Antifouling diketopiperazines produced by a deep-sea bacterium, Streptomyces fungicidicus

References

• Adamczeski , M , Reed , A R and Crews , P . 1995 . New and known diketopiperazines from the Caribbean sponge Calyx Cf. podatypa . J Nat Prod , 58 : 201 – 208 .
   PubMed Web of Science ®Google Scholar
• Burgess , J G , Boyd , K G , Armstrong , E , Jiang , Z , Yan , L , Berggren , M , May , U , Pisacane , T , Granmo , A and Adams , D R . 2003 . The development of a marine natural product-based antifouling paint . Biofouling , 19 : 197 – 205 .
   PubMed Web of Science ®Google Scholar
• Clare , A S , Rittschof , D , Gerhart , D J and Maki , J S . 1992 . Molecular approaches to non-toxic antifouling . Invert Reprod Dev , 22 : 67 – 76 .
   Web of Science ®Google Scholar
• Dobretsov , S and Qian , P Y . 2004 . The role of epibotic bacteria from the surface of the soft coral Dendronephthya sp. in the inhibition of larval attachment . J Exp Mar Biol Ecol , 299 : 35 – 50 .
   Web of Science ®Google Scholar
• Dobretsov , S , Dahms , H U and Qian , P Y . 2006 . Inhibition of biofouling by marine microorganisms and their metabolites . Biofouling , 22 : 43 – 54 .
   PubMed Web of Science ®Google Scholar
• Evans , S M . 1999 . TBT or not TBT?: that is the question . Biofouling , 14 : 117 – 129 .
   Web of Science ®Google Scholar
• Fdhila , F , Vázquez , V , Sánchez , J L and Riguera , R . 2003 . DD-diketopiperazines: antibiotics active against Vibrio anguillarum isolated from marine bacteria associated with cultures of Pecten maximus . J Nat Prod , 66 : 1299 – 1301 .
   PubMed Web of Science ®Google Scholar
• Gunther , K . 1988 . Thin-layer chromatographic enantiomeric resolution via ligand exchange . J Chromatogr , 448 : 11 – 30 .
   PubMed Web of Science ®Google Scholar
• Harder , T , Vengatesen , T and Qian , P Y . 2001 . Effect of cyprid age on the attachment of Balanus amphitrite Darwin in response to natural biofilms . Biofouling , 17 : 211 – 219 .
   Web of Science ®Google Scholar
• Holmstroem , C and Kjelleberg , S . 1999 . Marine Pseudoalteromonas species are associated with higher organisms and produce biologically active extracellular agents . FEMS Microbiol Ecol , 30 : 285 – 293 .
   PubMed Web of Science ®Google Scholar
• Jamie , H , Kilian , G , Dyason , K and Milne , P J . 2002 . The effect of the isomers of cyclo-(Trp-Pro) on heart and ion-channel activity . J Pharm Pharmacol , 54 : 1659 – 1665 .
   PubMed Web of Science ®Google Scholar
• Jayatilake , G S , Thornton , M P , Leonard , A C , Grimwade , J E and Baker , B J . 1996 . Metabolites from an Antarctic sponge-associated bacterium, Pseudomonas aeruginosa . J Nat Prod , 59 : 293 – 296 .
   PubMed Web of Science ®Google Scholar
• Kelecom , A . 2002 . Secondary metabolites from marine microorganisms . Ann Brazil Acad Sci , 74 : 151 – 170 .
   PubMed Web of Science ®Google Scholar
• Kon-ya , K , Shimidzu , N , Otaki , N , Yokoyama , A , Adachi , K and Miki , W . 1995 . Inhibitory effect of bacterial ubiquinones on the settling of barnacle, Balanus amphitrite . Experientia , 51 : 153 – 155 .
   Google Scholar
• Krchnak , V , Weichse , A S , Cabe , D , Flegelova , Z and Leb , M . 1996 . Structurally homogeneous and heterogeneous synthetic combinatorial libraries . Mol Divers , 1 : 149 – 164 .
   PubMed Web of Science ®Google Scholar
• Little , B J and Wagner , P A . 1997 . Spatial relationships between bacteria and mineral surfaces . Rev Mineral , 35 : 123 – 160 .
