Encyclopedia of marine natural products
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| 100 | 1 | |a Kornprobst, Jean-Michel |e Verfasser |4 aut | |
| 245 | 1 | 0 | |a Encyclopedia of marine natural products |c Jean-Michel Kornprobst |
| 264 | 1 | |a Weinheim |b Wiley-VCH | |
| 336 | |b txt |2 rdacontent | ||
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CONTENTS
FOREWORD XXI PREFACE AND ACKNOWLEDGEMENTS XXIII
LIST OF FIGURES XXV
LIST OF TABLES XXXV
ABBREVIATIONS, ACRONYMS, AND CELL LINES XXXIX
VOLUME 1
PARTI GENERAL ASPECTS AND DOCUMENTARY RESOURCES
L SYSTEMS OF CLASSIFICATION OF LIVING ORGANISMS: GREAT STEPS IN CHEMICAL
AND BIOLOGICAL EVOLUTION 3
WHITTAKEFS FIVE KINGDOMS SYSTEM 3
DISCOVERY OF ARCHAEAFARCHAEBACTERIA): 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 10 REFERENCES 10 WEBSITES 12
GENERAL INFORMATION ON THE MARINE ENVIRONMENT 13
PHYSICOCHEMICAL ASPECTS 13 CHEMICAL COMPOSITION OF SEAWATER 13
OPTICAL PROPERTIES OF SEAWATER 15 RAPID ABSORPTION OF LIGHT IN RELATION
TO DEPTH SELECTIVE ABSORPTION OF THE WAVELENGTHS 15 15
BIOLOGICAL AND ECOLOGICAL ASPECTS 16 PRIMARY AND SECONDARY METABOLITES
16 ECOMONES: VECTORS OF CHEMICAL COMMUNICATION PHENOMENA OF DEPENDENCE
16
DEPENDENCE ON LIGHT 16 DEPENDENCE ON TEMPERATURE 17 DEPENDENCE ON
SALINITY 17 MAIN TYPES OF INTERSPECIFIC RELATIONS 17
COMMENSALISM 17 SYMBIOSIS 17 PARASITISM 17 THE HIERARCHY OF ECOLOGICAL
LEVELS AND SPACE
DISTRIBUTION OF MARINE ORGANISMS 18 PLANT BIODIVERSITY: PHYLOGENY OF THE
ALGAE 18 ANIMAL BIODIVERSITY 21 BIOCHEMICAL CHARACTERISTICS OF SESSILE
ANIMALS 23
ESTIMATION OF BIOMASS 23
16
SELECTION OF DOCUMENTARY RESOURCES REFERENCES 24 WEBSITES 25
24
CHEMISTRY OF MARINE NATURAL SUBSTANCES: ORIGINALITY, DIVERSITY,
DISTRIBUTION 27
GENERAL INTRODUCTION 27
DISTRIBUTION OF NITROGENOUS AND NON-NITROGENOUS SECONDARY METABOLITES 27
DISTRIBUTION OF SECONDARY METABOLITES BY CHEMICAL CLASS 28
CHARACTERISTICS OF THE SECONDARY METABOLITES OF MARINE ORGANISMS 29
INCORPORATION OF HALOGENS 30
INCORPORATION OF SULFUR 31 INCORPORATION OF SILICON 32
BIBLIOGRAFISCHE INFORMATIONEN HTTP://D-NB.INFO/997573376
DIGITALISIERT DURCH
IMAGE 2
VIII CONTENTS
RARE CHEMICAL ELEMENTS ENCOUNTERED IN MARINE SUBSTANCES: AS, B, NI, V,
ZN 32 ARSENIC 32 BORON 32
NICKEL 33 VANADIUM 33 ZINC 33
SELECTION OF DOCUMENTARY RESOURCES 34 REFERENCES 34 WEBSITES 36
BASIC MARINE PHARMACOLOGY 37
THE HOPES OF THE PAST 37
THE REALITIES OF THE PRESENT 39 1. ETHNOPHARMACOLOGY 39 2. THE TRIPTYCH:
BIODIVERSITY-CHEMODIVERSITY- PHARMACODIVERSITY 40
3. METHODS 44
FUTURE DIRECTIONS 46
SELECTION OF DOCUMENTARY RESOURCES 53 REFERENCES 53 WEBSITES 56
DOCUMENTARY RESOURCES 59
SHORT HISTORICAL BACKGROUND 59
PRINTED DOCUMENTATION 60 CHEMICAL ABSTRACTS, BIOLOGICAL ABSTRACTS,
CURRENT CONTENTS 60 BASIC WORKS 60
REFERENCE WORKS 61 ARTICLES PUBLISHED IN VOLUMES NOT ENTIRELY DEDICATED
TO MARINE ORGANISMS 61 SCIENTIFIC JOURNALS AND THE IMPACT FACTOR 62
SCIENTIFIC JOURNALS SPECIALIZING IN DEVELOPMENTS IN NATURAL MARINE
PRODUCTS 62 ARTICLES ABOUT DEVELOPMENT PUBLISHED IN SCIENTIFIC JOURNALS
65
PROCEEDINGS OF THE MAJOR INTERNATIONAL SYMPOSIA 66 GENERAL ARTICLES ON
THE SYNTHESIS OF MARINE NATURAL PRODUCTS 66
ELECTRONIC DOCUMENTATION 67 STATIC DATABASES 68 DYNAMIC DATABASES 68
SEARCHING FOR INFORMATION ON THE INTERNET 68
PART 2 ARCHAEA (ARCHEBACTERIA) AND EU BACTERIA
6 ARCHAEA (ARCHAEBACTERIA) 73
GENERAL INTRODUCTION 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 83 REFERENCES 83 EXPERIMENTAL
DOCUMENTATION 85 WEBSITES 85
SYNTHESIS 86
EUBACTERIA - 1 87
CELL WALLS AND GRAM REACTION 87 ANAEROBIC AND AEROBIC PHOTOSYNTHESIS:
BACTERIOCHLOROPHYLLS 88
BRIEF OVERVIEW OF MARINE BACTERIA 90
PIEZOPHILE (BAROPHILE) AND PSYCHROPHILE BACTERIA FROM EXTREME
ENVIRONMENTS 91
EXAMPLES OF METABOLITES ISOLATED FROM NON-PHOTOSYNTHETIC BACTERIA 91
LIPOPOLYSACCHARIDES AND OTHER CHARACTERISTICS OF SOME GRAM-NEGATIVE
BACTERIA 106
ANAEROBIC PHOTOSYNTHETIC BACTERIA 107
AEROBIC PHOTOSYNTHETIC BACTERIA 207
ANAMMOX BACTERIA AND LADDERANE LIPIDS 208
APPENDIX 2 110
SELECTION OF DOCUMENTARY RESOURCES 212 REFERENCES 221 WEBSITES 116
SYNTHESIS 116
IMAGE 3
CONTENTS IX
8
EU BACTERIA - 2 121
PROCHLOROPHYTA 122
TAXONOMY OF PROCHLOROPHYTA 121
UNIQUE CHARACTERISTICS OF PHOTOSYNTHESIS IN PROCHLOROCOCCUS 122
BIOCHEMICAL DATA ON PROCHLORON DIDEMNI 123
BIOCHEMICAL DATA ON PROCHLOROTHRIX HOLLANDICA 123
CYANOBACTERIA 124
TRADITIONAL CLASSIFICATION OF CYANOBACTERIA 124
PHOTOSYNTHETIC PIGMENTS 225
MEMBRANE LIPIDS 128
