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SUB Hamburg

Jean-Michel Kornprobst B/103660

Encyclopedia of Marine Natural Products

Volume 2: Porifera, Cnidaria, and Ctenophora

Translated from French by

T. B. Tarn Ha

WILEY-BLACKWELL

Contents

Foreword XXI

Preface and Acknowledgements XXIII

List of Figures XXV

List of Tables XXXV

Abbreviations, Acronyms, and Cell Lines XXXIX

Volume 1

PartiGeneral Aspects and DocumentaryResources

lSystems of Classification of Living Organisms:Great Steps in Chemical and BiologicalEvolution 3

Whittaker's five kingdoms system 3

Discovery of Archaea(Archaebacteria):ternary model of living organisms 4

Characteristics of cell membranes 5

Some recent data on terpenes 7

Main stages of evolution 8

Exceptional resources of marine biodiversity 9

Selection of documentary resourcess 10References 10Websites 12

General Information on the MarineEnvironment 13

Physicochemical aspects 13Chemical composition of seawater 13

Optical properties of seawater 25Rapid absorption of light in relation to depth 15Selective absorption of the wavelengths 25

Biological and ecological aspects 16Primary and secondary metabolites 16Ecomones: vectors of chemical communication 16Phenomena of dependence 26

Dependence on light 26Dependence on temperature 17Dependence on salinity 27

Main types of interspecific relations 27Commensalism 2 7Symbiosis 2 7Parasitism 17

The hierarchy of ecological levels and spacedistribution of marine organisms 28Plant biodiversity: phylogeny of the algae 28Animal biodiversity 21Biochemical characteristics of sessile animals 23Estimation of biomass 23

Selection of documentary resources 24References 24Websites 25

Chemistry of Marine Natural Substances:Originality, Diversity, Distribution 27

General introduction 27

Distribution of nitrogenous and non-nitrogenoussecondary metabolites 27

Distribution of secondary metabolites by chemicalclass 28

Characteristics of the secondary metabolitesof marine organisms 29Incorporation of halogens 30Incorporation of sulfur 31Incorporation of silicon 32

Encyclopedia of Marine Natural Products. Jean-Michel KornprobstCopyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, WeinheimISBN: 978-3-527-32703-4

V I Contents

Rare chemical elements encountered in marinesubstances: As, B, Ni, V, Zn 32

Arsenic 32Boron 32Nickel 33Vanadium 33Zinc 33


Basic Marine Pharmacology 37

The hopes of the past 37

The realities of the present 391. Ethnopharmacology 392. The triptych: biodiversity-chemodiversity-pharmacodiversity 403. Methods 44

Future directions 46


Documentary Resources 59

Short historical background 59

Printed documentation 60Chemical Abstracts, Biological Abstracts,Current Contents 60Basic works 60Reference works 62Articles published in volumes not entirelydedicated to marine organisms 62Scientific journals and the impact factor 62Scientific journals specializing in developmentsin natural marine products 62Articles about development publishedin scientific journals 65Proceedings of the major international symposia 66General articles on the synthesis of marine naturalproducts 66

Electronic documentation 67"Static" databases 68"Dynamic" databases 68Searching for information on the Internet 68

Part 2Archaea (Archebacteria) and Eubacteria

6

Archaea (Archaebacteria) 73


Membrane lipids 74

Pranylquinones 79

Cyclic polysulfides 80

Bacteriorhodopsin of halophiles 82

Extremozymes 82

Appendix i: Stereospecific numbering (sn) 83

Selection of documentary resources 83References 83Experimental documentation 85Websites 85Synthesis 86

Eu bacteria - 1 87

Cell walls and Gram reaction 87Anaerobic and aerobic photosynthesis:bacteriochlorophylls 88

Brief overview of marine bacteria 90

Piezophile (barophile) and psychrophile bacteriafrom extreme environments 91

Examples of metabolites isolatedfrom non-photosynthetic bacteria 91

Lipopolysaccharides and other characteristicsof some Gram-negative bacteria 206

Anaerobic photosynthetic bacteria 207

Aerobic photosynthetic bacteria 207

Anammox bacteria and "ladderane lipids" 108

Appendix 2 220

Selection of documentary resources 222References 222Webs i tes 226Synthes i s 226

Contents V I I

8

Eu bacteria - 2 222

Prochlorophyta 222

Taxonomy of Prochlorophyta 222

Unique characteristics of photosynthesisin Prochlorococcus 122

Biochemical data on Prochloron didemni 123

Biochemical data on Prochlorothrix hollandica 123

Cyanobacteria 224

Traditional classification of cyanobacteria 224

Photosynthetic pigments 225

Membrane lipids 228

General characteristics of the secondarymetabolites 229

Malyngamides and other chlorinated derivatives 230

Semiplenamides A-G and besarhanamides A-B 233

Aplysiatoxin, oscillatoxin-A

and other brominated derivatives 234

Other non-peptidic nitrogenous derivatives 235

Iipopeptides, peptides and depsipeptides 237

Other toxins 247

Sulfated compounds 248Polymethoxyalkenes and poly-/?-hydroxybutyricacids (PHBAs) 250