   Web of Science ®Google Scholar
• McCleland , K , Milne , P J , Lucieto , F R , Frost , C , Brauns , S C , Van De Venter , M , Du Plessiss , J and Dyason , K . 2004 . An investigation into the biological activity of the selected histidine-containing diketopiperazines cyclo(His-Phe) and cyclo(His-Tyr) . J Pharm Pharmacol , 56 : 1143 – 1153 .
   PubMed Web of Science ®Google Scholar
• Milne , P J , Hunt , A L , Rostoll , K , van der Walt , J J and Graz , C JM . 1998 . The biological activity of selected cyclic dipeptides . J Pharm Pharmacol , 50 : 1331 – 1335 .
   PubMed Web of Science ®Google Scholar
• Mitova , M , Tommonaro , G , Hentschel , U , Müller , W EG and De Rosa , S . 2004 . Exocellular cyclic dipeptides from a Ruegeria strain associated with cell cultures of Suberites domuncula . Mar Biotechnol , 6 : 95 – 103 .
   PubMed Web of Science ®Google Scholar
• Olguin-Uribe , G , Abou-Mansour , E , Boulander , A , Débard , H , Francisco , C and Combaut , G . 1997 . 6-bromoindole-3-carbaldehyde, from an Acinetobacter sp. bacterium associated with the ascidian Stomozoa murrayi . J Chem Ecol , 23 : 2507 – 2521 .
   Web of Science ®Google Scholar
• Prasad , C . 1995 . Bioactive cyclic dipeptides . Peptides , 1 : 151 – 164 .
   Google Scholar
• Rittschof , D . 1999 . “ Fouling and natural products as antifoulants ” . In Recent advances in marine biotechnology , Edited by: Fingerman , M , Nagabhushanam , R and Thompson , M F . Vol. 3 , 245 – 257 . Enfield, USA : Science Publishers Inc. . Biofilms, bioadhesion, corrosion, and biofouling
   Google Scholar
• Schmitz , F J , Vanderah , D J , Hollenbeak , K H , Enwall , C E , Gopichand , Y , Sengupta , P K , Hossain , M B and van der Helm , D . 1983 . Metabolites from the marine sponge Tedania ignis. A new atisanediol and several known diketopiperazines . J Org Chem , 48 : 3941 – 3945 .
   Web of Science ®Google Scholar
• Ström , K , Sjögren , J , Broberg , A and Schnürer , J . 2002 . Lactobacillus plantarum MiLAB 393 produces the antifungal cyclic dipeptides cyclo(L-Phe-L-Pro) and cyclo- (L-Phe-trans-4-OH-L-Pro) and 3-phenyllactic acid . Appl Environ Microbiol , 68 : 4322 – 4327 .
   PubMed Web of Science ®Google Scholar
• Venter , J C , Remington , K , Heidelberg , J F , Halpern , A L , Rusch , D , Eisen , J A , Wu , D , Paulsen , I , Nelson , K E , Nelson , W , Fouts , D E , Levy , S , Knap , A H , Lomas , M W , Nealson , K , White , O , Peterson , J , Hoffman , J , Parsons , R , Baden-Tillson , H , Pfannkoch , C , Roger , Y H and Smith , H O . 2004 . Environmental genome shotgun sequencing of the Sargasso Sea . Science , 304 : 66 – 74 .
   PubMed Web of Science ®Google Scholar
• Wahl , M . 1989 . Marine epibiosis. I. Fouling and antifouling: some basic aspects . Mar Ecol Prog Ser , 58 : 175 – 189 .
   Web of Science ®Google Scholar
• Yebra , D M , Kill , S and Dam-Johansen , K . 2004 . Antifouling technology: past, present and future steps towards efficient and environmentally friendly antifouling coatings . Prog Org Coat , 50 : 75 – 104 .
   Web of Science ®Google Scholar
• Young , P E , Madison , V and Blout , E R . 1976 . Cyclic peptides. 15. Lanthanide-assisted 13C and 1H NMR analysis of preferred side-chain rotamers in proline-containing cyclic dipeptides . J Am Chem Soc , 98 : 5365 – 5371 .
   PubMed Web of Science ®Google Scholar
• Zar , J H . 1996 . Biostatistical analysis. , 3rd ed. , Upper Saddle River, NJ, , USA : Prentice Hall .
   Google Scholar