GENERAL CHARACTERISTICS OF THE SECONDARY METABOLITES 129
MALYNGAMIDES AND OTHER CHLORINATED DERIVATIVES 130
SEMIPLENAMIDES A-G AND BESARHANAMIDES A-B 133
APLYSIATOXIN, OSCILLATOXIN-A
AND OTHER BROMINATED DERIVATIVES 134
OTHER NON-PEPTIDIC NITROGENOUS DERIVATIVES 135
LIPOPEPTIDES, PEPTIDES AND DEPSIPEPTIDES 237
OTHER TOXINS 247
SULFATED COMPOUNDS 248 POLYMETHOXYALKENES AND POLY-/?-HYDROXYBUTYRIC
ACIDS (PHBAS) 250
OTHER MOLECULES 252
APPENDIX 3 253
APPENDIX 4 254
SELECTION OF DOCUMENTARY RESOURCES 155 REFERENCES 155 WEBSITES 162
SYNTHESIS 163
PART 3 PHOTOSYNTHETIC EUKARYOTES
BACILLARIOPHYCEAE (DIATOMS) 173 FRUSTULES: FUNDAMENTAL CHARACTERISTICS
OF DIATOMS 1 73
BASES OF CLASSIFICATION OF DIATOMS 1 74
PRIMARY METABOLITES 1 74
PHOTOSYNTHETIC PIGMENTS 174
MEMBRANE LIPIDS 175
TERPENIC HYDROCARBONS 177
OTHER TERPENIC DERIVATIVES: DESCRIPTION OF THE TWO BIOSYNTHETIC PATHWAYS
179
GENERA NITZSCHIA AND PSEUDO-NITZSCHIA: DOMOIC ACID 180
OTHER MOLECULES 181
APPENDIX 5 183
APPENDIX 6 184
SELECTION OF DOCUMENTARY RESOURCES 185 REFERENCES 285 WEBSITES 287
SYNTHESIS 288
10 CHRYSOPHYCEAE, RAPHIDOPHYCEAE, HAPTOPHYCEAE 292
CHRYSOPHYCEAE 292 GENERAL PRESENTATION: SIMPLIFIED CLASSIFICATION 292
PHOTOSYNTHETIC PIGMENTS AND STORAGE POLYSACCHARIDES 192
FATTY ACIDS 191 STEROLS 191 OTHER DERIVATIVES 192
RAPHIDOPHYCEAE 1 93
HAPTOPHYCEAE 1 93 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
IMAGE 4
CONTENTS
APPENDIX 7 198
SELECTION OF DOCUMENTARY RESOURCES 199 REFERENCES 199 WEBSITES 200
SYNTHESIS 200
11
DINOPHYCEAE (DINOFLAGELLATES) 201
GENERAL ASPECTS 201
CLASSIFICATION OF DINOFLAGELLATES 202
PHOTOSYNTHETIC PIGMENTS 202
SULFATED EXOPOLYSACCHARIDES 203
STEROLS 204
FATTY ACIDS 204
GLYCOLIPIDS 207 AMPHIDINOLS AND OTHER POLYHYDROXYLATED POLYENIC
DERIVATIVES 207
TOXIC PROLIFERATIONS: ENDO- AND EXOTOXINS 211
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 NITROGENOUS TOXINS 229
PFIESTERIA PISCIDDA: A PARTICULARLY TOXIC DINOFLAGELLATE 232
SULFUR-CONTAINING DERIVATIVES 232
PHOSPHORUS DERIVATIVES 233
SELECTION OF DOCUMENTARY RESOURCES 233 REFERENCES 233 WEBSITES 242
SYNTHESIS 242
12 CHLOROPHYCEAE (GREEN ALGAE) AND MARINE SPERMATOPHYTA 251
GENERAL ASPECTS 251
ELEMENTS OF CLASSIFICATION OF MARINE MACROALGAE 251
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 METABOLITES OF 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
SULFUR-CONTAINING DERIVATIVES 267
MARINE SPERMATOPHYTA (PHANEROGAMS) 267
SELECTION OF DOCUMENTARY RESOURCES 268 REFERENCES 268 WEBSITES 272
SYNTHESIS 273
13
RHODOPHYCEAE (RED ALGAE) 275
SPECIAL FEATURES OF RED ALGAE 275
CLASSIFICATION OF RHODOPHYCEAE 275
PHOTOSYNTHETIC PIGMENTS 277
STORAGE MONOSACCHARIDES AND POLYSACCHARIDES 278
SKELETON POLYSACCHARIDES 278
MATRIX POLYSACCHARIDES: CARRAGEENANS AND AGARS 278
CARRAGEENOPHYTES AND AGAROPHYTES 281
GELLING AGENTS AND THICKENERS 281
IMAGE 5
CONTENTS
XI
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 291
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 SERMTUS (GIGARTINALES,
SOLIERIACEAE) 298
HALOGENATED PHLOROGLUCINOLS OF RHABDONIA VERTIDLLATA (GIGARTINALES,
SOLIERIACEAE) 299
SULFATED AROMATIC DERIVATIVES OF LICHOCARPUS CRINITUS (GIGARTINALES,
TICHOCARPACEAE) 299
NITROGEN-CONTAINING DERIVATIVES OF GIGARTINALES 299
HALOGENATED COMPOUNDS OF CERAMIALES: GENERAL COMMENTS 300
POLYHALOGENATED MONOTERPENES OF PANTONEURA PLOCAMIOIDES (CERAMIALES,
DELESSERIACEAE) 301
SESQUITERPENES OF LAURENDA (CERAMIALES, RHODOMELACEAE) 301
HALOGENATED DITERPENES OF LAURENDA 310
NON-HALOGENATED HYDROPEROXYDITERPENES OI LAURENDA 319
SQUALENOIDS OF LAURENDA SPECIES AND CHONDRIA ARMATA 319
CYCLIC HALOGENATED C I5 ETHERS AND POLYETHERS OF LAURENDA AND CHONDRIA
322
BROMO- AND POLYBROMOPHENOLS OF CERAMIALES 325
NITROGEN-CONTAINING BROMOPHENOLS OF RHODOMELA CONFERVOIDES 328
OTHER NITROGEN-CONTAINING DERIVATIVES OF CERAMIALES 329
CYCLIC POLYSULFIDES OF CHONDRIA CALIFORNICA 332
ARSENIC-CONTAINING DERIVATIVE OF CHONDRIA CRASSICAULIS 332
SOME ATYPICAL DERIVATIVES OF LAURENDA SPEDES 333
HALOGENATED DERIVATIVES OF NEMALIALES 333
ACETYLENIC ACIDS OF LIAGORA FARINOSA 335
SULFATED TRITERPENE ALCOHOLS OF TRIDEOCARPA FIAGILIS 336
CYCLIC PEPTIDE FROM GALAXAURA FILAMENTOSA 337
APPENDIX 8 337
APPENDIX 9 338
SELECTION OF DOCUMENTARY RESOURCES 338 REFERENCES 338 WEBSITES 352
SYNTHESIS 353
14
PHAEOPHYCEAE (BROWN ALGAE) 361
GENERAL INTRODUCTION; 361
CLASSIFICATION OF PHAEOPHYCEAE 361
PHOTOSYNTHETIC PIGMENTS 363
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 371
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 SPOROCHNUS BOLLEANUS 390
