Anti-microfouling properties of compounds isolated from several Mediterranean Dictyota spp.

Abstract

Brown algae of the genus Dictyota are widespread around the world and are common along the coasts of the Mediterranean Sea. These marine organisms keep their surface relatively free from biofouling and are known for their ability to produce a wide array of bioactive compounds, mostly diterpenes, whose ecological functions are not clearly defined. In this study, an evaluation of the chemodiversity of the Dictyota genus was conducted on three samples, harvested on both NW and SW Mediterranean coasts (France and Algeria, respectively). Ten compounds were purified from the organic extracts of these samples; their chemical structures were elucidated by 1D and 2D NMR spectroscopy and were compared with literature data. Among them, three new diterpenes [one dolabellane (1), one xenicane (2), and one prenylated guaiane (3)] were characterized together with five previously described compounds [3,4-epoxy-14-oxo-7,18-dolabelladiene (4), acetoxycrenulide (5), dictyol E (6), 10,18-dihydroxydolabella-2,7-diene (7), and 10-acetoxy-18-hydroxydolabella-2,7-diene (8)]. In addition, the occurrence of two known glycerol derivatives [1-Ο-octadecenoylglycerol (9) and sn-3-Ο-(geranylgeranyl)glycerol (10)] was also determined. Some of the isolated compounds (4–6 and 8–10) were screened for their potential to prevent the adhesion of three bacterial strains isolated from marine biofilms in comparison with four commercial antifoulants (TBTO, Zineb, ZnPT, and CuPT): those bearing a glycerol moiety (compounds 9 and 10) exhibited the strongest anti-adhesion effects, whatever the strain, and with a moderate toxicity. Thus, these chemical structures should be further explored for both their putative involvement in keeping the algal surface free of biofouling and the development of effective and environmentally benign antifoulants.