Marine antifoulants from bifurcaria bifurcata (phaeophyceae, cystoseiraceae) and other brown macroalgae

References

• Abarzua , S and Jakubowski , S . 1995 . Biotechnological investigation for the prevention of biofouling I. Biological and biochemical principles for the prevention of biofouling . Mar Ecol Prog Ser , 123 : 301 – 312 .
   Web of Science ®Google Scholar
• Armstrong , E , Boyd , K and Burgess , J . 2000a . Prevention of marine biofouling using natural compounds from marine organisms . Biotechnol Ann Rev , 6 : 221 – 241 .
   PubMedGoogle Scholar
• Armstrong , E , Boyd , K G , Piscane , A , Pepiatt , C J and Burgess , J G . 2000b . Marine microbial natural products in antifouling coatings . Biofouling , 16 : 215 – 224 .
   Web of Science ®Google Scholar
• Barkay , T . 1987 . Adaptation of aquatic microbial communities to Hg stress . Appl Environ Microbiol , 53 : 2725 – 2732 .
   PubMed Web of Science ®Google Scholar
• Biard , JF , Verbist , JF , Floch , R and Letourneux , Y . 1980 . Epoxyélé‐ganolone et éléganediol, deux nouveaux diterpènes de Bifurcaria bifurcata Ross (Cystoseiracées) . Tetrahedron Lett , 21 : 1849 – 1852 .
   Web of Science ®Google Scholar
• Clare , A S . 1996 . Marine natural product antifoulants: status and potential . Biofouling , 9 : 211 – 229 .
   Web of Science ®Google Scholar
• Clare , A S , Rittschof , D , Gerhart , D J and Maki , J . 1992 . Molecular approaches to non‐toxic antif ouling . Invertebr Reprod Dev , 22 : 67 – 76 .
   Web of Science ®Google Scholar
• Combaut , G and Piovetti , L . 1983 . A novel acyclic diterpene from the brown alga Bifurcaria bifurcata . Phytochemistry (Oxf) , 22 : 1787 – 1789 .
   Web of Science ®Google Scholar
• Culioli , G , Mesguiche , V , Piovetti , L and Vails , R . 1999a . Geranylgeraniol and geranylgeraniol‐derived diterpenes from the brown alga Bifurcaria bifurcata (Cystoseiraceae) . Biochem Syst Ecol , 27 : 665 – 668 .
   Web of Science ®Google Scholar
• Culioli , G , Di Guardia , S , Vails , R and Piovetti , L . 2000 . Geranylgeraniol‐derived diterpenes from the brown alga Bifurcaria bifurcata: comparison with two other Cystoseiraceae species . Biochem Syst Ecol , 28 : 185 – 187 .
   Web of Science ®Google Scholar
• Culioli , G , Daoudi , M , Mesguiche , V , Vails , R and Piovetti , L . 1999b . Geranylgeraniol‐derived diterpenoids from the brown alga Bifurcaria bifurcata . Phytochemistry (Oxf) , 52 : 1447 – 1454 .
   Web of Science ®Google Scholar
• Culioli , G , Daoudi , M , Ortalo‐Magné , A , Vails , R and Piovetti , L . 2001a . (S)‐12‐hydroxygeranylgeraniol‐derived diterpenes from the brown alga Bifurcaria bifurcata . Phytochemistry (Oxf) , 57 : 529 – 535 .
   PubMed Web of Science ®Google Scholar
• Culioli , G , Ortalo‐Magné , A , Richou , M , Vails , R and Piovetti , L . in press . Seasonal variations in the chemical composition of Bifurcaria bifurcata (Cystoseiraceae) . Biochem Syst Ecol ,
   Web of Science ®Google Scholar
• Dalley , R . 1989 . Legislation affecting tributylin antifoulings . Biofouling , 1 : 363 – 366 .
   Google Scholar
• Daoudi , M , Bakkas , S , Culioli , G , Ortalo‐Magne , A , Piovetti , L and Guiry , M D . 2001 . Acyclic diterpenes and sterols from the genera Bifurcaria and Bifurcariopsis (Cystoseiraceae Phaeophyceae) . Biochem Syst Ecol , 29 : 973 – 978 .
