Abstract
Despite the many publications concerning the isolation of substances and the many reviews of marine natural products, some groups of organisms remain poorly studied, including “Polychaeta”. In response, this review covers articles published through December 2016 that address marine natural products produced from polychaetes, with a focus on antipredatory strategies, competitors, fouling, and pathogens. A total of 121 compounds were isolated from 1934 to 2016, which includes halogenated aromatics, proteins, amino acids and Lumazine derivatives most notably—with a defensive function were found in the literature, most frequently in the families Sabellidae, Terebellidae, Glyceridae, and Nereididae. The period of highest discovery of natural products in defensive actions for the group was the 2000s. Polychaetes were addressed in 26 revisions of the total 51 articles analyzed and are less reported than other marine invertebrates such as sponges, cnidarians, mollusks, and tunicates. In sum, the present review provides a basis for future research on the marine chemical ecology of polychaetes.
Similar content being viewed by others
References
Agatsuma Y, Endo H, Taniguchi K (2008) Inhibitory effect of 2,4-dibromophenol and 2,4,6-tribromophenol on larval survival and metamorphosis of the sea urchin Strongylocentrotus nudus. Fish Sci 74:837–841
Amsler CD, Iken K, McClintock JB, Amsler MO, Peters KJ, Hubbard JM, Furrow FB, Baker BJ (2005) Comprehensive evaluation of the palatability and chemical defenses of subtidal macroalgae from the Antarctic Peninsula. Mar Ecol Prog Ser 294:141–159
Anctil M (1979) The epithelial luminescent system of Chaetopterus variopedatus. Can J Zool 57:1290–1310
Anctil M (1981) Luminescence control in isolated notopods of the tube-worm Chaetopterus variopedatus: effects of cholinergic and GABAergic drugs. Comp Biochem Physiol C 68:187–194
Andersen RJ, Wolfe MS, Faulkner DJ (1974) Autotoxic antibiotic production by a marine Chromobacterium. Mar Biol 27:281–285
Anderson RS, Chain BM (1982) Antibacterial activity in the coelomic fluid of a marine annelid, Glycera dibranchiata. J Invertebr Pathol 40:320–326
Assmann M, Lichte E, Köck M (2004) Multiple defensive roles for bromopyrrole alkaloids from Caribbean Agelas sponges. Boll Mus Ist Biol Univ Genova 68:187–193
Asworth RB, Cormier MJ (1967) Isolation of 2,6-dibromophenol from the marine hemichordate, Balanoglossus biminiensis. Science 155:1558–1559
Bandaranayake WM (2006) The nature and role of pigments of marine invertebrates. Nat Prod Rep 23:223–255. https://doi.org/10.1039/b307612c
Barsby T, Kicklighter CE, Hay ME, Sullards MC, Kubanek J (2003) Defensive 2-alkylpyrrole sulfamates from the marine annelid Cirriformia tentaculata. J Nat Prod 66:1110–1112. https://doi.org/10.1021/np030149z
Bassot JM (1987) A transient intracellular coupling explains the facilitation of responses in the bioluminescent system of scale worms. J Cell Biol 105:2235–2243
Bassot JM, Nicolas MT (1995) Bioluminescence in scale-worm photosomes: the photoprotein polynoidin is specific for the detection of superoxide radicals. Histochem Cell Biol 104:199–210
Becerro MA, López NI, Turón X, Uriz J (1994) Antimicrobial activity and surface bacterial film in marine sponges. J Exp Mar Biol Ecol 179:195–205
Benkendorff K, Davis AR, Bremner JB (2001) Chemical defense in the egg masses of benthic invertebrates: an assessment of antibacterial activity in 39 mollusks and 4 polychaetes. J Invertebr Pathol 78:109–118. https://doi.org/10.1006/jipa.2001.5047
Bhosale SH, Jagtap TG, Naik CG (1999) Antifungal activity of some marine organisms from India, against food spoilage Aspergillus strains. Mycopathologia 147:133–138
Bianco EM, Rogers R, Teixeira VL, Pereira RC (2009) Antifoulant diterpenes produced by the brown seaweed Canistrocarpus cervicornis. J Appl Phycol 21(3):341–346. https://doi.org/10.1007/s10811-008-9374-9
Bleidorn C, Vogt L, Bartolomaeus T (2003) New insights into polychaete phylogeny (Annelida) inferred from 18S rDNA sequences. Mol Phylogenet Evol 29:279–288
Blunden G (1988) Metabolites from marine algae. Prog Oceanogr 21:217–226
Blunt JW, Copp BR, Munro MHG, Northcote PT, Prinsep MR (2003) Marine natural products. Nat Prod Rep 20:1–48. https://doi.org/10.1039/b207130b
Blunt JW, Copp BR, Munro MHG, Northcote PT, Prinsep MR (2004) Marine natural products. Nat Prod Rep 21:1–49. https://doi.org/10.1039/b305250h
Blunt JW, Copp BR, Munro MHG, Northcote PT, Prinsep MR (2005) Marine natural products. Nat Prod Rep 22:15–61. https://doi.org/10.1039/b415080p
Blunt JW, Copp BR, Munro MHG, Northcote PT, Prinsep MR (2006) Marine natural products. Nat Prod Rep 23:26–78. https://doi.org/10.1039/b502792f
Blunt JW, Copp BR, Hu WP, Munro MHG, Northcote PT, Prinsep MR (2007) Marine natural products. Nat Prod Rep 24:31–86. https://doi.org/10.1039/b603047p
Blunt JW, Copp BR, Hu WP, Munro MHG, Northcote PT, Prinsep MR (2008) Marine natural products. Nat Prod Rep 25:35–94. https://doi.org/10.1039/b701534h
Blunt JW, Copp BR, Hu WP, Munro MHG, Northcote PT, Prinsep MR (2009) Marine natural products. Nat Prod Rep 26:170–244. https://doi.org/10.1039/b805113p
Blunt JW, Copp BR, Munro MHG, Northcote PT, Prinsep MR (2010) Marine natural products. Nat Prod Rep 27:165–237. https://doi.org/10.1039/b906091j
Blunt JW, Copp BR, Munro MHG, Northcote PT, Prinsep MR (2011) Marine natural products. Nat Prod Rep 28:196–268. https://doi.org/10.1039/c005001f
Blunt JW, Copp BR, Keyzers RA, Munro MHG, Prinsep MR (2012) Marine natural products. Nat Prod Rep 29:144–222. https://doi.org/10.1039/c2np00090c
Blunt JW, Copp BR, Keyzers RA, Munro MHG, Prinsep MR (2013) Marine natural products. Nat Prod Rep 30:237–323. https://doi.org/10.1039/c2np20112g
Blunt JW, Copp BR, Keyzers RA, Munro MHG, Prinsep MR (2014) Marine natural products. Nat Prod Rep 31:160–258. https://doi.org/10.1039/c3np70117d
Blunt JW, Copp BR, Keyzers RA, Munro MHG, Prinsep MR (2015) Marine natural products. Nat Prod Rep 32:116–211. https://doi.org/10.1039/c4np00144c
Blunt JW, Copp BR, Keyzers RA, Munro MHG, Prinsep MR (2016) Marine natural products. Nat Prod Rep 33:382–431. https://doi.org/10.1039/c5np00156k
Bolser RC, Hay ME (1996) Are tropical plants better defended? Palatability and defenses of temperate vs. tropical seaweeds. Ecology 77(8):2269–2286
Boman HG (1995) Peptide antibiotics and their role in innate immunity. Annu Rev Immunol 13:61–92
Bon C, Saliou B, Thieffry M, Manaranch R (1985) Partial purification of α-Glycerotoxin, a presynaptic neurotoxin from the venom glands of the polychaete annelid Glycera convoluta. Neurochem Int 7(1):63–75
