Antifouling activity of bromotyrosine-derived sponge metabolites and synthetic analogues

S. Ortlepp, M. Sjögren, M. Dahlström, H. Weber, R. Ebel, R. Edrada, C. Thoms, P. Schupp, L. Bohlin, P. Proksch

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56 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)776-785
Number of pages10
JournalMarine Biotechnology
Volume9
Issue number6
DOIs
Publication statusPublished - Dec 2007

Keywords

  • antifouling
  • Balanus improvisus
  • bastadins
  • bastadin analogues
  • bromotyrosine derivatives
  • natural products

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