Fusetani / Clare Antifouling Compounds

1. Auflage 2006
ISBN: 978-3-540-30016-8
Verlag: Springer Berlin Heidelberg
Format: PDF
Kopierschutz: 1 - PDF Watermark

E-Book, Englisch, Band 42, 226 Seiten

Reihe: Progress in Molecular and Subcellular Biology

Awareness of the dangers of toxic components in antifouling coatings has raised interest in the potential for nontoxic alternatives. Marine organisms from bacteria to invertebrates and plants use chemicals to communicate and defend themselves. This book explores natural based antifoulants, their ecological functions, methods of characterisation and possible uses in antifouling. The text takes on the challenge of identifying such compounds, designing sustainable production and incorporating them into antifouling coatings.

Autoren/Hrsg.

Fusetani, Nobuhiro

Clare, Anthony S.

Inhaltsverzeichnis

1;Contents;10
2;Defense of Benthic Invertebrates Against Surface Colonization by Larvae: A Chemical Arms Race;15
2.1;Introduction;15
2.1.1;1.1;15
2.1.2;Multiple Levels of Antifouling Defense;15
2.1.3;1.2;16
2.1.4;Overview of the Fouling Process;16
2.1.5;1.3;17
2.1.6;Biofouling as a Sequential Ecological Process;17
2.1.7;1.4;19
2.1.8;Ecological Importance of Antifouling Defense;19
2.1.9;Mechanisms;19
2.2;The Role of Biofilms and their Constituent Microbes in;20
2.3;The Role of Biofilms and their Constituent Microbes in Fouling;20
2.3.1;2.1;21
2.3.2;Interpreting the Effects of Biofilms on Larval Settlement;21
2.3.3;2.2;23
2.3.4;Specific Bacterial Strains within Biofilms as Positive Cues for;23
2.3.5;Settlement of Fouling Larvae;23
2.4;Modulation of Surface Bacteria by Invertebrates: Direct and Indirect Effects on Fouling;23
2.4.1;3.1;24
2.4.2;Antibiotic Chemistry: Maintaining a Bacteria-Free Surface as a;24
2.4.3;Defense against Fouling;24
2.4.4;3.2;25
2.4.5;Maintaining a Community of Host-Specific Bacteria to Block;25
2.4.6;Inductive Biofilm Formation;25
2.4.7;3.3;28
2.4.8;Attracting Strains that Chemically Deter Settlement of Fouling;28
2.4.9;Larvae;28
2.5;Eukaryotic Propagules;31
2.5.1;4.1;31
2.5.2;Sponges;31
2.6;Role of Basibont-Derived Chemistry in Defense against;31
2.6.1;4.2;35
2.6.2;Cnidarians;35
2.6.3;4.3;39
2.6.4;Ascidians;39
2.6.5;4.4;42
2.6.6;Bryozoans;42
2.7;Investigating Larval Behavior to Understand and Combat Fouling;42
2.7.1;5.1;43
2.7.2;Waterborne Signals and Chemically Mediated Navigation;43
2.7.3;5.2;44
2.7.4;Measuring Production and Release of Chemical Deterrents in;44
2.7.5;Situ;44
2.7.6;5.3;45
2.7.7;Behavior of Larvae around Chemically Defended Surfaces;45
2.7.8;5.4;47
2.7.9;Interpreting the Ecological Importance of Larval Toxicity in;47
2.7.10;Laboratory Assays;47
2.7.11;5.5;50
2.7.12;An Alternative Bioassay Design to Avoid Artifacts and;50
2.7.13;Concentration Effects;50
2.8;The Importance of Alternative Hypothesis Testing: Mechanical and Physical Defense;52
2.9;Conclusions;54
2.10;References;55
3;Furanones;68
3.1;Natural Furanones from Delisa;69
3.2;Natural Antifouling Activity of Furanones;71
3.2.1;2.1;71
3.2.2;Surface Delivery and Surface Quantification of Furanones;71
3.2.3;2.2;74
3.2.4;Bacterial Fouling;74
3.2.5;2.3;75
3.2.6;Macrofouling;75
3.3;The Mode of Action of Furanones – Inhibition of Bacterial Signalling Systems;76
3.4;The Development and Application of Furanones;79
3.4.1;4.1;80
3.4.2;Chemical Synthesis;80
3.4.3;4.2;84
3.4.4;Delivery;84
3.4.5;4.3;85
3.4.6;Inhibition of Pathogenic Phenotypes and the Development of;85
3.4.7;Anti-Infectives;85
3.4.8;4.4;88
3.4.9;Alternative Modes of Activity;88
3.4.10;4.5;90
3.4.11;Biomaterials and Biofilms;90
3.4.12;4.6;91
3.4.13;Alternative Quorum Sensing Inhibitor Applications;91
3.4.14;4.7;92
3.4.15;Macrofouling – Coatings and Polymers;92
3.4.16;4.8;94
3.4.17;Furanones, Biofouling and Biosignal Ltd.;94
3.5;References;94
4;Isocyano Compounds as Non-Toxic Antifoulants;100
4.1;Introduction;100
4.2;Natural Marine Isocyanides;101
4.3;Natural Antifouling Isocyanoterpenes;101
4.3.1;3.1;101
4.3.2;Sesquiterpenes;101
4.3.3;3.2;103
4.3.4;Diterpenes;103
4.4;The Structure-Activity Relationships of Synthetic Isocyano Compounds;103
4.4.1;4.1;104