Branchini BR, Behney CE, Southworth TL, Rawat R, Deheyn DD (2014) Chemical analysis of the luminous slime secreted by the marine worm Chaetopterus (Annelida, Polychaeta). Photochem Photobiol 90:247–251. https://doi.org/10.1111/php.12169
Bryan PJ, Rittschof D, McClintock JB (1996) Bioactivity of echinoderm ethanolic body-wall extracts: an assessment of marine bacterial attachment and macroinvertebrate larval settlement. J Exp Mar Biol Ecol 196:79–96
Bryan PJ, McClintock JB, Hopkins TS (1997) Structural and chemical defenses of echinoderms from the northern Gulf of Mexico. J Exp Mar Biol Ecol 210:173–186
Burns E, Ifrach I, Carmeli S, Pawlik JR, Ilan M (2003) Comparison of anti-predatory defenses of Red Sea and Caribbean sponges. I. Chemical defense. Mar Ecol Prog Ser 252:105–114
Canicattì C, Ville P, Pagliara P, Roch P (1992) Hemolysins from the mucus of Spirographis spalllanzanii (Polychaeta: Sabellidae). Mar Biol 114:453–458
Casillas E, Myers MS (1989) Effect of bromobenzene and O-bromophenol on kidney and liver of english sole (Parophrys velutus). Camp. Biochem Physiol 93C(1):4348–1989
Chain BM, Anderson RS (1983a) Antibacterial activity of the coelomic fluid from the polychaete, Glycera dibranchiata. II. Partial purification and biochemical characterization of the active factor. Biol Bull 164:41–49
Chain BM, Anderson RS (1983b) A bactericidal and cytotoxic factor in the coelomic fluid of the polychaete, Glycera dibranchiata. Dev Comp Immunol 7:625–628
Chen YP, Lincoln DE, Woodin SA, Lovell CR (1991) Purification and properties of a unique flavin-containing chloroperoxidase from the capitellid polychaete Notomastus lobatus. J Biol Chem 266(35):23909–23915
Chen YP, Woodin SA, Lincoln DE, Lovell CR (1996) An unusual dehalogenating peroxidase from the marine terebellid polychaete Amphitrite ornata. J Biol Chem 271(9):4609–4612. https://doi.org/10.1074/jbc.271.9.4609
Chung HY, Ma WCJ, Ang PO Jr, Kim JS, Chen F (2003) Seasonal variations of bromophenols in brown algae (Padina arborescens, Sargassum siliquastrum, and Lobophora variegata) collected in Hong Kong. J Agric Food Chem 51:2619–2624
Clavico EEG, Da Gama BAP, Soares AR, Cassiano KM, Pereira RC (2013) Interaction of chemical and structural components providing defences to sea pansies Renilla reniformis and Renilla muelleri. Mar Biol Res 9(3):285–292. https://doi.org/10.1080/17451000.2012.739693
Connaughton VP, Schuur A, Targett NM, Epifanio CE (1994) Chemical suppression of feeding in larval weakfish (Cynoscion regalis) by trochophores of the serpulid polychaete Hydroides dianthus. J Chem Ecol 20(7):1763–1771
Cowart JD, Fielman KT, Woodin SA, Lincoln DE (2000) Halogenated metabolites in two polychaetes and their planktotrophic and lecithotrophic larvae. Mar Biol 136:993–1002
Cronin G (2001) Resource allocation in seaweeds and marine invertebrates: chemical defense patterns in relation to defense theories. In: McClintock JB, Baker BJ (eds) Marine chemical ecology. CRC Press, Boca Raton, pp. 325–353
Czeczuga B (1971) The coloration of specimens of Nereis zonata Mal. (Annelides, Polychaeta) from the Black Sea. Hydrobiologia 37(2):301–307
Dales RP (1962) The nature of the pigments in the crowns of sabellid and serpulid polychaetes. J Mar Biol Assoc UK 42:259–274
Dales RP (1971) Bioluminescence in pelagic polychaetes. J Fish Res Board Can 28(10):1487–1489
Dales RP, Kennedy GY (1954) On the diverse colours of Nereis diversicolor. J Mar Biol Assoc UK 33:699–708
Davis JM, Viney C (1998) Water-mucin phases: conditions for mucus liquid crystallinity. Thermochim Acta 315:39–49
De Nys R, Steinberg PD, Willemsen P, Dworjanyn SA, Gabelish CL, King RJ (1995) Broad spectrum effects of secondary metabolites from the red alga Delisea pulchra in antifouling assays. Biofouling 8:259–271
Deheyn DD, Latz MI (2009) Internal and secreted bioluminescence of the marine polychaete Odontosyllis phosphorea (Syllidae). Invertebr Biol 128(1):31–45. https://doi.org/10.1111/j.1744-7410.2008.00149.x
Deheyn DD, Enzor LA, Dubowitz A, Urbach JS, Blair D (2013) Optical and physicochemical characterization of the luminous mucous secreted by the marine worm Chaetopterus sp. Physiol Biochem Zool 86(6):702–715. https://doi.org/10.1086/673869
Dimarcq JL, Bulet P, Hetru C, Hoffmann J (1998) Cysteine-rich antimicrobial peptides in invertebrates. Biopolymers 47:465–477
Dworjanyn AS, De Nys R, Steinberg PD (1999) Localisation and surface quantification of secondary metabolites in the red alga Delisea pulchra. Mar Biol 133:727–736
Dworjanyn AS, De Nys R, Steinberg PD (2006) Chemically mediated antifouling in the red alga Delisea pulchra. Mar Ecol Prog Ser 318:153–163
Eklöf J (2010) Taxonomy and phylogeny of polychaetes. Dissertation, University of Gothenburg
Elayaraja S, Murugesan P, Vijayalakshmi S, Balasubramanian T (2010) Antibacterial and antifungal activities of polychaete Perinereis cultrifera. Indian J Geo-Mar Sci 39(2):257–261
Emrich R, Weyland H, Weber K (1990) 2,3,4-Tribromopyrrole from the marine polychaete Polyphysia crassa. J Nat Prod 53(3):703–705
Engel S, Pawlik JR (2000) Allelopathic activities of sponge extracts. Mar Ecol Prog Ser 207:273–281
Epifanio RA, Maia LF, Fenical W (2000) Chemical defenses of the endemic Brazilian gorgonian Lophogorgia violacea Pallas (Octocorallia, Gorgonacea). J Braz Chem Soc 11(6):584–591
Epifanio RA, Maia LF, Pawlik JR, Fenical W (2007) Antipredatory secosterols from the octocoral Pseudopterogorgia americana. Mar Ecol Prog Ser 329:307–310
Esser F, Winterberg M, Sebesvari Z, Harder T (2008) Effects of halogenated metabolites from infaunal polychaetes on larval settlement of the spionid polychaete Streblospio benedicti. Mar Ecol Prog Ser 355:161–172. https://doi.org/10.3354/meps07226
Fan X, NJ X, Shi JG (2003) Bromophenols from the red alga Rhodomela confervoides. J Nat Prod 66:455–458
Fattorini D, Regoli F (2004) Arsenic speciation in tissues of the Mediterranean polychaete Sabella spallanzanii. Environ Toxicol Chem 23:1881–1887
Fattorini D, Notti A, Halt MN, Gambi MC, Regoli F (2005) Levels and chemical speciation of arsenic in polychaetes: A review. Mar Ecol 26:255–264. https://doi.org/10.1111/j.1439-0485.2005.00057.x
Fattorini D, Notti A, Nigro M, Regoli F (2010) Hyperaccumulation of vanadium in the Antarctic polychaete Perkinsiana littoralis as a natural chemical defense against predation. Environ Sci Pollut Res 17:220–228. https://doi.org/10.1007/s11356-009-0243-0
