Marine natural product antifoulants: Status and potential

Biofouling

Volumn 9, Issue 3, 1996, Pages 211-229

  Clare, Anthony S ^a  

^a THE LABORATORY   (United Kingdom)

Author keywords

Antifoulants; Biocides; Biofouling; Coatings; Marine natural products; Organotins; Settlement

Indexed keywords

EID: 0001181477     PISSN: 08927014     EISSN: None     Source Type: Journal    
DOI: 10.1080/08927019609378304     Document Type: Article

References (105)

1. Acar J F (1980) The disc susceptibility test. In: Lorian V (ed) Antibiotics in Laboratory Medicine. Williams and Wilkins, London, pp 24-54
2. Albert A (1968) Selective Toxicity. Methuen & Company Ltd. London, pp 162-168
3. Anthoni U, Nielsen P H, Pereira M, Christophersen C (1990) Bryozoan secondary metabolites: a chemotaxonomical challenge. Camp Biochem Physiol 96B: 431-437
4. Avelin S, Vitalina S, Rittschof D, Nagabhushanam R (1993) Bacterial-barnacle interaction: potential of using juncellins and antibiotics to alter the structure of bacterial communities. J Chem Ecol 19: 2155-2167
5. Avelin S, Vitalina S, Sarojini R, Nagabhushanam R (1994) Broad spectrum natural products from the Indian Ocean octocoral Euptexaura nuttingi. In: Thompson M-F, Nagabhushanam R, Sarojini R, Fingerman M (eds) Recent Developments in Biofouling Control. A A Balkema, Rotterdam, pp 241-249
6. Bak R P M, Borsboom J L A (1984) Allelopathic interaction between a reef coelenterate and benthic algae. Oecologia 63: 194-198
7. Bakus G J, Kawaguchi M (1984) Toxins from marine organisms: studies on antifouling, In: Bolis L, Zadunaisky J, Gilles R (eds) Toxins, Drugs, and Pollutants in Marine Animals. Springer-Verlas, Berlin, pp 43-46
8. Bakus G J, Schulte B, Jhu S, Wright M, Green G, Gomez P (1990) Antibiosis and antifouling in marine sponges: Laboratory versus field studies. In: Rutzler K (ed) New Perspectives in Sponge Biology. Smithsonian Institution Press, Washington, D C, pp 102-108
9. Bakus G J, Wright M, Khan A K, Ormsby B, Gulko D A, Licuanan W, Carriazo E, Ortiz A, Chan D B, Lorenzana D, Huxley M P (1994) Experiments seeking marine natural antifouling compounds. In: Thompson M-F, Nagabhushanam R, Sarojini R, Fingerman M (eds) Recent Developments in Biofouling Control. A A Balkema, Rotterdam, pp 373-381
10. Bandurraga M M, Fenical W (1985) Isolation of the muricins. Evidence of a chemical adaptation against fouling in the marine octocoral Muricea fruticosa (Gorgonacea). Tetrahedron 41: 1057-1065
11. Becerro M A, Lopez N I, Turon X, Uriz M J (1994) Antimicrobial activity and surface bacterial film in marine sponges. J Exp Mar Biol Ecol 179: 195-205
12. Berking S (1987) Homarine (N-methylpicolinic acid) and trigonelline (N-methylnicotimc acid) appear to be involved in pattern control in a marine hydroid. Development 99: 211-220
13. Bobzin S C, Faulkner D J (1992) Chemistry and chemical ecolosy of the Bahamian sponge Aphsilla glacialis. J Chem Ecol 18: 309-332
14. Bultman J D, Griffith J R (1994) Fluoropolymer and silicone fouling-release coatings. In: Thompson M-F, Nagabhushanam R, Sarojini R, Fingerman M (eds) Recent Developments in Biofouling Control. A A Balkema, Rotterdam, pp 383-389
15. Caccamese S, Azzolina R, Furnari G, Cormaci M, Grasso S (1981) Antimicrobial and antiviral activities of some marine algae from eastern Sicily. Bot Mar 24: 365-367
16. Ciereszko L S, Guillard R R L (1989) The influence of some cembranoudes from gorgonian corals on motility of some flagellates. J Exp Mar Biol Ecol 127: 205-210
17. Claisse D, Alzieu C (1993) Copper contamination as a result of antifoulma paint regulations? Mar Poll Bull 26: 395-397
18. Clare A S (1995) Natural ways to banish barnacles. New Sci February: 38-41
19. Clare A S, Rittschof D, Gerhart D J. Maki J S (1992) Molecular approaches to nontoxic antifouling. Invert Reprod Devel 22: 67-76
