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Evaluation of the activity of the sponge metabolites avarol and avarone and their synthetic derivatives against fouling micro- and macroorganisms

Lookup NU author(s): Dr Jean-Philippe Marechal, Dr Claire Hellio, Professor Tony Clare

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Abstract

The sesquiterpene hydroquinone avarol (1) was isolated from the marine sponge Dysidea avara, whereas the corresponding quitione, avarone (2), was obtained by oxidation of avarol, and the significantly more lipophilic compounds [3 '-(P-chlorophenyl)avarone (3), 3 ',4 '-ethylenedithioavarone (4), 4 '-isopropylthioavarone (5), 4 '-tertbutylthioavarone (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 mu g/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).


Publication metadata

Author(s): Tsoukatou M, Marechal JP, Hellio C, Novakovic I, Tufegdzie S, Sladic D, Gasic MJ, Clare AS, Vagias C, Roussis V

Publication type: Article

Publication status: Published

Journal: Molecules

Year: 2007

Volume: 12

Issue: 5

Pages: 1022-1034

ISSN (print): 1420-3049

ISSN (electronic): 1431-5165

Publisher: Molecular Diversity Preservation International

URL: http://dx.doi.org/10.3390/12051022

DOI: 10.3390/12051022


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