Comprehensive Natural Products II: Chemistry and Biology

Description

This work presents a definitive interpretation of the current status of and future trends in natural products—a dynamic field at the intersection of chemistry and biology concerned with isolation, identification, structure elucidation, and chemical characteristics of naturally occurring compounds such as pheromones, carbohydrates, nucleic acids, and enzymes. With more than 1,800 color figures, Comprehensive Natural Products II features 100% new material and complements rather than replaces the original work (©1999).

Reviews the accumulated efforts of chemical and biological research to understand living organisms and their distinctive effects on health and medicine
Stimulates new ideas among the established natural products research community—which includes chemists, biochemists, biologists, botanists, and pharmacologists
Informs and inspires students and newcomers to the field with accessible content in a range of delivery formats
Includes 100% new content, with more than 6,000 figures (1/3 of these in color) and 40,000 references to the primary literature, for a thorough examination of the field
Highlights new research and innovations concerning living organisms and their distinctive role in our understanding and improvement of human health, genomics, ecology/environment, and more
Adds to the rich body of work that is the first edition, which will be available for the first time in a convenient online format giving researchers complete access to authoritative Natural Products content

e9780080453811v1 2
- Cover 2
- Title Page 5
- Copyright Page 6
- Contents 7
- Contributors 9
- Preface 13
- Introduction 15
- Editors in Chief 19
- Volume Editors 21
- 1.01 Overview and Introduction 27
- 1.02 Unsaturated Fatty Acids 31
  - 1.02.1 Introduction 31
  - 1.02.2 Monounsaturated Fatty Acids 33

e9780080453811v1 2
- Cover 2
- Title Page 5
- Copyright Page 6
- Contents 7
- Contributors 9
- Preface 13
- Introduction 15
- Editors in Chief 19
- Volume Editors 21
- 1.01 Overview and Introduction 27
- 1.02 Unsaturated Fatty Acids 31
  - 1.02.1 Introduction 31
  - 1.02.2 Monounsaturated Fatty Acids 33
  - 1.02.3 Methylene-Interrupted Polyunsaturated Fatty Acids 46
  - 1.02.4 Unusual Unsaturated Fatty Acids 50
  - 1.02.5 Summary and Future Prospects 54
  - Abbreviations 54
  - References 55
- 1.03 Prostaglandin Endoperoxide Synthases: Structure, Function, and Synthesis of Novel Lipid Signaling Molecules 61
  - 1.03.1 Introduction 62
  - 1.03.2 Physiological Functions and Regulation of PGHS Isoforms 63
  - 1.03.3 Structural Determinants for Arachidonic Acid Metabolism by PGHS 67
  - 1.03.4 Role of PGHS in the Biosynthesis of Novel Acidic Eicosanoids 73
  - 1.03.5 Biosynthesis, Degradation, and Pharmacology of Prostaglandin-Glycerylesters 79
  - 1.03.6 Biosynthesis, Degradation, and Pharmacology of Prostaglandin-Ethanolamides 81
  - Abbreviations 82
  - 1.03.7 Metabolism of Other Arachidonoyl Amides by PGHS 82
  - 1.03.8 Conclusions 82
  - References 83
- 1.04 Mycolic Acid/Cyclopropane Fatty Acid/Fatty Acid Biosynthesis and Health Relations 91
  - 1.04.1 Introduction 92
  - 1.04.2 Structural Variation, Biosynthesis, and Function of the Core Cell Envelope Mycolic Acids 93
  - 1.04.3 Trehalose-Based Glycolipids 108
  - 1.04.4 Phthiocerol-Based Glycolipids 127
  - 1.04.5 Lipoarabinomannan and Phosphatidylinositides 134
  - 1.04.6 Exotic Glycolipids and Glycopeptidolipids 138
  - 1.04.7 Conclusions and Outlook 157
  - Abbreviations 157
  - References 159