Other molecules 252

Appendix 3 253

Appendix 4 254

Selection of documentary resources 255References 255Websites 262Synthesis 263

Part 3Photosynthetic Eukaryotes

Bacillariophyceae (Diatoms) 273

Frustules: fundamental characteristics of diatoms 2 73

Bases of classification of diatoms 2 74

Primary metabolites 274


Membrane lipids 275

Terpenic hydrocarbons 277

Other terpenic derivatives: descriptionof the two biosynthetic pathways 279

Genera Nitzschia and Pseudo-nitzschia: domoicacid 180

Other molecules 282

Appendix 5 283

Appendix 6 284


10Chrysophyceae, Raphidophyceae,Haptophyceae 292

Chrysophyceae 292General presentation: simplified classification 292Photosynthetic pigmentsand storage polysaccharides 292Fatty acids 292Sterols 292Other derivatives 292

Raphidophyceae 2 93

Haptophyceae 2 93General presentation: simplified classification 293Photosynthetic pigments 294Sterols 294Fatty acids and other linear derivatives 295Prymnesins 296Particular characteristics of Pavlova pinguisand Pleurochrysis carterae 197

V I M Contents

Appendix 7 298

Selection of documentary resources 299References 2 99Websites 200Synthesis 200

11

Dinophyceae (Dinoflagellates) 202

General aspects 202

Classification of dinoflagellates 202


Sulfated exopolysaccharides 203

Sterols 204

Fatty acids 204

Glycolipids 207

Amphidinols and other polyhydroxylated polyenicderivatives 207

Toxic proliferations: endo- and exotoxins 222

Main types of dinoflagellate toxins 222

Cyclic polyethers 222

Okadaic acid and derivatives 220

Toxic macrolides: amphidinolides, caribenolide, gonio-domin A, hoffmanniolide 222

Complexity of the biosynthesis of polyketides 225

Saxitoxin and its derivatives 225

Nitrogenous toxins with imine function 228

Zooxanthellatoxins (ZTs) and other nitrogenoustoxins 229

Pfiesteria piscicida: a particularly toxicdinoflagellate 232

Sulfur-containing derivatives 232

Phosphorus derivatives 233


12Chlorophyceae (Green Algae)and Marine Spermatophyta 252

General aspects 252

Elements of classification of marine macroalgae 252

Classification of Chlorophyceae 252

Chlorophylls, carotenes and xanthophylls 252

Storage polysaccharides: starches 254

Cell-wall polysaccharides 255

Matrix polysaccharides 255

Membrane lipids: fatty acids and sterols 255

Oxylipins 258

Background on the secondary metabolitesof Chlorophyceae 259

Terpenes 259

Meroterpenes of Dasycladales 262

Aromatic derivatives 263

Amino acids, amines, betaines 264

Peptides and depsipeptides: kahalalides 264

Other nitrogen-containing derivatives 265


Marine Spermatophyta (phanerogams) 267


13

Rhodophyceae (Red Algae) 275

Special features of red algae 275

Classification of Rhodophyceae 275


Storage monosaccharides and polysaccharides 278

Skeleton polysaccharides 278

Matrix polysaccharides: carrageenans and agars 278

Carrageenophytes and agarophytes 281

Gelling agents and thickeners 282

Contents IX

Other types of matrix polysaccharides 282

Phospholipids and fatty acids 282

Oxylipins and prostaglandins 284

Sterols and ecdysteroids 285

General comments on the secondary metabolites 286

Secondary metabolites of Cryptonemiales 287

Secondary metabolites of Gelidiales 290

Secondary metabolites of Rhodymeniales 290

Polyhalogenated monoterpenes of Gigartinales 292

Diterpenes of Sphaerococcus coronopifolius(Gigartinales, Sphaerococcaceae) 293

Macrocyclic pyrones of Phacelocarpus labillardieri(Gigartinales, Sphaerococcaceae) 297

Polycavernosides of Polycavernosa tsudai(Gigartinales, Gracilariaceae) 297

Brominated meroditerpenes of Callophycus serratus(Gigartinales, Solieriaceae) 298

Halogenated phloroglucinols of Rhabdonia verticillata(Gigartinales, Solieriaceae) 299

Sulfated aromatic derivatives of Tichocarpus crinitus(Gigartinales, Tichocarpaceae) 299