IMAGE 6
X II CONTENTS
MEROSESQUITERPENES OF DICTYOPTERIS SPECIES 391
MERODITERPENES OF THE GENERA TAONIA AND STYPOPODIUM 392
MERODITERPENES OF CYSTOSEIRA SPECIES: CHEMOTAXONOMY OF CYSTOSEIRACEAE
396
NAHOCOLS AND ISONAHOCOLS: REARRANGED LINEAR MERODITERPENES OF SARGASSUM
AUTUMNALE 401
DERIVATIVES OF NITROGEN, PHOSPHORUS AND ARSENIC 402
SULFUR-CONTAINING DERIVATIVES 404
IODINATED DERIVATIVES 405
APPENDIX IO 406
APPENDIX N 407
SELECTION OF DOCUMENTARY RESOURCES 407 REFERENCES 407 WEBSITES 417
SYNTHESIS 428
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 431
ANTIVIRAL AND IMMUNOSTIMULANT SULFATED POLYSACCHARIDES OF RED, BROWN AND
GREEN ALGAE 432
ANTICOAGULANT AND ANTITHROMBOTIC PROPERTIES OFFUCOIDANS 432
ANTITUMOURAL, IMMUNOMODULATORY AND ANTIVIRAL PROPERTIES OFFUCOIDANS 433
OTHER EXAMPLES OF BIOLOGICAL ACTIVITIES OF MACROALGAE 434
USES OF ALGAE IN COSMETICS 434
USES OF ALGAE IN AGRICULTURE AND LIVESTOCK PRODUCTION 435
SELECTION OF DOCUMENTARY RESOURCES 435 REFERENCES 435 PROCEEDINGS OF THE
LATEST INTERNATIONAL SEAWEED SYMPOSIA 440 WEBSITES 440
PART 4 FUNGI AND OTHER EUKARYOTIC UNICELLULAR NON-PHOTOSYNTHETIC
ORGANISMS
16 FUNGI 445
THE FUNGAL KINGDOM: THE CONCEPT OF MARINE FUNGI 445
MASTIGOMYCETES AND EUMYCETES (TRUE FUNGI) 446
ELEMENTS OF CLASSIFICATION OF EUMYCETES 446
BACKGROUND INFORMATION ON THE STRUCTURE OF CHITIN 446
FATTY ACIDS 446
STEROLS 446
MEMBRANE PEPTIDES OF FUNGI: PEPTAIBOLS 448
GENERAL COMMENTS ON SECONDARY METABOLITES OF MARINE FUNGI 449
SUBSTANCES ISOLATED FROM FUNGI COLLECTED FROM THE SURFACE OF THE SEA 449
SUBSTANCES ISOLATED FROM FUNGI FROM SEDIMENTS AND OTHER INERT SUBSTRATES
450
SUBSTANCES ISOLATED FROM FUNGI ASSOCIATED WITH CYANOBACTERIA 454
ALGICOLOUS FUNGI: GENERAL REMARKS 454
SUBSTANCES ISOLATED FROM FUNGI ASSOCIATED WITH GREEN ALGAE AND MARINE
SPERMATOPHYTA 454
SUBSTANCES ISOLATED FROM FUNGI ASSOCIATED WITH RED ALGAE 458
SUBSTANCES ISOLATED FROM FUNGI ASSOCIATED WITH BROWN ALGAE 459
SUBSTANCES ISOLATED FROM LIGNICOLOUS FUNGI 462
SUBSTANCES ISOLATED FROM FUNGI ASSOCIATED WITH SPONGES 465
IMAGE 7
CONTENTS X I II
SUBSTANCES ISOLATED FROM FUNGI ASSOCIATED WITH CNIDARIANS 473
SUBSTANCES ISOLATED FROM FUNGI ASSOCIATED WITH MOLLUSCS 474
SUBSTANCES ISOLATED FROM FUNGI ASSOCIATED WITH BRYOZOANS 476
SUBSTANCES ISOLATED FROM FUNGI ASSOCIATED WITH ECHINODERMS 476
SUBSTANCES ISOLATED FROM FUNGI ASSOCIATED WITH CRUSTACEANS 478
SUBSTANCES ISOLATED FROM FUNGI ASSOCIATED WITH TUNICATES (ASCIDIANS) 478
SUBSTANCES ISOLATED FROM FUNGI ASSOCIATED WITH FISH 480
SELECTION OF DOCUMENTARY RESOURCES 482 REFERENCES 482 WEBSITES 488
SYNTHESIS 489
17 THRAUSTOCHYTRIDS AND CILIATES 493
TAXONOMIC POSITION OF THRAUSTOCHYTRIDS AND OVERVIEW OF THE GROUP 493
CAROTENOIDS OF THRAUSTOCHYTRIDS 493
LONG-CHAIN (N-3) POLYUNSATURATED FATTY ACIDS OF THRAUSTOCHYTRIDS 493
LONG-CHAIN FATTY ACID COMPOSITION AND PHYLOGENY OF THRAUSTOCHYTRIDS 495
A-GLUCOSYLCERAMIDES OF THRAUSTOCHYTRIDS 495
INTRODUCTION TO THE CHEMISTRY OF CILIATES 496
TERPENES OF EUPLOTES 497
KERONOPSINS OF PSEUDOKERONOPSIS RUBRA 498
SELECTION OF DOCUMENTARY RESOURCES 499 REFERENCES 499 WEBSITES 502
SYNTHESIS 502
18 INTRODUCTION TO MARINE BIOTECHNOLOGY 503
INTRODUCTION 503
RECENT DEVELOPMENTS IN THE CULTURE OF INVERTEBRATES 503
LIPIDS AND PIGMENTS: EXAMPLES OF NUTRITIONAL APPLICATIONS 504
NEW SUBSTANCES AND BIOMATERIALS: EXAMPLES OF BIOMEDICAL APPLICATIONS 506
BIOREMEDIATION AND BIOFOULING: EXAMPLES OF 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 510 GENERAL REFERENCES 510 REFERENCES
510 WEBSITES 526
VOLUME 2
PART 5 PORIFERA, CNIDARIA, AND CTENOPHORA
19 PORIFERA (SPONGES) 522
OVERVIEW OF THE UNIVERSE OF SPONGES 521
METABOLITES OF CALCAREA (CALCAREOUS SPONGES) 524 GENERAL CHARACTERISTICS
OF CALCAREA 524 FATTY ACIDS 524 STEROLS 524 NON-NITROGENOUS DERIVATIVES
OF SPECIES OF THE GENUS LEUCETTA 525
IMIDAZOLE ALKALOIDS AND ZINC COMPLEXES ISOLATED FROM THE GENERA
LEUCETTA, LEUCOSOLENIA AND CLATHRINA 526 A, (W-BIS LONG-CHAIN
AMINOALCOHOLS 528 NITROGEN-CONTAINING MACROLIDES AND CYCLIC PEPTIDES 529
OTHER NITROGEN-CONTAINING COMPOUNDS OF CALCAREA 529
METABOLITES OF HEXACTINELLIDA 530
CLASSIFICATION AND MEMBRANE CONSTITUENTS OF DEMOSPONGIAE 531
CLASSIFICATION 531
IMAGE 8
XIV CONTENTS
SOME PHYSICAL OBSERVATIONS ON DEMOSPONGES 532 SHAPE AND SIZE 532
CONSISTENCY 532 COLOUR AND ODOUR 532 DIVERSITY OF MEMBRANE CONSTITUENTS:
SOME EXAMPLES 536
PHOSPHOLIPIDS AND DEMOSPONGIC ACIDS 538 FATTY ACIDS WITH 5,9 DIENIC