20. Clare A S, Rittschof D, Price R R, Gerhart D J (1995) Khellin, a natural product analogue with antifouling activity: laboratory and field studies. In: Bousher A, Edyvean R G J (eds) Biodeterioration and Biodegradation, Vol 9. Institute of Chemical Engineers, pp 573-580
21. Coll J C, Price I R, Konig G M, Bowden B F (1987) Algal overgrowth of alcyonacean soft corals. Mar Biol 96: 129-135
22. Davis A R (1991) Alkaloids and ascidian defense: evidence for the ecological role of natural products from Eudistoma olivaceum. Mar Biol 111: 375-379
23. Davis A R, Targett N M, McConnell O J, Young C M (1989) Epibiosis of marine algae and benthic invertebrates: Natural products chemistry and other mechanisms inhibiting settlement and overgrowth. In: Scheuer PJ (ed) Bioorganic Marine Chemistry, Vol 3. Springer-Verlag, Berlin, pp 85-114
24. Davis A R, White G A (1994) Epibiosis in a guild of sessile subtidal invertebrates in south-eastern Australia: a quantitative survey. J Exp Mar Biol Ecol 177: 1-14
25. Davis A R, Wright A E (1989) Interspecific differences in fouling of two congeneric ascidians (Eudistoma olivaceum and E. capsulatum): is surface acidity an effective defense? Mar Biol 102: 491-497
26. Davis A R, Wright A E (1990) Inhibition of larval settlement by natural products from the ascidian, Eudistoma olivaceum (van Name). J Chem Ecol 16: 1349-1357
27. de Nys R, Steinberg P D, Willemsen P, Dworjanyn S A, Gabelish C L, King R J (1995) Broad spectrum effects of secondary metabolites from the red alga Delisea pulchra in antifouling assays. Biofouling 8: 259-271
28. Dyrynda P E J (1985) Chemical defences and the structure of subtidal epibenthic communities. In: Gibbs P E (ed) Proc 19th Eur Mar Biol Symp. Cambridge University Press, Cambridge, pp 411-424
29. Ellis D V (1991) New dangerous chemicals in the environment: lessons from TBT. Mar Poll Bull 22: 8-10
30. Faulkner D J (1992) Biomedical uses for natural marine chemicals. Oceanus Spring: 29-35
31. Faulkner D J (1994) Marine natural products. Nat Prod Rep 11: 355-394
32. Garson M J (1994) The biosynthesis of sponge secondary metabolites: Why it is important. In: van Soest R W M, van Kempen Th M G, Braekman J-C (eds) Sponges in Time and Space. A A Balkema, Rotterdam, pp 427-440
33. Gatenholm P, Holmström C, Maki J S, Kjelleberg S (1995) Toward biological antifouling surface coatings: marine bacteria immobilized in hydrogel inhibit barnacle larvae. Biofouling 8: 293-301
34. Gerhart D J, Rittschof D, Mayo S W (1988) Chemical ecology and the search for marine antifoulants. Studies of a predator-prey symbiosis. J Chem Ecol 14: 1905-1917
35. Goto R, Kado R, Muramoto K, Kamiya H (1992) Fatty acids as antifoulants in a marine sponge. Biofouling 6: 61-68
36. Goto R, Kado R, Muramoto K, Kamiya H (1993) Furospongolide, an antifouling substance from the marine sponge Phyllospongia papyracea against the barnacle Balanus amphitrite. Nippon Suisan Gakkaishi 59: 1953
37. Gough M A, Fothergill J, Hendrie J D (1994) A survey of southern England coastal waters for the s-triazine antifouling compound Irgarol 1051. Mar Poll Bull 28: 613-620
38. Hadfield M G, Ciereszko L S (1978) Action of cembranolides derived from octocorals on larvae of the nudibranch Phestilla sibogae. In: Kaul P N, Sinderman C J (eds) Drugs and Food from the Sea: Myth or Reality? University of Oklahoma Press, Norman, pp 145-150
39. Harrison P G (1982) Control of microbial growth and of amphipod grazing by water-soluble compounds from leaves of Zostera marina. Mar Biol 67: 225-230
40. Harrison P G, Chan A T (1980) Inhibition of the growth of micro-algae by extracts of eelgrass (Zosiera marina) leaves. Mar Biol 61: 21-26
41. Harrison P G, Durance C D (1985) Reductions in photosynthetic carbon uptake in epiphytic diatoms by water-soluble extracts of leaves of Zostera marina. Mar Biol 90: 117-119
