The nature and role of pigments of marine invertebrates.

Marine animals, especially those from tropical waters, are often brilliantly coloured, and bright colouration is widespread in both sessile and non-sessile invertebrates. These spectacular natural colours are common in species inhabiting shallow waters, and appear not only in animals exposed to bright light, but also in those living in dark areas where colours are visible only with artificial illumination. Marine organisms also show variation in colour with depth and geographical location, and display great variety in colour patterning. These colour characteristics are the result of several different processes, and serve various purposes - the distribution and function of pigments seems to vary between invertebrate groups. In addition to playing an important role in how marine organisms interact, pigments may be involved in physiological processes. Although nitrogenous pigments predominate, marine organisms contain pigments belonging to all the major structural classes of natural products, as well as some that are unique to the marine environment. This review discusses the nature and significance of such pigments, the chemical and biological processes involved, the factors responsible for and affecting bright colourations, as well as their evolution and speculation as to their function.

[1]  A. Gray Darwin on the origin of species , 1860 .

[2]  C. Munn The pigments of Aplysia Punctata , 1899, The Journal of physiology.

[3]  P. Friedlaender Zur Kenntnis des Farbstoffes des antiken Purpurs aus Murex brandaris , 1907 .

[4]  P. Friedländer Über den Farbstoff des antiken Purpurs aus murex brandaris , 1909 .

[5]  R. Jones,et al.  The lipochromes of sea anemones: Carotenoid pigments of Actinia equina, Anemonia sulcata, Actinoloba dianthus and Tealia felina. , 1935, The Biochemical journal.

[6]  E. Fauré-Fremiet THE FOLLICULINIDÆ (INFUSORIA HETEROTRICHA) OF THE BRETON COAST , 1936 .

[7]  D. A. Webb Observations on the blood of Certain Ascidians, with Special Reference to the Biochemistry of Vanadium , 1939 .

[8]  Par E. Lederer LES PIGMENTS DES INVERTÉBRÉS: (À L'EXCEPTION DES PIGMENTS RESPIRATOIRES) , 1940 .

[9]  C. Pantin,et al.  The colours of the plumose anemone Metridium senile (L.) , 1941, Philosophical Transactions of the Royal Society of London. Series B, Biological Sciences.

[10]  D. L. Fox,et al.  PIGMENTS IN THE COELENTERATA , 1944 .

[11]  A. Comfort THE PIGMENTATION OF MOLLUSCAN SHELLS , 1951 .

[12]  E. Beerstecher The nutrition of the Crustacea. , 1952, Vitamins and hormones.

[13]  D. L. Fox,et al.  The pigmentation of the jellyfish, Pelagia noctiluca (Forskål) var. panopyra Péron & Lesueur , 1954, Proceedings of the Royal Society of London. Series B - Biological Sciences.

[14]  R. Nicolaus,et al.  The structure of melanins and melanogenesis—I: The structure of melanin in Sepia☆ , 1961 .

[15]  A. Fontaine The Colours of Ophiocomina Nigra (Abildgaard): II. The Occurrence of Melanin and Fluorescent Pigments , 1962, Journal of the Marine Biological Association of the United Kingdom.

[16]  Y. Hirata,et al.  Structures of aplysin and aplysinol, naturally occurring bromo-compounds , 1963 .

[17]  P. F. Zagalsky,et al.  CAROTENOPROTEINS IN INVERTEBRATES , 1967 .

[18]  G. J. Bakus Defensive mechanisms and ecology of some tropical holothurians , 1968 .

[19]  B. M. Gilchrist Distribution and relative abundance of carotenoid pigments in anostraca (Crustacea: Branchiopoda). , 1968, Comparative biochemistry and physiology.

[20]  A. C. Giese,et al.  STUDIES ON THE RED AND BLUE FORMS OF THE PIGMENT OF BLEPHARISMA * , 1970 .

[21]  P. Herring Biliprotein coloration of Physalia physalis , 1971 .

