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Zebra Mussel Antifouling Activity of the Marine Natural Product Aaptamine and Analogs

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Abstract

Several aaptamine derivatives were selected as potential zebra mussel (Dreissena polymorpha) antifoulants because of the noteworthy absence of fouling observed on Aaptos sponges. Sponges of the genus Aaptos collected in Manado, Indonesia consistently produce aaptamine-type alkaloids. To date, aaptamine and its derivatives have not been carefully evaluated for their antifoulant properties. Structure–activity relationship studies were conducted using several aaptamine derivatives in a zebra mussel antifouling assay. From these data, three analogs have shown significant antifouling activity against zebra mussel attachment. Aaptamine, isoaaptamine, and the demethylated aaptamine compounds used in the zebra mussel assay produced EC50 values of 24.2, 11.6, and 18.6 μM, respectively. In addition, neither aaptamine nor isoaaptamine produced a phytotoxic response (as high as 300 μM) toward a nontarget organism, Lemna pausicostata, in a 7-day exposure. The use of these aaptamine derivatives from Aaptos sp. as potential environmentally benign antifouling alternatives to metal-based paints and preservatives is significant, not only as a possible control of fouling organisms, but also to highlight the ecological importance of these and similar biochemical defenses.

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Acknowledgments

We thank J. Schetz, Ph.D., from the University of North Texas in Fort Worth, for initiating a zebra mussel antifouling program at the University of Mississippi. D. Molloy Ph.D., D. Mayer, and the staff of the New York State History Museum, Field Research Laboratory for providing zebra mussels. C. Dunbar, Ph.D. and F. Wiggers for MS and NMR spectral measurement; R. Johnson from the USDA, Agriculture Research Service (NPURU) for conducting phytotoxicity bioassays; A. Feldhaus for assistance with the antifouling assays; H. Pennaka for assistance with preparation of compounds for antifouling research.

This work was supported by EPA (GR01290-02).

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Authors and Affiliations

  1. Department of Pharmacognosy, Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi, University, MS, 38677, USA

    Jeffrey A. Diers, John J. Bowling & Mark T. Hamann

  2. Department of Pharmacology, Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi, University, MS, 38677, USA

    Jeffrey A. Diers & Mark T. Hamann

  3. Department of Chemistry and National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi, University, MS, 38677, USA

    Mark T. Hamann

  4. U.S. Department of Agriculture, Agriculture Research Service, NPURU, The University of Mississippi, University, MS, 38677, USA

    Stephen O. Duke

  5. The Department of Pharmaceutical Biology, Gadjah Mada University, Yogyakarta, 55281, Indonesia

    Subagus Wahyuono

  6. National Institute of Water & Atmospheric Research (NIWA) Ltd., Taihoro Nukurangi, Newmarket, Auckland, New Zealand

    Michelle Kelly

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  1. Jeffrey A. Diers
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  2. John J. Bowling
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  3. Stephen O. Duke
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  4. Subagus Wahyuono
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  5. Michelle Kelly
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  6. Mark T. Hamann
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Correspondence to Mark T. Hamann.

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Diers, J.A., Bowling, J.J., Duke, S.O. et al. Zebra Mussel Antifouling Activity of the Marine Natural Product Aaptamine and Analogs. Mar Biotechnol 8, 366–372 (2006). https://doi.org/10.1007/s10126-005-6055-4

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  • DOI: https://doi.org/10.1007/s10126-005-6055-4

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