STRUCTURE 541 OTHER MONO- AND POLYUNSATURATED FATTY ACIDS 543 BRANCHED
FATTY ACIDS 544
ISOPRENIC ACIDS 547 CYCLOPROPANIC ACIDS 548 BROMINATED ACIDS 550 2-O
SUBSTITUTED ACIDS 551
SULFUR DERIVATIVES OF DEMOSPONGIC ACIDS 553 INTRACELLULAR LOCALIZATION
AND BIOLOGICAL ACTIVITY OF DEMOSPONGIC ACIDS 555 BRIEF REMINDER ABOUT
CONVENTIONAL STEROLS 555
UNCONVENTIONAL STEROLS PRODUCED BY CHANGES IN THE TETRACYCLIC SYSTEM 556
UNCONVENTIONAL STEROLS PRODUCED BY POLYMETHYLATION OF THE SIDE CHAIN 562
STEROLS WITH DEGRADED SIDE CHAINS 564 STEROLS AND STANOLS WITH
CYCLOPROPANIC AND CYCLOPROPENIC SIDE CHAINS 564 SECOSTEROLS 566
POLYHYDROXYLATED STEROIDS AND DERIVATIVES, PEROXYSTEROLS 569 SULFATED
STEROLS 572 CHLORINATED STEROLS AND STERONES 574
NITROGEN-CONTAINING STEROLS 576 GLYCOLIPIDS 577
SECONDARY METABOLITES OF HOMOSDEROMORPHA 582 FATTY ACIDS, POLYKETIDES
AND OXYLIPINS OF PLAKINASTRELLA AND PLAKORTIS 582 CYCLIC PEROXIDES AND
PEROXYLACTONES
OF PLAKINASTRELLA AND PLAKORTIS 584 GLYCOSIDES 587 POLYHYDROXYLATED
STEROLS OF OSCARELLA LOBULARIS 587 ALKALOIDS AND OTHER ORIGINAL NITROGEN
DERIVATIVES OF PLAKORTIS AND CORTIDUM 587
SECONDARY METABOLITES OF ASTROPHORIDA 590 ACETYLENIC FATTY ACIDS OF
STELLETTA 591 GLYCOLIPIDS: CAMINOSIDES AND PACHYMOSIDES 592 TRITERPENES
OF MALABARICANE AND ISOMALABARICANE:
SESTERTERPENES 591 TRITERPENIC GLYCOSIDES AND STEROIDAL GLYCOSIDES 593
SUBSTITUTED TETRAMIC ACIDS AND DERIVED GLYCOSIDES 596 ERYLUSAMINES,
ERYLUSINE AND ERYLUSIDINE 598
CYCLIC DEPSIPEPTIDES, PEPTOLIDES AND MACROLACTONES 598
NITROGEN-CONTAINING TERPENES 602
BENGAZOLES AND BENGAMIDES 603 ATYPICAL NITROGENOUS DERIVATIVES 605
PHOSPHORUS-CONTAINING DERIVATIVES SIMILAR TO CALYCULIN A 607 AROMATIC
SULFATED DERIVATIVES 608
ISOTACTIC POLYMETHOXYDIENES OF MYRIASTRA CLAVOSA 608
SECONDARY METABOLITES OF HADROMERIDA AND CHONDROSIDA 609 PERFORATING
POWER OF CLIONAIDAE 609 LYSO-PHOSPHOLIPIDS AND SULFATED SPHINGOSINES
OF SPIRASTRELLA ABATA 610 BROMINATED ACETYLENIC DERIVATIVES OF
DIPLASTRELLA 611 CYCLIC PEROXIDES 612 TERPENES 613
UNCONVENTIONAL STEROLS 624 MACROLACTONES: LATRUNCULINS AND SPONGISTATINS
615 ATYPICAL GLYCOSIDES OF LATRUNCULIA CORTICATA 617 OTHER NITROGEN-FREE
TOXINS 627
PEPTIDES AND DEPSIPEPTIDES 628 PYRROLE DERIVATIVES AND OTHER
NITROGEN-CONTAINING HETEROCYCLES 619 ATYPICAL NUCLEOSIDES 622
SECONDARY METABOLITES OF LITHISTIDA 622 PARTICULAR CHARACTERISTICS OF
LITHISTID SPONGES 622 NITROGEN-CONTAINING SESQUITERPENES OF THEONELLA
623 SPECIFIC GLYCOLIPIDS OF THEONELLA SWINHOD,
DISCODERMIA CALYX AND D. DISSOLUTA 623 LONG-CHAIN POLYACETYLENIC
DERIVATIVES OF THEONELLA SP. 624 3/?-METHOXYSTEROLS OF JEREICOPSIS
GRAPHIDIOPHORA 624
4-METHYLENESTEROLS AND STERONES OF THEONELLA 624 MACROLIDES 626 EXAMPLES
OF ACETOGENINS: DISCODERMOLIDE, CALYCULINS AND ONNAMIDES 629
LINEAR PEPTIDES 630 MONO- AND BICYCLIC PEPTIDES 632 SYMBIOTIC ORIGIN OF
SOME POLYPEPTIDES 635 CYCLIC AND LINEAR DEPSIPEPTIDES 635 ATYPICAL
NITROGENOUS DERIVATIVES 639
SECONDARY METABOLITES OF SPIROPHORIDA 640 ATYPICAL STEROLS OF CINACHYRA,
MICROSCLERODERMA, AND SCLERITODERMA 640
CINACHYROLIDE A 640 MICROSCLERODERMINS AND ACICULITINS 641 EXAMPLES OF
ATYPICAL DERIVATIVES OF SOME SPONGES OF THE TETILLIDAE 641
SECONDARY METABOLITES OF AGELASIDA 642 STEROLS 642 DITERPENES AND
CAROTENOIDS 642 MEROSESQUITERPENES AND NITROGEN-CONTAINING
MERODITERPENES 643
IMAGE 9
CONTENTS XV
GALACTOSYLCERAMIDES AND GLYCOLIPIDS 644 OROIDIN AND RELATED C N N 5
BROMOPYRROLE ALKALOIDS 646 AGELASTATIN A SERIES 649 OTHER SERIES 650
PYRROLE-2-CARBOXYLIC ACID DERIVATIVES 650 OTHER EXAMPLES OF
NITROGEN-CONTAINING HETEROCYCLES 650 BETAINES 651
SECONDARY METABOLITES OF HALICHONDRIDA 652 A-NOR-STEROIDS AND OTHER
NON-CONVENTIONAL STEROLS 652 CONVENTIONAL TERPENES 654
NITROGEN-CONTAINING TERPENES: ISONITRILES AND RELATED DERIVATIVES 659
OTHER TERPENES 666 LONG-CHAIN LINEAR POLYAMINES AND
A,CO-BIS-ISOTHIOCYANATES 668 POLYETHERS: HALICHONDRINS, OKADAIC
AND GLYCOOKADAIC ACIDS 668 VARIOUS LIPIDS 670 LINEAR PEPTIDES OF THE
GENERA AULETTA AND CYMBASTELA 672
DEPSIPEPTIDES AND CYCLIC PEPTIDES 672 PYRROLE, IMIDAZOLE, PYRIDINE,
ISOQUINOLINE AND INDOLE DERIVATIVES 678 PYRROLE DERIVATIVES 678
IMIDAZOLE DERIVATIVES 678 PYRIDINE AND ISOQUINOLINE DERIVATIVES 679
INDOLE DERIVATIVES 679 HETEROCYCLES RELATED TO THE OROIDIN FAMILY 681
ATYPICAL HALOGENATED AND SULFUR-CONTAINING DERIVATIVES 682
SECONDARY METABOLITES OF HAPLOSCLERIDA 683 ACETYLENIC DERIVATIVES 685
ATYPICAL FATTY ACIDS 691 TERPENES AND MEROTERPENES 693