   PubMed Web of Science ®Google Scholar
• De Nys , R , Steinberg , P D , Willemsen , P , Dworjanyn , S A , Gabelish , C L and King , R J . 1995 . Broad spectrum effects of secondary metabolites from the red alga Delisea pulchra in antifouling assays . Biofouling , 8 : 259 – 271 .
   Web of Science ®Google Scholar
• Devi , P , Soilimabi , W , D'Souza , L , Sonak , S , Kamat , S and Singbal , S . 1997 . Screening of some marine plants for activity against marine fouling bacteria . Bot Mar , 40 : 87 – 91 .
   Web of Science ®Google Scholar
• Duxbury , T and Bicknell , B . 1983 . Metal‐tolerant bacterial populations from natural and metal‐polluted soils . Soil Biochem , 15 : 243 – 250 .
   Web of Science ®Google Scholar
• Ellis , D V . 1991 . New dangerous chemicals in the environment: lessons from TBT . Mar Pollut Bull , 22 : 8 – 10 .
   Web of Science ®Google Scholar
• Evans , L . 1990 . Underwater foul play . Biol Sci Rep. , 2 : 35 – 38 .
   Google Scholar
• Fletcher , R . 1980 . Studies on the recently introduced brown alga Sargassum muticum (Yendo) Fensholt III. Periodicity in gamete release and incubation of early germlings stages . Bot Mar , 23 : 425 – 432 .
   Web of Science ®Google Scholar
• Fletcher , R . 1989 . A bioassay technique using the marine fouling green alga Enteromorpha . Int Biodeterior Biode‐grad , 25 : 407 – 422 .
   Web of Science ®Google Scholar
• Gotschalk , C and Allredge , A . 1989 . Enhanced primary production and nutrient generation with aggregated marine diatoms . Mar Biol , 103 : 119 – 129 .
   Web of Science ®Google Scholar
• Guillard , R and Ryther , J . 1962 . Studies of marine planktonic diatoms I. Cyclotella nana (Hustedt), and Detonula confervacea (Cleve) . Can J Microbiol , 8 : 229 – 239 .
   PubMed Web of Science ®Google Scholar
• Hattori , T and Shizuri , Y . 1996 . A screening method for antifouling substances using spores of the fouling macroalga Ulva conglobata and new antifouling technology . Biofouling , 8 : 147 – 160 .
   Google Scholar
• Hellio , C . 2000 . Recherche de nouvelles substances à activité antifouling à partir de macroalgues du littoral breton 280 PhD Thesis
   Google Scholar
• Hellio , C and Le Gal , Y . 1998 . Histidine utilization by the unicellular alga Dunaliella tertiolecta . Comp Biochem Physiol , 119A : 753 – 758 .
   Google Scholar
• Hellio , C and Le Gal , Y . 1999 . Histidase from the unicellular green alga Dunaliella tertiolecta: purification and partial characterization . Eur J Phycol , 34 : 71 – 78 .
   Web of Science ®Google Scholar
• Hellio , C , Bourgougnon , N and Le Gal , Y . 2000a . Phenoloxidase (.E.C.1.1.4.1.8.) from Mytilus edulis byssus gland: purification, partial characterization and application for screening products with potential antifouling activities . Biofouling , 16 : 235 – 244 .
   Web of Science ®Google Scholar
• Hellio , C , Bremer , G , Pons , A M , Le Gal , Y and Bourgougnon , N . 2000b . Inhibition of the development of microorganisms (bacteria and fungi) by extracts of marine algae from Brittany (France) . Appl Microbiol Biotechnol , 54 : 543 – 549 .
   PubMed Web of Science ®Google Scholar
• Hellio , C , De La Broise , D , Dufossé , L , Le Gal , Y and Bourgougnon , N . 2001 . Inhibition of marine bacteria by extracts of macroalgae: potential use for environmentally friendly antifouling paints . Mar Environ Res , 52 : 231 – 247 .
   PubMed Web of Science ®Google Scholar
• Higgs , M D and Mulheirn , L J . 1981 . Six new metabolites from the brown alga Halidrys siliquosa (Phaeophyta, Fucales) . Tetrahedron , 37 : 3209 – 3213 .