- 1.05 Microbial Type III Polyketide Synthases 173
  - 1.05.1 Introduction 173
  - 1.05.2 Plant Type III PKSs 175
  - 1.05.3 Type III PKSs from Actinobacteria 177
  - 1.05.4 Type III PKSs from Proteobacteria 185
  - 1.05.5 Type III PKSs from Eukaryotic Microbes 189
  - 1.05.6 Conclusions and Future Perspectives 191
  - Abbreviations 193
  - References 194
- 1.06 Plant Type III PKS 197
  - 1.06.1 Introduction 197
  - 1.06.2 Functional Diversity and Catalytic Potential 200
  - 1.06.3 Enzyme Structure and Site-Directed Mutagenesis 231
  - 1.06.4 Protein Engineering 240
  - 1.06.5 Combinational Biosynthesis 241
  - 1.06.6 Conclusions 246
  - Acknowledgments 246
  - Abbreviations 246
  - References 247
- 1.07 Type II PKS 253
  - 1.07.1 Introduction 254
  - 1.07.2 Enzymes of Type II PKS-Derived Natural Products 254
  - 1.07.3 Natural Structural Diversity 265
  - 1.07.4 Artificial Structural Diversity through Combinatorial Biosynthesis 296
  - Glossary 318
  - 1.07.5 Conclusions 318
  - Acknowledgments 318
  - References 319
- 1.08 Structural Enzymology of Polyketide Synthase: The Structure–Sequence–Function Correlation 331
  - 1.08.1 Introduction 331
  - 1.08.2 Fatty Acid Biosynthesis and Fatty Acid Synthase 333
  - 1.08.3 The Type II PKS 336
  - 1.08.4 Structural Enzymology of Individual Type II PKS Enzymes 340
  - 1.08.5 Protein–Protein Interactions and Transport of Polyketide Intermediates between Enzymes 365
  - 1.08.6 Summary and Future Prospects 366
  - Acknowledgments 366
  - Glossary 367
  - Abbreviations 367
  - References 368
  - Nomenclature 368
- 1.09 Fungal Type I Polyketides 373
  - 1.09.1 Introduction 373
  - 1.09.2 Diversity of Fungal Polyketides 374
  - 1.09.3 Biosynthesis of Fungal Polyketides 380
  - 1.09.4 Mixed Polyketide/Nonribosomal Peptides 398
  - 1.09.5 Meroterpenoids 400
  - 1.09.6 Post-PKS Reactions in Fungi 402
  - 1.09.7 Conclusions 404
  - References 406
- 1.10 Type I Modular PKS 411
  - 1.10.1 Introduction to Polyketides 412
  - 1.10.2 Fatty Acid Biosynthesis – Reactions and Enzymes 414
  - 1.10.3 Polyketide Biosynthesis – Reactions and Enzymes 418
  - 1.10.4 Mechanism and Structural Specificity of Precursor Loading within the Modules of the DEBS 425
  - 1.10.5 Experimental Investigation of Stereospecificity of the Reactions of the DEBS Chain-Extension Cycles 429
  - 1.10.6 Studies of the Quaternary Structure of the Type I FAS 435
  - 1.10.7 Studies of the Structure of the DEBS Modules 441
  - 1.10.8 Current Proposals for the Topology of the DEBS Modules and Multienzymes 444
  - 1.10.9 Other Polyketide Synthases 449
  - 1.10.10 Commercial Applications of Genetic Engineering of Modular Polyketide Synthases 464
  - 1.10.11 Future Perspectives 470
  - Abbreviations 472
  - References 473
  - Nomenclature 473
- 1.11 NRPS/PKS Hybrid Enzymes and Their Natural Products 479
  - 1.11.1 Introduction 480
  - 1.11.2 Medicinally Important PK/NRP Natural Products and Pathways 484
  - 1.11.3 Trans-AT Domain Pathways – a Rich Source of Unusual Biochemistry 493
  - 1.11.4 Engineering, Technology Development, and Other Future Directions for Hybrid PK/NRP Systems 507
  - 1.11.5 Conclusions 509
  - Abbreviations 510
  - Acknowledgment 510
  - References 511
- 1.12 Mevalonate Pathway in Bacteria and Archaea 519
  - 1.12.1 Introduction 519
  - 1.12.2 Overview of the Mevalonate Pathway 520
  - 1.12.3 Two Classes of HMG-CoA Reductase 523
  - 1.12.4 Two Types of IPP Isomerase 528
  - 1.12.5 Biosynthetic Gene Clusters of Secondary Metabolites from Actinomycetes 536
  - 1.12.6 Mevalonate Fermentation 537
  - Nomenclature 538
  - 1.12.7 Conclusions 538