Fauchald K (1977) The polychaete worms – definitions and keys to the orders, families and genera. Natural History Museum of Los Angeles County, Los Angeles
Faulkner D J (1977) Interesting aspects of marine natural products chemistry. Tetrahedron 33(12):1421–1443
Faulkner DJ (1984) Marine natural products: Metabolites of marine invertebrates. Nat Prod Rep 1:551–598
Faulkner DJ (1986) Marine natural products. Nat Prod Rep 3:1–33
Faulkner DJ (1987) Marine natural products. Nat Prod Rep 4:539–576
Faulkner DJ (1988) Marine natural products. Nat Prod Rep 5:613–663
Faulkner DJ (1990) Marine natural products. Nat Prod Rep 7:269–309
Faulkner DJ (1991) Marine natural products. Nat Prod Rep 8:97–147
Faulkner DJ (1992) Marine natural products. Nat Prod Rep 9:323–364
Faulkner DJ (1993) Marine natural products. Nat Prod Rep 10:497–539
Faulkner DJ (1994) Marine natural products. Nat Prod Rep 1:355–394
Faulkner DJ (1995) Marine natural products. Nat Prod Rep 12:223–269
Faulkner DJ (1996) Marine natural products. Nat Prod Rep 13:75–125
Faulkner DJ (1997) Marine natural products. Nat Prod Rep 14:259–302
Faulkner DJ (1998) Marine natural products. Nat Prod Rep 15:113–158
Faulkner DJ (1999) Marine natural products. Nat Prod Rep 16:155–198
Faulkner DJ (2000a) Marine natural products. Nat Prod Rep 17:7–55
Faulkner DJ (2000b) Marine Pharmacology. Antonie Van Leeuwenhoek 77:135–145
Faulkner DJ (2000c) Highlights of marine natural products chemistry (1972-1999). Nat Prod Rep 17:1–6
Faulkner DJ (2001) Marine natural products. Nat Prod Rep 18:1–49
Faulkner DJ (2002) Marine natural products. Nat Prod Rep 19:1–48
Fielman KT, Targett NM (1995) Variation of 2,3,4-tribromopyrrole and its sodium sulfamate salt in the hemichordate Saccoglossus kowalevskii. Mar Ecol Prog Ser 116:125–136
Fielman KT, Woodin SA, Walla MD, Lincoln DE (1999) Widespread occurrence of natural halogenated organics among temperate marine infauna. Mar Ecol Prog Ser 181:1–12
Fielman KT, Woodin SA, Lincoln DE (2001) Polychaete indicator species as a source of natural halogenated organic compounds in marine sediments. Environ Toxicol Chem 20(4):738–747
Fischer A, Fischer U (1995) On the life-style and life-cycle of the luminescent polychaete Odontosyllis enopla (Annelida, Polychaeta). Invertebr Biol 114:236–247
Francis WR, Powers ML, Haddock SHD (2014) Characterization of an anthraquinone fluor from the bioluminescent, pelagic polychaete Tomopteris. Lumin J Biol Chem Lumin 29:1135–1140
Gaion A, Sartori D, Scuderi A, Fattorini D (2014) Bioaccumulation and biotransformation of arsenic compounds in Hediste diversicolor (Muller 1776) after exposure to spiked sediments. Environ Sci Pollut Res 21:5952–5959
Garson MJ (2001) Ecological perspectives on marine natural product biosynthesis. In: McClintock B, Baker BJ (eds) Marine chemical ecology, CRC Press LLC, pp 71–114
Gaston GR, Hall J (2000) Lunar periodicity and bioluminescence of swarming Odontosyllis luminosa (Polychaeta: Syllidae) in Belize. Gulf Caribb Res 12:47–51
Gaston GR, Slattery M (2002) Ecological function of chemical deterrents in a tropical polychaete, Eupolymnia crassicornis (Annelida, Terebellidae), in Belize. Bull Mar Sci 70(3):891–897
Geiszinger AE, Goessler W, Francesconi KA (2002a) Biotransformation of arsenate to the tetramethylarsonium ion in the marine polychaetes Nereis diversicolor and Nereis virens. Environ Sci Technol 36:2905–2910
Geiszinger AE, Goessler W, Francesconi KA (2002b) The marine polychaete Arenicola marina: its unusual arsenic compound pattern and its uptake of arsenate from seawater. Mar Environ Res 53:37–50
Gerhart DJ, Rittschof D, Mayo SW (1988) Chemical ecology and the search for marine antifoulants- studies of a predator-prey symbiosis. J Chem Ecol 14(10):1905–1916
Giangrande A, Licciano M, Pagliara P, Gambi MC (2000) Gametogenesis and larval development in Sabella spallanzanii (Polychaeta: Sabellidae) from the Mediterranean Sea. Mar Biol 136:847–861
Giangrande A, Cavallo A, Licciano M, Mola E, Pierri C, Trianni L (2005) Utilization of the filter feeder polychaete Sabella spallanzanii Gmelin (Sabellidae) as bioremediator in aquaculture. Aquac Int 13:129–136
Giangrande A, Licciano M, Schirosi R, Musco L, Stabili L (2014) Chemical and structural defensive external strategies in six sabellid worms (Annelida). Mar Ecol 35:36–45
Giangrande A, Licciano M, Pasqua M, Fanizzi FP, Migoni D, Stabili L (2016) Heavy metals in five Sabellidae species (Annelida, Polychaeta): ecological implications. Environ Sci Pollut Res 24:3759–3768. https://doi.org/10.1007/s11356-016-8089-8
Gibbs PE, Langston WJ, Burt GR, Pascoe PL (1983) Tharyx marioni (Polychaeta): a remarkable accumulator of arsenic. J Mar Biol Assoc UK 63:313–325
Giray C, King GM (1997) Predator deterrence and 2,4-dibromophenol conservation by the enteropneusts Saccoglossus bromophenolosus and Protoglossus graveolens. Mar Ecol Prog Ser 159:229–238
Goerke H, Weber K (1990) Locality-dependent concentrations of bromophenols in Lanice conchilega (Polychaeta: Terebellidae). Comp Biochem Physiol B 97(4):741–744
Goerke H, Weber K (1991) Bromophenols in Lanice conchilega (Polychaeta, Terebellidae): the influence of sex, weight and season. Bull Mar Sci 48(2):517–523
Goerke H, Emrich R, Weber K, Duchêne JC (1991) Concentrations and localization of brominated metabolites in the genus Thelepus (Polychaeta: Terebellidae). Comp Biochem Physiol B 99(1):203–206
Gouveneaux A, Mallefet J (2013) Physiological control of bioluminescence in a deep-sea planktonic worm, Tomopteris helgolandica. J Exp Biol 216:4285–4289
Haddock SHD, Moline MA, Case JF (2010) Bioluminescence in the sea. Annu Rev Mar Sci 2:443–493
Hardege JD, Bentley MG, Snape L (1998) Sediment selection by juvenile Arenicola marina. Mar Ecol Prog Ser 166:187–195
Hay ME (1984) Predictable spatial escapes from herbivory: How do these affect the evolution of herbivore resistance in tropical marine communities? Oecologia 64:396–407
Hay ME (1996) Marine chemical ecology: What’s known and what’s next? J Exp Mar Biol Ecol 200:103–134
Hay ME (1997) The ecology and evolution of seaweed-herbivore interactions on coral reefs. Coral Reefs 16(Suppl 1):67–76
Hay ME (2009) Marine chemical ecology: chemical signals and cues structure marine populations, communities, and ecosystems. Annu Rev Mar Sci 1:193–212
Hay ME (2011) Crustaceans as powerful models in aquatic chemical ecology. In: Breithaupt T, Thiel M (eds) Chemical communication in crustaceans, 1st edn. Springer-Verlag, New York, pp 41–62. https://doi.org/10.1007/978-0-387-77101-4_3