   Web of Science ®Google Scholar
• Hirota , H , Tomono , Y and Fusetani , N . 1996 . Terpenoids with antifouling activity against barnacle larvae from the marine sponge Acanthella cavernosa . Tetrahedron , 52 : 2359 – 2368 .
   Web of Science ®Google Scholar
• Hirota , H , Okino , T , Yoshimura , E and Fusetani , N . 1998 . Five new antifouling sesquiterpenes from two marine sponges of the genus Axinyssa and the nudibranch Phyllidia pustulosa . Tetrahedron , 54 : 13971 – 13980 .
   Web of Science ®Google Scholar
• HolmStröm , C and Kjelleberg , S . 1994 . The effect of external biological factors on settlement of marine invertebrate larvae and new antifouling technology . Biofouling , 8 : 147 – 160 .
   Web of Science ®Google Scholar
• HolmStröm , C and Kjelleberg , S . 1999 . “ Factors influencing the settlement of macrofoulers ” . In Recent Advances in Marine Biotechnology. Volume 3, Biofilms, Bioadhesion, Corrosion and Biofouling , Edited by: Fingerman , M , Nagab‐hushanam , R and Thompson , M F . 173 – 201 . Enfield, New Hampshire : Science Publishers Incorporated .
   Google Scholar
• Horeau , A and Nouaille , A . 1971 . Extension et simplification de la méthode de détermination de la configuration des alcools secondaires par dédoublement partiel Part. VIII: application à la génépine . Tetrahedron Lett , 22 : 1939 – 1942 .
   Google Scholar
• Hougaard , L , Anthoni , U , Christophersen , C and Nielsen , P H . 1991a . Eleganolone derived diterpenes from Bifurcaria bifurcata . Phytochemistry (Oxf) , 30 : 3049 – 3051 .
   Web of Science ®Google Scholar
• Hougaard , L , Anthoni , U , Christophersen , C and Nielsen , P H . 1991b . Two new diterpenoid dihydroxy‐γ‐butyrolactones from Bifurcaria bifurcata (Cystoseiraceae) . Tetrahedron Lett , 32 : 3577 – 3578 .
   Web of Science ®Google Scholar
• Jackson , S . 1991 . Microalgae: their status as fouling organisms . Oebalia , 17 : 295 – 303 .
   Google Scholar
• Keifer , P A , Rinehart , K L and Hooper , I R . 1986 . Renillafoulins, antifouling diterpenes from the sea pansy Renilla reniformis (Octocorallia) . J Org Chem , 51 : 4450 – 4454 .
   Web of Science ®Google Scholar
• Little , B , Ray , R , Wagner , P , Jones‐Meehan , J , Lee , C and Mansfeld , F . 1999 . Spatial relationship between marine bacteria and localized corrosion on polymer coated steel . Biofouling , 31 : 301 – 321 .
   Google Scholar
• Maki , J . 1999 . “ The influence of marine microbes on biofouling ” . In Recent Advances in Marine Biotechnology. Volume 3, Biofilms, Bioadhesion, Corrosion and Biofouling , Edited by: Fingerman , M , Nagabhushanam , R and Thompson , M F . 147 – 171 . Enfield, New Hampshire : Science Publishers Incorporated .
   Google Scholar
• National Comittee for Clinical Laboratory Standards . 1993 . Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically , Third edition , Villanova, PA : National Comittee for Clinical Laboratory Standards . Approved Standard M7‐A3
   Google Scholar
• Okino , T , Yoshimura , E , Hirota , H and Fusetani , N . 1995 . Antifouling kalihinenes from the marine sponge Acanthella cavernosa . Tetrahedron Lett , 36 : 8637 – 8640 .
   Web of Science ®Google Scholar
• Okino , T , Yoshimura , E , Hirota , H and Fusetani , N . 1996 . New antifouling kalihipyrans from the marine sponge Acanthella cavernosa . J Nat Prod , 59 : 1081 – 1083 .
   Web of Science ®Google Scholar
• Peppiatt , C J , Armstrong , E , Piscane , A and Burgess , J G . 2000 . Antibacterial activity of resin based coatings containing marine microbial extracts . Biofouling , 16 : 225 – 234 .
   Web of Science ®Google Scholar
• Phillips , D W and Towers , G H N . 1982 . Chemical ecology of red alga bromophenols I. Temporal, interpopulationnal and within‐thallus measurements of lanosol levels in Rhodomela larix (Turner) C. Agardh . J Exp Mar Biol Ecol , 58 : 285 – 293 .