TRITERPENIC GLYCOSIDES 699 HOPANOIDS, STEROIDS AND STEROSIDES 701
MACROLIDES, DEPSIPEPTIDES AND CYCLIC PEPTIDES 704 AMMO ALCOHOLS AND
GLYCOSPHINGOLIPIDS
(CEREBROSIDES) 705 MANZAMINES AND RELATED DERIVATIVES 707 QUINOLIZIDINE
AND 1-OXAQUINOLIZIDINE DERIVATIVES 707 PYRIDINE DERIVATIVES AND
3-ALKYLPYRIDINIUM SALTS 714 PYRIDOACRIDINE ALKALOIDS 716
PYRROLOQUINONES AND OTHER EXAMPLES OF NITROGEN-CONTAINING HETEROCYCLES
727 QUINONES AND SULFATED HYDROQUINONES 722 VERY LONG-CHAIN LINEAR
SULFATED DERIVATIVES 722 THIOCYANATINS: A,CO-DITHIOCYANATES
OF OCEANAPIA SP. 722 SOME INFORMATION ON FRESHWATER HAPLOSCLERID SPONGES
723
SECONDARY METABOLITES OF POECILOSCLERIDA 724 STEROLS, STEROIDS AND
STEROSIDES 725 TERPENES AND TRITERPENIC GLYCOSIDES 727 POLYBROMINATED
ACETOGENINS AND OXYLIPINS 732
LONG-CHAIN ACETYNENIC DERIVATIVES: RASPAILYNES 732 GLYCOLIPIDS 733
BROMINATED AROMATIC DERIVATIVES OF HAMIGERA TARANGAENSIS 733
MACROLIDES 734 CHONDROPSINS: CYCLIC DEPSIPEPTIDES OF CHONDROPSIS SP. 736
EURYPAMIDES (MICROCIONA EURYPA), MICROCIONAMIDES
(CLATHRIA ABIETINA) AND OTHER CYCLIC PEPTIDES 737 LINEAR AMIDES 738
EXAMPLES OF SOME ATYPICAL SULFUR-CONTAINING DERIVATIVES 739 PYRROLE AND
INDOLE DERIVATIVES 742 PYRIDINES, QUINOLIZINES AND PYRIDOACRIDINES 742
GUANIDINE DERIVATIVES 743 PYRROLOIMINOQUINONES AND PYRROLOQUINONES 747
AZASUGARS 748
OTHER EXAMPLES OF POLYCYDIC ALKALOIDS 748 PHOSPHORUS AND
ARSENIC-CONTAINING DERIVATIVES, BETAINES 750
GENERAL INFORMATION ON THE METABOLITES OF SPONGES LACKING MINERAL
SPICULES 752
SECONDARY METABOLITES OF DENDROCERATIDA 753 TERPENES AND MEROTERPENES
754 STEROLS 760
POLYBROMOPHENOLS AND POLYBROMODIPHENYL ETHERS OF DYSIDEA 761 NITROGEN
COMPOUNDS 763
SECONDARY METABOLITES OF DICTYOCERATIDA 768 TERPENES AND MEROTERPENES
768 STEROLS 788
GLYCOLIPIDS 789 POLYBROMODIPHENYL ETHERS AND OTHER HALOGENATED AROMATIC
DERIVATIVES 789 MACROLIDES: LAULIMALIDE, ALTOHYRTINS, CHONDROPSINS
AND HATERUMALIDES 790 LINEAR AND CYCLIC PEPTIDES, DEPSIPEPTIDES 791
ALKALOIDS AND OTHER NITROGEN-CONTAINING COMPOUNDS 793
PHOSPHORUS DERIVATIVES 795 ATYPICAL SULFUR DERIVATIVES 796
SECONDARY METABOLITES OF VERONGIDA 796 3,5-DIBROMOTYROSINE DERIVATIVES
797 OTHER NITROGEN-CONTAINING COMPOUNDS 805 GLYCEROL ETHERS AND
GLYCOSPHINGOLIPIDS 807
SULFATED AROMATIC COMPOUNDS 807 METABOLITES SPECIFIC TO THE FAMILY
IANTHELLIDAE 808
IMAGE 10
XVI
CONTENTS
SELECTION OF DOCUMENTARY RESOURCES 822
REFERENCES 82 2 SOME PROCEEDINGS OF THE INTERNATIONAL SPONGE CONFERENCES
875 WEBSITES 875
SYNTHESIS 875
20
CNIDARIA AND CTENOPHORA 925
GENERAL INTRODUCTION 925
SIMPLIFIED CLASSIFICATION OF CNIDARIA 925 HERMATYPIC AND AHERMATYPIC
CORALS: CORAL BLEACHING 928
GENERAL INFORMATION ON METABOLITES OF CNIDARIA 929
MEMBRANE CONSTITUENTS AND SECONDARY METABOLITES OF OCTOCORALLIA
(ANTHOZOA) 930 PROSTAGLANDINS AND PROSTANOIDS 930 PHOSPHOLIPID FATTY
ACIDS, GLYCOLIPIDS
AND OTHER LIPIDIE DERIVATIVES 935 GENERAL REMARKS ON THE STEROLS OF
OCTOCORALLIA 939 GORGOSTEROL AND OTHER CYCLOPROPANE-CONTAINING STEROLS
940
POLYOXYGENATED STEROIDS 944 STERONES AND CHLORINATED STERONES 948
SULFUR-CONTAINING STEROIDS 952
CYCLIZED SIDE-CHAIN STEROLS 951 SECOSTEROLS 952 STEROSIDES, PREGNANE AND
NOR-PREGNANE DERIVATIVES 955 SESQUITERPENIC HYDROCARBONS 958 HALOGENATED
AND NITROGEN-CONTAINING SESQUITERPENES 959
SESQUITERPENES WITH ORIGINAL CARBON SKELETONS 962 EXAMPLES OF
SESQUITERPENES WITH A CLASSICAL CARBON SKELETON 968 GENERAL ACCOUNT OF
DITERPENES 974
LINEAR AND MONOCYCLIC DITERPENES 975 GENERAL INFORMATION ON BICYDIC
DITERPENES 991 CHLORINATED DITERPENES 995 OTHER EXAMPLES OF BRIARANE
DERIVATIVES 996 NITROGEN-CONTAINING DITERPENES OF CLADIELLANE/
EUNICELLANE: ELEUTHEROBIN AND ANALOGUES, LABIATAMIDES 999
OTHER EXAMPLES OF CLADIELLANE/EUNICELLANE DITERPENES 1004 DITERPENES OF
SERRULATANE AND OTHER BICYCLIC CARBON SKELETONS 1005
BICYCLIC C5/C11 DITERPENES 1005 BICYCLIC DITERPENES CONTAINING A
CYCLOPROPANE 1006 SOME OTHER EXAMPLES OF BICYCLIC DITERPENES 1011
GENERAL ACCOUNT OF TRICYCLIC DITERPENES 1014 PSEUDOPTEROSINS, OTHER
AMPHILECTANE DERIVATIVES AND ANALOGUES 2024 OTHER EXAMPLES OF TRICYCLIC
AND TETRACYCLIC DITERPENES 2029
COMMENTS ON THE ORIGIN OF TERPENES 2023 NON-TERPENIC NITROGENOUS
DERIVATIVES OF OCTOCORALLIA 2023
MEMBRANE CONSTITUENTS AND SECONDARY METABOLITES OF HEXACORALLIA
(ANTHOZOA) 1027 FATTY ACIDS, OXYLIPINS AND ACETYLENIC DERIVATIVES 1027
STEROLS AND ECDYSTEROIDS 1029
TERPENES 1031 CAROTENOIDS OF SEA ANEMONES 2033 AROMATIC DERIVATIVES 2033
CERAMIDES 2033
EXAMPLES OF NITROGENOUS PIGMENTS: ZOANTHOXANTHINS AND CALLIACTIN 2034