42. Hay M E (1991) The natural function of seaweed secondary metabolites. In: Thompson M-F, Sarojmi R, Nagabhushanam R (eds) Bioactive Compounds from Marine Organisms. A A Balkema, Rotterdam, pp 19-22
43. Holmström C, Kjelleberg S (1994) The effect of external biological factors on settlement of marine in venebrate and new antifouling technology. Biofouling 8: 147-160
44. Isensee J, Watermann B, Berger H-D (1994) Emissions of antifouling-biocides into the North Sea-an estimation. Deutsche Hydrographische Zeitschrift 46: 355-364
45. Iwata H, Tanabe S, Miyazaki N, Tatsukawa R (1994) Detection of butyltin compound residues in the blubber of marine mammals. Mar Poll Bull 28: 607-612
46. Izac R R, Bandurraga M M, Wasylyk J M, Dunn F W, Fenical W (1982) Germacrene derivatives from diverse marine soft-corals (Octocorallia). Tetrahedron 38: 301-304
47. Keifer P A, Rinehart K L, Hooper I R (1986) Renillafoulins, antifouling diterpenes from the sea pansy Renilla reniformis (Octocorallia). J Org Chem 51: 4450-4454
48. Kjaer E B (1992) Bioactive materials for antifouling coatings. Prog Org Coalings 20: 339-352
49. Kjelleberg S, Holmström C. (1994) Antifoulants from bacteria. In: Kjelleberg S, Steinberg P (eds) Biofouling: Problems and Solutions. Proc Int Workshop. The University of New South Wales, Sydney, pp 65-69
50. Kon-ya K, Shimidzu N, Miki W, Endo M (1994) Indole derivatives as potent inhibitors of larval settlement by the barnacle, Balanus amphitrite. Biosci Biotech Biochem 58: 2178-2181
51. Kon-ya K, Shimidzu N, Otaki N, Yokoyama A, Adachi K, Miki W (1995) Inhibitory effect of bacterial ubiquinones on the settling of barnacle. Balanus amphitrite. Experientia 51: 153-155
52. Martin D, Uriz M J (1993) Chemical bioactivity of Mediterranean benthic in vertebrate organisms against embryos and larvae of marine invertebrates. J Exp Mar Biol Ecol 173: 11-27
53. Mathews C K, van Holde K E (1990) Biochemistry The Benjamin/Cummings Publishing Company. Inc., Redwood City, CA, pp 614-615
54. McCaffrey E J, Endean R (1985) Antimicrobial activity of tropical and subtropical sponges. Mar Biol 89: 1-8
55. Missakian M G, Burreson B J, Scheuer P J (1975) Pukalide, a furanocembranolide from the soft coral Sinularia abupta. Tetrahedron 31: 2513-2515
56. Mizobuchi S, Kon-ya K, Adachi K, Sakai M. Miki W (1994) Antifouling substances from a Palauan octocoral Sinularia sp.. Fisheries Science 60: 345-346
57. Mizobuchi S, Shimidzu N, Katsuoka M, Adachi K, Miki W (1993) Antifouling substances against the mussel in an octocoral Denaronephthya sp.. Nippon Suisan Gakkaishi 59: 1195-1199
58. Mokashe S S, Tulaskar A S, Venkat K, Wagh A B (1994) Antimicrobial properties of poriferan species from Indian Waters. In: Thompson M-F, Nagabhushanam R, Sarojini R, Fingerman M (eds) Recent Developments in Biofouling Control. A A Balkema, Rotterdam, pp 263-268
59. Munro M H G, Blunt J W, Lake R J, Litaudon M, Battershill C N, and Page M J (1994) From seabed to sickbed: What are the prospects ? In: van Soest R W M, van Kempen Th M G, Braekman J-C (eds) Sponges in Time and Space. A A Balkema, Rotterdam, pp 473-484
60. Nakatsu T, Walker R P, Thompson J E, Faulkner D J (1983) Biologically-active sterol sulfates from the marine sponge Toxadocia zumi. Experientia 39: 759-761
61. Oclarit J M, Ohta S, Kamimura K, Yamaoka Y, Ikegami S (1994) Production of an antibacterial agent, o-aminophenol, by a bacterium isolated from the marine sponge, Adocia sp.. Fisheries Science 60: 559-562
62. Paul V J (1992) Chemical defenses of benthic marine invertebrates In: Paul V J (ed) Ecological Roles of Marine Natural Products. Comstock Publishing Associates, Ithaca, pp 164-188
63. Pennings S C, Pablo S R, Paul V J, Duffy J E (1994) Effects of sponge secondary metabolites in different diets on feeding by three groups of consumers. J Exp Mar Biol Ecol 180: 137-149
