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Antifouling compounds from the Sub-Arctic ascidian Synoicum pulmonaria: Synoxazolidinones A and C, Pulmonarins A and B, and synthetic analogues.

Journal article
Authors Rozenn Trepos
Gunnar Cervin
Claire Hellio
Henrik Pavia
Wenche Stensen
Klara Stensvåg
John-Sigurd Svendsen
Tor Haug
Johan Svenson
Published in Journal of natural products
Volume 77
Issue 9
Pages 2105-2113
ISSN 0163-3864
Publication year 2014
Published at Department of Biological and Environmental Sciences, Tjärnö Marine Biological Laboratory
Centre for Marine Chemical Ecology
Pages 2105-2113
Language en
Links dx.doi.org/10.1021/np5005032
Subject categories Organic synthesis, Bioorganic chemistry, Marine ecology

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.

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