[22]  Sutherland,et al.  Pigments of marine animals. XI. Angular naphthopyrones from the crinoid Comanthus parvicirrus timorensis , 1971 .

[23]  P. Herring Porphyrin Pigmentation in Deep-sea Medusae , 1972, Nature.

[24]  L. Mazzarella,et al.  Zoanthoxanthin, a heteroaromatic base from Parazoanthus cfr. axinellae(zoantharia): structure confirmation by X-ray crystallography , 1973 .

[25]  G. Prota,et al.  Zoanthoxanthins of a new structural type from Epizoanthus arenaceus (zoantharia) , 1974 .

[26]  J. T. Baker Tyrian purpie: an ancient dye, a modern problem , 1974 .

[27]  G. Cimino,et al.  Occurrence of hydroxyhydroquinone and 2-aminoimidazole in sponges. , 1974, Comparative biochemistry and physiology. B, Comparative biochemistry.

[28]  Baker Tyrian Purple : an ancient dye, a modern ploblem , 1974 .

[29]  G. Y. Kennedy PORPHYRINS IN INVERTEBRATES , 1975, Annals of the New York Academy of Sciences.

[30]  H. G. Vevers,et al.  A survey of avian eggshell pigments. , 1976, Comparative biochemistry and physiology. B, Comparative biochemistry.

[31]  D. L. Fox Relative chemical stability of inorganically conjugated astaxanthin. , 1976, Comparative biochemistry and physiology. B, Comparative biochemistry.

[32]  P. Schembri,et al.  Bonellin, a most unusual chlorin , 1976 .

[33]  M. Kimura,et al.  The neutral theory of molecular evolution. , 1983, Scientific American.

[34]  I. Macara,et al.  Isolation, properties and structural studies on a compound from tunicate blood cells that may be involved in vanadium accumulation. , 1979, The Biochemical journal.

[35]  G. Y. Kennedy Pigments of Marine Invertebrates , 1979 .

[36]  N. Krinsky Carotenoid protection against oxidation , 1979 .

[37]  Ka Francesconi Pigments of some echinoderms collected from Western Australian waters , 1980 .

[38]  P. Scheuer,et al.  Halogenated phenol and indole constituents of acorn worms , 1980 .

[39]  L. Zanetti,et al.  Developmental aberrations in sea-urchin eggs induced by avarol and two cogeners, the main sesquiterpenoid hydroquinones from the marine sponge, Dysidea avara. , 1980, Comparative biochemistry and physiology. C: Comparative pharmacology.

[40]  P. Falkowski,et al.  Light-shade adaptation of Stylophora pistillata, a hermatypic coral from the Gulf of Eilat , 1981, Nature.

[41]  Sutherland,et al.  Pigments of marine animals. XIV. Polyketide sulfates from the crinoid Comatula pectinata , 1981 .

[42]  G. Bakus Chemical defense mechanisms on the Great Barrier Reef, Australia. , 1981, Science.

[43]  G. Pettit,et al.  Isolation of geodiastatins 1 and 2 from the marine sponge Geodia mesotriaena. , 1981, Journal of natural products.

[44]  P. Gentien,et al.  Carotenoids of Temora turbinata, Centropages furcatus, Undinula vulgaris and Euchaeta russelli , 1982 .

[45]  T. Doyle,et al.  Isolation of lavendamycin, a new antibiotic from Streptomyces lavendulae. , 1982, The Journal of antibiotics.

[46]  J. Clardy,et al.  Halenaquinone, a pentacyclic polyketide from a marine sponge , 1983 .

[47]  Y. Kyōgoku,et al.  Marine Natural Products. XII. On the Chemical Constituents of the Okinawan Marine Sponge Hymeniacidon aldis , 1983 .

[48]  M. Ghiselin,et al.  Chemical defense and evolutionary ecology of dorid nudibranchs and some other opisthobranch gastropods , 1983 .

[49]  I. Shimizu,et al.  Carotenoids of Sea Squirts. I. New Marine Carotenoids, Halocynthiaxanthin and Mytiloxanthinone from Halocynthia roretzi , 1984 .