  - Abbreviations 538
  - References 539
- 1.13 Methylerythritol Phosphate Pathway 543
  - 1.13.1 Introduction 544
  - 1.13.2 Identification of the Genes and the Enzymes 548
  - 1.13.3 Distribution of the MEP Pathway 568
  - 1.13.4 Openings and Further Developments 570
  - Abbreviations 574
  - Acknowledgments 574
  - References 575
- 1.14 Prenyltransferase 583
  - 1.14.1 Introduction 583
  - 1.14.2 (E)-Prenyltransferases 587
  - 1.14.3 (Z)-Prenyl Diphosphate Synthases 595
  - 1.14.4 Conclusions 605
  - References 606
  - Glossary 606
- 1.15 Advances in the Enzymology of Monoterpene Cyclization Reactions 611
  - 1.15.1 Introduction 611
  - 1.15.2 Cyclization Chemistry 614
  - 1.15.3 Structural Studies 621
  - 1.15.4 Conclusions 631
  - Acknowledgments 631
  - References 632
- 1.16 Sesquiterpenes 635
  - 1.16.1 Introduction 635
  - 1.16.2 Classification of Sesquiterpenes 636
  - 1.16.3 Decorating the Sesquiterpene Scaffolds 656
  - 1.16.4 Future Challenges 661
  - Glossary 662
  - References 664
- 1.17 Diterpenes 669
  - 1.17.1 Introduction 669
  - 1.17.2 Labdane-Type Diterpenes 670
  - 1.17.3 Clerodane- and Halimane-Type Diterpenes 686
  - 1.17.4 Other types of Diterpenes 688
  - 1.17.5 Summary and Future Prospects 694
  - Abbreviations 695
  - References 695
- 1.18 Triterpenes 699
  - 1.18.1 Introduction 699
  - 1.18.2 Cyclization Mechanism 700
  - 1.18.3 Lanosterol/Cycloartenol Synthases 702
  - 1.18.4 Plant Triterpene Synthases 710
  - 1.18.5 Triterpene Tailoring Steps 727
  - 1.18.6 Summary and Future Perspectives 730
  - Abbreviations 731
  - References 731
- 1.19 Bacterial Squalene Cyclase 735
  - 1.19.1 Introduction 735
  - 1.19.2 The Reaction Mechanism 737
  - 1.19.3 The Enzyme Structure 738
  - 1.19.4 Site-Directed Mutagenesis 742
  - 1.19.5 Substrate Recognition and Catalytic Potential 745
  - 1.19.6 Conclusions 755
  - Abbreviations 756
  - References 756
  - Acknowledgments 756
- 1.20 Carotenoids 759
  - 1.20.1 Introduction 759
  - 1.20.2 Biosynthesis of Basic Structures of Carotenoids 760
  - 1.20.3 Biosynthesis of C30 Carotenoids 762
  - 1.20.4 Biosynthesis of C40 Carotenoids 762
  - 1.20.5 Pathway Engineering for Useful Carotenoid Formation in Escherichia coli 771
  - 1.20.6 Pathway Engineering for Useful Carotenoid Formation in Higher Plants 772
  - Acknowledgment 776
  - Nomenclature 776
  - 1.20.7 Conclusion 776
  - References 776
- 1.21 Sterol and Steroid Biosynthesis and Metabolism in Plants and Microorganisms 781
  - 1.21.1 Introduction 781
  - 1.21.2 Sterol and Steroid Biosynthetic Pathways 782
  - 1.21.3 Sterol and Steroid Conjugates 800
  - 1.21.5 Transport 802
  - 1.21.4 Sterol Degradation 802
  - 1.21.6 Molecular Regulation of Sterol Biosynthesis 803
  - 1.21.7 Functions of Steroids 804
  - Abbreviations 805
  - References 806
- 1.22 Isoprenoid in Actinomycetes 815
  - 1.22.1 Introduction 815
  - 1.22.2 Cyclic Isoprenoids 816
  - 1.22.3 Hybrid Isoprenoids 827
  - Abbreviations 837
  - References 837
- 1.23 Lignans (Neolignans) and Allyl/Propenyl Phenols: Biogenesis, Structural Biology, and Biological/Human Health Considerations 841
  - 1.23.1 Introduction 843
  - 1.23.2 Definition and Nomenclature 844
  - 1.23.3 Chemotaxonomical Diversity: Evolutionary Considerations 847
  - 1.23.4 Lignan Early Biosynthetic Steps: 8–89 Phenylpropanoid Coupling 873
  - 1.23.5 Downstream Lignan Metabolism 882
  - 1.23.6 Other Phenylpropanoid Coupling Modes: 8–29, 8–39 (8–59), and 8–O–49-Linked Lignans 904
  - 1.23.7 Allylic (Phenylpropenal) Double Bond Reductases and Phenylcoumaran Benzylic Ether Reductases 906