4.4.2;Antifouling Activities of 3-Isocyanotheonellin and Analogues;104
4.4.3;4.2;107
4.4.4;Isocyanocyclohexanes;107
4.4.5;4.3;109
4.4.6;Isocyanobenzenes;109
4.4.7;4.5;110
4.4.8;4.4;110
4.4.9;Simple Linear Alkyl Isocyanides;110
4.4.10;A Large-Scale Synthesis of Isocyanide 44;110
4.5;Field Experiments with Isocyanide 44;112
4.5.1;Test Panel Preparation;112
4.5.2;5.2;113
4.5.3;Field Experiments;113
4.6;References;116
4.7;6 Conclusion;116
5;3-Alkylpyridinium Compounds as Potential Non-Toxic Antifouling Agents;118
5.1;Introduction;118
5.2;Origin, General Characteristics and Biological Activities of;119
5.3;3-Alkylpyridinium Compounds;119
5.4;Monomeric 3-Alkylpyridinium Compounds;121
5.5;Dimeric and Trimeric 3-Alkylpyridinium Compounds;122
5.6;Polymeric 3-Alkylpyridinium Compounds;122
5.6.1;5.1;123
5.6.2;Halitoxin and Amphitoxin;123
5.6.3;5.2;125
5.6.4;EGF-Active Factors;125
5.6.5;5.3;125
5.6.6;Polymeric Alkylpyridinium Salts (Poly-APS);125
5.7;Ecological Significance of 3-Alkylpyridinium Compounds;132
5.8;Perspectives;133
5.9;References;134
6;5, 6-Dichloro-1-Methylgramine, a Non-Toxic Antifoulant Derived from a Marine Natural Product;138
6.1;Introduction;139
6.2;Antifouling Assay;139
6.2.1;2.1;139
6.2.2;Laboratory Culture of;139
6.2.3;2.2;140
6.2.4;Comparison of the Effect of TBTO on the Settlement Behavior;140
6.2.5;of Cyprids from Reared and Wild Adult Barnacles;140
6.3;Isolation of 2,5,6-Tribromo-1-Methylgramine from the Marine Bryozoan Zoobotryon pellucidum;142
6.4;Structure-Activity Relationships;143
6.5;Production of Antifouling Paints;145
6.6;Performance Evaluation Tests (Panel Tests);146
6.7;Development of an Effective Antifouling Paint;147
6.7.1;7.1;147
6.7.2;Duration of Antifouling Performance;147
6.7.3;7.2;148
6.7.4;Control of DCMG-Release and Demonstration Tests;148
6.8;Public Acceptance (Risk Management);149
6.8.1;8.1;149
6.8.2;Safety Test;149
6.8.3;8.2;150
6.8.4;Risk Evaluation;150
6.9;Summary and Future Perspectives;150
6.10;References;151
7;Biofilms;153
7.1;Introduction;153
7.2;Structure and Functional Properties of Marine Biofilms;155
7.2.1;2.1;155
7.2.2;Introduction;155
7.2.3;2.2;157
7.2.4;Phylogenetic Identification in Complex Microbial Communities;157
7.2.5;2.3;158
7.2.6;Algal Biofilms;158
7.3;Ulva Zoospores – a Model for Studying the Influence of Marine Microbial Biofilms on Biofouling Processes;159
7.3.1;3.1;160
7.3.2;Influence of Microbial Biofilms on Zoospore Settlement;160
7.3.3;3.2;161
7.3.4;Recognition of;161
7.3.5;acylhomoserine Lactones by Zoospores;161
7.3.6;3.3;164
7.3.7;Ecological and Applied Significance of Interspecific AHL;164
7.3.8;Signalling in Complex Marine Communities;164
7.4;Interactions of Biofilms and Bacterial Metabolites with Invertebrate Larvae;166
7.4.1;4.1 Mixed and Single Species Biofilms;166
7.4.2;4.2;169
7.4.3;Bacterial Products and Secondary Metabolites;169
7.4.4;4.3;170
7.5;Conclusions and Future Directions;171
7.6;References;173
8;Adrenoceptor and Other Pharmacoactive Compounds as Putative Antifoulants;182
8.1;Introduction;182
8.1.1;1.1;183
8.1.2;Some Basic Aspects of Pharmacoactive Compounds;183
8.2;G Protein-Coupled Receptors;184
8.3;Biogenic Amine Signaling and Implications in the Settlement of Barnacle Larvae;187
8.3.1;3.1;189
8.3.2;Serotonin (5-Hydroxytryptamine (5-HT));189
8.3.3;3.2;191
8.3.4;Histamine;191
8.3.5;3.3;192
8.3.6;Aminobutyric Acid (GABA);192
8.3.7;3.4;192
8.3.8;Octopamine and Tyramine;192
8.3.9;3.5;194
8.3.10;The Catecholamines;194
8.4;Adrenoceptor Compounds;198
8.4.1;4.1;198
8.4.2;Settlement Inhibition of;198
8.4.3;Cypris Larvae;198
8.4.4;4.2;203
8.4.5;Surface Affinity and the Antifouling Approach;203
8.5;Conclusions;206
8.6;References;208
9;State-of-Art Methodology of Marine Natural Products Chemistry: Structure Determination with Extremely Small Sample Amounts;214
9.1;Introduction;214
9.2;Structural Determination from Terrestrial Sources;215
9.3;Structure Studies on Marine Natural Products;217
9.4;Structure Determination of an Ascidian Sperm-Attracting and -Activating Factor (SAAF);220
9.5;Synthesis of Sperm-attracting and -activating Factor and its Epimer;224
9.6;Conclusion and Outlook;228
9.7;References;229
10;Subject Index;232