[50]  Y. Ohizumi,et al.  Keramadine, a novel antagonist of serotonergic receptors isolated from the okinawan sea sponge Agelas sp.☆ , 1984 .

[51]  R. Trench,et al.  Speciation and Symbiotic Dinoflagellates , 1985, Science.

[52]  Sutherland,et al.  Pigments of Marine Animals. XV. Bianthrones and Related Polyketides from Lamprometra palmata gyges and Other Species of Crinoids , 1985 .

[53]  Y. Ohizumi,et al.  Eudistomidin-A, a novel calmodulin antagonist from the okinawan tunicate eudistoma glaucus , 1986 .

[54]  K. Nakanishi,et al.  Isolation of tunichrome B-1, a reducing blood pigment of the sea squirt, Ascidia nigra. , 1986, Journal of natural products.

[55]  C. Christophersen,et al.  Organic Sulfur Compounds from Marine Organisms , 1986 .

[56]  R. R. Olson Photoadaptations of the Caribbean colonial Ascidian-cyanophyte symbiosis Trididemnum solidum. , 1986 .

[57]  T. Molinski,et al.  Metabolites of the antarctic sponge Dendrilla membranosa , 1987 .

[58]  C. Young,et al.  Chemical defense and aposematic coloration in larvae of the ascidian Ecteinascidia turbinata , 1987 .

[59]  D. Blasberger,et al.  Marine natural products: new results from Red Sea invertebrates , 1988 .

[60]  J. Clardy,et al.  Fascaplysin, an unusual antimicrobial pigment from the marine sponge Fascaplysinopsis sp , 1988 .

[61]  J. Porter,et al.  Allelochemical Interactions Between Sponges and Corals , 1988 .

[62]  C. Hawkins Unusual chelates isolated from Ascidiacea , 1988 .

[63]  P. Kelley,et al.  Functional significance of preserved color patterns of mollusks from the Gosport Sand (Eocene) of Alabama , 1988, Journal of Paleontology.

[64]  G. Cimino,et al.  Naturally occurring prostaglandin-1,15-lactones , 1989 .

[65]  P. F. Zagalsky,et al.  Studies on a blue carotenoprotein, linckiacyanin, isolated from the starfish Linckia laevigata (Echinodermata: Asteroidea) , 1989 .

[66]  C. Debitus,et al.  Corallistin A, a second example of a free porphyrin from a living organism. Isolation from the demosponge Corallistes sp. of the coral see and inhibition of abnormal cells , 1989 .

[67]  T. Reimchen Shell colour ontogeny and tubeworm mimicry in a marine gastropod Littorina mariae , 1989 .

[68]  A. Davis,et al.  Direct observations of larval dispersal in the colonial ascidian Podoclavella moluccensis Sluiter: evidence for closed populations☆ , 1989 .

[69]  M. Wicksten Adaptive coloration in invertebrates : proceedings of a symposium , 1990 .

[70]  M. McFall-Ngai Crypsis in the Pelagic Environment , 1990 .

[71]  Y. Ohizumi,et al.  Rigidin, a novel alkaloid with calmodulin antagonistic activity from the okinawan marine tunicate Eudistoma cf. rigida , 1990 .

[72]  J. McClintock,et al.  Chemical defense in the eggs and embryos of antarctic sea stars (Echinodermata) , 1990 .

[73]  S. Liaaen-Jensen Marine Carotenoids ‐ Selected Topics , 1991 .

[74]  P. Herring,et al.  Imidazolopyrazine bioluminescence in copepods and other marine organisms , 1990 .

[75]  A. Ansell,et al.  Oogenesis in the articulate brachiopodTerebratulina retusa , 1991 .

[76]  Andrew J. Young,et al.  The photoprotective role of carotenoids in higher plants , 1991 .

[77]  I. Cuthill,et al.  THE EVOLUTION OF APOSEMATISM IN MARINE GASTROPODS , 1991, Evolution; international journal of organic evolution.