  - 1.23.8 Norlignan Biosynthesis 915
  - 1.23.9 Allyl-/Propenylphenol Biosynthesis 918
  - 1.23.10 Biological Properties in Planta and in Human Usage 932
  - Acknowledgments 942
  - References 942
- 1.24 Plant Phenolics: Phenylpropanoids 955
  - 1.24.1 Introduction 955
  - 1.24.2 New Enzyme Functions in Phenylpropanoid Metabolism 957
  - 1.24.3 Flavonoids 963
  - 1.24.4 Functional Genomics and Evolution of Phenylpropanoid/Flavonoid Biosynthesis 992
  - References 994
- 1.25 Alkaloids 1003
  - 1.25.2 Classes of Alkaloids 1003
  - 1.25.1 What Is an Alkaloid? 1003
  - 1.25.3 Function and Diversity of Alkaloids 1004
  - 1.25.4 Strategies for Elucidating Alkaloid Biosynthesis 1008
  - 1.25.5 Benzylisoquinoline Alkaloid Biosynthesis 1013
  - 1.25.6 Monoterpene Indole Alkaloid Biosynthesis 1018
  - 1.25.7 Tropane Alkaloid Biosynthesis 1025
  - 1.25.8 Purine Alkaloid Biosynthesis 1027
  - 1.25.9 Conclusions and Outlook 1027
  - Glossary 1029
  - References 1029
- e9780080453811v2 1035
  - Cover 1035
  - Title page 1038
  - Copyright page 1039
  - Contents 1040
  - Contributors 1042
  - Preface 1046
  - Introduction 1048
  - Editors-In-Chief 1052
  - Volume Editors 1054
  - 2.01 Overview and Introduction 1060
  - 2.02 Terrestrial Plants as a Source of Novel Pharmaceutical Agents 1064
    - 2.02.3 Anticancer Compounds 1065
    - 2.02.1 Introduction 1065
    - 2.02.2 Plants as a Source of Bioactive Compounds 1065
    - 2.02.4 Anti-HIV Agents 1081
    - 2.02.5 Antimalarial Compounds 1084
    - 2.02.6 Cardiovascular and Metabolic Diseases 1085
    - 2.02.7 CNS Active Agents 1088
    - References 1091
    - 2.02.8 Outlook and Future Prospects 1091
  - 2.03 Marine Macroalgal Natural Products 1100
    - 2.03.1 Introduction 1100
    - 2.03.2 Isoprenoids 1101
    - 2.03.3 Fatty Acid and Polyketide Metabolites 1110
    - 2.03.4 Shikimate Metabolites 1114
    - 2.03.5 Nonribosomal Peptide Metabolites 1115
    - 2.03.6 Alkaloid Metabolites 1116
    - 2.03.7 Glycolipids 1118
    - Acknowledgments 1120
    - Abbreviations 1120
    - 2.03.8 Conclusion 1120
    - References 1121
    - Nomenclature 1121
  - 2.04 Insect Natural Products 1126
    - 2.04.1 Introduction 1126
    - 2.04.2 Challenges in Arthropod Natural Products Chemistry 1129
    - 2.04.3 Terpenoids 1130
    - 2.04.4 Fatty Acid and Other Polyacetate Derivatives 1137
    - 2.04.5 Polyketides 1142
    - 2.04.6 Alkaloids and Amines 1144
    - 2.04.7 Nucleoside Derivatives 1158
    - 2.04.8 Miscellaneous Compounds 1159
    - 2.04.9 Outlook 1160
    - References 1162
  - 2.05 Terrestrial Microorganisms – Filamentous Bacteria 1168
    - 2.05.1 Introduction 1168
    - 2.05.2 Historical Bacterial Metabolites 1169
    - 2.05.3 Newer Compounds or Compounds with Recently Described Mechanism of Action 1175
    - Abbreviations 1193
    - References 1193
  - 2.06 The Natural Products Chemistry of Cyanobacteria 1200
    - 2.06.1 Introduction 1201
    - 2.06.2 Trends in the Structures of Cyanobacterial Natural Products 1202
    - 2.06.3 Fatty Acid Derivatives from Cyanobacteria 1209
    - 2.06.4 Terpenes 1212
    - 2.06.5 Saccharides and Glycosides 1213
    - 2.06.6 Peptides 1217
    - 2.06.7 Polyketides 1224
    - 2.06.8 Lipopeptides 1228
    - 2.06.9 Conclusion 1241
    - Acknowledgments 1242
    - References 1242
  - 2.07 Myxobacteria – Unique Microbial Secondary Metabolite Factories 1248
    - 2.07.1 Myxobacteria as Producers of Bioactive Secondary Metabolites 1248
    - 2.07.2 Approaches to Exploring the Biosynthetic Potential of Myxobacteria 1251

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