Nitrogen-containing derivatives of Gigartinales 299

Halogenated compounds of Ceramiales:general comments 300

Polyhalogenated monoterpenes of Pantoneuraphcamioides (Ceramiales, Delesseriaceae) 301

Sesquiterpenes of Laurenda(Ceramiales, Rhodomelaceae) 302

Halogenated diterpenes of Laurenda 310

Non-halogenated hydroperoxyditerpenesof Laurenda 319

Squalenoids of Laurenda speciesand Chondria armata 319

Cyclic halogenated CI5 ethers and polyethersof Laurenda and Chondria 322

Bromo- and polybromophenols of Ceramiales 325

Nitrogen-containing bromophenolsof Rhodomela confervoides 328

Other nitrogen-containing derivativesof Ceramiales 329

Cyclic polysulfides of Chondria californica 332

Arsenic-containing derivativeof Chondria crassicaulis 332

Some atypical derivatives of Laurenda species 333

Halogenated derivatives of Nemaliales 333

Acetylenic acids of Liagora farinosa 335

Sulfated triterpene alcohols of Trideocarpa fragilis 336

Cyclic peptide from Galaxaura jilamentosa 337

Appendix 8 337

Appendix 9 338


14

Phaeophyceae (Brown Algae) 362

General introduction; 361

Classification of Phaeophyceae 362


Laminarans and other storage osides 363

Matrix polysaccharides: alginic acids and alginates 364

Fucoidans (sulfated fucans) 365

Lipids and fatty acids 367

Oxylipins of Laminariales 367

Epoxy lipids of Notheia anomala (Chordariales) 370

Sterols 372

Volatile hydrocarbons and sexual chemotaxy 372

Background on the secondary metabolites 376

Sesquiterpenes of Dictyotales 376

Cyclic diterpenes of Dictyotales 377

Linear diterpenes of Fucales and other derivatives 382

Phenols and phlorotannins 385

Other aromatic derivatives 388

Meroterpenes: general comments 389

Prenylated quinones and hydroquinones 389

Meromonoterpenes of Sporodtnus bolleanus 390

Contents

Merosesquiterpenes of Dictyopteris species 392

Meroditerpenes of the genera Taoniaand Stypopodium 392

Meroditerpenes of Cystosdra species: chemotaxonomyof Cystoseiraceae 396

Nahocols and isonahocols: rearranged linearmeroditerpenes of Sargassum autumnale 401

Derivatives of nitrogen, phosphorus and arsenic 402


Iodinated derivatives 405

Appendix io 406

Appendix n 407


15

Major Uses of Macroalgae 423

Overview 423

Estimate of resources 423

Edible seaweeds 425

Dietary properties of marine algae 425

Physicochemical aspects of phycocolloids 426

Economic aspects of phycocolloids 428

Major producing countries of phycocolloids 428

Main applications of agars 428

Main applications of carrageenans and furcellar-

ans 430

Main applications of alginic acid and alginates 430

Summary of research in the field of healthcare 431Antiviral and immunostimulant sulfatedpolysaccharides of red, brown and green algae 431Anticoagulant and antithrombotic propertiesoffucoidans 432

Antitumoural, immunomodulatory and antiviralproperties offucoidans 433

Other examples of biological activitiesof macroalgae 434

Uses of algae in cosmetics 434

Uses of algae in agriculture and livestockproduction 435

Selection of documentary resources 435References 435Proceedings of the latest International SeaweedSymposia 440Websites 440

Part 4Fungi and Other Eukaryotic UnicellularNon-photosynthetic Organisms

16Fungi 445

The Fungal Kingdom: the conceptof marine fungi 445

Mastigomycetes and Eumycetes (true fungi) 446

Elements of classification of Eumycetes 446

Background information on the structureof chitin 446

Fatty acids 446

Sterols 446

Membrane peptides of fungi: peptaibols 448

General comments on secondary metabolitesof marine fungi 449

Substances isolated from fungi collectedfrom the surface of the sea 449

Substances isolated from fungi from sedimentsand other inert substrates 450

Substances isolated from fungi associatedwith cyanobacteria 454

Algicolous fungi: general remarks 454

Substances isolated from fungi associatedwith green algae and marine Spermatophyta 454

