Probing the Structure–Activity Relationship of the Natural Antifouling Agent Polygodial against both Micro- and Macrofoulers by Semisynthetic Modification

Moodie, Lindon W. K.; Trépos, Rozenn; Cervin, Gunnar; Larsen, Lesley; Larsen, David S.; Pavia, Henrik; Hellio, Claire; Cahill, Patrick; Svenson, Johan

doi:10.1021/acs.jnatprod.6b01056

Cited by 42 publications

(60 citation statements)

References 73 publications

(167 reference statements)

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“…Natural compounds that inhibit larval metamorphosis may be useful antifoulants in shellfish aquaculture (Cahill et al 2012;Cahill, Burritt, et al 2013;Moodie et al 2017). These products typically have a contact active mode of action, whereby they are effective while remaining bound within a stable matrix, so effects are limited to coated surfaces (Cahill and Kuhajek 2014).…”

Section: Novel Antifouling Control Technologiesmentioning

confidence: 99%

Biofouling in marine aquaculture: a review of recent research and developments

et al. 2019

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Biofouling in marine aquaculture is one of the main barriers to efficient and sustainable production. Owing to the growth of aquaculture globally, it is pertinent to update previous reviews to inform management and guide future research. Here, the authors highlight recent research and developments on the impacts, prevention and control of biofouling in shellfish, finfish and seaweed aquaculture, and the significant gaps that still exist in aquaculturalists' capacity to manage it. Antifouling methods are being explored and developed; these are centred on harnessing naturally occurring antifouling properties, culturing fouling-resistant genotypes, and improving farming strategies by adopting more sensitive and informative monitoring and modelling capabilities together with novel cleaning equipment. While no simple, quick-fix solutions to biofouling management in existing aquaculture industry situations have been developed, the expectation is that effective methods are likely to evolve as aquaculture develops into emerging culture scenarios, which will undoubtedly influence the path for future solutions. ARTICLE HISTORY

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Section: Novel Antifouling Control Technologiesmentioning

confidence: 99%

Biofouling in marine aquaculture: a review of recent research and developments

et al. 2019

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“…These observations are consistent with other studies identifying P. purpureum as a particularly robust microalgae. 39,43 Both C. closterium and H.…”

mentioning

confidence: 99%

“…51,52 The dose-response behavior and inhibitory constants are presented in Figure 5 and Table 5. 43 Of particular interest, 9 exerted its inhibitory activity via a non-toxic mode of action, with active and swimming larvae still present after five days of incubation but no successfully settled or metamorphosed larvae. The remaining compounds killed the C. savignyi larvae outright, with no active or swimming larvae present after 5 days.…”

mentioning

confidence: 99%

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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“…Antifouling compounds, such as polygodial from the canelo tree Drimys winteri [ 65 , 66 ], synthetic 3-alkylpyridinium oligomers and polymers (3-APS) [ 32 ] and linoleic acid from the semi-evergreen plant Dryopteris crassirhizoma [ 67 ], show surfactant properties known to disrupt or solubilize the cell membrane of fouling organisms. In addition, cationic antifouling chemicals can interact with negatively-charged bacterial cells to cause lysis of cell membranes and leakage of cellular contents [ 57 , 58 , 60 , 68 , 69 , 70 ].…”

Section: Antifouling Compounds With Proposed General Targetsmentioning

confidence: 99%

Review on Molecular Mechanisms of Antifouling Compounds: An Update since 2012

Chen

Qian

2017

Marine Drugs

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Better understanding of the mechanisms of antifouling compounds is recognized to be of high value in establishing sensitive biomarkers, allowing the targeted optimization of antifouling compounds and guaranteeing environmental safety. Despite vigorous efforts to find new antifouling compounds, information about the mechanisms of antifouling is still scarce. This review summarizes the progress into understanding the molecular mechanisms underlying antifouling activity since 2012. Non-toxic mechanisms aimed at specific targets, including inhibitors of transmembrane transport, quorum sensing inhibitors, neurotransmission blockers, adhesive production/release inhibitors and enzyme/protein inhibitors, are put forward for natural antifouling products or shelf-stable chemicals. Several molecular targets show good potential for use as biomarkers in future mechanistic screening, such as acetylcholine esterase for neurotransmission, phenoloxidase/tyrosinase for the formation of adhesive plaques, N-acyl homoserine lactone for quorum sensing and intracellular Ca2+ levels as second messenger. The studies on overall responses to challenges by antifoulants can be categorized as general targets, including protein expression/metabolic activity regulators, oxidative stress inducers, neurotransmission blockers, surface modifiers, biofilm inhibitors, adhesive production/release inhibitors and toxic killing. Given the current situation and the knowledge gaps regarding the development of alternative antifoulants, a basic workflow is proposed that covers the indispensable steps, including preliminary mechanism- or bioassay-guided screening, evaluation of environmental risks, field antifouling performance, clarification of antifouling mechanisms and the establishment of sensitive biomarkers, which are combined to construct a positive feedback loop.

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Probing the Structure–Activity Relationship of the Natural Antifouling Agent Polygodial against both Micro- and Macrofoulers by Semisynthetic Modification

Cited by 42 publications

References 73 publications

Biofouling in marine aquaculture: a review of recent research and developments

Biofouling in marine aquaculture: a review of recent research and developments

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

Review on Molecular Mechanisms of Antifouling Compounds: An Update since 2012

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