[78]  R. Castenholz,et al.  CHARACTERIZATION AND BIOLOGICAL IMPLICATIONS OF SCYTONEMIN, A CYANOBACTERIAL SHEATH PIGMENT 1 , 1991 .

[79]  J. Bada,et al.  Biogeochemistry of Brachiopod Intracrystalline Molecules [and Discussion] , 1991 .

[80]  P. Crews,et al.  Novel sponge-derived amino acids. 12. Tryptophan-derived pigments and accompanying sesterterpenes from Fascaplysinopsis reticulata , 1991 .

[81]  G. Rosenberg APOSEMATISM AND SYNERGISTIC SELECTION IN MARINE GASTROPODS , 1991, Evolution; international journal of organic evolution.

[82]  Peter J. McCarthy,et al.  Discodermide: a new bioactive macrocyclic lactam from the marine sponge Discodermia dissoluta , 1991 .

[83]  R. Castenholz,et al.  EVIDENCE FOR AN ULTRAVIOLET SUNSCREEN ROLE OF THE EXTRACELLULAR PIGMENT SCYTONEMIN IN THE TERRESTRIAL CYANOBACTERIUM Chiorogloeopsis sp. , 1992, Photochemistry and photobiology.

[84]  J. J. Gauthier,et al.  Antimicrobial activities of Antarctic sponges , 1992, Antarctic Science.

[85]  G. Abbott,et al.  An intracrystalline chromoprotein from red brachiopod shells: implications for the process of biomineralization. , 1992, Comparative biochemistry and physiology. B, Comparative biochemistry.

[86]  B. Demmig‐Adams,et al.  Photoprotection and Other Responses of Plants to High Light Stress , 1992 .

[87]  N. Lindquist,et al.  Defense of Ascidians and Their Conspicuous Larvae: Adult vs. Larval Chemical Defenses , 1992 .

[88]  B. Robison Bioluminescence in the benthopelagic holothurian Enypniastes eximia , 1992, Journal of the Marine Biological Association of the United Kingdom.

[89]  N. Turro,et al.  Reactivity of tunichromes : reduction of vanadium(V) and vanadium(IV) to vanadium(III) at neutral pH , 1992 .

[90]  T. Molinski Marine pyridoacridine alkaloids: structure, synthesis, and biological chemistry , 1993 .

[91]  B. E. Tucker,et al.  Isolation of the nickel-chlorin chelate tunichlorin from the South Pacific ocean sea hare Dolabella auricularia. , 1993, Journal of natural products.

[92]  R. Castenholz,et al.  Evidence Regarding the UV Sunscreen Role of a Mycosporine-Like Compound in the Cyanobacterium Gloeocapsa sp , 1993, Applied and environmental microbiology.

[93]  A. Carroll,et al.  Studies of Australian Ascidians. I. Six New Lamellarin-Class Alkaloids From a Colonial Ascidian, Didemnum sp. , 1993 .

[94]  H. Kotsuki,et al.  Gorgiabisazulene and Gorgiagallylazulene, Two New Guaiazulenoid Pigments from a Gorgonian Acalycigorgia sp. , 1993 .

[95]  Joseph R. Pawlik Marine invertebrate chemical defenses , 1993 .

[96]  G. Pattenden,et al.  Marine Metabolites and Metal Ion Chelation: The Facts and the Fantasies , 1993 .

[97]  H. Fricke,et al.  Influence of light on algal symbionts of the deep water coral Leptoseris fragilis , 1993 .

[98]  P. Crews,et al.  13C-NMR assignments and cytotoxicity assessment of zoanthoxanthin alkaloids from zoanthid corals. , 1993, Journal of natural products.

[99]  C. Debitus,et al.  On the Novel Free Porphyrins Corallistin B, C, D, and E: Isolation from the demosponge Corallistes sp. of the Coral Sea and Reactivity of Their Nickel 55 (II) Complexes toward Formylating Reagents , 1993 .

[100]  J. Veron Corals of Australia and the Indo-Pacific , 1993 .