Substances isolated from fungi associatedwith red algae 458

Substances isolated from fungi associatedwith brown algae 459

Substances isolated from lignicolous fungi 462

Substances isolated from fungi associatedwith sponges 465

Contents X I

Substances isolated from fungi associatedwith cnidarians 473

Substances isolated from fungi associatedwith molluscs 474

Substances isolated from fungi associatedwith bryozoans 476

Substances isolated from fungi associatedwith echinoderms 476

Substances isolated from fungi associatedwith crustaceans 478

Substances isolated from fungi associatedwith tunicates (ascidians) 478

Substances isolated from fungi associatedwith fish 480


18Introduction to Marine Biotechnology 503

Introduction 503

Recent developments in the cultureof invertebrates 503

Lipids and pigments: examplesof nutritional applications 504

New substances and biomaterials: examplesof biomedical applications 506

Bioremediation and biofouling: examplesof environmental applications 507

Dialkylphthalates in marine organisms 508

Another type of application: bioadhesives 508

Some examples of biotechnology in Prokaryotes 509

Selection of documentary resources 520General references 520References 520Websites 526

17Thraustochytrids and Ciliates 493

Taxonomic position of thraustochytridsand overview of the group 493

Carotenoids of thraustochytrids 493

Long-chain (n-3) polyunsaturated fatty acidsof thraustochytrids 493

Long-chain fatty acid composition and phylogenyof thraustochytrids 495

a-Glucosylceramides of thraustochytrids 495

Introduction to the chemistry of ciliates 496

Terpenes of Euplotes 497

Keronopsins of Pseudokeronopsis rubra 498


Volume 2

Part5Porifera, Cnidaria, and Ctenophora

19

Porifera (Sponges) 522

Overview of the universe of sponges 522

Metabolites of Calcarea (calcareous sponges) 524General characteristics of Calcarea 524Fatty acids 524Sterols 524Non-nitrogenous derivatives of speciesof the genus Leucetta 525Imidazole alkaloids and zinc complexes isolated fromthe genera Leucetta, Leucosolenia and Clathrina 526a.co-Bis long-chain aminoalcohols 528Nitrogen-containing macrolides and cyclicpeptides 529Other nitrogen-containing compounds of Calcarea 529

Metabolites of Hexactinellida 530

Classification and membrane constituentsof Demospongiae 53 2Classification 532

.a.

XII Contents

Some physical observations on demosponges 532Shape and size 532Consistency 532Colour and odour 532

Diversity of membrane constituents:some examples 536Phospholipids and demospongic acids 538Fatty acids with 5,9 dienic structure 542Other mono- and polyunsaturated fatty acids 543Branched fatty acids 544Isoprenic acids 547Cyclopropanic acids 548Brominated acids 5502-0 substituted acids 552Sulfur derivatives of demospongic acids 553Intracellular localization and biological activityof demospongic acids 555Brief reminder about conventional sterols 555Unconventional sterols produced by changesin the tetracydic system 556Unconventional sterols produced by polymethylationof the side chain 562Sterols with degraded side chains 564Sterols and stanols with cyclopropanicand cydopropenic side chains 564Secosterols 566Polyhydroxylated steroids and derivatives,peroxysterols 569Sulfated sterols 572Chlorinated sterols and sterones 574Nitrogen-containing sterols 576Glycolipids 577

Secondary metabolites of Homoscleromorpha 582Fatty acids, polyketides and oxylipinsof Plakinastrella and Plakortis 582Cyclic peroxides and peroxylactonesof Plakinastrella and Plakortis 584Glycosides 587Polyhydroxylated sterols of Oscarella lobularis 587Alkaloids and other original nitrogen derivativesof Plakortis and Cortidum 587

Secondary metabolites of Astrophorida 590Acetylenic fatty acids of Stelletta 591Glycolipids: caminosides and pachymosides 592Triterpenes of malabaricane and isomalabaricane:sesterterpenes 591Triterpenic glycosides and steroidal glycosides 593Substituted tetramic acids and derived glycosides 596Erylusamines, erylusine and erylusidine 598Cyclic depsipeptides, peptolidesand macrolactones 598Nitrogen-containing terpenes 602

Bengazoles and bengamides 603Atypical nitrogenous derivatives 605Phosphorus-containing derivatives similarto calyculin A 607Aromatic sulfated derivatives 608Isotactic polymethoxydienes of Myriastra davosa 608

Secondary metabolites of Hadromeridaand Chondrosida 609Perforating power of Clionaidae 609lyso-Phospholipids and sulfated sphingosinesof Spirastrella abata 610Brominated acetylenic derivatives of Diplastrella 611Cyclic peroxides 622Terpenes 623Unconventional sterols 624Macrolactones: latrunculins and spongistatins 625Atypical glycosides of Latrunculia corticata 617Other nitrogen-free toxins 627Peptides and depsipeptides 628Pyrrole derivatives and other nitrogen-containingheterocycles 629Atypical nucleosides 622

