Abstract
The variation of the brominated indole and diterpenoid content within single and different colonies of the bryozoan Flustra foliacea was investigated. The secondary metabolite profile and concentrations of individual components of F. foliacea samples were established using GC–MS. Samples from 17 different collecting sites were analyzed. The alkaloid and diterpene composition of F. foliacea varied greatly depending upon the site of collection. Investigation of F. foliacea samples from a single site (Helgoland, North Sea) over a period of time showed that the alkaloid and diterpenoid profile remained constant, however concentrations of individual components varied significantly. The alkaloid and diterpenoid composition of different segments of a single colony was found to be constant. Only small differences could be detected in the essential oil composition of different colonies and segments of single colonies of F. foliacea. Two of the F. foliacea alkaloids were found in the gastropods Hydrobia ulva and Gibbula cinerea, and one alkaloid in the common starfish Asteria rubens, all collected from the surface of the bryozoan.
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REFERENCES
Al-Ogily, S. M. and Knight-Jones, E. W. 1977. Anti-fouling role of antibiotics produced by marine algae and bryozoans. Nature 265:728–729.
Anthoni, U., Nielsen, P. H., Pereira, M., and Christophersen, C. 1990. Bryozoan secondary metabolites: A chemotaxonomical challenge. Comp. Biochem. Physiol. 96B:431–437.
Blackmann, A. J. and Fu, S.-L. 1989. A β-phenylethylamine-derived possible biosynthetic precursor to the amathamides, alkaloids from the bryozoan Amathia wilsoni. J. Nat. Prod. 52:436–438.
Blackmann, A. J. and Green, R. D. 1987. Further amathamide alkaloids from the bryozoan Amathia wilsoni. Aust. J. Chem. 40:1655–1662.
Blackmann, A. J. and Mathews, D. J. 1985. Amathamide alkaloids from the marine bryozoan Amathia wilsoni Kirkpatrick. Heterocycles 23:2829–2833.
CarlÉ, J. S. and Christophersen, C. 1979. Bromo-substituted physostigmine alkaloids from a marine bryozoa Flustra foliacea. J. Am. Chem. Soc. 101:4012–4013.
CarlÉ, J. S. and Christophersen, C. 1980. Marine alkaloids. 2. Bromo alkaloids from the marine bryozoan Flustra foliacea. Isolation and structure elucidation. J. Am. Chem. Soc. 102:5107–5108.
CarlÉ, J. S. and Christophersen, C. 1981. Marine alkaloids. 3. Bromo-substituted alkaloids from the marine bryozoan Flustra foliacea, flustramine C and flustraminol A and B. J. Org. Chem. 46:3440–3443.
Christophersen, C. 1991. Evolution in molecular structure and adaptive variance in metabolism. Comp. Biochem. Physiol. 98B:427–432.
Christophersen, C. and CarlÉ, J. S. 1978. Chemical signals from a marine bryozoan. Naturwissenschaften 65:440–441.
Davidson, S. D. and Haygood, M. G. 1999. Identification of sibling species of the bryozoan Bugula neritina that produce different anticancer bryostatins and harbor distinct strains of the bacterial symbiont “Canditatus Endobugula sertula.” Biol. Bull. 196:273–280.
Dworjanyn, S. A., De Nys, R., and Steinberg, P. D. 1999. Localisation and surface quantification of secondary metabolites in the red alga Delisea pulchra. Mar. Biol. B 133:727–736.
Givskov, M., De Nys, R., Manefield, M., Gram, L., Maximilien, R., Eberl, L., Molin, S., Steinberg, P. D., and Kjelleberg, S. 1996. Eukaryotic interference with homoserine lactone-mediated prokaryotic signalling. J. Bacteriol. 278:6618–6622.
Hentzer, M., Riedel, K., Rasmussen, T. B., Heydorn, A., Andersen, J. B., Parsek, M. R., Rice, S. A., Eberl, L., Molin, S., HØiby, N., Kjelleberg, S., and Givskov, M. 2002. Inhibition of quorum sensing in Pseudomonas aeruginosa biofilm bacteria by a halogenated furanone compound. Microbiology 148:87–102.
Holst, P. B., Anthoni, U., Christophersen, C., and Nielsen, P. H. 1994a. Two alkaloids, flustramine E and debromoflustramine B, from the marine bryozoan Flustra foliacea. J. Nat. Prod. 57:997–1000.
Holst, P. B., Anthoni, U., Christophersen, C., Nielsen, P. H., and Bock, K. 1994b. A racemic diterpene from the marine bryozoan Flustra foliacea, natural product or artefact? Acta Chem. Scand. 48:765–768.
Laycock, M. V., Wright, J. L. C., Findlay, J. A., and Patil, A. D. 1986. New physostigmine related bromoalkaloids from the marine bryozoan Flustra foliacea. Can. J. Chem. 64:1312–1316.
Manefield, M., De Nys, R., Kumar, N., Read, R., Givskov, M., Steinberg, P., and Kjelleberg, S. 1999. Evidence that halogenated furanones from Delisea pulchra inhibit acylated homoserine lactone (AHL)-mediated gene expression by displacing the AHL signal from its receptor protein. Microbiology 145:283–291.
Melkani, A. B., Beauchamp, P. S., Dev, V., Whalen, C., and Mathela, C. S. 1994. Rosefuran epoxide from Elsholtzia densa Benth. J. Essent. Oil Res. 6:475–479.
Peters, L., KÖnig, G. M., Terlau, H., and Wright, A. D. 2002. Four new bromo-tryptamine derivatives from the marine bryozoan Flustra foliacea. J. Nat. Prod. 65:1633–1637.
Peters, L., KÖnig, G. M., Wright, A. D., Pukall, R., Stackebrandt, E., Eberl, L., and Riedel, K. 2003. Secondary metabolites of Flustra foliacea and their influence on bacteria. Appl. Environ. Microbiol. 69:3469–3475.
Stebbing, A. R. D. 1971. Growth of Flustra foliacea (bryozoa). Mar. Biol. 9:267–273.
Walls, J. T., Blackmann, A. J., and Ritz, D. A. 1991. Distribution of amathamide alkaloids within single colonies of the bryozoan Amathia wilsoni. J. Chem. Ecol. 17:1871–1881.
Wright, J. L. C. 1984. A new antibiotic from the marine bryozoan Flustra foliacea. J. Nat. Prod. 47:893–895.
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Peters, L., Wright, A.D., Krick, A. et al. Variation of Brominated Indoles and Terpenoids Within Single and Different Colonies of the Marine Bryozoan Flustra foliacea . J Chem Ecol 30, 1165–1181 (2004). https://doi.org/10.1023/B:JOEC.0000030270.65594.f4
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DOI: https://doi.org/10.1023/B:JOEC.0000030270.65594.f4