Antifouling Compounds from the Sub-Arctic Ascidian <i>Synoicum pulmonaria</i>: Synoxazolidinones A and C, Pulmonarins A and B, and Synthetic Analogues

Trépos, Rozenn; Cervin, Gunnar; Hellio, Claire; Pavia, Henrik; Stensen, Wenche; Stensvåg, Klara; Svendsen, John S.; Haug, Tor; Svenson, Johan

doi:10.1021/np5005032

Cited by 82 publications

(116 citation statements)

References 53 publications

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“…48 bastadin-9 (IC50 = 1.0 µM) 49 and synoxazolidinone C (IC50 = 2 µM). 29 The compounds also share similar structural features and antifouling activities with the natural antifouling phenyl ethers recently reported by Wang and co-workers. 50 The high inhibitory effect on barnacle cyprid settlement illustrates that the dihydrostilbenes also exhibit potent biological effects in higher organisms.…”

supporting

confidence: 70%

Prevention of Marine Biofouling Using the Natural Allelopathic Compound Batatasin-III and Synthetic Analogues

Moodie¹,

Trépos

Cervin

et al. 2017

J. Nat. Prod.

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The current study reports the first comprehensive evaluation of a class of allelopathic terrestrial natural products as antifoulants in a marine setting. To investigate the antifouling potential of the natural dihydrostilbene scaffold, a library of 22 synthetic dihydrostilbenes with varying substitution patterns, many of which occur naturally in terrestrial plants, were prepared and assessed for their antifouling capacity. The compounds were evaluated in an extensive screen against 16 fouling marine organisms. The dihydrostilbene scaffold was shown to possess powerful general antifouling effects against both marine microfoulers and macrofoulers with inhibitory activities at low concentrations. The species of microalgae examined displayed a particular sensitivity toward the evaluated compounds at low ng/mL concentrations. It was shown that several of the natural and synthetic compounds exerted their repelling activities via nontoxic and reversible mechanisms. The activities of the most active compounds such as 3,5-dimethoxybibenzyl (5), 3,4-dimethoxybibenzyl (9), and 3-hydroxy-3′,4,5′-trimethoxybibenzyl (20) were comparable to the commercial antifouling booster biocide Sea-nine, which was employed as a positive control. The investigation of terrestrial allelopathic natural products to counter marine fouling represents a novel strategy for the design of “green” antifouling technologies, and these compounds offer a potential alternative to traditional biocidal antifoulants.

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supporting

confidence: 70%

Prevention of Marine Biofouling Using the Natural Allelopathic Compound Batatasin-III and Synthetic Analogues

Moodie¹,

Trépos

Cervin

et al. 2017

J. Nat. Prod.

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“…Several peptides displayed high settling deterrent effects at 5 μg ml −1 and below (Table 2). Peptide 13 displayed a IC 50 value of 0.5 μg ml −1 (0.7 μM), which is lower than many of the reported naturally occurring AF compounds (Fusetani 2011;Hanssen et al 2014;Trepos et al 2014;Qian et al 2015). Peptides 6 and 10-12 are highly active and a clear link between the antibacterial activity, the settlement inhibition and the hydrophobicity of the most active peptides is seen, with IC 50 values ≤2.5 μg ml −1 for the peptides displaying a CLogP >1.49 (Table 2).…”

Section: Discussionmentioning

confidence: 65%

“…Marine biofouling organisms Nineteen different marine organisms involved in marine biofouling in estuarine and marine environments were included in the present study (Hanssen et al 2014;Trepos et al 2014) and the microfoulers are presented in Table 1. The 10 marine bacterial strains were obtained from the ATCC bacterial collection.…”

Section: Materials and Methods Materialsmentioning

confidence: 99%

“…previously (Hanssen et al 2014;Trepos et al 2014). Briefly, the bacteria were grown at 26°C in a marine medium, composed of 0.5 % peptone (neutralised bacteriological peptone, Oxoid Ltd, Basingstoke, UK) in filtered (Whatman 1001-270, pore size 11 μm) natural seawater from the Solent (Portsmouth, UK).…”

Section: Antibacterial Assaysmentioning

confidence: 97%

“…The current research offers a relevant comparison for further studies into the underlying mechanisms (Hanssen et al 2014;Trepos et al 2014). The current investigation represents the first study of the effects of compounds initially derived from the innate immune system on marine biofouling and on organisms in a marine setting, and extends recent studies towards biofilms (Ammons & Copie 2013;Alves & Olivia Pereira 2014).…”

mentioning

confidence: 99%

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Evaluation of cationic micropeptides derived from the innate immune system as inhibitors of marine biofouling

et al. 2015

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A series of 13 short synthetic amphiphilic cationic micropeptides, derived from the antimicrobial iron-binding innate defence protein lactoferrin, have been evaluated for their capacity to inhibit the marine fouling process. The whole biofouling process was studied and microfouling organisms such as marine bacteria and microalgae were included as well as the macrofouling barnacle Balanus improvisus. In total 19 different marine fouling organisms (18 microfoulers and one macrofouler) were included and both the adhesion and growth of the microfoulers were investigated. It was shown that the majority of the peptides inhibited barnacle cyprid settlement via a reversible nontoxic mechanism, with IC50 values as low as 0.5 μg ml(-1). Six peptides inhibited adhesion and growth of microorganisms. Two of these were particularly active against the microfoulers with MIC-values ranging between 0.01 and 1 μg ml(-1), which is comparable with the commercial reference antifoulant SeaNine.

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Functional Enzyme Mimics for Oxidative Halogenation Reactions that Combat Biofilm Formation

et al. 2018

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Transition-metal oxide nanoparticles and molecular coordination compounds are highlighted as functional mimics of halogenating enzymes. These enzymes are involved in halometabolite biosynthesis. Their activity is based upon the formation of hypohalous acids from halides and hydrogen peroxide or oxygen, which form bioactive secondary metabolites of microbial origin with strong antibacterial and antifungal activities in follow-up reactions. Therefore, enzyme mimics and halogenating enzymes may be valuable tools to combat biofilm formation. Here, halogenating enzyme models are briefly described, enzyme mimics are classified according to their catalytic functions, and current knowledge about the settlement chemistry and adhesion of fouling organisms is summarized. Enzyme mimics with the highest potential are showcased. They may find application in antifouling coatings, indoor and outdoor paints, polymer membranes for water desalination, or in aquacultures, but also on surfaces for food packaging, door handles, hand rails, push buttons, keyboards, and other elements made of plastic where biofilms are present. The use of natural compounds, formed in situ with nontoxic and abundant metal oxide enzyme mimics, represents a novel and efficient "green" strategy to emulate and utilize a natural defense system for preventing bacterial colonization and biofilm growth.

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Antifouling Compounds from the Sub-Arctic Ascidian Synoicum pulmonaria: Synoxazolidinones A and C, Pulmonarins A and B, and Synthetic Analogues

Cited by 82 publications

References 53 publications

Prevention of Marine Biofouling Using the Natural Allelopathic Compound Batatasin-III and Synthetic Analogues

Prevention of Marine Biofouling Using the Natural Allelopathic Compound Batatasin-III and Synthetic Analogues

Evaluation of cationic micropeptides derived from the innate immune system as inhibitors of marine biofouling

Functional Enzyme Mimics for Oxidative Halogenation Reactions that Combat Biofilm Formation

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