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

Molecules

Maria Tsoukatou⁴  Jean Philippe Marຜhal³  Claire Hellio¹  Irena Novaković²  Srdan Tufegdzic²  Dusan Sladić²  Miroslav J. Gašić²  Anthony S. Clare³  Constantinos Vagias⁴ 

[1] Portsmouth University, School of Biological Sciences, King Henry Building, Portsmouth PO1 2DY, U.K.; E-mail:;Institute of Chemistry, Technology and Metallurgy, Department of Chemistry, Njegoseva 12, 11000 Belgrade, Serbia and Montenegro; E-mails:;Newcastle University, School of Marine Science and Technology, Ridley Building, Newcastle upon Tyne NE1 7RU, U.K.; E-mail:;University of Athens, School of Pharmacy, Department of Pharmacognosy & Chemistry of Natural Products, Panepistimiopolis Zografou, Athens, GR 15771, Greece; E-mails:

关键词: Antifouling activity;    settlement inhibition;    antimicrobial activity;    avarol;    avarone;   

DOI  :  10.3390/12051022

来源: mdpi

【 摘 要 】

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).

【 授权许可】

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