Hay ME, Fenical W (1988) Marine plant-herbivore interactions: The ecology of chemical defense. Annu Rev Ecol Syst 19:111–145
Hay ME, Fenical W (1996) Chemical ecology and marine biodiversity: insights and products from the sea. Oceanography 9(1):10–20
Hay ME, Duffy E, Pfister CA, Fenical W (1987) Chemical defense against different marine herbivores: Are amphipods insect equivalents? Ecology 68(6):1567–1580
Herrera AA (1979) Electrophysiology of bioluminescent excitable epithelial cells in a polynoid polychaete worm. J Comp Physiol A 129:67–78
Higa T, Scheuer PJ (1974) Thelepin, a new metabolite from the marine annelid Thelepus setosus. J Amer Chem Soc 96(7):2246–2248
Higa T, Scheuer PJ (1975) Constituents of the marine annelid Thelepus setosus. Tetrahedron 31:2379–2381
Higa T, Fujiyama T, Scheuer PJ (1980) Halogenated phenol and indole constituents of acorn worms. Comp Biochem Physiol 65B:525–530
Hill RA (2003) Marine natural products. Annu Rep Prog Chem Sect B 99:183–207
Hill RA (2004) Marine natural products. Annu Rep Prog Chem Sect B 100:169–189
Hill RA (2005) Marine natural products. Annu Rep Prog Chem Sect B 101:124–136
Hill RA (2006) Marine natural products. Annu Rep Prog Chem Sect B 102:123–137
Hill RA (2007) Marine natural products. Annu Rep Prog Chem Sect B 103:125–139
Hill RA (2008) Marine natural products. Annu Rep Prog Chem Sect B 104:127–141
Hill RA (2009) Marine natural products. Annu Rep Prog Chem Sect B 105:150–166
Hill RA (2010) Marine natural products. Annu Rep Prog Chem Sect B 106:156–173
Hill RA (2011) Marine natural products. Annu Rep Prog Chem Sect B107:138–156
Hill RA (2012) Marine natural products. Annu Rep Prog Chem Sect B Org Chem 108:131–146
Hill RA (2013) Marine natural products. Annu Rep Prog Chem Sect B Org Chem 109:146–166
Hu Y, Chen J, Hu G, Yu J, Zhu X, Lin Y, Chen S, Yuan J (2015) Statistical research on the bioactivity of new marine natural products discovered during the 28 years from 1985 to 2012. Mar Drugs 13(1):202–221
Huber ME, Arneson CA, Widder EA (1989) Extremely blue bioluminescence in the polychaete Polycirrus perplexus (Terebellidae). Bull Mar Sci 44:1236–1239
Ianora A, Boersma M, Casotti R, Fontana A, Harder J, Hoffmann F, Pavia H, Potin P, Poulet SA, Toth G (2006) The H. T. Oodum synthesis essay: new trends in marine chemical ecology. Estuar Coasts 29(4):531–551
Inoue S, Okada K, Tanino H, Kakoi H, Horii N (1990) 6-Propionyllumazines from the marine polychaete, Odontosyllis undecimdonta. Chem Lett 19(3):367–368
Inoue S, Okada K, Tanino H, Kakoi H, Ohnishi Y, Horii N (1991) New lumazines from the marine polychaete, Odontosyllis undecimdonta. Chem Lett 20:563–564
Inoue S, Okada K, Tanino H, Kakoi H (1993) A new hexagonal cyclic enol phosphate of 6-β-hydroxypropionyllumazines from the marine swimming polychaete, Odontosyllis undecimdonta. Heterocycles 35(1):147–150
Iori D, Forti L, Massamba-N’Siala G, Prevedelli D, Simonini R (2014) Toxicity of the purple mucus of the polychaete Halla parthenopeia (Oenonidae) revealed by a battery of ecotoxicological bioassays. Sci Mar 78(4):589–595
Ishii T, Otake T, Okoshi K, NakaharaM NR (1994) Intracellular localization of vanadium in the fan worm Pseudopotamilla occelata. Mar Biol 121:143–151
Israel M, Lesbats B (1981) Chemiluminescent determination of acetylcholine and continuous detection of its release from torpedo eletric organ synapses and synaptosomes. Neurochem Int 3(1):81–90
Jensen PR, Fenical W (1994) Strategies for the discovery of secondary metabolites from marine bacteria: ecological perspectives. Annu Rev Microbiol 48:559–584
Jensen PR, Fenical W (1996) Marine bacterial diversity as a resource for novel microbial products. J Ind Microbiol 17:346–351
Jumars PA, Dorgan KM, Lindsay SM (2015) Diet of worms emended: an update of polychaete feeding guilds. Annu Rev Mar Sci 7:497–520
Kakoi H, Tanino H, Okada K, Inoue S (1995) 6-Acyllumazines from the marine polychaete, Odontosyllis undecimdonta. Heterocycles 41(4):789–797
Kamanos KAD, Withey JM (2012) Enantioselective total synthesis of (R)-(−)-complanine. Beilstein J Org Chem 8:1695–1699. https://doi.org/10.3762/bjoc.8.192
Kennedy GY, Nicol JAC (1959) Pigments of Chaetopterus variopedatus (Polychaeta). Proc R Soc Lond B Biol Sci 150(941):509–538
Kicklighter CE, Hay ME (2006) Integrating prey defensive traits: contrasts of marine worms from temperate and tropical habitats. Ecol Monogr 76(2):195–215
Kicklighter CE, Hay ME (2007) To avoid or deter: interactions among defensive and escape strategies in sabellid worms. Oecologia 151:161–173. https://doi.org/10.1007/s00442-006-0567-0
Kicklighter CE, Kubanek J, Barsby T, Hay ME (2003) Palatability and defense of some tropical infaunal worms: alkylpyrrole sulfamates as deterrents to fish feeding. Mar Ecol Prog Ser 263:299–306
Kicklighter CE, Fisher CR, Hay ME (2004a) Chemical defense of hydrothermal vent and hydrocarbon seep organisms: A preliminary assessment using shallow-water consumers. Mar Ecol Prog Ser 275:11–19
Kicklighter CE, Kubanek J, Hay ME (2004b) Do brominated natural products defend marine worms from consumers? Some do, most don’t. Limnol Oceanogr 49(2):430–441
King GM (1986) Inhibition of microbial activity in marine sediments by a bromophenol from a hemichordate. Nature 323:257–259
King GM (1988) Dehalogenation in marine sediments containing natural sources of halophenols. Appl Environ Microbol 54(12):3079–3085
Kubanek J, Whalen KE, Engel S, Kelly SR, Henkel TP, Fenical W, Pawlik JR (2002) Multiple defensive roles for triterpene glycosides from two Caribbean sponges. Oecologia 131:125–136. https://doi.org/10.1007/s00442-001-0853-9
Kubanek J, Jensen PR, Keifer PA, Sullards MC, Collins DO, Fenical W (2003) Seaweed resistance to microbial attack: A targeted chemical defense against marine fungi. Proc Natl Acad Sci USA 100(12):6916–6921
Kudenov JD (1995) Family Amphinomidae Lamarck 1818. In: Blake JA, Hilbig B, Scott PH (eds) Taxonomic atlas of the benthic fauna of the Santa Maria Basin and Western Santa Barbara Channel, Volume 5. The Annelida part 2–Polychaeta: Phyllodocida (Syllidae and Scale bearing families), Amphinomida and Eunicida. Santa Barbara Museum of Natural History, Santa Barbara, California, pp 207–215
Kuffner IB, Paul VJ (2004) Effects of the benthic cyanobacterium Lyngbya majuscula on larval recruitment of the reef corals Acropora surculosa and Pocillopora damicornis. Coral Reefs 23:455–458
Kurata K, Taniguchii K, Takashima K, Hayashi I, Suzuki M (1997) Feeding-deterrent bromophenols from Odonthalia corymbifera. Phytochemistry 45(3):485–4487