PALYTOXINS 1034
MYCOSPORINES 1036 BETAINES, PHOSPHOBETAINES, PURINES AND OTHER
NITROGEN-CONTAINING DERIVATIVES 1037 ZOANTHAMINE ALKALOIDS 1039
CYTOLYSINS, NEUROPEPTIDES AND OTHER VENOMS OF SEA ANEMONES 2042
VENOMS AND OTHER METABOLITES OF MEDUSOZOA 1042 SOME DATA ON THE CUBOZOA
AND OTHER JELLYFISH 1043 BIOLUMINESCENCE OF JELLYFISH AND OTHER CNIDARIA
2044 SOME RESULTS ON THE SECONDARY METABOLITES OF OTHER HYDROZOA 2045
CTENOPHORA 2049
SELECTION OF DOCUMENTARY RESOURCES 2049 REFERENCES 1049 WEBSITES 2082
SYNTHESIS 2083
VOLUME 3
PART 6 PROTOSTOMES
21 WORM-LIKE ORGANISMS: 1 2097
PLATYHELMINTHES 2097 MACROLIDES AND OTHER COMPOUNDS FROM SYMBIOSIS WITH
AMPHIDINIUM SP. 2097 STAUROSPORINE DERIVATIVES AND OTHER METABOLITES
FROM PLATYHELMINTHES 2200
IMAGE 11
CONTENTS X V II
NEMERTEA 2202
BACKGROUND ON ANNELIDA AND ECHIURA 1102 LIPIDS AND SEXUAL PHEROMONES OF
POLYCHAETES 1103 PIGMENTS OF POLYCHAETES AND ECHIURANS 1104 BROMOPHENOLS
OF POLYCHAETES AND OF THE PHORONID PHOWNOPSIS VIRIDIS 1105
EXAMPLES OF NITROGEN- AND SULFUR-CONTAINING DERIVATIVES FROM POLYCHAETES
1105
SELECTION OF DOCUMENTARY RESOURCES 1107 REFERENCES 1107 WEBSITES 1112
SYNTHESIS 2213
22 BRYOZOA, PHORONIDA AND BRACHIOPODA 2225
BRYOZOANS (BRYOZOA, ECTOPROCTA) 2225 BACKGROUND AND CLASSIFICATION 2115
LIPIDS AND AROMATIC COMPOUNDS 1226 BRYOSTATINS 2228 PYRROLE AND
PYRROLIDINE ALKALOIDS 2222
INDOLE AND PHYSOSTIGMINE ALKALOIDS 2223 QUINOLINE, ISOQUINOLINE AND
/?-CARBOLINE DERIVATIVES 2224 ORIGINAL HETEROCYCLIC SYSTEMS 2226 NITRO
COMPOUNDS 2226
SULFOXONIUM SALTS AND DOGGER BANK ITCH 2226
PHORONIDA AND BRACHIOPODA 2227
SELECTION OF DOCUMENTARY RESOURCES 2227 REFERENCES 2227 WEBSITES 2232
SYNTHESIS 1131
23 MOLLUSCS 1135
GENERAL CHARACTERISTICS AND CLASSIFICATION 1135
GENERAL INFORMATION ON LIPIDS: HYDROCARBONS, FATTY ACIDS, OXYLIPINS AND
STEROLS 1136
METABOLITES OF PROSOBRANCH GASTROPODS 1140 SOME CHEMICAL DATA ON
ARCHAEOGASTROPODA 1140 KEYHOLE LIMPET HAEMOCYANIN 1143 CHEMICAL DATA ON
MESOGASTROPODA 1143
SECONDARY METABOLITES OF NEOGASTROPODA 1145 A BRIEF HISTORY OF TYRIAN
PURPLE 1146 INDIRUBINS 1 147 CONOPEPTIDES AND CONOTOXINS 1148
TOXIC SALIVARY SECRETIONS: TETRODOTOXIN, SURUGATOXIN AND NEOSURUGATOXIN
1151
METABOLITES OF OPISTHOBRANCH GASTROPODS 1152 GENERAL CHARACTERISTICS OF
THE ORDER ANASPIDEA 2253 EXAMPLES OF FOOD CHAINS BETWEEN SEA HARES
AND ALGAE 2153 APLYSIOVIOLIN AND CAROTENOID PIGMENTS 1159
NITROGEN-CONTAINING MEROTERPENES 1159
MACROLACTONES: APLYOLIDES, APLYSIATOXINS, AURISIDES, DOLABELIDES,
APLYRONINES AND SYPHONOSIDE 1160 PEPTIDES AND DEPSIPEPTIDES: DOLASTATINS
AND AURILIDES 1162 OTHER EXAMPLES OF NITROGENOUS DERIVATIVES OF
ANASPIDEA 1166 ANTIMICROBIAL AND ANTI-TUMOUR GLYCOPROTEINS OF THE GENERA
APLYSIA AND DOLABELLA 1168
POLYPROPIONATES OF DOLABELLA AURICULARIA AND DOLABRIFERA DOLABRIFERA
1168 GENERAL INFORMATION ON THE SECONDARY METABOLITES OF CEPHALASPIDEA
2269 ALKYLBENZENES AND 2- AND 3-ALKYLPYRIDINES OF CEPHALASPIDEA 2 2 70
PEPTIDES AND DEPSIPEPTIDES OF PHILINOPSIS SPEDOSA 1171 POLYKETIDES OF
CLIONE ANTARCTICA 1172 SECONDARY METABOLITES OF NOTASPIDEA 2273
BACKGROUND ON THE CHEMISTRY OF NUDIBRANCHS 2275 TERPENES, TERPENOIDS AND
STEROIDS OF NUDIBRANCHS 2 2 75
PROSTAGLANDIN LACTONES OF TETHYS FIMBRIA 1187 CYTOTOXIC MACROLIDES OF
NUDIBRANCHS 1288 CHLORINATED POLYACETYLENIC DERIVATIVES OF DIAULULA
SANDIEGENSIS 1189
RELATIONS BETWEEN NUDIBRANCHS AND CALCAREOUS SPONGES: AMINO-2-IMIDAZOLE
DERIVATIVES 2290 RELATIONS BETWEEN NUDIBRANCHS AND BRYOZOANS: PYRROLE
DERIVATIVES 2 2 90 GUANIDINE DERIVATIVES AND OTHER ALKALOIDS OF
NUDIBRANCHS 2292
NUCLEOSIDES AND PEPTIDES OF NUDIBRANCHS 2192 SIMPLIFIED ASSESSMENT OF
NUDIBRANCH CHEMISTRY 2 2 93 GENERAL REMARKS ON METABOLITES OF
SACOGLOSSANS 2193 TERPENES OF SACOGLOSSANS 2 2 94
POLYPROPIONATE DERIVATIVES OF SACOGLOSSANS 2294 KAHALALIDES: CYTOTOXIC
DEPSIPEPTIDES OF THE COUPLED ELYSIA/BRYOPSIS SP. 2296
METABOLITES OF PULMONATE GASTROPODS 2197 SESQUITERPENES AND DITERPENES
OF THE GENERA ONCHIDELLA AND TRIMUSCULUS 1197 POLYPROPIONATE DERIVATIVES
OF PULMONATES 2 2 98 CYTOTOXIC DEPSIPEPTIDES OF ONCHIDIUM SP. 2199
IMAGE 12
XVIII CONTENTS
METABOLITES OF BIVALVIA (LAMELLIBRANCHIATA) 1200 DEGRADATION PRODUCTS OF
CHLOROPHYLL A OF RUDITAPES PHILLIPINARUM 1201 CAROTENOIDS 1203
SOME DATA ON POLAR LIPIDS (PLASMALOGENS AND CARDIOLIPIDS) 2203 POLAR
STEROLS OF PATINOPECTEN YESSOENSIS
AND 20-ISOSTEROLS OF MACOMA BALTHICA 1204 FATTY ACIDS AND OTHER LIPID
DERIVATIVES 1206 AZASPIRACIDS AND OTHER TOXINS 1206 POLYAMINES,