[101]  J. Tanaka,et al.  Bioactive compounds from marine sponges , 1994 .

[102]  M. Guyot,et al.  Trikendiol, an unusual red pigment from the sponge Trikentrion loeve, anti-HIV-1 metabolite , 1994 .

[103]  S. Urban,et al.  Lamellarins-O and Lamellarin-P - New Aromatic Metabolites From the Australian Marine Sponge Dendrilla-Cactos , 1994 .

[104]  P. Proksch,et al.  Defensive roles for secondary metabolites from marine sponges and sponge-feeding nudibranchs. , 1994, Toxicon : official journal of the International Society on Toxinology.

[105]  Sean Parkin,et al.  Alkaloids from the antarctic sponge Kirkpatrickia varialosa. , 1994 .

[106]  Pawlik,et al.  Defenses of Caribbean sponges against predatory reef fish. II. Spicules, tissue toughness, and nutritional quality , 1995 .

[107]  G. Guella,et al.  Novel Naamidine‐Type Alkaloids and Mixed‐Ligand Zinc(II) Complexes from a Calcareous Sponge, Leucetta sp., of the Coral Sea , 1995 .

[108]  A. Leonard,et al.  Discorhabdin alkaloids from the Antarctic sponge Latrunculia apicalis , 1995 .

[109]  M. Tsushima,et al.  Comparative biochemical studies of carotenoids in sea cucumbers , 1995 .

[110]  J. Rho,et al.  Isolation of guaianoid pigments from the gorgonian Calicogorgia granulosa. , 1996, Journal of natural products.

[111]  J. Clardy,et al.  Tridentatols A-C, novel natural products of the marine hydroid Tridentata marginata , 1996 .

[112]  M. Gordon Dietary antioxidants in disease prevention. , 1996, Natural product reports.

[113]  J. Tanaka,et al.  New cytotoxic carotenoids from the sponge Phakellia stelliderma , 1996 .

[114]  Heonjoong Kang,et al.  Polycarpine dihydrochloride: A cytotoxic dimeric disulfide alkaloid from the indian ocean ascidian Polycarpa clavata , 1996 .

[115]  W. Wickramasinghe,et al.  BENZYLMERCAPTAN (BENZYLTHIOL) AND DIBENZYLDISULPHIDE FROM THE MARINE SPONGE CRELLA SPINULATA, (HENTSCHEL) (POECILOSCLERIDA: CRELLIDAE) , 1996 .

[116]  K. Nakanishi,et al.  Reactions between tunichrome Mm-1, a tunicate blood pigment, and vanadium ions in acidic and neutral media. , 1996, Biochemistry.

[117]  D. van der Helm,et al.  Alkaloids from the Tunicate Polycarpa aurata from Chuuk Atoll. , 1996, The Journal of organic chemistry.

[118]  J. Clardy,et al.  Didemnimides A−D: Novel, Predator-Deterrent Alkaloids from the Caribbean Mangrove Ascidian Didemnum conchyliatum , 1997 .

[119]  G. Hofmann,et al.  Z-Axinohydantoin and Debromo-Z-Axinohydantoin from the Sponge Stylotella aurantium: Inhibitors of Protein Kinase C , 1997 .

[120]  B. Davidson,et al.  Plakinidine D, a new pyrroloacridine alkaloid from the ascidian Didemnum rubeum. , 1997, Journal of natural products.

[121]  G. Cimino,et al.  MORPHOLOGICAL AND CHEMICAL CAMOUFLAGE OF THE MEDITERRANEAN NUDIBRANCH DISCODORIS INDECORA ON THE SPONGES IRCINIA VARIABILIS AND IRCINIA FASCICULATA , 1997 .

[122]  Anette Ekendahl Colour polymorphic prey (Littorina saxatilis Olivi) and predatory effects of a crab population (Carcinus maenas L.) , 1998 .

[123]  S. Merilaita Crypsis through disruptive coloration in an isopod , 1998, Proceedings of the Royal Society of London. Series B: Biological Sciences.