Kurisaki E, Kato N, Ishida T, Matsumoto A, Shinohara K, Hiraiwa K (2010) Fatal human poisoning with Padan TM: A cartap-containing pesticide. Clin Toxicol 48:153–155. https://doi.org/10.3109/15563650903505166
Lane AL, Moore BS (2011) A sea of biosynthesis: marine natural products meet the molecular age. Nat Prod Rep 28:411–428. https://doi.org/10.1039/c0np90032j
Lane AL, Nyadonga L, Galhenaa AS, Shearerb TL, Stouta EP, Parryc RM, Kwasnika M, Wangc MD, Hayb ME, Fernandeza FM, Kubanek J (2009) Desorption electrospray ionization mass spectrometry reveals surface-mediated antifungal chemical defense of a tropical seaweed. Proc Natl Acad Sci USA 106(18):7314–7319
Latz MI, Frank TM, Case JF (1988) Spectral composition of bioluminescence of epipelagic organisms from the Sargasso Sea. Mar Biol 98:441–446
Leal MC, Puga J, Serôdio J, Gomes NCM, Calado R (2012) Trends in the discovery of new marine natural products from invertebrates over the last two decades – Where and what are we bioprospecting? PLoS ONE 7(1):e30580. https://doi.org/10.1371/journal.pone.0030580
Lebar MD, Heimbegner JL, Baker BJ (2007) Cold-water marine natural products. Nat Prod Rep 24:774–797. https://doi.org/10.1039/b516240h
Li JY, Endo H, Agatsuma Y, Taniguchi K (2011) Inhibition of larval survival and metamorphosis of the sea urchin Strongylocentrotus intermedius by 2,4-dibromophenol and 2,4,6-tribromophenol. Aquac Sci 59(2):247–253
Licciano M, Stabili L, Giangrande A (2005) Clearance rates of Sabella spallanzanii and Branchiomma luctuosum (Annelida: Polychaeta) on a pure culture of Vibrio alginolyticus. Water Res 39:4375–4384. https://doi.org/10.1016/j.watres.2005.09.003
Licciano M, Stabili L, Giangrande A, Cavallo RA (2007) Bacterial accumulation by Branchiomma luctuosum (Annelida: Polychaeta): a tool for biomonitoring marine systems and restoring polluted waters. Mar Environ Res 63:291–302. https://doi.org/10.1016/j.marenvres.2006.11.003
Lichtenegger HC, Schöberl T, Bartl MH, Waite H, Stucky GD (2003) High abrasion resistance with sparse mineralization: copper biomineral in worm jaws. Science 298:389–392. https://doi.org/10.1073/pnas.1632658100
Lincoln DE, Fielman KT, Marinelli RL, Woodin SA (2005) Bromophenol accumulation and sediment contamination by the marine annelids Notomastus lobatus and Thelepus crispus. Biochem Syst Ecol 33:559–570. https://doi.org/10.1016/j.bse.2004.12.006
Lindquist N (2002) Chemical defense of early life stages of benthic marine invertebrates. J Chem Ecol 28(10):1987–2000
Lindquist N, Hay ME (1996) Palatability and chemical defense of marine invertebrate larvae. Ecol Monogr 66(4):431–450
Lovell CR, Steward CC, Phillips T (1999) Activity of marine sediment bacterial communities exposed to 4-bromophenol, a polychaete secondary metabolite. Mar Ecol Prog Ser 179:241–246
Lumbang WA, Paul VJ (1996) Chemical defenses of the tropical green seaweed Neomeris anndata Dickie: effects of multiple compounds on feeding by herbivores. J Exp Mar Biol Ecol 201:185–195
Mahon AR, Amsler CD, McClintock JB, Amsler MO, Baker BJ (2003) Tissue-specific palatability and chemical defenses against macropredators and pathogens in the common articulate brachiopod Liothyrella uva from the Antarctic Peninsula. J Exp Mar Biol Ecol 290:197–210. https://doi.org/10.1016/S0022-0981(03)00075-3
Maltseva AL, Kotenko ON, Kokryakov VN, Starunov VV, Krasnodembskaya AD (2014) Expression pattern of arenicins—the antimicrobial peptides of polychaete Arenicola marina. Front Physiol 5(497):1–11. https://doi.org/10.3389/fphys.2014.00497
Manaranche R, Thieffry M, Israel M (1980) Effect of the venom of Glycera convoluta on the spontaneous quantal release of transmitter. J Cell Biol 85:446–458
Marcano L, Nusetti O, Rodriguez-Grau J, Briceno J, Vilas J (1997) Coelomic fluid lysozyme activity induction in the polychaete Eurythoe complanata as a biomarker of heavy metal toxicity. Bull Environ Contam Toxicol 59:22–28
Martin M, Anctil M (1984) Luminescence control in the tubeworm Chaetopterus variopedatus: role of the nerve cord and photogenic gland. Biol Bull 166:583–593
Martin D, Uriz MJ (1993) Chemical bioactivity of Mediterranean benthic organisms against embryos and larvae of marine invertebrates. J Exp Mar Biol Ecol 173:11–27
Martin D, Le Nourichel C, Uriz MJ, Bhaud M, Duchêne JC (2000) Ontogenic shifts in chemical defenses of the northwest Mediterranean Sea Eupolymnia nebulosa (Polychaeta, Terebellidae). Bull Mar Sci 67(1):287–298
Mastrodonato M, Lepore E, Gherardi M, Zizza S, Sciscioli M, Ferri D (2005) Histochemical and ultrastructural analysis of the epidermal gland cells of Branchiomma luctuosum (Polychaeta, Sabellidae). Invertebr Biol 124(4):303–309. https://doi.org/10.1111/j.1744-7410.2005.00028.x
Mastrodonato M, Gherardi M, Todisco G, Sciscioli M, Lepore E (2006) The epidermis of Timarete filigera (Polychaeta, Cirratulidae): histochemical and ultrastructural analysis of the gland cells. Tissue Cell 38:279–284. https://doi.org/10.1016/j.tice.2006.06.003
McClintock JB, Baker BJ (1997) A review of the chemical ecology of antartic marine invertebrates. Am Zool 37:329–342
Meredith TL, Cowart JD, Henkel TP, Pawlik JR (2007) The polychaete Cirriformia punctata is chemically defended against generalist coral reef predators. J Exp Mar Biol Ecol 353:198–202. https://doi.org/10.1016/j.jembe.2007.08.023
Meunier FA, Feng ZP, Molgó J, Zamponi GW, Schiavo G (2002) Glycerotoxin from Glycera convoluta stimulates neurosecretion by up-regulating N-type Ca2+ channel activity. EMBO J 21(24):6733–6743
Meunier FA, Nguyen TH, Colasante C, Luo F, Sullivan RKP, Lavidis NA, Molgó J, Meriney SD, Schiavo G (2010) Sustained synaptic-vesicle recycling by bulk endocytosis contributes to the maintenance of high-rate neurotransmitter release stimulated by glycerotoxin. J Cell Sci 123(7):1131–1140. https://doi.org/10.1242/jcs.049296
Michel C, Keil B (1975) Biologically active proteins in venomous glands of polychaetous annelid, Glycera convoluta Keferstein. Comp Biochem Physiol 50:29–32
Miron MJ, La Rivière L, Bassot JM, Anctil M (1987) Immunohistochemical and radioautographic evidence of monoamine-containing cells in bioluminescent elytra of the scale-worm Harmothoe imbricata (Polychaeta). Cell Tissue Res 249:547–556
Molinski TF, Dalisay DS, Lievens SL, Saludes JP (2009) Drug development from marine natural products. Nat Rev 8:69–85. https://doi.org/10.1038/nrd2487
Morel N, Thieffry M, Manaranche R (1983) Binding of Glycera convoluta neurotoxin to cholinergic nerve terminal plasma membranes. J Cell Biol 97:1737–1744
