Contents Foreword XXI Optical properties of seawater 15 Rapid absorption of light in relation to depth 15 Preface and Acknowledgements XXIII Selective absorption of the wavelengths 15 List of Figures XXV Biological and ecological aspects 16 List of Tables XXXV Primary and secondary metabolites 16 Ecomones: vectors of chemical communication 16 Abbreviations, Acronyms, and Cell Lines XXXIX Phenomena of dependence 16 Dependence on light 16 Volume 1 Dependence on temperature 17 Dependence on salinity 17 Main types of interspecific relations 17 Part 1 Commensalism 17 General Aspects and Documentary Symbiosis 17 Resources Parasitism 17 The hierarchy of ecological levels and space 1 distribution of marine organisms 18 Systems of Classification of Living Organisms: Plant biodiversity: phylogeny of the algae 18 Great Steps in Chemical and Biological Animal biodiversity 21 Evolution 3 Biochemical characteristics of sessile animals 23 Estimation of biomass 23 Whittaker’s five kingdoms system 3 Selection of documentary resources 24 Discovery of Archaea(Archaebacteria): References 24 ternary model of living organisms 4 Websites 25 Characteristics of cell membranes 5 Some recent data on terpenes 7 3 Main stages of evolution 8 Chemistry of Marine Natural Substances: Originality, Diversity, Distribution 27 Exceptional resources of marine biodiversity 9 General introduction 27 Selection of documentary resourcess 10 References 10 Distribution of nitrogenous and non-nitrogenous Websites 12 secondary metabolites 27 Distribution of secondary metabolites by chemical class 28 2 General Information on the Marine Characteristics of the secondary metabolites of marine organisms 29 Environment 13 Incorporation of halogens 30 Physicochemical aspects 13 Incorporation of sulfur 31 Chemical composition of seawater 13 Incorporation of silicon 32 Encyclopedia of Marine Natural Products. Jean-Michel Kornprobst Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim ISBN: 978-3-527-32703-4 VIII Contents Rare chemical elements encountered in marine Part 2 substances: As, B, Ni, V, Zn 32 Archaea (Archebacteria) and Eubacteria Arsenic 32 Boron 32 6 Nickel 33 Archaea (Archaebacteria) 73 Vanadium 33 Zinc 33 General introduction 73 Selection of documentary resources 34 Membrane lipids 74 References 34 Pranylquinones 79 Websites 36 Cyclic polysulfides 80 Bacteriorhodopsin of halophiles 81 4 Basic Marine Pharmacology 37 Extremozymes 82 The hopes of the past 37 Appendix 1: Stereospecific numbering (sn) 83 The realities of the present 39 Selection of documentary resources 83 1. Ethnopharmacology 39 References 83 2. The triptych: biodiversity–chemodiversity– Experimental documentation 85 pharmacodiversity 40 Websites 85 3. Methods 44 Synthesis 86 Future directions 46 Selection of documentary resources 53 7 References 53 Eubacteria – 1 87 Websites 56 Cell walls and Gram reaction 87 Anaerobic and aerobic photosynthesis: bacteriochlorophylls 88 5 Documentary Resources 59 Brief overview of marine bacteria 90 Short historical background 59 Piezophile (barophile) and psychrophile bacteria from extreme environments 91 Printed documentation 60 Chemical Abstracts, Biological Abstracts, Examples of metabolites isolated Current Contents 60 from non-photosynthetic bacteria 91 Basic works 60 Lipopolysaccharides and other characteristics Reference works 61 of some Gram-negative bacteria 106 Articles published in volumes not entirely dedicated to marine organisms 61 Anaerobic photosynthetic bacteria 107 Scientific journals and the impact factor 62 Aerobic photosynthetic bacteria 107 Scientific journals specializing in developments in natural marine products 62 Anammox bacteria and “ladderane lipids” 108 Articles about development published Appendix 2 110 in scientific journals 65 Proceedings of the major international symposia 66 Selection of documentary resources 111 General articles on the synthesis of marine natural References 111 products 66 Websites 116 Synthesis 116 Electronic documentation 67 “Static” databases 68 “Dynamic” databases 68 Searching for information on the Internet 68 Contents IX 8 Part 3 Eubacteria – 2 121 Photosynthetic Eukaryotes Prochlorophyta 121 Taxonomy of Prochlorophyta 121 9 Unique characteristics of photosynthesis Bacillariophyceae (Diatoms) 173 in Prochlorococcus 122 Frustules: fundamental characteristics of diatoms 173 Biochemical data on Prochloron didemni 123 Bases of classification of diatoms 174 Biochemical data on Prochlorothrix hollandica 123 Primary metabolites 174 Cyanobacteria 124 Photosynthetic pigments 174 Traditional classification of cyanobacteria 124 Membrane lipids 175 Photosynthetic pigments 125 Terpenic hydrocarbons 177 Membrane lipids 128 Other terpenic derivatives: description General characteristics of the secondary of