Natural Products -- Contents -- Contributors -- Section I Natural Products in the Natural World -- Part 1 Role and Reason -- 1 The Role of Phytochemicals in Relationships of Plants with Other Organisms -- 1.1 Introduction -- 1.2 Glucosinolates -- 1.2.1 Glucosinolates Affect Insect-Plant Relationship -- 1.2.2 Glucosinolates in Plant Immunity -- 1.3 Benzoxazinone Glucosides -- 1.4 Strigolactones -- 1.5 Phytoalexins - Inducible Defense Metabolites -- 1.5.1 Phenyalanine-derived Phytoalexins -- 1.5.2 Phytoalexins in Brassicaceae -- 1.6 Conclusions -- References -- 2 Designer Microbial Ecosystems - Toward Biosynthesis with Engineered Microbial Consortia -- 2.1 Introduction -- 2.2 Bacterial Cell-to-Cell Communication via Quorum-Sensing Systems -- 2.3 Engineering Population Control into Designer Bioproduction Consortia -- 2.4 Control and Optimization of Bioproduction Consortia -- 2.5 Design of Synthetic Microbial Consortia for Biosynthesis -- 2.6 Conclusions -- Acknowledgments -- References -- 3 Marine Natural Products - Chemical Defense/Chemical Communication in Sponges and Corals -- 3.1 Introduction -- 3.2 Chemical Communication between the Organism and Its Environment -- 3.2.1 Feeding Deterrents -- 3.2.2 Compounds Inducing Larvae Settlement -- 3.2.3 Photoprotective and Antioxidant Compounds -- 3.2.4 Antifouling Compounds -- 3.2.5 Antimicrobial Compounds -- 3.3 Mediating Communication between Host and Microbial Associates -- 3.3.1 Chemical Control by the Host of Its Microbial Partners -- 3.3.2 Chemical Resistance of the Microbial Partners to the Host Digestion -- 3.3.3 Chemical Defense of the Host by Associated Microorganisms -- 3.4 Chemical Communication within the Host Microbial Compartment -- 3.4.1 Molecules Involved in Quorum Sensing -- 3.4.2 Molecules Involved in Bacterial Antagonisms -- 3.5 Conclusions and Perspectives -- References.

Part 2 Self-Protection - Avoiding Autotoxicity -- 4 How Plants Avoid the Toxicity of Self-Produced Defense Bioactive Compounds -- 4.1 Introduction -- 4.2 Sequestration and Excretion -- 4.2.1 Vacuolar Sequestration -- 4.2.2 Extracellular Excretion -- 4.3 Genomic Clustering -- 4.4 Target Mutation-based Mechanism -- 4.5 Predicting Drug Resistance in Other Organisms -- Acknowledgments -- References -- Part 3 Fishing and Pharming -- 5 Marine Bioprospecting -- 5.1 Introduction -- 5.2 International Treaties and Permit Issues -- 5.3 Techniques and Types of Collection -- 5.4 Screening Extracts vs. Fractions vs. Compounds -- 5.5 Chemical and Biological Screening Methods -- 5.6 Innovations on the Horizon -- 5.7 Conclusions -- Acknowledgments -- References -- 6 Myxobacteria: Chemical Diversity and Screening Strategies -- 6.1 Introduction -- 6.2 Natural Products from Myxobacteria: Chemistry and Biological Activity, a Review of Publications Since 2009 -- 6.2.1 Peptides -- 6.2.2 Macrolides -- 6.2.3 Polyketides -- 6.2.4 Miscellaneous -- 6.3 Screening for New Scaffolds -- 6.3.1 Screening for New Antimicrobials (Bioassay-Guided Fractionation) -- 6.3.2 Mining New Myxobacterial Taxa and Structure-Guided Isolation: The Aethearmides -- 6.3.3 Genome- and Metabolome-Mining: Myxoprincomide -- 6.4 Conclusions -- Acknowledgment -- References -- 7 Fungal Endophytes of Grasses and Morning Glories, and Their Bioprotective Alkaloids -- 7.1 Introduction -- 7.2 Taxonomy of Clavicipitaceae and Host Grasses -- 7.3 Symbiosis Growth, Fruiting, and Pathogenesis -- 7.4 Endobiotic, Epibiotic, and Ectobiotic Growth -- 7.5 Phylogenetic Relationships -- 7.6 Ergot Alkaloids -- 7.7 Indole-Diterpenes -- 7.8 Peramine -- 7.9 Loline Alkaloids -- 7.10 Conclusions -- References.

8 Fungal-Actinomycete Interactions - Wakening of Silent Fungal Secondary Metabolism Gene Clusters via Interorganismic Interactions -- 8.1 Introduction -- 8.2 Microbial Regulatory Interactions -- 8.3 Interorganismal Interaction and Chromatin-Based Gene Regulation -- 8.4 Conclusions -- References -- 9 Secondary Metabolites Produced by Plant Pathogens -- 9.1 Introduction -- 9.2 Bacterial Secondary Metabolites and Plant Disease -- 9.3 Fungal Secondary Metabolites as Host-Selective Toxins -- 9.4 A Secondary Metabolite as a Fungal Avirulence Factor -- 9.5 Non-Host-Selective Toxins and Plant Disease -- 9.6 Secondary Metabolite Gene Clusters and Horizontal Gene Transfer -- 9.7 Secondary Metabolite Toxins as Protection Against Predation -- 9.8 Conclusions and Future Directions -- Acknowledgments -- References -- Section II From Genes to Molecules -- Part 1 Reading the Genome -- 10 Analyzing Fungal Secondary Metabolite Genes and Gene Clusters -- 10.1 Introduction -- 10.2 Tools for Bioinformatics Analyses of Fungal SM Biosynthetic Pathways -- 10.3 From Genes to Chemical Structures -- 10.3.1 Polyketide Synthases -- 10.3.2 Nonribosomal Peptide Synthetases -- 10.3.3 PKS-NRPS Hybrids -- 10.3.4 Terpenoids -- 10.3.5 Cooperation among Classes of Core SM Genes -- 10.4 Prospects -- Acknowledgments -- References -- Part 2 Biosynthesis and Heterologous Expression -- 11 RiPPs: Ribosomally Synthesized and Posttranslationally Modified Peptides -- 11.1 Introduction -- 11.2 Lanthipeptides -- 11.2.1 Bioengineering Studies in Native Producers and Heterologous Hosts -- 11.2.2 In vivo engineering of lanthipeptides in E. coli -- 11.2.3 In vitro engineering of lanthipeptides -- 11.3 Linear Azol(in)e-Containing Peptides (LAPs) -- 11.4 Thiopeptides -- 11.5 Cyanobactins -- 11.6 Lasso Peptides -- 11.7 Microviridins -- 11.8 Sactipeptides: Peptides Crosslinked by Cys to a-Carbon Linkages.