Mouneyrac C, Mastain O, Amiard JC, Amiard-Triquet C, Beaunier P, Jeantet AY, Smith BD, Rainbow PS (2003) Trace-metal detoxification and tolerance of the estuarine worm Hediste diversicolor chronically exposed in their environment. Mar Biol 143:731–744. https://doi.org/10.1007/s00227-003-1124-6
Nagawa Y, Saji Y, Chiba S, Yui T (1971) Neuromuscular blocking actions of Nereistoxin and its derivatives and antagonism by sulfhydryl compounds. Jpn J Pharmacol 21:185–197
Nakamura K, Tachikawa Y, Kitamura M, Ohno O, Suganuma M, Uemura D (2008) Complanine, an inflammation-inducing substance isolated from the marine fireworm Eurythoe complanata. Org Biomol Chem 6:2058–2060. https://doi.org/10.1039/b803107j
Nakamura K, Tachikawa Y, Uemura D (2009) (−)-Complanine, an inflammatory substance of marine fireworm: a synthetic study. Beilstein J Org Chem 5(12):1–4. https://doi.org/10.3762/bjoc.5.12
Nakamura K, Tachikawa Y, Ohno O, Kitamura M, Suganuma M, Uemura D (2010) Neocomplanines A and B, a Complanine family isolated from the marine fireworm. J Nat Prod 73:303–305. https://doi.org/10.1021/np900694j
Namera A, Watanabe T, Yashiki M, Kojima T (1999) Simple and sensitive analysis of Nereistoxin and its metabolites in human serum using headspace solid-phase microextraction and gas chromatography–mass spectrometry. J Chromatogr Sci 37:77–82
Nicol JAC (1952a) Studies on Chaetopterus variopedatus (Renier). I. The light-producing glands. J Mar Biol Assoc XXX:417–431
Nicol JAC (1952b) Studies on Chaetopterus variopedatus (Renier). II. Nervous control of light production. J Mar Biol Assoc XXX:433–452
Nicol JAC (1957) Luminescence in polynoids. III Propagation of excitation through the nerve cord. J Mar Biol Assoc UK 36:271–273
Nitta S (1934) Uber Nereistoxin, einen giftigen Bestandteil von Lumbriconereis heteropoda Marenz (Eunicidae). Yakugaku Zasshi 54:648–652
Notti A, Fattorini D, Razzetti EM, Regoli F (2007) Bioaccumulation and biotransformation of arsenic in the Mediterranean Polychaete Sabella spallanzanii: experimental observations. Environ Toxicol Chem 26(6):1186–1191
Nygren A, Norlinder E, Panova M, Pleijel F (2011) Colour polymorphism in the polychaete Harmothoe imbricata (Linnaeus, 1767). Mar Biol Res 7(1):54–62. https://doi.org/10.1080/17451001003713555
Nylund GM, Pavia H (2005) Chemical versus mechanical inhibition of fouling in the red alga Dilsea carnosa. Mar Ecol Prog Ser 299:111–121
Nylund GM, Gribben PE, De Nys R, Steinberg PD, Pavia H (2007) Surface chemistry versus whole-cell extracts: antifouling tests with seaweed metabolites. Mar Ecol Prog Ser 329:73–84
Osborn KJ, Haddock SHD, Pleijel F, Madin LP, Rouse GW (2009) Deep-sea, swimming worms with luminescent “Bombs”. Science 325(5943):964. https://doi.org/10.1126/science.1172488
Ovchinnikova TV, Aleshina GM, Balandin SV, Krasnosdembskaya AD, Markelov ML, Frolova EI, Leonova YF, Tagaev AA, Krasnodembsky EG, Kokryakov VN (2004) Purification and primary structure of two isoforms of arenicin, a novel antimicrobial peptide from marine polychaeta Arenicola marina. FEBS Lett 577:209–214. https://doi.org/10.1016/j.febslet.2004.10.012
Pan W, Liu X, Ge F, Han J, Zheng T (2004) Perinerin, a novel antimicrobial peptide purified from the clamworm Perinereis aibuhitensis Grube and its partial characterization. J Biochem 135:297–304. https://doi.org/10.1093/jb/mvh036
Pardo EV, Amaral ACZ (2004) Feeding behavior of the cirratulid Cirriformia filigera (Delle Chiaje, 1825) (Annelida: Polychaeta). Braz J Biol 64(2):283–288
Park Y, Choe S, Lee H, Jo J, Park Y, Kim E, Pyo J, Jung JH (2015) Advanced analytical method of Nereistoxin using mixed-mode cationic exchange solid-phase extraction and GC/MS. Forensic Sci Int 252:143–149. https://doi.org/10.1016/j.forsciint.2015.04.010
Paul VJ, Fenical W (1986) Chemical defense in tropical green algae, order Caulerpales. Mar Ecol Prog Ser 34:157–169
Paul VJ, Puglisi MP (2004) Chemical mediation of interactions among marine organisms. Nat Prod Rep 21:189–209. https://doi.org/10.1039/b302334f
Paul VJ, Ritson-Williams R (2008) Marine chemical ecology. Nat Prod Rep 25:662–695. https://doi.org/10.1039/b702742g
Paul VJ, Van Alstyne KL (1988) Chemical defense and chemical variationin some tropical Pacific species of Halimeda (Halimedaceae: Chlorophyta). Coral Reefs 6:263–269
Paul VJ, Lindquist N, Fenical W (1990) Chemical defenses of the tropical ascidian Atapozoa sp. and its nudibranch predators Nembrotha spp. Mar Ecol Prog Ser 59:109–118
Paul VJ, Puglisi MP, Ritson-Williams R (2006) Marine chemical ecology. Nat Prod Rep 23:153–180. https://doi.org/10.1039/b404735b
Paul VJ, Ritson-Williams R, Sharp K (2011) Marine chemical ecology in benthic environments. Nat Prod Rep 28:345–387. https://doi.org/10.1039/c0np00040j
Pavia H, Toth GB, Lindgren A, Aberg P (2003) Intraspecific variation in the phlorotannin content of the brown alga Ascophyllum nodosum. Phycologia 42(4):378–383
Pawlik JR (1993) Marine invertebrate chemical defenses. Chem Rev 93(5):1911–1922
Pawlik JR (2012) Antipredatory defensive roles of natural products from marine invertebrates. In: Fattorusso E, Gerwick WH, Taglilatela-Scarfati O (eds) Handbook of marine natural products, 1st edn. Springer, Netherlands, pp 677–710. https://doi.org/10.1007/978-90-481-3834-0_12
Pawlik JR, Chanas B, Toonen RJ, Fenical W (1995) Defenses of Caribbean sponges against predatory reef fish. I. Chemical deterrency. Mar Ecol Prog Ser 127:183–194
Pennings SC, Siska EL, Bertness MD (2001) Latitudinal differences in plant palatability in Atlantic coast salt marshes. Ecology 82(5):1344–1359
Pennings SC, Ho CK, Salgado CS, Wieski K, Davé N, Kunza AE, Wason EL (2009) Latitudinal variation in herbivore pressurein Atlantic Coast salt marshes. Ecology 90(1):183–195
Pereira RC, Da Gama BAP, Teixeira VL, Yoneshigue-Valentin Y (2003) Ecological roles of natural products of the Brazilian red seaweed Laurencia obtusa. Braz J Biol 63(4):665–672
Pereira DM, Valentão P, Andrade PB (2014) Marine natural pigments: chemistry, distribution and analysis. Dyes Pigments 111:124–134. https://doi.org/10.1016/j.dyepig.2014.06.011
Petrash DA, Lalonde SV, Gingras MK, Konhauser KO (2011) A surrogate approach to studying the chemical reactivity of burrow mucous linings in marine sediments. Palaios 26(9):594–600. https://doi.org/10.2110/palo.2010.p10-140r
Plyuscheva M, Martin D (2009) On the morphology of elytra as luminescent organs in scale-worms (Polychaeta, Polynoidae). Zoosymposia 2:379–389