ALKALOIDS
AND VARIOUS NITROGEN-CONTAINING DERIVATIVES 1212 ARSENIC-CONTAINING
DERIVATIVES OF TRIDACNA MAXIMA 1213 EXAMPLES OF BIOPOLYMERS 2223
METABOLITES OF CEPHALOPODS 1213
SELECTION OF DOCUMENTARY RESOURCES 1215 REFERENCES 1215 WEBSITES 1237
SYNTHESIS 1238
24
ARTHROPODA 1249
CHITIN AND CHITOSANS 1249
CAROTENOID PIGMENTS 1251
LIPID DERIVATIVES 2253 HORMONES CONTROLLING CRUSTACEAN MOULTING AND
OTHER STEROIDS 2253
SOME EXAMPLES OF SULFUR-, NITROGEN- AND ARSENIC- CONTAINING METABOLITES
OF CRUSTACEANS 2256
SOME DATA ON MARINE CHELICERIFORMS 2257
SELECTION OF DOCUMENTARY RESOURCES 2258 REFERENCES 1258 WEBSITES 1261
SYNTHESIS 1261
25 INTRODUCTION TO CHEMICAL ECOLOGY 1263
EXAMPLES OF INTRASPECIFIC RELATIONS 1264 SEXUAL PHEROMONES:
SPERM-ACTIVATING PEPTIDES OF URCHINS AND MOLLUSCS 1264 EXAMPLES OF ALARM
PHEROMONES 1265
EXAMPLES OF INTERSPECIFIC RELATIONSHIPS 1265 PREDATOR-PREY
RELATIONSHIPS: DEFENCE ALLOMONES OF ALGAE AND INVERTEBRATES 1266
DEFENCE ALLOMONES IN ASSOCIATIONS BETWEEN MICROORGANISMS AND
INVERTEBRATES 1267 ELICITORS AND DEFENCE ALLOMONES OF ALGAE 1271
SUBSTANCES INDUCING METAMORPHOSIS OF LARVAE 1272 FORMATION OF EPIBIOSIS
(BIOFOULING) AND ANTIFOULING SUBSTANCES 1273 FOOD ATTRACTANTS AND
STIMULANTS 1274
SELECTION OF DOCUMENTARY RESOURCES 1274 REFERENCES 1274 WEBSITES 1280
SYNTHESIS 1280
PART 7 DEUTEROSTOMES 26 ECHINODERMS 1283
GENERAL REMARKS AND CLASSIFICATION 1283
GENERAL COMMENTS ON THE CHEMISTRY OF ECHINODERMS 1284
METABOLITES OF CRINOIDS (FEATHER STARS AND SEA LILIES) 1287 QUINONIC
PIGMENTS 1287 STEROLS, GLYCOLIPIDS AND PHOSPHOCERAMIDES 2288
3,5-DIBROMOTYROSINE DERIVATIVES 1289
METABOLITES OF ECHINIDS (SEA URCHINS) 2290 ECHINOCHROME A, SPINOCHROMES
AND CAROTENOIDS 1290 FATTY ACIDS, PROSTAGLANDINS, GLYCOSPHINGOLIPIDS AND
OTHER LIPIDS 2292
NITROGEN- AND SULFUR-CONTAINING METABOLITES 2296 SULFATED FUCANS AND
GALACTANS 2297
METABOLITES OF OPHIUROIDS (BRITTLE STARS AND BASKET STARS) 2297 LIPIDS
2298 SULFATED CAROTENOIDS 2299
STEROLS AND SULFATED STEROLS 2300 ALKALOIDS 2302
METABOLITES OF ASTEROIDS (SEA STARS AND STARFISH) STEROLS AND SULFATED
STEROLS 1304 FREE AND SULFATED POLYHYDROXYSTEROLS 1309 NITROGEN- AND
PHOSPHORUS-CONTAINING POLYHYDROXYSTEROLS 1313
STEROIDAL GLYCOSIDES AND ASTEROSAPONINS 1313 CAROTENOIDS 1328 FATTY
ACIDS AND OXYLIPINS 2328 GLYCOLIPIDS, CERAMIDES, CEREBROSIDES AND
GANGLIOSIDES 2329
NITROGEN-CONTAINING DERIVATIVES 2329
2304
IMAGE 13
CONTENTS X IX
METABOLITES OF HOLOTHUROIDS (SEA CUCUMBERS) 2335 FATTY ACIDS 1336
STEROLS, 4A-METHYLSTEROLS AND TRITERPENES 2336 HOLOTHURINS 1336
CAROTENOIDS 2347 TREPANG 2348 CEREBROSIDES AND GANGLIOSIDES 2348
ATYPICAL NITROGEN-CONTAINING DERIVATIVES
OF CUCUMARIA FRONDOSA 1351 OLIGOSACCHARIDES AND SULFATED POLYSACCHARIDES
1352
SELECTION OF DOCUMENTARY RESOURCES 1352 REFERENCES 1353 WEBSITES 1366
SYNTHESIS 1367
27 WORM-LIKE ORGANISMS: 2. CHAETOGNATHA AND HEMICHORDATA (ENTEROPNEUSTA
AND PTEROBRANCHIA) 1369
SHORT DESCRIPTION OF CHAETOGNATHA 1369
SHORT DESCRIPTION OF HEMICHORDATA 1369
AROMATIC AND HETEROAROMATIC DERIVATIVES OF ENTEROPNEUSTS 1370
CEPHALOSTATINS OF CEPHALODISCUS GILCHRISTI (PTEROBRANCHIA) 1372
SELECTION OF DOCUMENTARY RESOURCES 1373 REFERENCES 1373 WEBSITES 1374
SYNTHESIS 1374
28 ASCIDIANS (TUNICATES) 1377
REMINDER ABOUT THE CONCEPT OF THE CHORDATE 1377
DESCRIPTION OF TUNICATES AND CLASSIFICATION OF THE ASCIDIACEA 1377
GENERAL INFORMATION ON THE CHEMISTRY OF ASCIDIANS 1379
LIPIDS: FATTY ACIDS, ACYLTUNICHLORINS, POLYKETIDES AND OXYLIPINS 1380
AMINO ALCOHOLS, SPHINGANINES, SERINOLIPIDS, CERAMIDES AND CEREBROSIDES
1382
STEROLS AND STEROIDS 1384
CAROTENOIDS 1386
SULFATED POLYSACCHARIDES OF ASCIDIAN TUNICS 1386
NITROGENOUS BIOPOLYMERS AND LECTINS 1387
METABOLITES OF DIDEMNIDAE 1388 DIDEMNAKETALS AND CHLORINATED DITERPENES
OF LISSOCLINUM SPECIES 1388 AROMATIC POLYSULFANES AND OTHER ATYPICAL
SULFUR DERIVATIVES 1390 LAMELLARINS AND OTHER PYRROLE ALKALOIDS 1392
DERIVATIVES OF QUINOLINE, PYRIDOACRIDINE
AND PYRROLOACRIDINE 1394 DERIVATIVES OF TYRAMINE, TRYPTOPHAN, INDOLE AND
SS-CARBOLINE 1396 CYTOTOXIC LINEAR AMIDES: BISTRATENE A AND BISTRAMIDES
1400
LINEAR PEPTIDES AND 1,4-DIKETOPIPERAZINES 1401 CYCLIC PEPTIDES 1402
MACROLIDES: PATELLAZOLES 1408 CYCLIC DEPSIPEPTIDES: DIDEMNINS, APLIDIN
(PLITIDEPSIN) AND OTHER DERIVATIVES 1409
PURINES, NUDEOSIDES AND ANALOGUES 1413
METABOLITES OF POLYCITORIDAE 1414 TERPENES OF CYSTODYTES SP. AND
POLYCITOR ADRIATICUS 1414
AROMATIC POLYSULFANES OF POLYCITOR ADRIATICUS 1414 NITROGENOUS
