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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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References

  • Bowling JJ (2005) The Rational Optimization of Aaptamine: A DNA Binding Marine Alkaloid. Masters Thesis, Department of Pharmacognosy, University of Mississippi, USA

    Google Scholar 

  • SA Brady RB Johns JD Smith (1994) ArticleTitleTrace metal geochemistry associated in sediment from the Cairns Region of the Great Barrier Reef, Australia Mar Poll Bull 28 230–234 Occurrence Handle10.1016/0025-326X(94)90098-1

    Article  Google Scholar 

  • L Calcul A Longeon AA Mourabit M Guyot ML Bourguet-Kondracki (2003) ArticleTitleNovel alkaloids of the aaptamine class from an Indonesian marine sponge of the genus Xestospongia Tetrahedron 59 6539–6544 Occurrence Handle10.1016/S0040-4020(03)01069-X

    Article  Google Scholar 

  • GW Cope MR Bartsch LL Marking (1997) ArticleTitleEfficacy of candidate chemicals for preventing attachment of zebra mussels (Dreissena polymorpha) Environ Toxicol Chem 16 IssueID9 1930–1934 Occurrence Handle10.1897/1551-5028(1997)016<1930:EOCCFP>2.3.CO;2

    Article  Google Scholar 

  • A Coutinho B Chanas T Souza I Frugrulhetti R Epifanio (2002) ArticleTitleAnti HSV-1 alkaloids from a feeding deterrent marine sponge of the genus Aaptos Heterocycles 57 IssueID7 1265–1272 Occurrence Handle10.3987/COM-02-9466

    Article  Google Scholar 

  • JA Diers HK Pennaka J Peng JJ Bowling SO Duke MT Hamann (2004) ArticleTitleStructural activity relationship studies of zebra mussel antifouling and antimicrobial agents from verongid sponges J Nat Prod 67 IssueID12 2117–2120 Occurrence Handle10.1021/np040097t

    Article  Google Scholar 

  • TH Dietz SJ Wilcox RA Byrne H Silverman (1997) ArticleTitleEffects of hyperosmotic challenge on the freshwater bivalve Dreissena polymorpha: importance of K+ Can J Zool 75 697–705

    Google Scholar 

  • Fedoreev S, Prokof'eva N, Denisenko V, Rebachuk N (1988) Cytotoxic activity of aaptamines derived from Suberitidae sponges. Khim Farm Zhurn 22(8), 943–946

  • N Fusetani (2004) ArticleTitleBiofouling and antifouling Nat Prod Rep 21 94–104 Occurrence Handle10.1039/b302231p

    Article  Google Scholar 

  • D Gochfeld K Sayed ParticleEl M Yousaf J Hu P Bartyzel D Dunbar S Wilkins J Zjawiony R Schinazi S Wirtz P Tharnish M Hamann (2003) ArticleTitleMarine natural products as lead anti-HIV agents Mini Rev Med Chem 3 IssueID5 451–475 Occurrence Handle10.2174/1389557033487962

    Article  Google Scholar 

  • Ioffina D, Volkovitskaya O, Gorkin V, Rebachuk N, Utkina N, Fedoreev S (1990) Aaptamine, a new selective type A monoamine oxidase inhibitor. Khim Farm Zhurn 24(7), 15–16

    Google Scholar 

  • RE Longley O McConnell E Eberhard D Harmody (1993) ArticleTitleEvaluation of marine sponge metabolites for cytotoxicity and signal transduction activity J Nat Prod 56 IssueID6 915–920 Occurrence Handle10.1021/np50096a015

    Article  Google Scholar 

  • GL Mackie (1991) ArticleTitleBiology of the exotic zebra mussel, Dreissena polymorpha, in relation to native bivalves and its potential impact in Lake St. Clair Hydrobiologia 219 251–268

    Google Scholar 

  • A Michael RD Johnson SO Duke BE Scheffler (2004) ArticleTitleDose-response relationships between herbicides with different modes of action and growth of Lemna Paucicostrata: an improved ecotoxicological method Environ Toxicol Chem 23 1074–1079 Occurrence Handle10.1897/03-256

    Article  Google Scholar 

  • B Morton (1969) ArticleTitleStudies on the biology of Dreissena polymorpha Pall. I. General anatomy and morphology Proc Malacol Soc Lond 38 301–321

    Google Scholar 

  • Y Ohizumi A Kajiwara H Nakamura J Kobayashi (1984) ArticleTitleα-Adrenoceptor blocking action of aaptamine, a novel marine natural product, in vascular smooth muscle J Pharm Pharmacol 36 IssueID11 785–786

    Google Scholar 

  • I Omae (2003) ArticleTitleGeneral aspects of tin-free antifouling paints Chem Rev 103 3431–3488 Occurrence Handle10.1021/cr030669z

    Article  Google Scholar 

  • HK Pennaka M Yousaf KV Rao M Kelly RT Hill SG Franzblau MT Hamann (2004) ArticleTitleSolving limited supplies of marine pharmaceuticals through the rational and high throughput modification of high-yielding marine natural product scaffolds Mar Biotech 6 S273–S280

    Google Scholar 

  • LM Rzepecki JH Waite (1993) ArticleTitleThe byssus of the zebra mussel, Dreissena polymorpha. I: Morphology and in situ protein processing during maturation Mol Mar Biol Biotechnol 2 IssueID5 255–266

    Google Scholar 

  • LM Rzepecki SS Chin JH Waite (1991) ArticleTitleMolecular diversity of marine glues: polyphenolic proteins from five mussel species Mol Mar Biol Biotechnol 1 IssueID1 78–88

    Google Scholar 

  • Y Shen T Lin J Sheu C Duh (1999) ArticleTitleStructures and cytotoxicity relationship of isoaaptamine and aaptamine derivatives J Nat Prod 62 IssueID9 1264–1267 Occurrence Handle10.1021/np990156g

    Article  Google Scholar 

  • Sova V, Fedoreev S (1990) Metabolites from sponges: inhibitors of alpha-1,3-glucanase. Khim Pri Soed 26,497–500

    Google Scholar 

  • MD Stephenson GH Leonard (1994) ArticleTitleEvidence for the decline of silver and lead and the increase of copper from 1977–1990 in the coastal marine waters of California Mar Poll Bull 28 148–153 Occurrence Handle10.1016/0025-326X(94)90390-5

    Article  Google Scholar 

  • Sundberg DC, Vasishtha N, Zimmerman RC, Smith CM (1998) Selection, design and delivery of environmentally benign antifouling agents. In: Naval Research Reviews. (Arlington, VA: Office of Naval Research) pp 51–59

  • S Takamatsu T Hodges I Rajbhandari W Gerwick M Hamann D Nagle (2003) ArticleTitleMarine natural products as novel antioxidant prototypes J Nat Prod 66 605–608 Occurrence Handle10.1021/np0204038

    Article  Google Scholar 

  • GT Taylor D Zheng (1996) Preliminary report on use of marine natural products as repellents antifouling for zebra mussels (Dreissena polymorpha) F D'itri (Eds) Zebra Mussels and Other Aquatic Nuisance Species Ann Arbor Press Ann Arbor

    Google Scholar 

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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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