Prezant RS (1980) An antipredation mechanism of the polychaete Phyllodoce mucosa with notes on similar mechanisms in other potential prey. Fish Bull 77:605–616
Prota G, D'Agostino M, Misuraca G (1970) Isolation and characterization of Hallachrome, a red pigment from the sea worm Halla parthenopeia. Specialia 27(1):15–16
Prota G, D’Agostino M, Misuraca G (1972) The structure of Hallachrome: 7-Hydroxy-8-methoxy-6-methyl-1,2-anthraquinone. J Chem Soc Perkin Trans 1 13:1614–1616
Puglisi MP, Sneed JM, Sharp KH, Ritson-Williams R, Paul VJ (2014) Marine chemical ecology in benthic environments. Nat Prod Rep 31:1510–1553. https://doi.org/10.1039/c4np00017j
Rasher DB, Hay ME (2010) Chemically rich seaweeds poison corals when not controlled by herbivores. Proc Natl Acad Sci USA 107(21):9683–9688
Rasher DB, Hay ME (2014) Competition induces allelopathy but suppresses growth and anti-herbivore defence in a chemically rich seaweed. Proc R Soc B 281:2013–2615
Rasher DB, Stout EP, Engel S, Kubanek J, Hay ME (2011) Macroalgal terpenes function as allelopathic agents against reef corals. Proc Natl Acad Sci USA 108(43):17726–17731
Ribeiro SM, Bianco EM, Rogers R, Teixeira VL, Pereira RC (2010) Chemical defense of Hymeniacidon heliophila (Porifera: Halichondrida) aganist tropical predators. Braz J Oceanogr 58(4):315–321
Rouse GW, Pleijel F (2001) Polychaetes. Oxford University Press, Oxford
Rouse GW, Pleijel F (2006) Annelid phylogeny and systematics. In: Rouse GW, Pleijel F (eds) Reproductive biology and phylogeny of Annelida. Science Publishers, Enfield, New Hampshire, pp 3–21
Rouse GW, Pleijel F (2007) Annelida. Zootaxa 1668:245–264
Schaum CE, Batty R, Last KS (2013) Smelling danger – alarm cue responses in the polychaete Nereis (Hediste) diversicolor (Müller, 1776) to potential fish predation. PLoS ONE 8(10):e77431. https://doi.org/10.1371/journal.pone.0077431
Schenning M, Proctor DT, Ragnarsson L, Barbier J, Lavidis NA, Molgó JJ, Zamponi GW, Schiavo G, Meunier FA (2006) Glycerotoxin stimulates neurotransmitter release from N-type Ca2+ channel expressing neurons. J Neurochem 98:894–904. https://doi.org/10.1111/j.1471-4159.2006.03938.x
Schmitt TM, Hay ME, Lindquist N (1995) Constraints on chemically mediated coevolution: multiple functions for seaweed secondary metabolites. Ecology 76(1):107–123
Sears MA, Gerhart DJ, Rittschof D (1990) Antifouling agents from marine sponge Lissodendoryx isodictyalis Carter. J Chem Ecol 16(3):791–799
Selander E, Jakobsenb HH, Lombarda F, Kiørboe T (2011) Grazer cues induce stealth behavior in marine dinoflagellates. Proc Natl Acad Sci USA 108(10):4030–4034
Selander E, Kubanek J, Hambergd M, Andersson MX, Cervinc G, Paviac H (2015) Predator lipids induce paralytic shellfish toxins inbloom-forming algae. Proc Natl Acad Sci USA 112(20):6395–6400
Seo JK, Nam BH, Go HJ, Jeong M, Lee KY, Cho SM, Lee IA, Park NG (2016) Hemerythrin-related antimicrobial peptide, msHemerycin, purified from the body of the lugworm, Marphysa sanguinea. Fish Shellfish Immunol 57:49–59. https://doi.org/10.1016/j.fsi.2016.08.018
Sheikh YM, Djerassi C (1975) 2,6-Dibromophenol and 2,4,6-tribromophenols – antiseptic secondary metabolites of Phoronopsis viridis. Experientia 31(3):265–266
Shibata T, Miyasaki T, Miyake H, Tanaka R, Kawaguchi S (2014) The Influence of phlorotannins and bromophenols on the feeding behavior of marine herbivorous gastropod Turbo cornutus. Am J Plant Sci 5:387–392
Shimomura O (2006) Annelida. In: Shimomura O (ed) Bioluminescence: chemical principles and methods, revised edition. World Scientific Publishing Co Pte Ltd, Singapore, pp 216–247
Skropeta D (2008) Deep-sea natural products. Nat Prod Rep 25(6):989–1216. https://doi.org/10.1039/b808743a
Skropeta D, Wei L (2014) Recent advances in deep-sea natural products. Nat Prod Rep 31(8):999–1025. https://doi.org/10.1039/c3np70118b
Slattery M, McClintock JB, Heineb JN (1995) Chemical defenses in Antarctic soft corals: evidence for antifouling compounds. J Exp Mar Biol Ecol 190:61–77
Stabili L, Licciano M, Giangrande A, Fanelli G, Cavallo RA (2006) Sabella spallanzanii filter-feeding on bacterial community: ecological implications and applications. Mar Environ Res 61:4–92. https://doi.org/10.1016/j.marenvres.2005.06.001
Stabili L, Schirosi R, Licciano M, Giangrande A (2009) The mucus of Sabella spallanzanii (Annelida, Polychaeta): its involvement in chemical defence and fertilization success. J Exp Mar Biol Ecol 374:144–149. https://doi.org/10.1016/j.jembe.2009.04.016
Stabili L, Schirosi R, Di Benedetto A, Merendino A, Villanova L, Giangrande A (2011) First insights into the biochemistry of Sabella spallanzanii (Annelida: Polychaeta) mucus: a potentially unexplored resource for applicative purposes. J Mar Biol Assoc UK 91(1):199–208. https://doi.org/10.1017/S0025315410001013
Stabili L, Schirosi R, Licciano M, Giangrande A (2014a) Role of Myxicola infundibulum (Polychaeta, Annelida) mucus: from bacterial control to nutritional home site. J Exp Mar Biol Ecol 461:344–349. https://doi.org/10.1016/j.jembe.2014.09.005
Stabili L, Giangrande A, Pizzolante G, Caruso G, Alifano P (2014b) Characterization of Vibrios diversity in the mucus of the polychaete Myxicola infundibulum (Annellida, Polichaeta). Microb Ecol 67:186–194. https://doi.org/10.1007/s00248-013-0312-2
Stachowicz JJ (2001) Chemical ecology of mobile benthic invertebrates: predators and prey, allies and competitors. In: McClintock JB, Baker BJ (eds) Marine chemical ecology. CRC Press, Boca Raton, pp. 157–194
Steinberg PD (1985) Feeding preferences of Tegula funebralis and chemical defenses of marine brown algae. Ecol Monogr 55(3):333–349
Steinberg PD (1988) Effects of quantitative and qualitative variation in phenolic compounds on feeding in three species of marine invertebrate herbivores. J Exp Mar Biol Ecol 120:221–237
Steward CC, Lovell CR (1997) Respiration and assimilation of 4-bromophenol by estuarine sediment bacteria. Microb Ecol 33:198–205
Steward CC, Pinckney J, Piceno Y, Lovell CR (1992) Bacterial numbers and activity, microalgal biomass and productivity, and meiofaunal distribution in sediments naturally contaminated with biogenic bromophenols. Mar Ecol Prog Ser 90:61–71
Steward CC, Nold SC, Ringelberg DB, White DC, Lovell CR (1996) Microbial biomass and community structures in the burrows of bromophenol producing and non-producing marine worms and surrounding sediments. Mar Ecol Prog Ser 133:149–165
Storch V, Welsch U (1972) Ultrastructure and histochemistry of the integument of air-breathing polychaetes from mangrove swamps of Sumatra. Mar Biol 17:137–144