64. Pidgeon J D (1993) Critical Review of Current and Future Marine Antifouling Coatings. Report No. 93/TIPEE/4787. Lloyd's Register Engineering Services
65. Price R R, Patchan M, Clare A S, Rittschof D, Bonaventura J (1992) Performance enhancement of natural antifouling compounds and their analogs through microencapsulation and controlled release. Biofouling 6: 207-216
66. Readman J W, Wee Kwong L L, Grondin D, Bartocci J, Villeneuve J-P, Mee L-D (1993) Coastal water contamination from a triazine herbicide used in antifouling paints. Environ Sci Technol 27: 1940-1942
67. Rittschof, D, Clare, A S, Gerhart, D J, Avelin, S, Bonaventura J (1992) Barnacle in vitro assays for biologically active substances: toxicity and settlement inhibition assays using mass cultured Balanus amphitrite amphitrite Darwin. Biofouling 6: 115-122
68. Rittschof D, Hooper I R, Branscomb E S, Costlow J D (1985) Inhibition of barnacle settlement and behavior by natural products from whip corals, Leptogorgia virgulata (Lamarck, 1815). J Chem Ecol 11: 551-563
69. Rittschof, D, Hooper, I R, Costlow, J D (1988) Settlement inhibition of marine invertebrate larvae: comparison of sensitivities of bryozoan and barnacle larvae. In: Thompson M-F, Sarojini R, Nagabhushanam R (eds) Marine Biodeterioration. A A Balkema, Rotterdam, pp 599-608
70. Rittschof D, Sasikumar N, Murlless D, Clare A S, Gerhart D, Bonaventura J (1994) Mixture interactions of lactones and furans and a commercial biocide: toxicity and antibarnacle settlement activity. In: Thompson M-F, Nagabhushanam R, Sarojini R, Fingerman M (eds) Recent Developments in Biofouling Control. A A Balkema, Rotterdam, pp 269-274
71. Sarma N S, Rao K S, Viswanadham B (1991) Settling responses and progression in community development of selected macrofouling organisms to recently isolated sponge metabolite, herbacin. at Visakhapatnam Harbor, Bay of Bengal. In: Thompson M-F, Sarojini R, Nagabhushanam R (eds) Bioactive Compounds from Marine Organisms. A A Balkema, Rotterdam, pp 341-350
72. Sears M A, Gerhart D J, Rittschof D (1990) Antifouling agents from marine sponge Lissodendoryx isodictyalis Carter. J Chem Ecol 16: 791-799
73. Shimidzu N, Katsuoka M, Mizobuchi S, Ina K, Miki W (1993) Isolation of (-)-beta-bisabolene as a repellent substance against blue mussel from an octocoral Sinularis sp.. Nippon Suisan Gakkaishi 59: 1951
74. Sieburth J M, Conover J T (1965) Sargassum tannin, an antibiotic which retards fouling. Nature 208: 52-53
75. Sieburth J M, Thomas C D (1973) Fouling on eelgrass (Zostera marina L.). J Phycol 9: 46-50
76. Slattery M, McClintock J B, Heine J N (1995) Chemical defenses in Antarctic soft corals: evidence for antifouling compounds. J Exp Mar Biol Ecol 190: 61-77
77. Standing J D, Hooper I R, Costlow J D (1984) Inhibition and induction of barnacle settlement by natural products present in octocorals. J Chem Ecol 10: 823-834
78. Steinberg P D, de Nys R (1994) Natural antifoulants from seaweeds. In: Kjelleberg S, Steinberg P (eds) Biofouling: Problems and Solutions. The University of New South Wales, Sydney, pp 70-76
79. Stewart C, de Mora S J (1990) A review of the degradation of tri(n-butyl)tin in the marine environment. Environ Technol 11: 565-570
80. Stoecker D (1978) Resistance of a tunicate to fouling. Biol Bull 155: 615-626
81. Targett N M (1988) Allelochemistry in marine organisms: Chemical fouling and antifouling strategies. In: Thompson M-F. Sarojini R, Nagabhushanam R (eds) Marine Biadeterioration. A A Balkema, Rotterdam. pp 609-617
82. Targett N M, Bishop S S, McConnell O J, Yoder J A (1983) Antifouling agents against the benthic marine diatom, Navicula salinicola Homarine from the gorgonians Leptogorgia virgulata and L. setacea and analogs. J Chem Ecol 9: 817-829
83. Targett N M, Stochaj W R (1994) Natural antifoulants and their analogs: Applying nature's defense strategies to problems of biofouiing control. In: Thompson M-F, Nagabhushanam R, Sarojini R, Fingerman M (eds) Recent Developments in Biofouling Control. A A Balkema, Rotterdam, pp 221-227
