Brominated skeletal components of the marine demosponges, Aplysina cavernicola and Ianthella basta: Analytical and biochemical investigations

Marine Drugs

Volumn 11, Issue 4, 2013, Pages 1271-1287

  Kunze, Kurt ^a   Niemann, Hendrik ^b   Ueberlein, Susanne ^a   Schulze, Renate ^a   Ehrlich, Hermann ^c   Brunner, Eike ^a   Proksch, Peter ^b   Van Pée, Karl Heinz ^a  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

^b HEINRICH HEINE UNIVERSITY   (Germany)

^c TU BERGAKADEMIE FREIBERG   (Germany)

Author keywords

Brominated tyrosine derivatives; Demosponges; Halogenase; HPLC; IR; NMR

Indexed keywords

ALKALOID; BROMINE; CHITIN; DNA; POLYSACCHARIDE;

AMINO ACID SEQUENCE; ANALYTIC METHOD; APLYSINA CAVERNICOLA; ARTICLE; CHEMICAL STRUCTURE; COVALENT BOND; DNA ISOLATION; DNA PURIFICATION; GEL PERMEATION CHROMATOGRAPHY; GENE CLUSTER; GENETIC ANALYSIS; GENETIC IDENTIFICATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IANTHELLA BASTA; INFRARED SPECTROMETRY; MARINE DESMOSPONGE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; POLYMERASE CHAIN REACTION; POTENTIOMETRY; PROTEIN PURIFICATION; QUANTITATIVE ANALYSIS; SPONGE (PORIFERA); SYMBIONT;

APLYSINA CAVERNICOLA; IANTHELLA BASTA; VERONGIDA;

EID: 84876993927     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md11041271     Document Type: Article

References (34)

