Outstanding Marine Molecules: Chemistry, Biology, Analysis -- Contents -- List of Contributors -- Foreword -- Preface -- Part One: Outstanding Marine Molecules from a Chemical Point of View -- 1 Marine Cyanotoxins Potentially Harmful to Human Health -- 1.1 Introduction -- 1.2 Marine Cyanobacteria as Causative Agent of Ciguatera-Like Poisoning -- 1.2.1 Ciguatera Fish Poisoning -- 1.2.2 Ciguatera Shellfish Poisoning (CSP): A New Ecotoxicological Phenomenon -- 1.2.3 Ciguatera-Like Poisonings Involve Complex Mixtures of Cyanotoxins -- 1.2.3.1 Ciguatoxins and Homoanatoxin -- 1.2.3.2 Ciguatoxins and Saxitoxins -- 1.2.3.3 Ciguatoxins and Palytoxins -- 1.3 Marine Cyanobacteria: A Potential Risk for Swimmers -- 1.4 Microcystins Could also be Found in the Sea -- 1.5 Risk of Neurodegenerative Disease in the Sea -- 1.6 Conclusion and Future Prospects -- Acknowledgments -- References -- 2 Outstanding Marine Biotoxins: STX, TTX, and CTX -- 2.1 Introduction -- 2.2 Saxitoxins (STXs) in Paralytic Shellfish Poisoning -- 2.2.1 Causes of Paralytic Shellfish Poisoning -- 2.2.2 Saxitoxins (STXs) -- 2.2.2.1 Chemical Aspects of the STXs -- 2.2.2.2 Detection of PSP Toxins -- 2.2.2.3 Poisoning Records -- 2.3 Tetrodotoxin (TTX) in Puffer Fish Poisoning (PFP) -- 2.3.1 Puffer Fish Poisoning (PFP) -- 2.3.1.1 Chemical Aspects of TTX -- 2.3.1.2 Detection of TTXs -- 2.4 Ciguatoxin (CTX) in Ciguatera Fish Poisoning (CFP) -- 2.4.1 Ciguatera Fish Poisoning (CFP) -- 2.4.2 Ciguatoxins -- 2.4.2.1 Chemical Aspects -- 2.4.2.2 Detection of CTX Toxins -- 2.4.2.3 Poisoning Records -- 2.4.2.4 Persistence and Recurrence of Symptoms -- 2.4.2.5 Fish Containing Ciguatoxins -- 2.4.2.6 Qualitative and Quantitative Methods for Toxins Detection -- 2.5 Conclusions -- References -- 3 Impact of Marine-Derived Penicillium Species in the Discovery of New Potential Antitumor Drugs -- 3.1 Introduction.

3.2 Molecules Isolated from Marine-Derived Penicillium Species With Potent Cytotoxic Activity -- 3.3 Marine-Derived Cytotoxic Penicillium -- 3.3.1 Where Were Marine-Derived Penicillium Searched and Isolated? -- 3.3.2 Which Penicillium Species? -- 3.4 What are these Promising Molecules from Marine Penicillium? -- 3.4.1 Statistics -- 3.4.2 Focus on Interesting Molecules -- 3.4.2.1 Cytotoxic Alkaloids: The Example of Communesins -- 3.4.3 Cytotoxic Alkaloids/Diketopiperazine Compounds: Examples of Fructigenine A and Verticillin Derivatives -- 3.4.3.1 Fructigenine A (= Rugulosovin B = Puberulin) -- 3.4.3.2 Verticillin A and Derivatives -- 3.4.4 Cytotoxic Sesquiterpenes: Ligerin, a Chlorinated Sesquiterpene -- 3.4.4.1 Ligerin is Produced by a New Species of Penicillium -- 3.4.4.2 Isolation of Ligerin -- 3.4.4.3 The Chlorine Atom: The Originality of Ligerin's Chemical Structure -- 3.4.4.4 The Many Structural Analogs of Ligerin -- 3.4.4.5 Ligerin Semisynthesis -- 3.4.4.6 Bioactivities -- 3.5 Conclusions -- References -- 4 Astonishing Fungal Diversity in Deep-Sea Hydrothermal Ecosystems: An Untapped Resource of Biotechnological Potential? -- 4.1 Introduction -- 4.2 Deep-Sea Hydrothermal Vents as Life Habitats -- 4.2.1 Generation of Marine Hydrothermal Systems: A Story of Interactions -- 4.2.2 Different Vent-Fluid Compositions Shaping Different Ecological Niches -- 4.2.3 Hydrothermal Lifestyles At the Macro- and Microscopic Scale -- 4.3 The Five "W"s of Marine Fungi: Who? What? When? Where? Why? -- 4.3.1 Definition and Novel Concept -- 4.3.2 Patterns of Distribution -- 4.3.3 Ecological Roles -- 4.3.4 Origin of Marine Fungi -- 4.4 Fungi in Deep-Sea Hydrothermal Vents -- 4.4.1 Hydrothermal Vents as Life Oases for Fungi -- 4.4.2 Physiological Adaptations -- 4.4.3 Biotechnological Potential -- 4.5 Conclusions -- Acknowledgments -- References.