Secondary metabolites of Lithistida 622Particular characteristics of lithistid sponges 622Nitrogen-containing sesquiterpenes of Theonella 623Specific glycolipids of Theonella swinhoei,Discodermia calyx and D. dissoluta 623Long-chain polyacetylenic derivatives of Theonellasp. 6243/?-Methoxysterols of Jereicopsis graphidiophora 6244-Methylenesterols and sterones of Theonella 624Macrolides 626Examples of acetogenins: discodermolide,calyculins and onnamides 629Linear peptides 630Mono- and bicydic peptides 632Symbiotic origin of some polypeptides 635Cyclic and linear depsipeptides 635Atypical nitrogenous derivatives 639

Secondary metabolites of Spirophorida 640Atypical sterols of Cinachyra, Microscleroderma,and Scleritoderma 640Cinachyrolide A 640Microsclerodermins and aciculitins 642Examples of atypical derivatives of some spongesof the Tetillidae 642

Secondary metabolites of Agelasida 642Sterols 642Diterpenes and carotenoids 642Merosesquiterpenes and nitrogen-containingmeroditerpenes 643

Contents XIII

Galactosylceramides and glycolipids 644Oroidin and related CnN5 bromopyrrole alkaloids 646

Agelastatin A series 649Other series 650

Pyrrole-2-carboxylic acid derivatives 650Other examples of nitrogen-containingheterocycles 650Betaines 652

Secondary metabolites of Halichondrida 652A-nor-steroids and other non-conventional sterols 652Conventional terpenes 654Nitrogen-containing terpenes: isonitrilesand related derivatives 659Other terpenes 666Long-chain linear polyaminesand a,cu-bis-isothiocyanates 668Polyethers: halichondrins, okadaicand glycookadaic acids 668Various lipids 670Linear peptides of the genera Aulettaand Cymbastela 672Depsipeptides and cyclic peptides 672Pyrrole, imidazole, pyridine, isoquinolineand indole derivatives 678

Pyrrole derivatives 678Imidazole derivatives 678Pyridine and isoquinoline derivatives 679Indole derivatives 679

Heterocycles related to the oroidin family 682Atypical halogenated and sulfur-containingderivatives 682

Secondary metabolites of Haplosclerida 683Acetylenic derivatives 685Atypical fatty acids 692Terpenes and meroterpenes 693Triterpenic glycosides 699Hopanoids, steroids and sterosides 702Macrolides, depsipeptides and cyclic peptides 704Amino alcohols and glycosphingolipids(cerebrosides) 705Manzamines and related derivatives 707Quinolizidine and 1-oxaquinolizidine derivatives 707Pyridine derivatives and 3-alkylpyridinium salts 724Pyridoacridine alkaloids 726Pyrroloquinones and other examplesof nitrogen-containing heterocycles 72 7Quinones and sulfated hydroquinones 721Very long-chain linear sulfated derivatives 722Thiocyanatins: a.codithiocyanatesof Oceanapia sp. 722Some information on freshwater haploscleridsponges 723

Secondary metabolites of Poecilosclerida 724Sterols, steroids and sterosides 725Terpenes and triterpenic glycosides 727Polybrominated acetogenins and oxylipins 732Long-chain acetynenic derivatives: raspailynes 732Glycolipids 733Brominated aromatic derivativesof Hamigera tarangaensis 733Macrolides 734Chondropsins: cyclic depsipeptidesof Chondropsis sp. 736Eurypamides (Microdona eurypa), microcionamides(Clathria abietina) and other cyclic peptides 737Linear amides 738Examples of some atypical sulfur-containingderivatives 739Pyrrole and indole derivatives 742Pyridines, quinolizines and pyridoacridines 742Guanidine derivatives 743Pyrroloiminoquinones and pyrroloquinones 747Azasugars 748Other examples of polycyclic alkaloids 748Phosphorus and arsenic-containing derivatives,betaines 750

General information on the metabolitesof sponges lacking mineral spicules 752

Secondary metabolites of Dendroceratida 753Terpenes and meroterpenes 754Sterols 760Polybromophenols and polybromodiphenyl ethersof Dysidea 761Nitrogen compounds 763

Secondary metabolites of Dictyoceratida 768Terpenes and meroterpenes 768Sterols 788Glycolipids 789Polybromodiphenyl ethers and other halogenatedaromatic derivatives 789Macrolides: laulimalide, altohyrtins, chondropsinsand haterumalides 790Linear and cyclic peptides, depsipeptides 792Alkaloids and other nitrogen-containingcompounds 793Phosphorus derivatives 795Atypical sulfur derivatives 796

Secondary metabolites of Verongida 7963,5-Dibromotyrosine derivatives 797Other nitrogen-containing compounds 805Glycerol ethers and glycosphingolipids 807Sulfated aromatic compounds 807Metabolites specific to the family Ianthellidae 808

X I V Contents

Selection of documentary resources 811References 822Some Proceedings of the International SpongeConferences 875Websites 875Synthesis 875