[124]  R. Andersen,et al.  Granulatimide and Isogranulatimide, Aromatic Alkaloids with G2 Checkpoint Inhibition Activity Isolated from the Brazilian Ascidian Didemnum granulatum: Structure Elucidation and Synthesis† , 1998 .

[125]  W. Dunlap,et al.  REVIEW—ULTRAVIOLET RADIATION‐ABSORBING MYCOSPORINE‐LIKE AMINO ACIDS IN CORAL REEF ORGANISMS: A BIOCHEMICAL AND ENVIRONMENTAL PERSPECTIVE , 1998 .

[126]  A. Carroll,et al.  Eudistomin V, a New β-Carboline from the Australian Ascidian Pseudodistoma aureum , 1998 .

[127]  A. Ishida,et al.  Effect of β, β-carotene, β-echinenone, astaxanthin, fucoxanthin, vitamin A and vitamin e on the biological defense of the sea urchin Pseudocentrotus depressus , 1998 .

[128]  D. Faulkner,et al.  Steinschwämme: Stars unter den Naturstoffproduzenten oder Wirte der Stars? , 1998 .

[129]  M. Joron,et al.  Diversity in mimicry: paradox or paradigm? , 1998, Trends in ecology & evolution.

[130]  W. Bandaranayake Mycosporines: are they nature's sunscreens? , 1998, Natural product reports.

[131]  M. Herderich,et al.  Bioactive pyridoacridine alkaloids from the micronesian sponge Oceanapia sp. , 1998, Journal of natural products.

[132]  Gabriella Gamberale,et al.  Aposematism and gregariousness: the combined effect of group size and coloration on signal repellence , 1998, Proceedings of the Royal Society of London. Series B: Biological Sciences.

[133]  R. Hettich,et al.  Cadiolides A and B, New Metabolites from an Ascidian of the Genus Botryllus , 1998 .

[134]  Vervoort,et al.  A cyclized didemnimide alkaloid from the caribbean ascidian didemnumconchyliatum , 1999, Journal of natural products.

[135]  James Mallet,et al.  EVOLUTION OF DIVERSITY IN WARNING COLOR AND MIMICRY: Polymorphisms, Shifting , 1999 .

[136]  J. Lown,,et al.  Pyrroloquinoline and pyridoacridine alkaloids from marine sources. , 1999, Current medicinal chemistry.

[137]  A. Rocher,et al.  Role of secondary metabolites and pigments in the epidermal tissues, ripe ovaries, viscera, gut contents and diet of the sea cucumber Holothuria atra , 1999 .

[138]  C. Cockell,et al.  Ultraviolet radiation screening compounds , 1999, Biological reviews of the Cambridge Philosophical Society.

[139]  Cho,et al.  New Bis(Indole) alkaloids of the topsentin class from the sponge spongosorites genitrix , 1999, Journal of natural products.

[140]  M. K. Harper,et al.  Neoamphimedine: A New Pyridoacridine Topoisomerase II Inhibitor Which Catenates DNA , 1999 .

[141]  W. Wickramasinghe,et al.  Structure and total synthesis of benzylthiocrellidone, a novel dimedone-based vinyl sulfide from the sponge Crella spinulata , 1999 .

[142]  T. Skjetne,et al.  Gyroxanthin—the First Allenic Acetylenic Carotenoid , 2000 .

[143]  M. Kelly,et al.  Sesquiterpene quinols/quinones from the Micronesian sponge Petrosaspongia metachromia. , 2000, Journal of natural products.

[144]  A. Zampella,et al.  New isomalabaricane derivatives from a new species of Jaspis sponge collected at the Vanuatu islands. , 2000, Journal of natural products.

[145]  Guy Cox,et al.  Fluorescent pigments in corals are photoprotective , 2000, Nature.

[146]  R. Manderville Synthesis, proton-affinity and anti-cancer properties of the prodigiosin-group natural products. , 2001, Current medicinal chemistry. Anti-cancer agents.

[147]  U. Pindur,et al.  Advances in marine natural products of the indole and annelated indole series: chemical and biological aspects. , 2001, Current medicinal chemistry.

