Studies in Natural Products Chemistry (eBook)

Front Cover 1
Studies in Natural Products Chemistry: Volume 34 Bioactive Natural Products (Part N) 4
Copyright Page 5
Table of Contents 10
Foreword 6
Preface 8
Contributors 12
Bioactive Natural Products 16
Chapter 1 Antitumor agent 248. Chemistry and antitumor activity of tylophorine-related alkaloids 18
INTRODUCTION 18
ISOLATION OF TYLOPHORA ALKALOIDS FROM MEDICINAL PLANTS 19
PHYSICAL & SPECTRAL DATA OF TYLOPHORA ALKALOIDS
TOTAL SYNTHESIS OF TYLOPHORINE-RELATED ALKALOIDS 25
SAR OF TYLOPHORINE-RELATED ALKALOIDS 36
ANTITUMOR ACTIVITY OF TYLOPHORA ALKALOIDS 40
MECHANISM OF ANTITUMOR ACTIVITY 42
CONCLUSION 47
ACKNOWLEDGEMENT 47
REFERENCES 47
Chapter 2 Antitumor and antimetastatic actions of various natural products 50
INTRODUCTION 50
REFERENCES 90
Chapter 3 Natural stilbenes and analogues as antineoplastic agents 92
INTRODUCTION 92
1. CHEMISTRY 95
2. BIOLOGICAL ACTIVITIES 126
ACKNOWLEDGEMENTS 139
REFERENCES 139
Chapter 4 Discoveries of the diels-alderases 144
1. INTRODUCTION 144
2. HISTORICAL BACKGROUND 145
3. BIOSYNTHETIC STUDIES OF DIELS-ALDER TYPE PHYTOTOXINS 154
4. DIELS-ALDERASE IN THE BIOSYNTHESIS OF SOLANAPYRONES 159
5. DIELS-ALDERASE IN BIOSYNTHESIS OF MACROPHOMIC ACID 165
6. DIELS-ALDERASE IN THE BIOSYNTHESIS OF LOVASTATIN 177
7. OTHER BIOSYNTHETIC AND SYNTHETIC STUDIES OF DIELS-ALDER TYPE NATURAL PRODUCTS 178
8. CONCLUSION AND PERSPECTIVES 180
ACKNOWLEDGMENTS 181
REFERENCES 182
Chapter 5 Lipids of membranes: Chemistry, biological role and applications as drug carriers 188
LIPIDS 188
THE STRUCTURE OF BIOMEMBRANES 199
LIPIDIC DRUG CARRIERS 207
REFERENCES 216
Chapter 6 Metabolism of plant hormones cytokinins and their function in signaling, cell differentiation and plant development 218
INTRODUCTION 218
STRUCTURAL DIVERSITY OF CYTOKININS 219
ANTICYTOKININS 222
PHYSIOLOGICAL FUNCTION OF CYTOKININS 223
CYTOKININ BIOSYNTHESIS 227
CYTOKININ METABOLISM 230
DEGRADATION OF CYTOKININS 234
CYTOKININ AS A SIGNAL MOLECULE 245
CYTOKININS AS REGULATORS OF GENE EXPRESSION 253
CYTOKININ TRANSPORT 256
INTERACTION WITH OTHER PHYTOHORMONES 257
CYTOKININ ANALYSIS 260
PRACTICAL APPLICATION OF CYTOKININS 263
ABBREVIATIONS 265
ACKNOWLEDGEMENTS 267
REFERENCES 267
Chapter 7 (+)-Biotin: A challenge for industrially viable total synthesis of natural products 280
INTRODUCTION 280
CYANOHYDRIN METHOD 285
STRECKER METHOD I 298
STRECKER METHOD II 302
CONCLUSION 316
ABBREVIATIONS 317
REFERENCES 318
Chapter 8 Biotechnology for the production of plant natural products 324
INTRODUCTION 324
GENETIC TRANSFORMATION TECHNIQUES 326
STRATEGIES FOR THE GENETIC MODIFICATION OF METABOLIC PATHWAYS 332
MODIFICATION OF METABOLIC PATHWAYS 340
FUTURE PERSPECTIVES 391
