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Antifouling Activity of Bromotyrosine-Derived Sponge Metabolites and Synthetic Analogues

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Abstract

Eighteen brominated sponge-derived metabolites and synthetic analogues were analyzed for antilarval settlement of Balanus improvisus. Only compounds exhibiting oxime substituents including bastadin-3 (4), −4 (1), −9 (2), and −16 (3), hemibastadin-1 (6), aplysamine-2 (5), and psammaplin A (10) turned out to inhibit larval settling at 1 to 10 μM. Analogues of hemibastadin-1 (6) were synthesized and tested for structure activity studies. Debromohemibastadin-1 (8) inhibited settling of B. improvisus, albeit at lower concentrations than hemibastadin-1 (6). Both 6 and 8 also induced cyprid mortality. 5,5′-dibromohemibastadin-1 (7) proved to be nontoxic, but settlement inhibition was observed at 10 μM. Tyrosinyltyramine (9), lacking the oxime function, was not antifouling active and was non-toxic at 100 μM. Hemibastadin-1 (6) and the synthetic products showed no general toxicity when tested against brine shrimp larvae. In contrast to the lipophilic psammaplin A (10), the hydrophilic sulfated psammaplin A derivative (11) showed no antifouling activity even though it contains an oxime group. We therefore hypothesize that the compound needs to cross membranes (probably by diffusion) and that the target for psammaplin A lies intracellularly.

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Acknowledgments

We thank BMBF (BiotechMarin) for financial support. C. Thoms acknowledges a Feodor Lynen Fellowship by the Alexander von Humboldt-Foundation, Bonn, Germany and P. Schupp acknowledges support by the National Institutes of Health MBRS SCORE grant S06-GM44796.

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Authors and Affiliations

  1. Institute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine University, Universitätstrasse 1, Geb. 26.23, D-40225, Düsseldorf, Germany

    Sofia Ortlepp, Rainer Ebel,  RuAngelie Edrada & Peter Proksch

  2. Division of Pharmacognosy, Department of Medicinal Chemistry, Biomedical Centre Uppsala University, SE-751 23, Uppsala, Sweden

    Sofia Ortlepp, Martin Sjögren & Lars Bohlin

  3. Department of Cell and Molecular Biology, Tjärnö Marine Biological Laboratory, Göteborg University, SE-452 96, Strömstad, Sweden

    Mia Dahlström

  4. Pharmaceutical and Medicinal Chemistry, Heinrich-Heine University, Universitätsstrasse 1, Geb. 26.23, D-40225, Düsseldorf, Germany

    Horst Weber

  5. University of Guam Marine Laboratory, UOG Station, Mangilao, Guam, 96923

    Carsten Thoms & Peter Schupp

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  1. Sofia Ortlepp
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  2. Martin Sjögren
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Correspondence to Peter Proksch.

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Ortlepp, S., Sjögren, M., Dahlström, M. et al. Antifouling Activity of Bromotyrosine-Derived Sponge Metabolites and Synthetic Analogues. Mar Biotechnol 9, 776–785 (2007). https://doi.org/10.1007/s10126-007-9029-x

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  • DOI: https://doi.org/10.1007/s10126-007-9029-x

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