| The Chemistry of Algal Secondary Metabolism | p. 1 |
| Introduction | p. 1 |
| Conceptual Framework | p. 1 |
| Natural Products | p. 1 |
| Natural Product Names | p. 3 |
| Bioactivity of Natural Products | p. 5 |
| Compound Classes | p. 7 |
| General Overview | p. 7 |
| Terpenes | p. 8 |
| Polyketides | p. 9 |
| Amino-Acid-Derived Natural Products | p. 10 |
| Shikimates | p. 11 |
| Miscellaneous Classes of Algal Natural Products | p. 11 |
| Algal Chemistry | p. 11 |
| Natural Products Chemistry of Rhodophyta | p. 12 |
| Natural Products Chemistry of Phaeophyta | p. 14 |
| Natural Products Chemistry of Chlorophyta | p. 16 |
| Natural Products Chemistry of Cyanobacteria and Microalgae | p. 17 |
| Summary | p. 19 |
| References | p. 20 |
| Macroalgal Chemical Defenses and Their Roles in Structuring Tropical Marine Communities | p. 25 |
| Introduction | p. 25 |
| The Tropical Marine Environment | p. 26 |
| Tropical Macroalgal Natural Products | p. 27 |
| Tropical Chemically Defended Macroalgae | p. 28 |
| Tropical Macroalgal Chemical Defenses and Community Structure | p. 29 |
| Are Tropical Macroalgae Better Defended Than Their Counterparts? | p. 39 |
| The Causes and Effects of Ecological Dominance | p. 39 |
| Associational Defenses | p. 40 |
| Chemically Defended Isomorphic Macroalgal Life Stages | p. 41 |
| Intrapopulational Variation | p. 42 |
| Surface Ecology | p. 43 |
| Is Inducible Resistance to Herbivores Common Among Tropical Macroalgae? | p. 45 |
| The Invasive Potential of Chemically Defended Tropical Macroalgae | p. 46 |
| Conclusions | p. 48 |
| References | p. 49 |
| Macroalgal Chemical Defenses and Their Roles in Structuring Temperate Marine Communities | p. 57 |
| Interactions in Diverse Macroalgal Communities | p. 57 |
| Defense Strategies | p. 58 |
| Induced Defenses against Herbivory | p. 60 |
| Within-Plant Variation in Defenses: Watch Your Valuables! | p. 66 |
| Consequences of Algal Defenses to Grazers | p. 68 |
| From Defenses to Herbivore Population Dynamics | p. 68 |
| Defenses as Selective Agents | p. 69 |
| Allelopathy in Space Competition and in Resisting Epibiotism | p. 71 |
| Epibiotism as a Natural Enemy | p. 72 |
| Community Context Matters: Interactions among Hosts, Epibiota, and Grazers | p. 74 |
| Case Study of F. vesiculosus in the Eutrophic Northern Baltic Sea: Genotypically Variable, Plastic Phlorotannins as Chemical Defenses | p. 76 |
| Conclusions | p. 80 |
| References | p. 81 |
| Macroalgal Chemical Defenses in Polar Marine Communities | p. 91 |
| Introduction | p. 91 |
| Western Antarctic Peninsula | p. 92 |
| McMurdo Sound, Antarctica | p. 98 |
| The Arctic | p. 99 |
| References | p. 100 |
| Macroalgal and Cyanobacterial Chemical Defenses in Freshwater Communities | p. 105 |
| Introduction | p. 105 |
| Cyanobacteria and Macroalgae: Evolutionary and Ecological Perspectives | p. 106 |
| Cyanotoxin Structure and Synthesis | p. 107 |
| Hepatotoxins | p. 107 |
| Neurotoxins | p. 108 |
| Macroalgal Secondary Metabolites | p. 110 |
| Inducible Synthesis of Secondary Metabolites | p. 111 |
| Effects on Consumers | p. 111 |
| Allelopathic Effects | p. 112 |
| Allelopathy in Cyanobacteria | p. 112 |
| Allelopathic Effects of A. flos-aquae on a Motile Alga | p. 113 |
| Allelopathy in Algae | p. 113 |
| Secondary Metabolites and Trophic Interactions | p. 114 |
| Bioaccumulation of Metabolites at Higher Trophic Levels | p. 115 |
| Summary | p. 115 |
| References | p. 116 |
| New Perspectives for Addressing Patterns of Secondary Metabolites in Marine Macroalgae | p. 121 |
| Interpreting Patterns of Chemical Defense in the Marine Environment | p. 121 |
| A Brief Review of Macroscale Patterns of Algal Chemical Defenses | p. 122 |
| Patterns of Secondary Metabolites at the Microscale | p. 125 |
| Metabolite Distribution Within the Thallus | p. 125 |
| Temporal Responses Within Algae: Seconds to Weeks | p. 128 |
| Advances in the Characterization of Patterns of Chemical Defenses | p. 130 |
| Phylogeny Meets Ecology | p. 130 |
| Metabolic Similarities Between Algal Groups | p. 132 |
| The Use of Molecular Tools to Characterize Patterns of Gene Response Involved in Macroalgal Defenses | p. 136 |
| Conclusion | p. 138 |
| References | p. 139 |
| Macroalgal Models in Testing and Extending Defense Theories | p. 147 |
| Introduction | p. 147 |
| Defense Theories | p. 148 |
| Optimal Defense Model | p. 148 |
| Carbon-Nutrient Balance Model | p. 149 |
| Growth-Differentiation Balance Model | p. 149 |
| The Status of Defense Models in Terrestrial Plant Ecology | p. 150 |
| Empirical Tests of Defense Theories in Marine Studies | p. 151 |
| Optimal Defense Model | p. 151 |
| Carbon-Nutrient Balance Model | p. 161 |
| Growth-Differentiation Balance Model | p. 163 |
