Comparative effects of indole derivatives as antifouling agents on the growth of two marine diatom species

Antifouling agents, used to prevent biofouling, need to be assessed for their impacts on marine organisms and environment before the application. Diatoms are one of the main components of fouling biofilms, which play important roles in the formation of biofouling. Particularly, diatoms are also the important ingredients of primary production and present interest as ecotoxicological models in marine environment. In this study, two benthic diatoms Nitzschia closterium f. minutissima and Navicula climacospheniae, widely distributed in fouling biofilm, were used as models for screening the activities of potential antifoulants. Nine indole derivatives were tested and CuSO4 was used as a reference. Indole derivatives showed significant anti-algal activities and the EC50 values of most indole derivatives were lower than that of CuSO4. Halogen substituent enhanced the anti-algal activities of compounds, and the most efficient compounds for N. closterium f. minutissima were gramine and 7-chloroindole with the EC50 values of 1.94 and 2.1 mg/L, while for N. climacospheniae, 7-chloroindole and 6-bromoindole were the most efficient and the EC50 values were 3.91 and 4.25 mg/L, respectively. In conclusion, indole derivatives would be one of the promising candidates as antifoulants and our results strengthened the need to perform antifouling activity assays and environment-friendly evaluations.

[1]  Yang Yu,et al.  Seasonal variations in fouling diatom communities on the Yantai coast , 2015, Chinese Journal of Oceanology and Limnology.

[2]  Chuanhai Xia,et al.  Indole derivatives inhibited the formation of bacterial biofilm and modulated Ca2+ efflux in diatom. , 2014, Marine pollution bulletin.

[3]  M. Faimali,et al.  Toxicity and transfer of metal oxide nanoparticles from microalgae to sea urchin larvae , 2014 .

[4]  G. Swain,et al.  Static vs dynamic settlement and adhesion of diatoms to ship hull coatings , 2014, Biofouling.

[5]  R. Marks,et al.  Coral-associated bacteria, quorum sensing disrupters, and the regulation of biofouling , 2013, Biofouling.

[6]  K. Tait,et al.  Investigating a possible role for the bacterial signal molecules N‐acylhomoserine lactones in Balanus improvisus cyprid settlement , 2013, Molecular ecology.

[7]  P. Qian,et al.  Antifouling Activity of Secondary Metabolites Isolated from Chinese Marine Organisms , 2013, Marine Biotechnology.

[8]  P. Anantharaman,et al.  Antifouling activity of the methanolic extract of Syringodium isoetifolium, and its toxicity relative to tributyltin on the ovarian development of brown mussel Perna indica. , 2013, Ecotoxicology and environmental safety.

[9]  Sujing Liu,et al.  Effects of ethyl 2-methyl acetoacetate (EMA) on the growth of Phaeodactylum tricornutum and Skeletonema costatum , 2012 .

[10]  J. Mouget,et al.  Comparative efficiency of macroalgal extracts and booster biocides as antifouling agents to control growth of three diatom species. , 2012, Marine pollution bulletin.

[11]  R. Guo,et al.  Access the toxic effect of the antibiotic cefradine and its UV light degradation products on two freshwater algae. , 2012, Journal of hazardous materials.

[12]  F. Sarti,et al.  The management of the effects of navigation on the marine environment: the case of tributyltin (TBT) , 2011 .

[13]  D. Häder,et al.  Toxicity assessment of a common laundry detergent using the freshwater flagellate Euglena gracilis. , 2011, Chemosphere.

[14]  John A. Lewis,et al.  Antifouling strategies: history and regulation, ecological impacts and mitigation. , 2011, Marine pollution bulletin.

[15]  J. Leflaive,et al.  Effects of 2E,4E-Decadienal on Motility and Aggregation of Diatoms and on Biofilm Formation , 2011, Microbial Ecology.

[16]  Ying Xu,et al.  Natural products as antifouling compounds: recent progress and future perspectives , 2009, Biofouling.

[17]  V. Paul,et al.  Mini-review: quorum sensing in the marine environment and its relationship to biofouling , 2009, Biofouling.

[18]  P. Qian,et al.  Antifouling and antibacterial compounds from a marine fungus Cladosporium sp. F14 , 2009 .