11.9 Summary and Outlook -- References -- 12 Polyketide Synthase: Sequence, Structure, and Function -- 12.1 Introduction -- 12.2 Similarity and Differences between PKS and FAS -- 12.3 Sequence-Structure-Function Relationship of PKS Domains -- 12.3.1 Acyltransferase (AT) -- 12.3.2 Ketosynthase (KS) -- 12.3.3 Ketoreductase (KR) -- 12.3.4 Dehydratase (DH) -- 12.3.5 Enoylreductase (ER) -- 12.3.6 Aromatase/Cyclase (ARO/CYC) -- 12.3.7 Product Template Domain (PT) -- 12.3.8 Thioesterase (TE) -- 12.3.9 Acyl Carrier Protein (ACP) -- 12.4 ACP and Sequestration Hypothesis of FAS and PKS -- 12.5 Conclusion and Future Directions -- References -- 13 Manipulation of Fungal Natural Product Pathways -- 13.1 Introduction -- 13.2 Precursor-Directed Biosynthesis and Mutasynthesis -- 13.3 Gene Knockout and Silencing -- 13.4 Heterologous Expression -- 13.5 Yeast Expression -- 13.6 Gene Cluster Expression -- 13.7 Epigenetic Remodeling -- 13.8 Perspective -- References -- 14 Production of Therapeutic Products -- 14.1 Introduction -- 14.2 The Production Host and the Influence on Process Development -- 14.2.1 Genetic, Metabolic, and Process Engineering of the Natural Product Production Host -- 14.2.2 Current Production Routes: How Are Common Natural Products Produced? -- 14.3 Heterologous Natural Product Biosynthesis -- 14.4 Conclusions and Future Directions -- References -- Part 3 Regulation: Waking Sleeping Pathways -- 15 Waking Sleeping Pathways in Filamentous Fungi -- 15.1 Introduction -- 15.2 Discovery -- 15.3 One Strain Many Compounds -- 15.4 Interspecies Crosstalk -- 15.5 Molecular Manipulation -- 15.6 Epigenetic Manipulation -- 15.7 Heterologous Expression -- 15.8 Conclusions and Future Directions -- References -- Section III Evolving Enzymes, Evolving Pathways: Synthetic Biology -- Part 1 Chemical Diversification.

16 The Oxidosqualene Cyclases: One Substrate, Diverse Products -- 16.1 Introduction -- 16.2 Animal and Fungal Oxidosqualene Cyclases -- 16.3 Plant Oxidosqualene Cyclases -- 16.4 Bacterial Squalene Cyclases -- 16.5 Conclusions and Future Directions -- References -- 17 Harnessing Sugar Biosynthesis and Glycosylation to Redesign Natural Products and to Increase Structural Diversity -- 17.1 Introduction -- 17.2 Deoxysugar Biosynthesis -- 17.3 Deoxysugar Transfer -- 17.4 Deoxysugar Modification -- 17.4.1 Altering the Glycosylation Pattern by Combinatorial Biosynthesis -- 17.5 In Vitro Glycorandomization -- 17.6 Conclusions and Prospects for the Future -- Acknowledgments -- References -- Part 2 Evolving Pathways -- 18 Evolutionary Mechanisms Involved in Development of Fungal Secondary Metabolite Gene Clusters -- 18.1 Introduction -- 18.2 Complex Evolution of Fungal Secondary Metabolism Gene Clusters: Two Case Studies -- 18.2.1 Genetic Rearrangements within Aflatoxin and Related Gene Clusters -- 18.2.2 Evolution of the ACE1 Gene Cluster in Ascomycetes -- 18.2.3 Similar Mechanisms Occur in Other Secondary Metabolism Gene Clusters -- 18.3 Conclusion -- References -- Part 3 Synthetic Biology -- 19 Synthetic Biology of Natural Products -- 19.1 Introduction -- 19.2 Computer-Aided Pathway Engineering -- 19.2.1 Predicting Pathways to Produce Desired Compounds -- 19.2.2 Enzyme Design for Novel Chemistry -- 19.2.3 Computational Detection of Biosynthetic Units in Microbial Genomes -- 19.3 Rewriting the Genetic Code -- 19.3.1 Chemical Synthesis of Huge Gene Clusters -- 19.3.2 Rapid Assembly of Engineered Pathways -- 19.3.3 Synthesis of Entire Microbial Genomes -- 19.4 Designer Cell Factories for Natural Products -- 19.4.1 Transplantation of Production Pathways to Heterologous Hosts -- 19.4.2 Optimization of Heterologous Pathways for Overproduction.

19.4.3 Refactoring of Natural Pathways for Facilitated Engineering.