The Ecological Role of Alkaloids

335 Pages·2007·8.04 MB·English

ALKALOIDS – SECRETS OF LIFE
ALKALOID CHEMISTRY, BIOLOGICAL SIGNIFICANCE, APPLICATIONS
AND ECOLOGICAL ROLE
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ALKALOIDS – SECRETS OF LIFE
ALKALOID CHEMISTRY, BIOLOGICAL
SIGNIFICANCE, APPLICATIONS
AND ECOLOGICAL ROLE
Tadeusz Aniszewski
Associate Professor in Applied Botany
Senior Lecturer
Research and Teaching Laboratory of Applied Botany
Faculty of Biosciences
University of Joensuu
Joensuu
Finland
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Firstedition2007
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Contents
List of Figures xi
List of Tables xv
Preface xvii
Chapter 1 Definition, Typology and Occurrence of Alkaloids 1
1. Definition 1
1.1. True alkaloids 6
1.2. Protoalkaloids 6
1.3. Pseudoalkaloids 11
2. Occurrence in nature 12
2.1. The Dogbane botanical family (Apocynaceae) 13
2.2. The Aster botanical family (Asteraceae) 17
2.3. The Logan botanical family (Loganiaceae) 19
2.4. The Poppy botanical family (Papaveraceae) 21
2.5. The Citrus botanical family (Rutaceae) 22
2.6. The Nightshade botanical family (Solanaceae) 25
2.7. The Coca botanical family (Erythroxylaceae) 27
2.8. The Borage botanical family (Boraginaceae) 28
2.9. The Legume botanical family (Fabaceae) 29
2.10. The Monseed botanical family (Menispermaceae) 45
2.11. The Berberry botanical family (Berberidaceae) 46
2.12. The Buttercup botanical family (Ranunculaceae) 47
2.13. The Lily botanical family (Liliaceae) 48
2.14. The Coffee botanical family (Rubiaceae) 49
2.15. The Amaryllis botanical family (Amaryllidaceae) 51
2.16. The Oleaster botanical family (Elaeagnaceae) 53
2.17. The Caltrop botanical family (Zygophyllaceae) 53
2.18. Mushroom 54
2.19. Moss 55
2.20. Fungus and bacter 55
2.21. Animals 57
Chapter 2 Alkaloid Chemistry 61
1. Alkaloids as secondary metabolism molecules 61
2. Synthesis and metabolism 66
2.1. Skeleton diversity 67
2.2. Ornithine-derived alkaloids 73
viii Contents
2.3. Tyrosine-derived alkaloids 76
2.3.1. Mescaline pathway 76
2.3.2. Kreysigine and colchicine pathway 77
2.3.3. Dopamine – cephaeline pathway 78
2.3.4. Galanthamine pathway 78
2.4. Tryptophan-derived alkaloids 78
2.4.1. Psilocybin pathway 79
2.4.2. Elaeagnine, harman and harmine pathway 80
2.4.3. Ajmalicine, tabersonine and catharanthine pathway 81
2.4.4. Vindoline, vinblastine and vincristine pathway 81
2.4.5. Strychnine and brucine pathway 83
2.4.6. Quinine, quinidine and cinchonine synthesis pathway 83
2.4.7. Eserine synthesis pathway 84
2.4.8. Ergotamine synthesis pathway 84
2.5. Nicotinic acid-derived alkaloids 85
2.6. Lysine-derived alkaloids 87
2.6.1. Pelletierine, lobelanine and piperine synthesis pathway 87
2.6.2. The swansonine and castanospermine synthesis pathway 88
2.6.3. The lupinine, lupanine, sparteine and cytisine
synthesis pathway 88
2.7. Methods of analysis 90
2.7.1. Methodological considerations 91
2.7.2 Structural approach 95
2.7.2.1. Piperidine alkaloids 95
2.7.2.2. Indolizidine alkaloids 96
2.7.2.3. Quinolizidine alkaloids 98
2.7.2.4. Pyrrolizidine alkaloids 101
2.7.2.5. Izidine alkaloids 103
2.7.2.6. Pyrrolidine alkaloids 103
2.7.2.7. Tropane alkaloids 103
2.7.2.8. Imidazole alkaloids 104
2.7.2.9. Quinazoline alkaloids 105
2.7.2.10. Acridone alkaloids 106
2.7.2.11. Pyridine alkaloids 107
2.7.2.12. Sesquiterpene pyridine alkaloids 107
2.7.2.13. Phenyl and phenylpropyl alkaloids 110
2.7.2.14. Indole alkaloids 111
2.7.2.15. Manzamine alkaloids 119
2.8. Biogenesis of alkaloids 122
2.8.1. Chemistry models 122
2.8.2. Biochemistry models 124
2.8.3. Molecular biology models 126
2.8.4. Analytical dilemmas 127
2.9. Methods of alkaloid analysis 128
2.9.1. Methods in history 129
2.9.2. Basic methods and instruments 129
2.9.3. From iodine to enzyme 129
Contents ix
2.9.4. Choice of method and confidence 136
2.9.5. Chemical modification of alkaloids 138
Chapter 3 Biological Significance of Alkaloids 141
1. Alkaloids in biology 141
1.1. From stimulators to inhibitors and destroyers of growth 143
1.2. The effects of stress and endogenous security mechanisms 146
2. Bioactivity 148
2.1. Secrets of life 148
2.2. Life regulation through the high and low cytotoxicity 150
2.3. Haemoglobinization of leukaemia cells 153
2.4. Estrogenic effects 155
2.5. Antimicrobial properties 156
2.6. Anti-parasitic activity 158
3. Biotoxicity 161
3.1. Research evidence 161
3.2. Influence on DNA 162
3.3. Selective effectors of death 163
3.4. Non-toxic to self but deformer for others 164
3.5. Degenerators of cells 166
3.6. Aberrations in cells 167
3.7. Causers of locoism 168
4. Narcotics 169
5. Alkaloids in the immune system 172
6. Genetic approach to alkaloids 175
7. Alkaloids in the evolution of organisms 178
Chapter 4 Applications 181
1. Medicinal applications 182
1.1. Regulation of Na+ ions and channels 184
1.2. Regulation of mescarinic cholinergic receptor 185
1.3. Regulation of acetylcholine esterase 185
1.4. Regulation of opioid and opiate receptors 186
1.5. Regulation of glycine receptors 186
1.6. Regulation of other receptors 186
1.7. Regulation of microtubules of the spindle apparatus 187
1.8. Regulation of microbial activity 187
1.9. Regulation of stimulation 187
1.10. Regulation of schizonticide activity 188
2. Alkaloids as drugs 188
3. Agricultural applications 191
3.1. Alkaloids in food 192
3.2. Alkaloids as biological fertilizers 194
3.3. Alkaloids in plant protection 195