Abstract
Marine organism-derived secondary metabolites are promising potential sources for discovering environmentally safe antifouling agents. In present study, 55 marine secondary metabolites and their synthesized derivatives were tested and evaluated for their antifouling activities and security. These compounds include 44 natural products isolated from marine invertebrates and their symbiotic microorganisms collected from the South China Sea and 11 structural modified products derived from the isolated compounds. The natural secondary metabolites, covering phenyl ether derivatives, terpenoids, 9, 11-secosteroids, anthraquinones, alkaloids, nucleoside derivatives and peptides, were isolated from two corals, one sponge and five symbiotic fungi. All of the isolated and synthesized compounds were tested for their antifouling activities against the cyprids of barnacle Balanus (Amphibalanus) amphitrite Darwin. Noticeably, five phenyl ether derivatives (9, 11, 13–15) exhibited potent anti-larval settlement activity with the EC50 values lower than 3.05 μM and the LC50/EC50 ratios higher than 15. The study of structure–activity relationship (SAR) revealed that the introduction of acetoxy groups and bromine atoms to phenyl ether derivatives could significantly improve their antifouling activities. This is the first report on the SAR of phenyl ether derivatives on antifouling activity against barnacle B. amphitrite. The polybrominated diphenyl ether derivative, 2, 4, 6, 2′, 4′, 6′-hexabromo-diorcinol (13), which displayed excellent antifouling activity, was considered as a promising candidate of environmentally friendly antifouling agents.Electronic supplementary materialThe online version of this article (doi:10.1186/s13568-016-0272-2) contains supplementary material, which is available to authorized users.
Highlights
Marine biofouling is still a thorny issue that brings tremendous losses in both marine technical and economic fields around the world
Isolated and synthesized compounds Fifty-five compounds were obtained for the antifouling bioassay
44 natural products were isolated from two gorgonians, one sponge and five coral-derived fungi, and 11 synthesized products were obtained by structural modification of the isolated natural compounds
Summary
Marine biofouling is still a thorny issue that brings tremendous losses in both marine technical and economic fields around the world. Paints containing toxic materials like copper, lead, mercury and arsenic were used to control biofouling until organotins such as tributyltin (TBT) and triphenyltin were introduced in the 1960s (Qian et al 2010; Omae 2003). Because of the hypertoxicity to the marine ecological environment, fishery and aquaculture (Rittschof 2001), an increasing number of countries have ratified an international treaty to ban the application of antifouling coatings based on organotin compounds since early 2008 (Qian et al 2010; Faӱ et al 2007; Kitano et al 2011). Wang et al AMB Expr (2016) 6:102 antifouling products, but have been found that they accumulate in marine environment and are deleterious to marine organisms (Konstantinou and Albanis 2004). The demand for environmentally benign, non-toxic or low toxic antifouling agents is urgently required
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