20

Cnidaria and Ctenophora 925


Simplified classification of Cnidaria 925

Hermatypic and ahermatypic corals:coral bleaching 928

General information on metabolites of Cnidaria 929

Membrane constituents and secondary metabolitesof Octocorallia (Anthozoa) 930Prostaglandins and prostanoids 930Phospholipid fatty acids, glycolipidsand other lipidic derivatives 935General remarks on the sterols of Octocorallia 939Gorgosterol and other cyclopropane-containingsterols 940Polyoxygenated steroids 944Sterones and chlorinated sterones 948Sulfur-containing steroids 951Cydized side-chain sterols 952Secosterols 952Sterosides, pregnane and wor-pregnane derivatives 955Sesquiterpenic hydrocarbons 958Halogenated and nitrogen-containingsesquiterpenes 959Sesquiterpenes with original carbon skeletons 962Examples of sesquiterpeneswith a classical carbon skeleton 968General account of diterpenes 974Linear and monocyclic diterpenes 975General information on bicyclic diterpenes 992Chlorinated diterpenes 995Other examples of briarane derivatives 996Nitrogen-containing diterpenes of dadiellane/eunicellane: eleutherobin and analogues,labiatamides 999Other examples of cladiellane/eunicellanediterpenes 2004Diterpenes of serrulatane and other bicyclic carbonskeletons 2005Bicyclic C5/Cn diterpenes 2005Bicyclic diterpenes containing a cyclopropane 2006Some other examples of bicyclic diterpenes 2022

General account of tricydic diterpenes 2024Pseudopterosins, other amphilectane derivativesand analogues 2024Other examples of tricyclic and tetracydicditerpenes 2029Comments on the origin of terpenes 1023Non-terpenic nitrogenous derivativesof Octocorallia 2023

Membrane constituents and secondary metabolitesof Hexacorallia (Anthozoa) 2027Fatty acids, oxylipins and acetylenic derivatives 1027Sterols and ecdysteroids 2029Terpenes 2032Carotenoids of sea anemones 2033Aromatic derivatives 2033Ceramides 2033Examples of nitrogenous pigments:zoanthoxanthins and calliactin 2034Palytoxins 2034Mycosporines 2036Betaines, phosphobetaines, purinesand other nitrogen-containing derivatives 2037Zoanthamine alkaloids 2039Cytolysins, neuropeptides and other venomsof sea anemones 2042

Venoms and other metabolites of Medusozoa 2042Some data on the Cubozoa and other jellyfish 2043Bioluminescence of jellyfish and other Cnidaria 2044Some results on the secondary metabolitesof other Hydrozoa 2045

Ctenophora 2049


Volume 3

Part 6Protostomes

21Worm-like Organisms: 1 1097

Platyhelminthes 2097Macrolides and other compounds from symbiosiswith Amphidinium sp. 2097Staurosporine derivatives and other metabolitesfrom Platyhelminthes 2200

Contents X V

Nemertea 2202

Background on Annelida and Echiura 2202Lipids and sexual pheromones of polychaetes 2203Pigments of polychaetes and echiurans 2204Bromophenols of polychaetesand of the phoronid Phoronopsis viridis 1105Examples of nitrogen- and sulfur-containing derivativesfrom polychaetes 2205


22Bryozoa, Phoronida and Brachiopoda 2225

Bryozoans (Bryozoa, Ectoprocta) 2 2 2 5Background and classification 2225Lipids and aromatic compounds 2226Bryostatins 2228Pyrrole and pyrrolidine alkaloids 2222Indole and physostigmine alkaloids 2223Quinoline, isoquinoline and /?-carbolinederivatives 2224Original heterocyclic systems 2226Nitro compounds 2226Sulfoxonium salts and "Dogger Bank itch" 2226

Phoronida and Brachiopoda 2227


23Molluscs 2235

General characteristics and classification 2235

General information on lipids: hydrocarbons,fatty acids, oxylipins and sterols 2236

Metabolites of prosobranch gastropods 2240Some chemical data on Archaeogastropoda 2240Keyhole limpet haemocyanin 2 243Chemical data on Mesogastropoda 2243Secondary metabolites of Neogastropoda 2245A brief history of Tyrian Purple 2246Indirubins 2 247Conopeptides and conotoxins 2248

