Antifouling compounds from the sub-arctic ascidian Synoicum pulmonaria: synoxazolidinones A and C, pulmonarins A and B, and synthetic analogues.

• Published in: Journal of Natural Products
• Main Authors: Trepos, Rozenn, Cervin, Gunnar, Hellio, Claire, Pavia, Henrik, Stensen, Wenche, Stensvåg, Klara, Svendsen, John-Sigurd, Haug, Tor, Svenson, Johan
• Other Authors: University of Portsmouth, Göteborgs Universitet = University of Gothenburg (GU), Laboratoire des Sciences de l'Environnement Marin (LEMAR) (LEMAR), Institut de Recherche pour le Développement (IRD)-Institut Français de Recherche pour l'Exploitation de la Mer (IFREMER)-Université de Brest (UBO)-Institut Universitaire Européen de la Mer (IUEM), Institut de Recherche pour le Développement (IRD)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), The Arctic University of Norway Tromsø, Norway (UiT)
• Format: Article in Journal/Newspaper
• Language: English
• Published: HAL CCSD 2014
• Subjects: ALKALOIDS; ACL; SPONGE GEODIA-BARRETTI; MARINE NATURAL-PRODUCTS; BARNACLE BALANUS-IMPROVISUS; 4-OXAZOLIDINONES; AQUACULTURE; ENVIRONMENT; COATINGS; SECONDARY METABOLITES; FUTURE; [SDV]Life Sciences [q-bio]; [SDE.BE]Environmental Sciences/Biodiversity and Ecology; Arctic
• Online Access: https://hal.univ-brest.fr/hal-01103850; https://doi.org/10.1021/np5005032

International audience The current study describes the antifouling properties of four members belonging to the recently discovered synoxazolidinone and pulmonarin families, isolated from the sub-Arctic sessile ascidian Synoicum pulmonaria collected off the Norwegian coast. Four simplified synthetic analogues were also prepared and included in the study. Several of the studied compounds displayed MIC values in the micro-nanomolar range against 16 relevant marine species involved in both the micro- and macrofouling process. Settlement studies on Balanus improvisus cyprids indicated a deterrent effect and a low toxicity for selected compounds. The two synoxazolidinones displayed broad activity and are shown to be among the most active natural antifouling bromotyrosine derivatives described. Synoxazolidinone C displayed selected antifouling properties comparable to the commercial antifouling product Sea-Nine-211. The pulmonarins prevented the growth of several bacterial strains at nanomolar concentrations but displayed a lower activity toward microalgae and no effect on barnacles. The linear and cyclic synthetic peptidic mimics also displayed potent antifouling activities mainly directed against bacterial adhesion and growth.