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Antifouling activity of bromotyrosine-derived sponge metabolites and synthetic analogues
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Division of Pharmacognosy.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Division of Pharmacognosy.
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2007 (English)In: Marine Biotechnology, ISSN 1436-2228, E-ISSN 1436-2236, Vol. 9, no 6, 776-785 p.Article in journal (Refereed) Published
Abstract [en]

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 microM. 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 microM. Tyrosinyltyramine (9), lacking the oxime function, was not antifouling active and was non-toxic at 100 microM. 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.

Place, publisher, year, edition, pages
2007. Vol. 9, no 6, 776-785 p.
Keyword [en]
antifouling, Balanus improvisus, bastadins, bastadin analogues, bromotyrosine derivatives, natural products
National Category
Biological Sciences
Identifiers
URN: urn:nbn:se:uu:diva-102016DOI: 10.1007/s10126-007-9029-xISI: 000251372400011PubMedID: 17713818OAI: oai:DiVA.org:uu-102016DiVA: diva2:213862
Available from: 2009-04-29 Created: 2009-04-29 Last updated: 2017-12-13Bibliographically approved

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