Toxic salivary secretions: tetrodotoxin, surugatoxinand neosurugatoxin 2252

Metabolites of opisthobranch gastropods 2252General characteristics of the order Anaspidea 2253Examples of food chains between sea haresand algae 2253Aplysioviolin and carotenoid pigments 2259Nitrogen-containing meroterpenes 2259Macrolactones: aplyolides, aplysiatoxins, aurisides,dolabelides, aplyronines and syphonoside 2260Peptides and depsipeptides: dolastatinsand aurilides 2262Other examples of nitrogenous derivativesof Anaspidea 2266Antimicrobial and anti-tumour glycoproteinsof the genera Aplysia and Dolabella 1168Polypropionates of Dolabella auriculariaand Dolabrifera dolabrifera 1168General information on the secondary metabolitesof Cephalaspidea 2269Alkylbenzenes and 2- and 3-alkylpyridinesof Cephalaspidea 2 2 70Peptides and depsipeptides of Philinopsis speciosa 1171Polyketides of Clione antarctica 1172Secondary metabolites of Notaspidea 2273Background on the chemistry of nudibranchs 2275Terpenes, terpenoids and steroidsof nudibranchs 2 2 75Prostaglandin lactones of Tethys flmbria 1187Cytotoxic macrolides of nudibranchs 2288Chlorinated polyacetylenic derivativesof Diaulula sandiegensis 1189Relations between nudibranchs and calcareoussponges: amino-2-imidazole derivatives 2290Relations between nudibranchsand bryozoans: pyrrole derivatives 2290Guanidine derivatives and other alkaloidsof nudibranchs 2292Nucleosides and peptides of nudibranchs 2 2 92Simplified assessment of nudibranch chemistry 2 2 93General remarks on metabolites of sacoglossans 2293Terpenes of sacoglossans 2294Polypropionate derivatives of sacoglossans 2294Kahalalides: cytotoxic depsipeptidesof the coupled Elysia/Bryopsis sp. 2296

Metabolites of pulmonate gastropods 2 2 97Sesquiterpenes and diterpenes of the generaOnchidella and Trimusculus 1197Polypropionate derivatives of pulmonates 2 2 98Cytotoxic depsipeptides of Onchidium sp. 2299

X V I Contents

Metabolites of Bivalvia (Lamellibranchiata) 1200Degradation products of chlorophyll aof Ruditapes phillipinarum 1201Carotenoids 1203Some data on polar lipids (plasmalogensand cardiolipids) 2203Polar sterols of Patinopecten yessoensisand 20-isosterols of Macoma balthica 1204Fatty acids and other lipid derivatives 2206Azaspiracids and other toxins 2206Polyamines, alkaloidsand various nitrogen-containing derivatives 2222Arsenic-containing derivativesof Tridacna maxima 1213Examples of biopolymers 2223

Metabolites of cephalopods 2223


24

Arthropoda 2249

Chitin and chitosans 2249

Carotenoid pigments 2252

Lipid derivatives 2253

Hormones controlling crustacean moultingand other steroids 2253

Some examples of sulfur-, nitrogen- and arsenic-containing metabolites of crustaceans 2256

Some data on marine cheliceriforms 2257


25Introduction to chemical ecology 2263

Examples of intraspecific relations 2264Sexual pheromones: sperm-activating peptidesof urchins and molluscs 2264Examples of alarm pheromones 2265

Examples of interspecific relationships 2 265Predator-prey relationships: defence allomonesof algae and invertebrates 2266

Defence allomones in associationsbetween microorganisms and invertebrates 2267Elicitors and defence allomones of algae 2272Substances inducing metamorphosis of larvae 2272Formation of epibiosis (biofouling)and antifouling substances 2273Food attractants and stimulants 2274


Part 7Deuterostomes

26Echinoderms 2283

General remarks and classification 2283

General comments on the chemistryof echinoderms 2 284

Metabolites of crinoids(feather stars and sea lilies) 1287Quinonic pigments 1287Sterols, glycolipids and phosphoceramides 22883,5-Dibromotyrosine derivatives 2289

Metabolites of echinids (sea urchins) 2290Echinochrome A, spinochromes and carotenoids 2290Fatty acids, prostaglandins, glycosphingolipidsand other lipids 2292Nitrogen- and sulfur-containing metabolites 2296Sulfated fucans and galactans 2297

Metabolites of ophiuroids(brittle stars and basket stars) 2297Lipids 1298Sulfated carotenoids 2299Sterols and sulfated sterols 2300Alkaloids 2302

Metabolites of asteroids (sea stars and starfish)Sterols and sulfated sterols 2304Free and sulfated polyhydroxysterols 1309Nitrogen- and phosphorus-containingpolyhydroxysterols 2323Steroidal glycosides and asterosaponins 2323Carotenoids 1328Fatty acids and oxylipins 2328Glycolipids, ceramides, cerebrosidesand gangliosides 2329Nitrogen-containing derivatives 2329

2304

Contents X V I I

Metabolites of holothuroids (sea cucumbers) 2335Fatty acids 2336Sterols, 4ct-methylsterols and triterpenes 1336Holothurins 1336Carotenoids 2347Trepang 2348Cerebrosides and gangliosides 2348Atypical nitrogen-containing derivativesof Cucumaria frondosa 1351Oligosaccharides and sulfated polysaccharides 2352