1. Blunt, J.W.; Copp, B.R.; Hu, W.P.; Munro, M.H.G.; Northcote, P.T.; Prinsep, M.R. Marine natural products. Nat. Prod. Rep. 2009, 26, 170-244.
2. Montaser, R.; Luesch, H. Marine natural products: A new wave of drugs? Future Med. Chem. 2011, 3, 1475-1489.
3. Proksch, P.; Putz, A.; Ortlepp, S.; Kjer, J.; Bayer, M. Bioactive natural products from marine sponges and fungal endophytes. Phytochem. Rev. 2010, 9, 475-489.
4. Müller, W.E.G. Origin of metazoa: Sponges as living fossils. Naturwissenschaften 1998, 85, 11-25.
5. Li, C.-W.; Chen, J.-Y.; Hua, T.-E. Precambrian sponges with cellular structures. Science 1998, 279, 879-882.
6. Thoms, C.; Wolff, M.; Padmakumar, K.; Ebel, R.; Proksch, P. Chemical defense of Mediterranean sponges Aplysina cavernicola and Aplysina aerophoba. Z. Naturforsch. C 2004, 59, 113-122.
7. Thoms, C.; Ebel, R.; Proksch, P. Activated chemical defense in Aplysina sponges revisited. J. Chem. Ecol. 2006, 32, 97-123.
8. Paul, V.J.; Ritson-Williams, R.; Sharp, K. Marine chemical ecology in benthic environments. Nat. Prod. Rep. 2011, 28, 345-387.
9. Wehner, R.; Gehring, W.J. Zoologie; Georg Thieme Verlag: Stuttgart, Germany, 2007; pp. 698-699.
10. Bergquist, P.R.; Cook, S.D.C. Order Verongida Bergquist, 1978. In Systema Porifera: A Guide to the Classification of Sponges; Hooper, J.N.A., van Soest, R.W.M., Eds.; Kluwer Academic/Plenum Publishers: New York, NY, USA, 2002; Volume I, pp. 1081-1096.
11. Ehrlich, H.; Maldonado, M.; Spindler, K.-D.; Eckert, C.; Hanke, T.; Born, R.; Goebel, C.; Simon, P.; Heinemann, S.; Worch, H. First evidence of chitin as a component of the skeletal fibers of marine sponges. Part I. Verongidae (Demospongia: Porifera). J. Exp. Zool. B Mol. Dev. Evol. 2007, 308, 347-356.
12. Brunner, E.; Ehrlich, H.; Schupp, P.; Hedrich, R.; Hunoldt, S.; Kammer, M.; Machill, S.; Paasch, S.; Bazhenov, V.V.; Kurek, D.V.; et al. Chitin-Based scaffolds are an integral part of the skeleton of the marine demosponge Ianthella basta. J. Struct. Biol. 2009, 168, 539-547.
13. Uriz, M.-J.; Turon, X.; Becerro, M.A.; Agell, G. Siliceous spicules and skeleton frameworks in sponges: Origin, diversity, ultrastructural patterns, and biological functions. Microsc. Res. Tech. 2003, 62, 279-299.
14. Ehrlich, H.; Ilan, M.; Maldonado, M.; Muricy, G.; Bavestrello, G.; Kljajic, Z.; Carballo, J.L.; Shiaparelli, S.; Ereskovsky, A.V.; Schupp, P.; et al. Three-Dimensional chitin-based scaffolds from Verongida sponges (Demospongiae: Porifera). Part I. Isolation and identification of chitin. Int. J. Biol. Macromol. 2010, 47, 132-140.
15. Teeyapant, R.; Woerdenbag, H.; Kreis, P.; Hacker, J.; Wray, V.; Witte, L.; Proksch, P. Antibiotic and cytotoxic activity of brominated compounds from the marine sponge Verongia aerophoba. Z. Naturforsch. C 1993, 48, 939-945.
16. Faulkner, D.J. Marine pharmacology. Antonie Van Leeuwenhoek 2000, 77, 135-145.
17. Weiss, B.; Ebel, R.; Elbrächter, M.; Kirchner, M.; Proksch, P. Defence metabolites from the marine sponge Verongia aerophoba. Biochem. Syst. Ecol. 1996, 24, 1-12.
18. Tabudravu, J.N.; Eijsink, V.G.H.; Gooday, G.W.; Jaspars, M.; Komander, D.; Legg, M.; Synstad, B.; van Aalten, D.M.F. Psammaplin A, a Chitinase Inhibitor Isolated from the Fijian Marine Sponge Aplysinella rhax. Bioorg. Med. Chem. 2002, 10, 1123-1128.
19. Thomson, J.E.; Barrow, K.D.; Faulkner, D.J. Localization of two brominated metabolites, aerothionin and homoaerothionin, in spherulous cells of the marine sponge Aplysina fistularis (=Verongia thiona) . Acta Zool. 1981, 64, 199-210.
20. Turon, X.; Becerro, M.A.; Uriz, M.J. Distribution of brominated compounds within the sponge Aplysina aerophoba: Coupling X-ray microanalysis with cryofixation techniques. Cell Tissue Res. 2000, 301, 311-322.
21. Tymiak, A.A.; Rinehart, L.R., Jr. Biosynthesis of dibromotyrosine-derived antimicrobial compounds by the marine sponge Aplysina fistularis (Verongia aurea). J. Am. Chem. Soc. 1981, 103, 6763-6765.
22. +-labelled Diaryl Ether Peptoids as Precursors of the Bastadins from the Marine Sponge Ianthella basta. PhD Thesis, Combined Faculties for the Natural Sciences and for Mathematics, Ruperto-Carola University of Heidelberg, Heidelberg, Germany, November 2001.
23. Bayer, K.; Scheuermayer, M.; Fieseler, L.; Hentschel, U. Genomic mining for novel FADH2-dependent halogenases in marine sponge-associated microbial consortia. Mar. Biotechnol. 2013, 15, 63-72.
24. Van Pée, K.-H. Enzymatic chlorination and bromination. Methods Enzymol. 2012, 516, 237-257.
25. Chow, T.Y.K. Purification of yeast - E. coli shuttle plasmid suitable for high transformation frequency in E. coli. Nucleic Acids Res. 1989, 17, 8391.
26. Bollet, C.; Gevaudan, M.J.; de Lamballerie, X.; Zandotti, C.; de Micco, P. A simple method for the isolation of chromosomal DNA from Gram positive or acid-fast bacteria. Nucleic Acids Res. 1991, 19, 1955.
27. Wang, H.; Zhang, L.; Zhang, F.; An, H.; Chen, S.; Li, H.; Wang, P.; Wang, X.; Wang, Y.; Yang, H. Investigation on the morphology of precipitated chemicals from TE buffer on solid substrates. Surf. Rev. Lett. 2007, 14, 1121-1128.
28. Ouyang, Y.; Dai, S.; Xie, L.; Ravi Kumar, M.S.; Sun, W.; Sun, H.; Tang, D.; Li, X. Isolation of high molecular weight DNA from marine sponge bacteria for BAC library construction. Mar. Biotechnol. 2010, 12, 318-325.
29. Schöniger, W. Eine mikroanalytische Schnellbestimmung von Halogenen in organischen Substanzen. Mikrochem. Acta 1995, 1, 123-129.
30. Ebada, S.S.; Edrada, R.A.; Lin, W.; Proksch, P. Methods of isolation, purification and structural elucidation of bioactive secondary metabolites from marine invertebrates. Nat. Protoc. 2008, 3, 1820-1831.
31. Pelzer, S.; Süßmuth, R.; Heckmann, D.; Recktenwald, J.; Huber, P.; Jung, G.; Wohlleben, W. Identification and analysis of the balhimycin biosynthetic gene cluster and its use for manipulating glycopeptide biosynthesis in Amycalotopsis mediterranei DSM5908. Antimicrob. Agents Chemother. 1999, 43, 1565-1573.
32. Institut für angewandte Hydrobiologie; HYDRA AG; HYDRA Institut für Meereswissenschaften AG; HYDRA Büro für Gewässerö kologie Mürle & Ortlepp GbR; HYDRA Wiesloch - Dipl-Biol. Andreas Becker. Available online: http://www.hydra-institute.com (accessed on 10 April 2013).
33. Fung, B.M.; Khitrin, A.K.; Ermolaev, J. An improved broadband decoupling sequence for liquid crystals and solids. J. Magn. Reson. 2002, 142, 97-101.
34. Schirmer, A.; Gadkari, R.; Reeves, C.D.; Ibrahim, F.; DeLong, E.F.; Hutchinson, C.R. Metagenomic analysis reveals diverse polyketide synthase gene clusters in microorganisms associated with the marine sponge Discodermia dissoluta. Appl. Environ. Microbiol. 2005, 71, 4840-4849.