ACKNOWLEDGEMENTS 393
REFERENCES 393
Chapter 9 Roles of insect and mammal pheromones: Vomeronasal receptors 408
1. INTRODUCTION AND CONCEPT OF PHEROMONES 408
2. CHEMICAL SIGNALS AS A COMMUNICATION PATHWAY. CHEMOSIGNALS AND DETECTION MODELS 410
3. BIOSYNTHESIS OF PHEROMONES 414
4. ISOLATION OF PHEROMONES 423
5. THE ROLE OF PHEROMONES IN INSECT CONTROL AND MONITORING OF PESTS 426
6. SYNTHESIS OF PHEROMONES 430
7. STEREOCHEMISTRY – BIOACTIVITY RELATIONSHIPS 437
8. SYNERGISM BETWEEN PHEROMONES AND HOST PLANT VOLATILES 439
9. PHEROMONES IN HUMANS (VNO) AND ANIMALS 444
10. BIOLOGICAL ASSAYS 450
11. CONCLUDING REMARKS 453
ACKNOWLEDGEMENTS 454
REFERENCES 455
Chapter 10 Stilbenoids: Chemistry and bioactivities 468
1. INTRODUCTION 468
2. STRUCTURES AND DISTRIBUTION 469
3. ISOLATION AND IDENTIFICATION TECHNIQUES APPLIED 574
4. CONFORMATION, ABSOLUTE CONFIGURATIONS AND SOME SPECTRAL CHARACTERISTICS 576
5. BIOSYNTHESIS 579
6. CHEMICAL SYNTHESIS 587
7. BIOLOGICAL ACTIVITY 601
ABBREVIATIONS 626
ACKNOWLEDGEMENTS 628
REFERENCES 628
Chapter 11 Tissue culture of medicinal plants: Micropropagation, transformation and production of useful secondary metabolites 662
INTRODUCTION 662
1. MICROPROPAGATION OF BRAZILIAN IPECAC 664
2. Production of useful secondary metabolites in callus and root organ cultures 699
3. Transformation and production of useful secondary metabolites 713
ABBREVIATIONS 763
ACKNOWLEDGEMENTS 763
REFERENCES 764
Chapter 12 Isoquinuclidines: A review of chemical and pharmacological properties 768
1. INTRODUCTION 768
2. PHARMACOLOGICAL PROPERTIES OF ISOQUINUCLIDINE ANALOGS 770
3. METHODS OF CHEMICAL SYNTHESIS OF ISOQUINUCLIDINE AND ANALOGS 783
CONCLUSION 798
ABBREVIATIONS 799
REFERENCES 799
Chapter 13 Hyaluronic acid: Its function and degradation in in vivo systems 804
INTRODUCTION 805
OCCURRENCE OF HA IN LIVING ORGANISMS AND ITS FUNCTIONS 806
BIOSYNTHESIS OF HA IN LIVING ORGANISMS AND IN VITRO 818
BIOLOGICAL ACTIVITY OF HA AND ITS USE IN MEDICINE 829
HA CATABOLISM IN LIVING ORGANISMS AND UNDER IN VITRO CONDITIONS 836
DEGRADATION OF HYALURONIC ACID BY ROS IN INFLAMMATORY DISEASES 844
METHODS OF CHARACTERIZATION OF PHYSICO-CHEMICAL PROPERTIES OF HYALURONAN 858
CHARACTERIZATION OF MOLAR MASS AND SIZE OF HA 863
METHODS OF DETECTION OF HA DEGRADATION PRODUCTS 878
CONCLUSION 886
ABBREVIATIONS AND SYMBOLS 887
ACKNOWLEDGEMENTS 889
REFERENCES 889
Chapter 14 High altitude plants, chemistry of acclimation and adaptation 898
1.- INTRODUCTION 898
2.- THE HIGH ELEVATION HABITATS 901
3.- CHALLENGES TO PLANT LIFE: THE PHYSICAL GRADIENTS 905
4.- THE CHEMISTRY OF NUTRIENTS AT HIGH ELEVATION 928
5.- UV-IRRADIANCE 958
6.- CONCLUDING REMARKS 983
7.- REFERENCES 984
Subject Index 998