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Antifouling Activity of a Dibrominated Cyclopeptide from the Marine Sponge Geodia barretti

2008; American Chemical Society; Volume: 71; Issue: 3 Linguagem: Inglês

10.1021/np0705209

1520-6025

Erik Hedner, Martin Sjögren, Said Hodzic, Rolf Andersson, Ulf Göransson, Per R. Jonsson, Lars Bohlin,

Synthetic Organic Chemistry Methods

Many sessile suspension-feeding marine organisms rely on chemical defense to keep their surfaces free from fouling organisms. The brominated cyclopeptides barettin (cyclo[(6-bromo-8-entryptophan)arginine]) (1) and 8,9-dihydrobarettin (cyclo[(6-bromotryptophan)arginine]) (2) from the cold-water sponge Geodia barretti have previously displayed settlement inhibition of barnacle larvae in a dose-dependent manner. In this paper, we describe a novel dibrominated cyclopeptide, bromobenzisoxazolone barettin (cyclo[(6-bromo-8-(6-bromobenzioxazol-3(1H)-one)-8-hydroxy)tryptophan)]arginine) (3), which we have isolated from G. barretti and which displays settlement inhibition of barnacle larvae (Balanus improvisus) with an EC50 value of 15 nM. The chemical structure was determined using MS and 2D-NMR.