5 Glycolipids from Marine Invertebrates -- 5.1 Introduction -- 5.2 Glycosphingolipids from Marine Invertebrates: Occurrence, Characterization, and Biological Activity -- 5.2.1 α-Glycopyranosylceramides -- 5.2.1.1 α-Monoglycosylceramides -- 5.2.1.2 α-Diglycosylceramides -- 5.2.1.3 α-Triglycosylceramides -- 5.2.1.4 α-Tetraglycosylceramides -- 5.2.2 β-Glycopyranosylceramides -- 5.2.2.1 β-Glycopyranosylceramides with Saturated, Mono-, and Diunsaturated Sphingoid Bases -- 5.2.2.2 β-Glycopyranosylceramides with Triunsaturated Sphingoid Bases -- 5.2.3 Biological and Pharmacological Properties of GSLs from Marine Invertebrates -- 5.2.3.1 Immunostimulating and Antitumor Properties of α-Galactosylceramides -- 5.2.3.2 Biological Activity of β-Glycosylceramides -- 5.3 Gangliosides -- 5.3.1 Occurrence and Structure -- 5.3.1.1 Inositolphosphoceramide Gangliosides -- 5.3.1.2 Lactosylceramide Gangliosides -- 5.3.1.3 Glucosylceramide Gangliosides -- 5.3.2 Biological Activity -- 5.3.3 Conclusion -- 5.4 Atypical Glycolipids -- 5.4.1 Occurrence and Structure -- 5.4.2 Biological Activity -- 5.4.3 Conclusion -- 5.5 General Conclusion -- List of Abbreviations -- References -- 6 Pigments of Living Fossil Crinoids -- 6.1 The Discovery of Stalked Crinoids -- 6.2 Anthraquinonic Pigments of Stalked Crinoids -- 6.3 Axial Chirality of Gymnochromes and Hypochromines -- 6.4 Towards a Fungal Origin of Gymnochromes? -- 6.5 Biological Activities of Gymnochromes -- 6.6 Perspectives -- References -- Part Two: Outstanding Marine Molecules from an Ecological Point of View -- 7 Bacterial Communication Systems -- 7.1 Coordination of Multicellular Behavior in Bacteria -- 7.2 The Repertoire of Chemical Signals -- 7.3 Molecular Mechanisms of QS -- 7.4 The Effective Range of QS-Regulated Processes -- 7.5 The Inhibition of QS: Quorum Quenching.