Suadicani SO, de Freitas JC, Sawaya MI (1993) Pharmacological evidence for the presence of a beta-adrenoceptor-like agonist in the amphinomid polychaete Eurythoe complanata. Comp Biochem Physiol 104C(2):327–332
Sudatti DB, Rodrigues SV, Pereira RC (2006) Quantitative GC-ECD analysis of halogenated metabolites: determination of elatol on surface and within-thallus of Laurencia obtusa. J Chem Ecol 32:835–843. https://doi.org/10.1007/s10886-006-9033-z
Taboada S, Núñez-Pons L, Avila C (2013) Feeding repellence of Antarctic and Sub-Antarctic benthic invertebrates against the omnivorous sea star Odontaster validus. Polar Biol 36:13–25. https://doi.org/10.1007/s00300-012-1234-z
Taghon GL (1982) Optimal foraging by deposit-feeding invertebrates: roles of particle size and organic coating. Oecologia (Berl) 52:295–304
Tanino H, Takakura H, Kakoi H, Okada K, Inoue S (1994) (S)-6-(1-hydroxypropyl) lumazine derivatives from the marine polychaete, Odontosyllis undecimdonta. Heterocycles 38(5):971–974
Tanino H, Takakura H, Kakoi H, Okada K, Inoue S (1996) (S)-2-methyl-1,5-bis(1,3-dimethyl-6-lumazinyl)-1,5-pentanedione from the marine polychaete, Odontosyllis undecimdonta. Heterocycles 42(1):125–128
Tasiemski A, Schikorsk D, Le Marrec-Croq F, Camp CPV, Boidin-Wichlacz C, Sautière PE (2007) Hedistin: a novel antimicrobial peptide containing bromotryptophan constitutively expressed in the NK cells-like of the marine annelid, Nereis diversicolor. Dev Comp Immunol 31(8):749–762. https://doi.org/10.1016/j.dci.2006.11.003
Thacker RW, Becerro MA, Lumbang WA, Paul VJ (1998) Allelopathic interactions between sponges on a tropical reef. Ecology 79(5):1740–1750
Thornburg CC, Zabriskie TM, McPhail KL (2010) Deep-sea hydrothermal vents: Potential hot spots for natural products discovery? J Nat Prod 73:489–499. https://doi.org/10.1021/np900662k
Toth GB, Pavia H (2000) Water-borne cues induce chemical defense in amarine alga (Ascophyllum nodosum). Proc Natl Acad Sci USA 97(26):14418–14420
Toth GB, Langhamer O, Pavia H (2005) Inducible and constitutive defenses of valuable seaweed tissues: consequences for herbivore fitness. Ecology 86(3):612–618
Tsuji FI, Hill E (1983) Repetitive cycles of bioluminescence and spawning in the polychaete, Odontosyllis phosphorea. Biol Bull 165(2):444–449
Unson MD, Holland ND, Faulkner DJ (1994) A brominated secondary metabolite synthesized by the cyanobacterial symbiont of a marine sponge and accumulation of the crystalline metabolite in the sponge tissue. Mar Biol 119:1–11
Uriz MJ, Martin D, Rosell D (1992) Relationships of biological and taxonomical characteristics to chemically mediated bioactivity in the Mediterranean littoral sponges. Mar Biol 113:287–297
von Reumont BM, Campbell LI, Richter S, Hering L, Sykes D, Hetmank J, Jenner RA, Bleidorn C (2014) A polychaete’s powerful punch: venom gland transcriptomics of Glycera reveals a complex cocktail of toxin homologs. Genome Biol Evol 6(9):2406–2423. https://doi.org/10.1093/gbe/evu190
Wahl M (1989) Marine epibiosis. I. Fouling and antifouling: some basic aspects. Mar Ecol Prog Ser 58:175–189
Wahl M, Hay ME (1995) Associational resistance and shared doom: effects of epibiosis on herbivory. Oecologia 102:329–340
Watson GJ, Hamilton KM, Tuffnail WE (2005) Chemical alarm signalling in the polychaete Nereis (Neanthes) virens (Sars) (Annelida: Polychaeta). Anim Behav 70:1125–1132. https://doi.org/10.1016/j.anbehav.2005.03.011
Watts MJ, Barlow TS, Button M, Sarkar SK, Bhattacharya BD, Alam MA, Gomes A (2013) Arsenic speciation in polychaetes (Annelida) and sediments from the intertidal mudflat of Sundarban mangrove wetland, India. Environ Geochem Health 35:13–25. https://doi.org/10.1007/s10653-012-9471-1
Weber K, Ernst W (1978) Occurrence of brominated phenols in the marine polychaete Lanice conchilega. Naturwissenschaften 65:262
Whitfield FB, Drew M, Helidoniotis F, Svoronos D (1999) Distribution of bromophenols in species of marine polychaetes and bryozoans from Eastern Australia and the role of such animals in the flavor of edible ocean fish and prawns (Shrimp). J Agric Food Chem 47:475–4762. https://doi.org/10.1021/jf9904719
Woodin SA, Walla MD, Lincoln DE (1987) Occurrence of brominated compounds in soft-bottom benthic organisms. J Exp Mar Biol Ecol 107:209–217
Woodin SA, Marinelli RL, Lincoln DE (1993) Allelochemical inhibition of recruitament in a sedimentary assemblage. J Chem Ecol 19(3):517–530
Woodin SA, Lindsay SM, Lincoln DE (1997) Biogenic bromophenols as negative recruitment cues. Mar Ecol Prog Ser 157:303–306
Wright JT, De Nys R, Poore AGB, Steinberg PD (2004) Chemical defense in a marine alga: heritability and the potential for selection by herbivores. Ecology 85(11):2946–2959
Yoon KS, Chen YP, Lovell CR, Lincoln DE, Knapp LW, Woodin SA (1994) Localization of the chloroperoxidase of the capitellid polychaete Notomastus lobatus. Biol Bull 187:215–222
Zapata-Vívenes E, Nusetti OA, Marcano L, Esclapes MM, Arredondo L (2005) Immunological responses and wound healing in the polychaete Eurythoe complanata (Annelida: Amphinomidae) exposed to copper. Cienc Mar 31:1–10
Zimmer RK, Butman CA (2000) Chemical signaling processes in the marine environment. Biol Bull 198(2):168–187. https://doi.org/10.2307/1542522
Zörner SA, Fischer A (2007) The spatial pattern of bioluminescent flashes in the polychaete Eusyllis blomstrandi (Annelida). Helgol Mar Res 61:55–66. https://doi.org/10.1007/s10152-006-0053-4
Acknowledgments
The authors gratefully acknowledge the financial support from CNPq (Conselho Nacional de Pesquisa e Desenvolvimento), CAPES (Coordenação de Aperfeiçoamento de Pessoal de Nível Superior) and FAPERJ (Fundação Carlos Chagas Filho de Amparo à Pesquisa ao Estado do Rio de Janeiro). Without it, this study would not have been possible. We are thankful to Diana Cavalcanti and Ana Claudia dos Santos Brasil whose comments helped to improve an earlier version of this manuscript. Two anonymous reviewers also contributed to improve the final version.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of Interest
The authors declare that they have no conflicts of interest.
Rights and permissions
About this article
Cite this article
Coutinho, M.C.L., Teixeira, V.L. & Santos, C.S.G. A Review of “Polychaeta” Chemicals and their Possible Ecological Role. J Chem Ecol 44, 72–94 (2018). https://doi.org/10.1007/s10886-017-0915-z
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10886-017-0915-z