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

Abstract

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-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 wereMolecules 2007, 12 1023 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).

Antifouling activity as a function of population variation in Sargassum vulgare from the littoral of Rio de Janeiro (Brazil)

“…Among these organisms, marine algae produce a wide variety of chemically active metabolites, potentially as an aid to protect themselves against other settling organisms that could prevent or reduce access to light and nutrients (Henrikson and Pawlik 1995;Wahl 2008;Hellio et al 2009). Active metabolites from several species of marine macro-and microalgae are reported as antibacterial, antifungal, antialgal and/or antimacrofouling agents that are effective in the prevention of biofouling (Fusetani 2004;Maréchal et al 2004;Barbosa et al 2007;Tsoukatou et al 2007;Cassano et al 2008;Culioli et al 2008;Mokrini et al 2008;Plouguerné et al 2010).…”

Palatability and chemical defenses of sponges from the western Antarctic Peninsula

“…Being sessile, sponges are at a distinct disadvantage when compared to motile organisms in terms of their ability to seek refuge or move away from threats that can include spatial competition (Engel & Pawlik 2000), fouling (Tsoukatou et al 2007), or predation. Consequently, sponges and other groups of sessile marine invertebrates have evolved alternate modes of defense, including the incorporation of physical defenses , Huang et al 2008) and/or the production of defensive secondary metabolites , Assmann et al 2000, Kubanek et al 2000, McClintock & Baker 2001, Furrow et al 2003.…”

Isolation and Structural Determination of the Antifouling Diketopiperazines from Marine-Derived <i>Streptomyces praecox</i> 291-11

“…Although many natural marine compounds with antifouling activity isolated from seaweeds [43][44][45][46] and invertebrates [47][48][49][50] have been reported, culturable marine microbes can be a good source for discovering antifouling compounds due to their relatively easy supply. Studying the optimal culture conditions will be valuable in future investigations.…”