7.6 Examples of Cross-Kingdom Signaling in the Marine Environment -- 7.6.1 Chemical Defense of the Red Seaweed Delisea pulchra -- 7.6.2 The Mutualistic Association of Vibrio .scheri with the Hawaiian Bobtail Squid -- 7.6.3 Exploitation of Bacterial QS During Settlement of Marine Spores and Invertebrate Larvae -- 7.7 "-Omic" Approaches to QS -- 7.8 Concluding Remarks -- References -- 8 Domoic Acid -- 8.1 Historical Background -- 8.2 Case Studies -- 8.2.1 Case Study #1: The 1987 Outbreak on Prince Edward Island -- 8.2.2 Case Study #2: The 1991 Bird Intoxication Event in California -- 8.2.3 Case Study #3: Massive Sea Lion Mortality in Just a Few Weeks -- 8.3 Chemistry -- 8.3.1 Physico-Chemical Properties -- 8.3.2 Structure Determination -- 8.3.2.1 The Kainic Acid Family -- 8.3.2.2 Nuclear Magnetic Resonance (NMR) Spectroscopy -- 8.3.2.3 Mass Spectrometry (MS) -- 8.3.2.4 UV spectroscopy (UV) -- 8.3.3 Extraction, Separation, Purification, and Detection of DA -- 8.3.3.1 Extraction and Cleanup -- 8.3.3.2 Separation and Purification -- 8.3.3.3 Detection, Quantification, and Monitoring in Food Samples -- 8.3.3.4 Immunological Method -- 8.3.4 Domoic Acid and Related Molecules -- 8.3.5 Synthesis -- 8.3.6 Biosynthesis -- 8.3.6.1 Labeled Precursor Investigations -- 8.3.6.2 Regulation of DA Production -- 8.3.7 Degradation -- 8.3.7.1 Photodegradation -- 8.3.7.2 Photo-oxidative Degradation -- 8.3.7.3 Bacterial and Enzymatic Degradation -- 8.4 DA-Producing Organisms -- 8.4.1 Red Algae -- 8.4.2 Diatoms -- 8.5 Molecular Basis of DA Acute and Chronic Poisoning -- 8.5.1 The Kainoids' Mode of Action -- 8.5.1.1 Glutamate Receptors -- 8.5.2 Short- and Long-term Neurological Problems Associated with DA -- 8.5.2.1 Mammal Studies -- 8.5.3 Cures Against ASP -- 8.6 Understanding and Predicting Toxigenic Diatom Blooms (Macroscopic Scale).

8.7 Natural Factors that Enhance Bloom Formation and/or DA Production -- 8.7.1 Silicon -- 8.7.2 Phosphorus -- 8.7.3 Nitrogen -- 8.7.4 Iron -- 8.7.5 The Role of Bacteria in the Biosynthesis of DA by Toxigenic Diatoms -- 8.8 Functional Genomics of Diatoms -- 8.8.1 The Key to the Evolutionary Success of Diatoms -- 8.8.2 Genomics of DA Biosynthesis and Regulation Networks -- 8.8.2.1 Genomic Aspects -- 8.8.2.2 Transcriptomics of DA-Producing Diatoms -- 8.9 Conclusions -- Acknowledgments -- References -- 9 Algal Morpho-Inducers -- 9.1 Introduction -- 9.1.1 Marine Macroalgae: Different Evolutionary Histories Leading to Similar Morphologies -- 9.1.2 Macroalgal Morphologies and Adaptation -- 9.1.3 What Exactly does the Term "Algal Morpho- Inducer" Cover? -- 9.2 Morpho-Inducers of Animals and Land Plants Produced by Macroalgae -- 9.2.1 Algal Compounds as Morpho-Inducers of Animals -- 9.2.2 Algal Compounds as Morpho-Inducers of Land Plants: Phytohormones -- 9.2.2.1 Auxins -- 9.2.2.2 Cytokinin -- 9.3 Morpho-Inducers of Macroalgae -- 9.3.1 Are Macroalgal Phytohormones also Morpho- Inducers on Algae? -- 9.3.2 Morpho-Inducers of Macroalgae Produced by Bacteria -- 9.4 Conclusions -- Acknowledgment -- References -- 10 Halogenation and Vanadium Haloperoxidases -- 10.1 Introduction -- 10.2 Biochemical Characterization of Vanadium- Dependent Haloperoxidases (VHPOs) -- 10.2.1 Occurrence of VHPO Activities in Living Organisms -- 10.2.2 Enzymatic Assays and Biochemical Properties -- 10.2.3 Biological Functions of VHPOs -- 10.3 Structural Characterization of VHPOs -- 10.3.1 Protein Sequences of VHPOs -- 10.3.2 Overall Quaternary Structures of VHPOs -- 10.3.3 Tertiary Structure of VHPOs -- 10.3.4 Active Site Structure of VHPOs -- 10.3.5 Fine Structure and Vanadate Coordination into the Active Site -- 10.4 Catalytic Cycle and Halide Specificity.

10.4.1 Acid Phosphatases, "Cousins" of VHPOs.