title: Antifouling compounds from the sub-arctic ascidian Synoicum pulmonaria: synoxazolidinones A and C, pulmonarins A and B, and synthetic analogues.
abstract: 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.
authors.affiliation: School of Biological Sciences, University of Portsmouth , Portsmouth PO1 2DY, U.K.
authors.forename: Rozenn
authors.initials: R
authors.lastname: Trepos
authors.forename: Gunnar
authors.initials: G
authors.lastname: Cervin
authors.forename: Claire
authors.initials: C
authors.lastname: Hellio
authors.forename: Henrik
authors.initials: H
authors.lastname: Pavia
authors.forename: Wenche
authors.initials: W
authors.lastname: Stensen
authors.forename: Klara
authors.initials: K
authors.lastname: Stensvåg
authors.forename: John-Sigurd
authors.initials: JS
authors.lastname: Svendsen
authors.forename: Tor
authors.initials: T
authors.lastname: Haug
authors.forename: Johan
authors.initials: J
authors.lastname: Svenson
mesh_terms: D000818:Animals; D057219:Biofouling; D001969:Bromobenzenes / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D019791:Guanidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D006146:Guanidines; D007814:Larva / Q000187:drug effects; D008386:Marine Biology; D015394:Molecular Structure; D023303:Oxazolidinones / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001468:Thoracica / Q000502:physiology; D014561:Urochordata / Q000737:chemistry*
chemical_list: D001969:Bromobenzenes; D006146:Guanidines; D023303:Oxazolidinones; C000590253:pulmonarin A; C000590254:pulmonarin B; C555088:synoxazolidinone A; C555089:synoxazolidinone B; C000594630:synoxazolidinone C; D019791:Guanidine