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Evaluation of the Activity of the Sponge Metabolites Avarol and Avarone and their Synthetic Derivatives Against Fouling Micro- and Macroorganisms

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Author(s): Maria Tsoukatou | Jean Philippe Maréchal | Claire Hellio | Irena Novaković | Srdan Tufegdzic | Dusan Sladić | Miroslav J Gašić | Anthony S Clare | Constantinos Vagias | Vassilios Roussis

Journal: Molecules
ISSN 1420-3049

Volume: 12;
Issue: 5;
Start page: 1022;
Date: 2007;
Original page

Keywords: Antifouling activity | settlement inhibition | antimicrobial activity | avarol | avarone

ABSTRACT
The sesquiterpene hydroquinone avarol (1) was isolated from the marine sponge Dysidea avara, whereas the corresponding quinone, avarone (2), was obtained by oxidation of avarol, and the significantly more lipophilic compounds [3’-(p-chloro-phenyl)avarone (3), 3’,4’-ethylenedithioavarone (4), 4’-isopropylthioavarone (5), 4’-tert-butylthioavarone (6), 4’-propylthioavarone (7), 4’-octylthioavarone (8)] were obtained by nucleophilic addition of thiols or p-chloroaniline to avarone. All these compounds were tested, at concentrations ranging from 0.5 to 50 μg/mL, for their effect on the settlement of the cyprid stage of Balanus amphitrite, for toxicity to both nauplii and cyprids and for their growth inhibitory activity on marine bacteria (Cobetia marina, Marinobacterium stanieri, Vibrio fischeri and Pseudoalteromonas haloplanktis) and marine fungi (Halosphaeriopsis mediosetigera, Asteromyces cruciatus, Lulworthia uniseptata and Monodictys pelagica).
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