the two biosynthetic pathways 179 metabolites 129 Genera Nitzschia and Pseudo-nitzschia: domoic Malyngamides and other chlorinated derivatives 130 acid 180 Semiplenamides A–G and besarhanamides A–B 133 Other molecules 181 Aplysiatoxin, oscillatoxin-A Appendix 5 183 and other brominated derivatives 134 Appendix 6 184 Other non-peptidic nitrogenous derivatives 135 Selection of documentary resources 185 Lipopeptides, peptides and depsipeptides 137 References 185 Websites 187 Other toxins 147 Synthesis 188 Sulfated compounds 148 Polymethoxyalkenes and poly-b-hydroxybutyric acids (PHBAs) 150 10 Other molecules 151 Chrysophyceae, Raphidophyceae, Haptophyceae 191 Appendix 3 153 Chrysophyceae 191 Appendix 4 154 General presentation: simplified classification 191 Selection of documentary resources 155 Photosynthetic pigments References 155 and storage polysaccharides 191 Websites 162 Fatty acids 191 Synthesis 163 Sterols 191 Other derivatives 192 Raphidophyceae 193 Haptophyceae 193 General presentation: simplified classification 193 Photosynthetic pigments 194 Sterols 194 Fatty acids and other linear derivatives 195 Prymnesins 196 Particular characteristics of Pavlova pinguis and Pleurochrysis carterae 197 X Contents Appendix 7 198 12 Selection of documentary resources 199 Chlorophyceae (Green Algae) References 199 and Marine Spermatophyta 251 Websites 200 General aspects 251 Synthesis 200 Elements of classification of marine macroalgae 251 11 Classification of Chlorophyceae 252 Dinophyceae (Dinoflagellates) 201 Chlorophylls, carotenes and xanthophylls 252 General aspects 201 Storage polysaccharides: starches 254 Classification of dinoflagellates 202 Cell-wall polysaccharides 255 Photosynthetic pigments 202 Matrix polysaccharides 255 Sulfated exopolysaccharides 203 Membrane lipids: fatty acids and sterols 255 Sterols 204 Oxylipins 258 Fatty acids 204 Background on the secondary metabolites Glycolipids 207 of Chlorophyceae 259 Amphidinols and other polyhydroxylated polyenic Terpenes 259 derivatives 207 Meroterpenes of Dasycladales 262 Toxic proliferations: endo- and exotoxins 211 Aromatic derivatives 263 Main types of dinoflagellate toxins 212 Amino acids, amines, betaines 264 Cyclic polyethers 212 Peptides and depsipeptides: kahalalides 264 Okadaic acid and derivatives 220 Other nitrogen-containing derivatives 265 Toxic macrolides: amphidinolides, caribenolide, gonio- Sulfur-containing derivatives 267 domin A, hoffmanniolide 222 Marine Spermatophyta (phanerogams) 267 Complexity of the biosynthesis of polyketides 225 Selection of documentary resources 268 Saxitoxin and its derivatives 225 References 268 Nitrogenous toxins with imine function 228 Websites 272 Synthesis 273 Zooxanthellatoxins (ZTs) and other nitrogenous toxins 229 Pfiesteria piscicida: a particularly toxic 13 dinoflagellate 232 Rhodophyceae (Red Algae) 275 Sulfur-containing derivatives 232 Special features of red algae 275 Phosphorus derivatives 233 Classification of Rhodophyceae 275 Selection of documentary resources 233 Photosynthetic pigments 277 References 233 Storage monosaccharides and polysaccharides 278 Websites 241 Synthesis 242 Skeleton polysaccharides 278 Matrix polysaccharides: carrageenans and agars 278 Carrageenophytes and agarophytes 281 Gelling agents and thickeners 281 Contents XI Other types of matrix polysaccharides 282 Cyclic polysulfides of Chondria californica 332 Phospholipids and fatty acids 282 Arsenic-containing derivative of Chondria crassicaulis 332 Oxylipins and prostaglandins 284 Some atypical derivatives of Laurencia species 333 Sterols and ecdysteroids 285 Halogenated derivatives of Nemaliales 333 General comments on the secondary metabolites 286 Acetylenic acids of Liagora farinosa 335 Secondary metabolites of Cryptonemiales 287 Sulfated triterpene alcohols of Tricleocarpa fragilis 336 Secondary metabolites of Gelidiales 290 Cyclic peptide from Galaxaura filamentosa 337 Secondary metabolites of Rhodymeniales 290 Appendix 8 337 Polyhalogenated monoterpenes of Gigartinales 291 Appendix 9 338 Diterpenes of Sphaerococcus coronopifolius (Gigartinales, Sphaerococcaceae) 293 Selection of documentary resources 338 References 338 Macrocyclic pyrones of Phacelocarpus labillardieri Websites 352 (Gigartinales, Sphaerococcaceae) 297 Synthesis 353 Polycavernosides of Polycavernosa tsudai (Gigartinales, Gracilariaceae) 297 14 Brominated meroditerpenes of Callophycus serratus (Gigartinales, Solieriaceae) 298 Phaeophyceae (Brown Algae) 361 Halogenated phloroglucinols of Rhabdonia verticillata General introduction; 361 (Gigartinales, Solieriaceae) 299 Classification of Phaeophyceae 361 Sulfated aromatic derivatives of Tichocarpus crinitus Photosynthetic pigments 363 (Gigartinales, Tichocarpaceae) 299 Laminarans and other storage osides 363