MACROLIDES: IEJIMALIDES 1415 SIMPLE PYRROLE AND INDOLE ALKALOIDS 1415
YS-CARBOLINE ALKALOIDS: EUDISTOMINS
AND RELATED DERIVATIVES 1416 DECAHYDROQUINOLINE ALKALOIDS: LEPADINS 1418
QUINOLIZIDINE AND INDOLIZINE ALKALOIDS 1420 PERHYDROPYRROLO[2,L-J] AND
PERHYDROPYRIDO[2,L-J] QUINOLINE ALKALOIDS: CYLINDRICINES 1420
PYRIDOACRIDINE ALKALOIDS AND RELATED DERIVATIVES 1421 OTHER TYPES OF
ALKALOIDS 1424 CYCLIC PEPTIDES 1426
METABOLITES OF POLYCLINIDAE 1426 LONG-CHAIN SULFATED ALKANES AND
TERPENES OF SIDNYUM TURBINATUM 1427 TERPENES AND MEROTERPENES 1427
PARA- AND METACYCLOPHANES: LONGITHORONES AND RELATED DERIVATIVES 1427
SIMPLE AROMATIC DERIVATIVES 1430
NITROGENOUS AND NON-NITROGENOUS MACROLIDES 1430 LONG-CHAIN AMINES AND
AMINO ALCOHOLS, SPHINGOSINES 1432 PIPERIDINE ALKALOIDS: PSEUDODISTOMINS
1433
INDOLE AND /?-CARBOLINE ALKALOIDS 1434 QUINOLINE AND PYRIDOACRIDINE
ALKALOIDS 1436 BIS-STEROIDAL ALKALOIDS OF RITTERELLA TOKIOKA:
RITTERAZINES 1436
PURINES AND NUCLEOSIDES 2437
IMAGE 14
XX CONTENTS
MISCELLANEOUS NITROGENOUS DERIVATIVES 1439
METABOLITES OF ASCIDIIDAE 1441 VANADIUM, INTRACELLULAR ACIDITY OF BLOOD
CELLS AND PEPTIDE LIGANDS 1441
METABOLITES OF CIONIDAE 1445
METABOLITES OF DIAZONIDAE 1446
METABOLITES OF PEROPHORIDAE 1447 METABOLITES ISOLATED FROM SPECIES OF
THE GENUS PEROPHORA 1447 TETRAHYDROISOQUINOLINE ALKALOIDS:
ECTEINASCIDINS
METABOLITES OF MOLGULIDAE AND PYURIDAE 1449 LIPIDS AND NON-NITROGENOUS
DERIVATIVES 1449 NITROGENOUS DERIVATIVES, ANTIMICROBIAL PEPTIDES AND
PROTEINS 1450
METABOLITES OF STYELIDAE 1453 NON-NITROGENOUS DERIVATIVES 1453
PHENYLETHYLAMINE DERIVATIVES, VARIOUS ALKALOIDS ANTIBACTERIAL PURINES
AND PEPTIDES 1456
SELECTION OF DOCUMENTARY RESOURCES 1456 REFERENCES 1456 WEBSITES 1477
SYNTHESIS 1477
1447
1453
29 VERTEBRATES: FISH, REPTILES AND MAMMALS 1489
FISH 1489 SQUALENE AND OTHER LIPID DERIVATIVES OF CHONDRICHTHYES AND
AGNATHA 1489 BILE STEROIDS OF SHARKS AND HAGFISH:
SCYMNOL, MYXINOL AND DERIVATIVES 1490 SQUALAMINE AND OTHER AMINOSTEROLS
OF SHARKS MIGRATORY PHEROMONES AND SEX HORMONES OF LAMPREYS 1493
INHIBITION OF ANGIOGENESIS BY SHARK CARTILAGE: NEOVASTAT 1494 GENERAL
ACCOUNT OF LIPID DERIVATIVES OF OSTEICHTHYES 1494 VENOMS AND TOXINS:
DEFENCE SUBSTANCES OFFISH ANTIFREEZE PROTEINS OF POLAR FISH 1501
SULFATED GLYCOSAMINOGLYCANS OF THE EXTRACELLULAR MATRIX 1502
REPTILES 1502
MAMMALS 1503 LIPID COMPOSITION AND RESIDUES OF CHLORINATED PESTICIDES
1503 AMBERGRIS, AMBREIN AND AMBROX 2504
SELECTION OF DOCUMENTARY RESOURCES 1504 REFERENCES 1504 WEBSITES 1511
SYNTHESIS 1522
2492
2497
INDEX 2525
|
| any_adam_object | 1 |
| author | Kornprobst, Jean-Michel |
| author_facet | Kornprobst, Jean-Michel |
| author_role | aut |
| author_sort | Kornprobst, Jean-Michel |
| author_variant | j m k jmk |
| building | Verbundindex |
| bvnumber | BV025584418 |
| classification_rvk | WI 4440 |
| classification_tum | CIT 680b BIO 070b WER 660b BIO 140b |
| ctrlnum | (DE-599)BVBBV025584418 |
| discipline | Chemie / Pharmazie Biologie Werkstoffwissenschaften / Fertigungstechnik |
| format | Book |
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| id | DE-604.BV025584418 |
| illustrated | Not Illustrated |
| indexdate | 2024-12-23T23:22:21Z |
| institution | BVB |
| isbn | 9783527327034 9783527334292 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-019102616 |
| open_access_boolean | |
| publishDateSort | 0000 |
| publisher | Wiley-VCH |
| record_format | marc |
| spellingShingle | Kornprobst, Jean-Michel Encyclopedia of marine natural products Pharmazeutische Biologie (DE-588)4045693-6 gnd Naturstoff (DE-588)4041418-8 gnd Meeresbiologie (DE-588)4169246-9 gnd |
| subject_GND | (DE-588)4045693-6 (DE-588)4041418-8 (DE-588)4169246-9 |
| title | Encyclopedia of marine natural products |
| title_auth | Encyclopedia of marine natural products |
| title_exact_search | Encyclopedia of marine natural products |
| title_full | Encyclopedia of marine natural products Jean-Michel Kornprobst |
| title_fullStr | Encyclopedia of marine natural products Jean-Michel Kornprobst |
| title_full_unstemmed | Encyclopedia of marine natural products Jean-Michel Kornprobst |
| title_short | Encyclopedia of marine natural products |
| title_sort | encyclopedia of marine natural products |
| topic | Pharmazeutische Biologie (DE-588)4045693-6 gnd Naturstoff (DE-588)4041418-8 gnd Meeresbiologie (DE-588)4169246-9 gnd |
| topic_facet | Pharmazeutische Biologie Naturstoff Meeresbiologie |
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