[148]  P. Molíst,et al.  Cytological study and immunohistochemical location of PSP toxins in foot skin of the ormer, Haliotis tuberculata, from the Galician coast (NW Spain) , 2001 .

[149]  D. Faulkner,et al.  Marine natural products. , 2000, Natural product reports.

[150]  S. Johnsen,et al.  Hidden in Plain Sight: The Ecology and Physiology of Organismal Transparency , 2001, The Biological Bulletin.

[151]  C. Amsler,et al.  Secondary Metabolites as Mediators of Trophic Interactions Among Antarctic Marine Organisms , 2001 .

[152]  E. Ivanova,et al.  Pseudoalteromonas maricaloris sp. nov., isolated from an Australian sponge, and reclassification of [Pseudoalteromonas aurantia] NCIMB 2033 as Pseudoalteromonas flavipulchra sp. nov. , 2002, International journal of systematic and evolutionary microbiology.

[153]  R. Mckillup,et al.  Flies that attack polymorphic snails on coloured backgrounds: selection for crypsis by a sarcophagid parasitoid of Littoraria filosa , 2002 .

[154]  H. Takata,et al.  Role of Cell Contact in the Specification Process of Pigment Founder Cells in the Sea Urchin Embryo , 2002, Zoological science.

[155]  Umbilic and Tangential Singularities on Configurations of Principal Curvature Lines , 2002 .

[156]  P. Scheuer,et al.  Natural Products from Three Nudibranchs: Nembrotha kubaryana, Hypselodoris infucata and Chromodoris petechialis , 2002, Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry.

[157]  P. Comba,et al.  Synthesis and structural properties of patellamide A derivatives and their copper(II) compounds. , 2002, Chemistry.

[158]  J. Pawlik,et al.  Anti-predatory chemical defenses of ascidians: secondary metabolites or inorganic acids? , 2002 .

[159]  M. Matz,et al.  Molecular basis and evolutionary origins of color diversity in great star coral Montastraea cavernosa (Scleractinia: Faviida). , 2003, Molecular biology and evolution.

[160]  C. Amsler,et al.  Surface sequestration of chemical feeding deterrents in the Antarctic sponge Latrunculia apicalis as an optimal defense against sea star spongivory , 2003 .

[161]  T. Goreau,et al.  Changes in zooxanthellae density, morphology, and mitotic index in hermatypic corals and anemones exposed to cyanide. , 2003, Marine pollution bulletin.

[162]  D. Sakurai,et al.  Direct evidence for the role of pigment cells in the brain of ascidian larvae by laser ablation , 2002, Journal of Experimental Biology.

[163]  R. Chakraborty,et al.  Isolation of Sesquiterpenoids from Sponge Dysidea Avara and Chemical Modification of Avarol as Potential Antitumor Agents , 2003, Natural product research.

[164]  Werner E. G. Müller,et al.  Biotechnological potential of marine sponges , 2004 .

[165]  N. Lindquist Chemical Defense of Early Life Stages of Benthic Marine Invertebrates , 2002, Journal of Chemical Ecology.

[166]  F. Pietra,et al.  Natural‐Product Diversity of the New Caledonian Marine Ecosystem Compared to Other Ecosystems: A Pharmacologically Oriented View , 2004, Chemistry & biodiversity.

[167]  L. Litman,et al.  The Time Course of the Camouflage Response of Cuttlefish (Sepia officinalis) , 2004, The Biological Bulletin.

[168]  J. Mather,et al.  Apparent movement in a visual display: the ‘passing cloud’ of Octopus cyanea (Mollusca: Cephalopoda) , 2004 .

[169]  K. M. Marshall,et al.  Biological activities of pyridoacridines. , 2004, Natural product reports.

[170]  Richard A. Cloney,et al.  Ultrastructure of cephalopod chromatophore organs , 2004, Zeitschrift für Zellforschung und Mikroskopische Anatomie.