| Tests of Hypotheses from More Than One Model | p. 164 |
| Summary and Conclusions | p. 166 |
| References | p. 167 |
| Ecological and Physiological Roles of Dimethylsulfoniopropionate and its Products in Marine Macroalgae | p. 173 |
| Introduction | p. 173 |
| Dimethylsulfoniopropionate | p. 174 |
| DMSP Synthesis | p. 174 |
| The Distribution of DMSP in Marine Macroalgae | p. 176 |
| Physiological and Ecological Functions of DMSP | p. 177 |
| The DMSP Cleavage Reaction and Its Products | p. 178 |
| The DMSP Cleavage Reaction | p. 178 |
| The Functional Significance of the DMSP Cleavage Reaction | p. 179 |
| Summary | p. 188 |
| References | p. 188 |
| Influence of Algal Secondary Metabolites on Plankton Community Structure | p. 195 |
| Introduction | p. 195 |
| Early Studies | p. 196 |
| General Considerations | p. 197 |
| Specific Aspects | p. 198 |
| Single Metabolites | p. 199 |
| Conclusions | p. 199 |
| References | p. 200 |
| Herbivore Offense in the Sea: The Detoxification and Transport of Secondary Metabolites | p. 203 |
| Introduction | p. 203 |
| Proximate Mechanisms of Herbivore Tolerance | p. 204 |
| Defining "Tolerance" | p. 204 |
| Mechanisms of Detoxification and Transport | p. 205 |
| Detoxification and Macroalgal-Herbivore Interactions | p. 214 |
| Do Detoxification Rates Limit Feeding Rates of Large Grazers? | p. 214 |
| Are Tropical Herbivores More Tolerant of Lipophilic Metabolites Than Are Temperate Herbivores? | p. 215 |
| Is Host Breadth Mediated by Tolerance of Lipophilic Metabolites? | p. 216 |
| Are There Phylogenetic Constraints on Tolerance of Lipophilic Metabolites? | p. 218 |
| Do Herbivores "Eavesdrop" on Their Macroalgal Hosts? | p. 219 |
| Using Population-Level Variation in Herbivore Traits as an Analytical Tool | p. 219 |
| Conclusion | p. 221 |
| References | p. 221 |
| Secondary Metabolite Defenses Against Pathogens and Biofoulers | p. 229 |
| Introduction | p. 229 |
| Defenses Against Settlement and Attachment | p. 230 |
| Larval Attachment Defenses of Ulva reticulata | p. 231 |
| Disruption of Microbial Communication Pathways: An Effective Inhibitor of Settlement and Attachment | p. 233 |
| Lethal and Growth-Inhibitory Antimicrobials | p. 234 |
| Lobophorolide: A Potent Antifungal Chemical Defense | p. 234 |
| Antifungal Chemical Defenses of Penicillus spp | p. 236 |
| Future Perspective and Conclusions | p. 238 |
| References | p. 239 |
| Oxidative Burst and Related Responses in Biotic Interactions of Algae | p. 245 |
| Introduction | p. 245 |
| Reactive Oxygen Species and Detection Methods | p. 246 |
| Inducers and Sources of ROS Emission in Biotic Interactions of Marine Algae | p. 248 |
| Elicitors and Sources of ROS in Terrestrial Plant-Pathogen Interactions | p. 248 |
| A Growing Repertoire of ROS Inducers | p. 249 |
| New Insights into ROS Sources in Algae | p. 249 |
| Oxidative-Burst-Associated Responses | p. 254 |
| Emission of Volatile Halogenated Organic Compounds | p. 254 |
| Lipid Peroxidation and Generation of Oxylipins | p. 255 |
| Phenolics, Cell-Wall Cross-Linking, and Responses to Wounding | p. 256 |
| Gene-Regulated Responses | p. 258 |
| Functions of the Oxidative Burst in an Ecological Context, the Hallmark of Parasite or Disease Resistance | p. 259 |
| Ecological Functions of the Oxidative Burst | p. 259 |
| Toward New Approaches to Test the Ecological Relevance of Oxidative-Burst-Associated Responses | p. 262 |
| Conclusions | p. 263 |
| References | p. 264 |
| Defense Strategies of Algae and Cyanobacteria Against Solar Ultraviolet Radiation | p. 273 |
| Introduction | p. 273 |
| Solar Spectrum and UVR | p. 274 |
| UVR in Aquatic Ecosystems | p. 275 |
| Effects of UVR on Algae | p. 276 |
| Molecular Targets | p. 276 |
| Induction of Reactive Oxygen Species | p. 277 |
| Ultrastructure of Cells | p. 277 |
| Physiological Processes | p. 278 |
| Ecological Consequences | p. 278 |
| Protective Mechanisms to Counteract Harmful UV Effects | p. 279 |
| Avoidance | p. 279 |
| Physiological Acclimation | p. 281 |
| Physical Properties | p. 281 |
| DNA Repair | p. 281 |
| De Novo Protein Biosynthesis | p. 282 |
| Antioxidative Potential | p. 282 |
| Photoprotective Substances | p. 283 |
| Conclusions | p. 291 |
| References | p. 291 |
| Algal Sensory Chemical Ecology | p. 297 |
| Introduction to Sensory Chemical Ecology | p. 297 |
| Sexual Communication | p. 298 |
| Gamete Attraction | p. 298 |
| Inducers of Gamete Production or Release | p. 299 |
| Chemoattraction to Nutrients | p. 300 |
| Sensory Ecology of Ulva Spores | p. 301 |
| Chemical and Physicochemical Modulation of Spore Settlement in Brown Algae | p. 303 |
| References | p. 305 |
| Index | p. 311 |
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