   Web of Science ®Google Scholar
• Ragan , M A and Glombitza , K W . 1986 . “ Phlorotannins, brown algal polyphenols ” . In Progress in Phycological Research , Edited by: Round , F E and Chapman , D J . 129 – 241 . Biopress Ltd .
   Google Scholar
• Schmitt , T M , Hay , M E and Lindquist , N . 1995 . Constraints on chemically mediated coevolution: multiple functions for seaweed secondary metabolites . Ecology , 76 : 107 – 123 .
   Web of Science ®Google Scholar
• Schmitt , T M , Lindquist , N and Hay , M E . 1998 . Seaweed secondary metabolites as antifoulants: effects of Dictyota spp. diterpenes on survivorship, settlement, and development of marine invertebrate larvae . Chemoecology , 8 : 125 – 131 .
   Web of Science ®Google Scholar
• Semmak , L , Zerzouf , A , Vails , R , Banaigs , B , Jeanty , G and Francisco , C . 1988 . Acyclic diterpenes from Bifurcaria bifurcata . Phytochemistry (Oxf) , 27 : 2347 – 2349 .
   Web of Science ®Google Scholar
• Shadomy , S , Espinel‐Ingroff , A and Cartwright , R Y . 1985 . “ Laboratory studies with antifungal agents: susceptibility tests and bioassays ” . In Manual of Clinical Microbiology , 4th Edition , Edited by: Lenette , E H , Balows , A , Hausler , W J and Shadomy , H J . 991 – 999 . Washington DC : American Society for Microbiology .
   Google Scholar
• Tagg , J R and Mc Given , A R . 1971 . Assay system for bacteriocin . Appl Microbiol , 21 : 943 – 944 .
   PubMedGoogle Scholar
• Vails , R , Banaigs , B , Piovetti , L and Zerzouf , A . 1993a . Variations géographiques de la composition en diterpènes de Bifurcaria bifurcata des côtes atlantiques marocaines . Ann Inst Oceanogr , 63 : 215 – 223 .
   Google Scholar
• Valls , R , Banaigs , B , Francisco , C , Codomier , L and Cave , A . 1986 . An acyclic diterpene from the brown alga Bifurcaria bifurcata . Phytochemistry (Oxf) , 25 : 751 – 752 .
   Web of Science ®Google Scholar
• Valls , R , Banaigs , B , Piovetti , L , Archavlis , A and Artaud , J . 1993b . Linear diterpene with antimitotic activity from the brown alga Bifurcaria bifurcata . Phytochemistry (Oxf) , 34 : 1585 – 1588 .
   Web of Science ®Google Scholar
• Valls , R , Piovetti , L , Banaigs , B , Archavlis , A and Pellegrini , M . 1995 . (S)‐13‐hydroxygeranylgeraniol‐derived furanoditer‐penes from Bifurcaria bifurcata . Phytochemistry (Oxf) , 39 : 145 – 149 .
   PubMed Web of Science ®Google Scholar
• Waite , J . 1987 . Natures underwater adhesive specialist . Chemtech , 13 : 692 – 697 .
   Google Scholar
• Waite , J and Tanzer , M . 1980 . The bioadhesive of Mytilus edulis byssus: a protein containing L‐Dopa . Biochem Biophys Res Commun , 96 : 1554 – 1556 .
   PubMed Web of Science ®Google Scholar
• Williams , G A and Seed , R . 1992 . “ Interactions between macro‐faunal epiphytes and their host algae ” . In Plant‐Animal Interactions in the Marine Benthos. Systematics Association , Edited by: John , D M , Hawkins , S J and Price , J H . 189 – 211 . Oxford, England : Clarendon Press .
   Google Scholar
• Corresponding author. Present address: Department of Marine Sciences and Coastal Management, University of Newcastle, Ridley Building, Newcastle upon Tyne NE17RU, UK; e‐mail: [email protected]
   Google Scholar
• Present address: Laboratoire de Biologie et Chimie Moleculaires, 12 Avenue Saint‐Symphorien, Universite de Bretagne Sud, 56017 Vannes, France
   Google Scholar