[171]  V. Paul,et al.  Chemical mediation of interactions among marine organisms. , 2004, Natural product reports.

[172]  G. Ruxton,et al.  What, if anything, is the adaptive function of countershading? , 2004, Animal Behaviour.

[173]  J. Endler,et al.  Predator Mixes and the Conspicuousness of Aposematic Signals , 2004, The American Naturalist.

[174]  C. Chiao,et al.  Visual Background Features That Elicit Mottled Body Patterns in Cuttlefish, Sepia officinalis , 2004, The Biological Bulletin.

[175]  M. Nishiguchi,et al.  Counterillumination in the Hawaiian bobtail squid, Euprymna scolopes Berry (Mollusca: Cephalopoda) , 2004 .

[176]  Laurent Meijer,et al.  Meridianins, a new family of protein kinase inhibitors isolated from the ascidian Aplidium meridianum. , 2004, Bioorganic & medicinal chemistry letters.

[177]  M. Härlin,et al.  Towards a historization of aposematism , 2003, Evolutionary Ecology.

[178]  T. Cronin,et al.  Fluorescent Enhancement of Signaling in a Mantis Shrimp , 2004, Science.

[179]  D. Mebs Chemical defense of a dorid nudibranch,Glossodoris quadricolor, from the red sea , 1985, Journal of Chemical Ecology.

[180]  H. Trapido-Rosenthal,et al.  Ichthyodeterrent Properties of Lipophilic Extracts from Bermudian Sponges , 1997, Journal of Chemical Ecology.

[181]  C. Chiao,et al.  Disruptive Body Patterning of Cuttlefish (Sepia officinalis) Requires Visual Information on Edges and Brightness of Objects on Natural Substrate Backgrounds , 2004, The Biological Bulletin.

[182]  E. Antunes,et al.  Pyrroloiminoquinone and related metabolites from marine sponges. , 2005, Natural product reports.

[183]  T. Hata,et al.  6H-anthra[1,9-bc]thiophene derivatives from a bryozoan,Dakaira subovoidea , 1993, Experientia.

[184]  P. Scheuer,et al.  The distribution of quinone pigments in echinoderms , 1967, Experientia.

[185]  C. Schnitzler,et al.  Bioluminescent and Red-Fluorescent Lures in a Deep-Sea Siphonophore , 2005, Science.

[186]  H. Fricke,et al.  Coral host improves photosynthesis of endosymbiotic algae , 1990, Naturwissenschaften.

[187]  G. Prota,et al.  Neobonellin, a new biologically active pigment fromBonellia viridis , 1978, Experientia.

[188]  O. Mcconnell,et al.  Staurosporine aglycone (K252-c) and arcyriaflavin A from the marine ascidian,Eudistoma sp , 1994, Experientia.

[189]  C. Amsler,et al.  Ecology of Antarctic Marine Sponges: An Overview1 , 2005, Integrative and comparative biology.

[190]  S. D. Rosa,et al.  Structure of two biologically active sesquiterpenoid amino-quinones from the marine spongeDysidea avara , 1982, Experientia.

[191]  J. Rideout,et al.  Chemical defense of crinoids by polyketide sulphates , 1979, Experientia.

[192]  C. Chiao,et al.  Disruptive Body Patterning of Cuttlefish (Sepia officinalis) Requires Visual Information Regarding Edges and Contrast of Objects in Natural Substrate Backgrounds , 2005, The Biological Bulletin.

[193]  A. Barbieri,et al.  Eilatin complexes of ruthenium and osmium. synthesis, electrochemical behavior, and near-IR luminescence. , 2005, Inorganic chemistry.

[194]  F. Garcia-Pichel,et al.  The structure of scytonemin, an ultraviolet sunscreen pigment from the sheaths of cyanobacteria , 1993, Experientia.

[195]  V. Poroikov,et al.  Novel antitumor agents: marine sponge alkaloids, their synthetic analogs and derivatives. , 2005, Mini reviews in medicinal chemistry.

[196]  E. Savazzi The colour patterns of cypraeid gastropods , 2007 .