Evaluation of the activity of the sponge metabolites avarol and avarone and their synthetic derivatives against fouling micro- and macroorganisms.
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 microg/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).
Tsoukatou
Maria
M
University of Athens, School of Pharmacy, Department of Pharmacognosy and Chemistry of Natural Products, Panepistimiopolis Zografou, Athens, GR 15771, Greece. mtsoukatou@yahoo.com
Maréchal
Jean Philippe
JP
Hellio
Claire
C
Novaković
Irena
I
Tufegdzic
Srdan
S
Sladić
Dusan
D
Gasić
Miroslav J
MJ
Clare
Anthony S
AS
Vagias
Constantinos
C
Roussis
Vassilios
V
D000818:Animals; D000900:Anti-Bacterial Agents / Q000494:pharmacology*; D000935:Antifungal Agents / Q000494:pharmacology*; D004353:Drug Evaluation, Preclinical; D008826:Microbial Sensitivity Tests; D011161:Porifera; D012717:Sesquiterpenes / Q000494:pharmacology*
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D012717:Sesquiterpenes; C023663:avarol