[19]  S. Sonak,et al.  Implications of the ban on organotins for protection of global coastal and marine ecology. , 2009, Journal of environmental management.

[20]  G. Culioli,et al.  Antifouling activity of meroditerpenoids from the marine brown alga Halidrys siliquosa. , 2008, Journal of natural products.

[21]  P. Proksch,et al.  Antifouling activity of sponge-derived polybrominated diphenyl ethers and synthetic analogues , 2008, Biofouling.

[22]  F. Pohleven,et al.  Influence of polymeric 3-alkylpyridinium salts from the marine sponge Reniera sarai on the growth of algae and wood decay fungi , 2008, Biofouling.

[23]  Zhan-Chang Wang,et al.  Antifouling Metabolites from the Mangrove Plant Ceriops tagal , 2008, Molecules.

[24]  P. Qian,et al.  Antifouling and antibacterial compounds from the gorgonians Subergorgia suberosa and Scripearia gracillis , 2008, Natural product research.

[25]  Hiroshi Aoyama,et al.  In vitro effect of agriculture pollutants and their joint action on Pseudokirchneriella subcapitata acid phosphatase. , 2007, Chemosphere.

[26]  P. Proksch,et al.  Antifouling Activity of Bromotyrosine-Derived Sponge Metabolites and Synthetic Analogues , 2007, Marine Biotechnology.

[27]  H. Lee,et al.  Isolation of antifouling compounds from the marine bacterium, Shewanella oneidensis SCH0402 , 2007 .

[28]  H. Lee,et al.  The study of antagonistic interactions among pelagic bacteria: a promising way to coin environmental friendly antifouling compounds , 2006, Hydrobiologia.

[29]  K. Dam-Johansen,et al.  Antifouling technology—past, present and future steps towards efficient and environmentally friendly antifouling coatings , 2004 .

[30]  C. Hellio,et al.  Isethionic Acid and Floridoside Isolated from the Red Alga, Grateloupia turuturu, Inhibit Settlement of Balanus amphitrite Cyprid Larvae , 2004, Biofouling.

[31]  Miguel Cámara,et al.  Cell-to-Cell Communication Across the Prokaryote-Eukaryote Boundary , 2002, Science.

[32]  Y. Ohizumi,et al.  Novel marine-derived halogen-containing gramine analogues induce vasorelaxation in isolated rat aorta. , 2001, European journal of pharmacology.

[33]  B. Banaigs,et al.  Structure–activity relationship for bromoindole carbaldehydes: Effects on the sea urchin embryo cell cycle , 2001, Environmental toxicology and chemistry.

[34]  Y. Ohizumi,et al.  Structure-activity relationship of gramine derivatives in Ca(2+) release from sarcoplasmic reticulum. , 1999, European journal of pharmacology.

[35]  E. Abou-Mansour,et al.  6-Bromoindole-3-Carbaldehyde, from an Acinetobacter Sp. Bacterium Associated with the Ascidian Stomozoa murrayi , 1997, Journal of Chemical Ecology.

[36]  K. Adachi,et al.  2, 5, 6-Tribromo-l-methylgramine, an Antifouling Substance from the Marine Bryozoan Zoobotryon pellucidum , 1994 .

[37]  S. Vincent,et al.  Antibiofilm activity of coconut (Cocos nucifera Linn.) husk fibre extract. , 2013, Saudi journal of biological sciences.

[38]  Ying Xu,et al.  Antifouling compounds from deep-sea bacteria and their potential mode of action , 2009 .

[39]  W. Miki,et al.  5,6-Dichloro-1-methylgramine, a non-toxic antifoulant derived from a marine natural product. , 2006, Progress in molecular and subcellular biology.

[40]  Iwao Omae,et al.  General aspects of natural products antifoulants in the environment , 2006 .

[41]  H. Morii,et al.  Factors Influencing Histamine Formation by Psychrotrophic Luminous Bacteria Photobacterium phosphoreum. , 1994 .

[42]  R. Rhoads,et al.  Progress in Molecular and Subcellular Biology , 1990, Progress in Molecular and Subcellular Biology.