84. Teo S L-M, Ryland J S (1995) Potential antifouling mechanisms using toxic chemicals in some British ascidians. J Exp Mar Biol Ecol 188: 49-62
85. Thompson J E (1985) Exudation of biologically-active metabolites in the sponge Aplysina fistularis. I. Biological evidence. Mar Biol 88: 23-26
86. Thompson J E, Walker R P, Faulkner D J (1985) Screening and bioassays for biologically-active substances from forty marine sponge species from San Diego, California. USA. Mar Biol 88: 11-21
87. Todd J S, Zimmerman R C, Crews P, Alberte R S (1993) The antifouling activity of natural and synthetic phenolic acid sulphate esters Phytochem 34: 401-404
88. Tsukamoto S, Hirota H, Kato H, Fusetani N (1993) Isolation of eicosapentaenoyl and arachidonoyl lysophosphatidylinositols from the ascidian Halocynthia roretzi (V. Drasche). Comp Biochem Physiol 106C: 151-153
89. Unson M D, Holland N D, Faulkner D J (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
90. Uriz M J, Martin D, Rosell D (1992) Relationships of biological and taxonomic characteristics to chemically mediated bioactivity in Meditteranean littoral sponges. Mar Biol 113: 287-297
91. van Altena I, Butler A J (1994) Antifoulants from marine invertebrates. In. Kjelleberg S, Steinberg P (eds) Biofouling: Problems and Solutions. The University of New South Wales, Sydney, pp 80-86
92. Vitalina S, Avelin S, Rittschof D, Sarojini R, Nagabhushanam R (1991) Compounds from octocorals that inhibit barnacle settlement: Isolation and biological potency. In: Thompson M-F, Sarojini R, and Nagabhushanam R (eds) Bioactive Compounds from Marine Organisms, A A Balkema, Rotterdam, pp 331-339
93. Wahl M (1989) Marine epibiosis. I. Fouling and antifouling:some basic aspects. Mar Ecol Progr Ser 58: 175-189
94. Wahl M, Banaigs B (1991) Marine epibiosis. III. Possible antifouling defense adaptations in Polysyncraton lacazei (Giard) (Didemnidae, Ascidiacea). J Exp Mar Biol Ecol 145: 49-63
95. Wahl M, Jensen P R, Fenical W (1994) Chemical control of bacterial epibiosis in ascidians. Mar Ecol Progr Ser 110: 45-57
96. Waite M E, Waldock M J, Thain J E, Smith D J, Milton S M (1991) Reductions in TBT concentrations following legislation in 1986 and 1987. Mar Environ Res 32: 89-111
97. Walker R P, Thompson J E, Faulkner D J (1985) Exudation of biologically-active metabolites in the sponge Aplysina fistularis. II.. Chemical evidence. Mar Biol 88: 27-32
98. Walls J T, Blackman A J, Ritz D A (1991) Distribution of amathamide alkaloids within single colonies of the bryozoan Amathia wilsoni. J Chem Ecol 17: 1871-1881
99. Walls J T, Ritz D A, Blackman A J (1993) Fouling, surface bacteria and antibacterial agents of four bryozoan species found in Tasmania, Australia. J Exp Mar Biol Ecol 169: 1-13
100. Wender P A, Koehler K F, Sharkey N A, Dell' Aquila M L, Blumberg P M (1986) Analysis of the phorbol ester pharmacophore on protein kinase C as a guide to the rational design of new classes of analogs. Proc Natl Acad Sci USA 83: 4214-4218
101. Willemsen P R (1994) Antifoulants from marine invertebrates - sponges. In: Kjelleberg S, Steinberg P (eds) Biofouling: Problems and Solutions. Proc lnt Workshop. The University of New South Wales, Sydney, pp 87-92
102. Willemsen P R, Ferrari G M (1993) The use of ami-fouling compounds from sponges in anti-fouling paints. Surface Coatings International Issue 10: 423-127
103. Woods Hole Oceanographic Institution (1952) Marine Fouling and its Prevention. U S Naval Institute, Annapolis
104. Young C M, Chia F S (1981) Laboratory evidence for delay of larval settlement in response to a dominant competitor. Int J Invert Reprod Devel 3: 221-226
105. Zapata O, McMillan C (1979) Phenolic acids in seagrasses. Aquat Bot 7: 307-317