Alkaloids 20
1. Definition 20
1.1. True alkaloids 25
1.2. Protoalkaloids 25
1.3. Pseudoalkaloids 30
2. Occurrence in nature 31
2.1. The Dogbane botanical family (Apocynaceae) 32
2.2. The Aster botanical family (Asteraceae) 36
2.3. The Logan botanical family (Loganiaceae) 38
2.4. The Poppy botanical family (Papaveraceae) 40
2.5. The Citrus botanical family (Rutaceae) 41
2.6. The Nightshade botanical family (Solanaceae) 44
2.7. The Coca botanical family (Erythroxylaceae) 46
2.8. The Borage botanical family (Boraginaceae) 47
2.9. The Legume botanical family (Fabaceae) 48
2.10. The Monseed botanical family (Menispermaceae) 64
2.11. The Berberry botanical family (Berberidaceae) 65
2.12. The Buttercup botanical family (Ranunculaceae) 66
2.13. The Lily botanical family (Liliaceae) 67
2.14. The Coffee botanical family (Rubiaceae) 68
2.15. The Amaryllis botanical family (Amaryllidaceae) 70
2.16. The Oleaster botanical family (Elaeagnaceae) 72
2.17. The Caltrop botanical family (Zygophyllaceae) 72
2.18. Mushroom 73
2.19. Moss 74
2.20. Fungus and bacter 74
2.21. Animals 76
Chapter 2 Alkaloid Chemistry 80
1. Alkaloids as secondary metabolism molecules 80
2. Synthesis and metabolism 85
2.1. Skeleton diversity 86
2.2. Ornithine-derived alkaloids 92
2.3. Tyrosine-derived alkaloids 95
2.3.1. Mescaline pathway 95
2.3.2. Kreysigine and colchicine pathway 96
2.3.3. Dopamine – cephaeline pathway 97
2.3.4. Galanthamine pathway 97
2.4. Tryptophan-derived alkaloids 97
2.4.1. Psilocybin pathway 98
2.4.2. Elaeagnine, harman and harmine pathway 99
2.4.3. Ajmalicine, tabersonine and catharanthine pathway 100
2.4.4. Vindoline, vinblastine and vincristine pathway 100
2.4.5. Strychnine and brucine pathway 102
2.4.6. Quinine, quinidine and cinchonine synthesis pathway 102
2.4.7. Eserine synthesis pathway 103
2.4.8. Ergotamine synthesis pathway 103
2.5. Nicotinic acid–derived alkaloids 104
2.6. Lysine-derived alkaloids 106
2.6.1. Pelletierine, lobelanine and piperine synthesis pathway 106
2.6.2. The swansonine and castanospermine synthesis pathway 107
2.6.3. The lupinine, lupanine, sparteine and cytisine synthesis pathway 107
2.7. Methods of analysis 109
2.7.1. Methodological considerations 110
2.7.2. Structural approach 114
2.7.2.1. Piperidine alkaloids 114
2.7.2.2. Indolizidine alkaloids 115
2.7.2.3. Quinolizidine alkaloids 117
2.7.2.4. Pyrrolizidine alkaloids 120
2.7.2.5. Izidine alkaloids 122
2.7.2.6. Pyrrolidine alkaloids 122
2.7.2.7. Tropane alkaloids 122
2.7.2.8. Imidazole alkaloids 123
2.7.2.9. Quinazoline alkaloids 124
2.7.2.10. Acridone alkaloids 125
2.7.2.11. Pyridine alkaloids 126
2.7.2.12. Sesquiterpene pyridine alkaloids 126
2.7.2.13. Phenyl and phenylpropyl alkaloids 129
2.7.2.14. Indole alkaloids 130
2.7.2.15. Manzamine alkaloids 138
2.8. Biogenesis of alkaloids 141
2.8.1. Chemistry models 141
2.8.2. Biochemistry models 143
2.8.3. Molecular biology models 145
2.8.4. Analytical dilemmas 146
2.9. Methods of alkaloid analysis 147
2.9.1. Methods in history 148
2.9.2. Basic methods and instruments 148
2.9.3. From iodine to enzyme 148
2.9.4. Choice of method and confidence 155
2.9.5. Chemical modification of alkaloids 157
Chapter 3 Biological Significance of Alkaloids 160
1. Alkaloids in biology 160
1.1. From stimulators to inhibitors and destroyers of growth 162
1.2. The effects of stress and endogenous security mechanisms 165
2. Bioactivity 167
2.1. Secrets of life 167
2.2. Life regulation through the high and low cytotoxicity 169
2.3. Haemoglobinization of leukaemia cells 172
2.4. Estrogenic effects 174
2.5. Antimicrobial properties 175
2.6. Anti-parasitic activity 177
3. Biotoxicity 180
3.1. Research evidence 180
3.2. Influence on DNA 181
3.3. Selective effectors of death 182
3.4. Non-toxic to self but deformer for others 183
3.5. Degenerators of cells 185
3.6. Aberrations in cells 186
3.7. Causers of locoism 187
4. Narcotics 188
5. Alkaloids in the immune system 191
6. Genetic approach to alkaloids 194
7. Alkaloids in the evolution of organisms 197
Chapter 4 Applications 200
1. Medicinal applications 201
1.1. Regulation of Na+ ions and channels 203
1.2. Regulation of mescarinic cholinergic receptor 204
1.3. Regulation of acetylcholine esterase 204
1.4. Regulation of opioid and opiate receptors 205
1.5. Regulation of glycine receptors 205
1.6. Regulation of other receptors 205
1.7. Regulation of microtubules of the spindle apparatus 206
1.8. Regulation of microbial activity 206
1.9. Regulation of stimulation 206
1.10. Regulation of schizonticide activity 207
2. Alkaloids as drugs 207
3. Agricultural applications 210
3.1. Alkaloids in food 211
3.2. Alkaloids as biological fertilizers 213
3.3. Alkaloids in plant protection 214
4. Biotechnology 216
4.1. Cell cultures 217
4.2. Root cultures 222
Chapter 5 The Ecological Role of Alkaloids 224
1. Animal sequestration of alkaloids 225
2. Sexual behaviour 231
3. Feeding attraction and deterrence 232
4. A case study: Alkaloids and population changes 233
4.1. Introduction 233
4.2. Material and methods 234
4.2.1. Method of QAs(+) indications 236
4.2.2. Mutational trajectories 237
4.3. Results 238
4.3.1. QAs(+) occurrence and frequency 238
4.3.2. Tendencies of QAs(+) plants to evolve and their MECs 238
4.3.3. Tendencies and dependencies of species 246
4.4. Discussion of case study results 250
Appendix Alkaloid Extraction Protocol 254
References 256
Indices 306
Alkaloid Index 308
Taxonomic Index 322
Author Index 334