27Worm-like Organisms: 2. Chaetognathaand Hemichordata (Enteropneustaand Pterobranchia) 2369

Short description of Chaetognatha 2369

Short description of Hemichordata 2369

Aromatic and heteroaromatic derivativesof enteropneusts 2 3 70

Cephalostatins of Cephalodiscus gilchristi(Pterobranchia) 2372


28Ascidians (Tunicates) 2377

Reminder about the concept of the chordate 2377

Description of tunicates and classificationof the Ascidiacea 2377

General information on the chemistryof ascidians 2379

Lipids: fatty acids, acyltunichlorins, polyketidesand oxylipins 2380

Amino alcohols, sphinganines, serinolipids,ceramides and cerebrosides 2382

Sterols and steroids 2384

Carotenoids 2386

Sulfated polysaccharides of ascidian tunics 2386

Nitrogenous biopolymers and lectins 2387

Metabolites of Didemnidae 2388Didemnaketals and chlorinated diterpenesof Lissoclinum species 2388Aromatic polysulfanes and other atypicalsulfur derivatives 2390Lamellarins and other pyrrole alkaloids 2392Derivatives of quinoline, pyridoacridineand pyrroloacridine 2394Derivatives of tyramine, tryptophan, indoleand /?-carboline 2396Cytotoxic linear amides: bistratene Aand bistramides 1400Linear peptides and 1,4-diketopiperazines 2402Cyclic peptides 2402Macrolides: patellazoles 2408Cyclic depsipeptides: didemnins, Aplidin® (plitidepsin)and other derivatives 2409Purines, nucleosides and analogues 2423

Metabolites of Polycitoridae 2424Terpenes of Cystodytes sp.and Polycitor adriaticus 2424Aromatic polysulfanes of Polycitor adriaticus 1414Nitrogenous macrolides: iejimalides 2425Simple pyrrole and indole alkaloids 2425/?-Carboline alkaloids: eudistominsand related derivatives 2426Decahydroquinoline alkaloids: lepadins 2428Quinolizidine and indolizine alkaloids 2420Perhydropyrrolo[2,l-j] and perhydropyrido[2,l-j]quinoline alkaloids: cylindricines 2420Pyridoacridine alkaloids and related derivatives 2422Other types of alkaloids 2424Cyclic peptides 2426

Metabolites of Polyclinidae 2426Long-chain sulfated alkanes and terpenesof Sidnyum turbinatum 1427Terpenes and meroterpenes 2427Para- and metacyclophanes: longithoronesand related derivatives 2427Simple aromatic derivatives 2430Nitrogenous and non-nitrogenous macrolides 2430Long-chain amines and amino alcohols,sphingosines 2432Piperidine alkaloids: pseudodistomins 2433Indole and /?-carboline alkaloids 2434Quinoline and pyridoacridine alkaloids 2436Bis-steroidal alkaloids of Ritterella tokioka:ritterazines 2436Purines and nucleosides 2437

XVII I Contents

Miscellaneous nitrogenous derivatives 2439

Metabolites of Ascidiidae 2442Vanadium, intracellular acidity of blood cellsand peptide ligands 2442

Metabolites of Cionidae 2445

Metabolites of Diazonidae 2446

Metabolites of Perophoridae 2447Metabolites isolated from speciesof the genus Perophora 1447Tetrahydroisoquinoline alkaloids: ecteinascidins

Metabolites of Molgulidae and Pyuridae 2449Lipids and non-nitrogenous derivatives 2449Nitrogenous derivatives, antimicrobial peptidesand proteins 2450

Metabolites of Styelidae 2453Non-nitrogenous derivatives 2453Phenylethylamine derivatives, various alkaloidsAntibacterial purines and peptides 2456


2447

2453

29Vertebrates: Fish, Reptilesand Mammals 2489

Fish 1489Squalene and other lipid derivativesof Chondrichthyes and Agnatha 2489Bile steroids of sharks and hagfish:scymnol, myxinol and derivatives 2490Squalamine and other aminosterols of sharksMigratory pheromones and sex hormonesof lampreys 2493Inhibition of angiogenesis by shark cartilage:Neovastat® 2494General account of lipid derivatives ofOsteichthyes 2494Venoms and toxins: defence substances offishAntifreeze proteins of polar fish 2502Sulfated glycosaminoglycans of the extracellularmatrix 2502

Reptiles 2502

Mammals 2503Lipid composition and residues of chlorinatedpesticides 2503Ambergris, ambrein and ambrox 1504


2492

2497

Index 2525

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