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Molecules 2007, 12(5), 1022-1034; doi:10.3390/12051022
Article

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

1
, 2
, 4
, 5
, 5
, 5
, 5
, 2
, 1
 and 1,*
1 University of Athens, School of Pharmacy, Department of Pharmacognosy and Chemistry of Natural Products, Panepistimiopolis Zografou, Athens, GR 15771, Greece 2 Newcastle University, School of Marine Science and Technology, Ridley Building, Newcastle upon Tyne NE1 7RU, U.K. 3 Observatoire de Milieu Marin Martiniquais, 3 Avenue Condorcet, 97200 Fort de France, Martinique, French West Indies 4 Portsmouth University, School of Biological Sciences, King Henry Building, Portsmouth PO1 2DY, U.K. 5 Institute of Chemistry, Technology and Metallurgy, Department of Chemistry, Njegoseva 12, 11000 Belgrade, Serbia and Montenegro 6 Faculty of Chemistry, University of Belgrade, Studentski trg 12-16, 11000 Belgrade, Serbia and Montenegro
* Author to whom correspondence should be addressed.
Received: 23 April 2007 / Revised: 13 May 2007 / Accepted: 14 May 2007 / Published: 15 May 2007
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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).
Keywords: Antifouling activity; settlement inhibition; antimicrobial activity; avarol; avarone Antifouling activity; settlement inhibition; antimicrobial activity; avarol; avarone
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Tsoukatou, M.; Maréchal, J.P.; Hellio, C.; Novaković, I.; Tufegdzic, S.; Sladić, D.; Gašić, M.J.; Clare, A.S.; Vagias, C.; Roussis, V. Evaluation of the Activity of the Sponge Metabolites Avarol and Avarone and their Synthetic Derivatives Against Fouling Micro- and Macroorganisms. Molecules 2007, 12, 1022-1034.

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