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Special Issue "Antifouling Marine Natural Products"

A special issue of Marine Drugs (ISSN 1660-3397).

Deadline for manuscript submissions: closed (30 June 2017)

Special Issue Editors

Guest Editor
Prof. Dr. Pei-Yuan Qian

Division of Life Sciences, Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong
Website | E-Mail
Fax: +852 2358 1559
Interests: larval omics; marine molecular ecology; microbial ecology; marine natural products; biofouling and antifouling; marine invertebrates
Guest Editor
Prof. Dr. Nobuhiro Fusetani

Director, Fisheries & Oceans Hakodate, Hakodate Research Center for Fisheries and Oceans, 20-5 Benten-cho, Hakodate 040-0051, Japan
E-Mail
Fax: +81 138 21 4601
Interests: marine natural products; drug discovery; antitumor; antimicrobial; enzyme inhibitors; chemical ecology; biofouling

Special Issue Information

Dear Colleagues,

Over the past decade, due to ban of TTB-containing antifouling coatings, substantial efforts have been made in identifying environmentally-friendly antifouling compounds from diverse sources of natural products, such as microbes, algae, invertebrates, vertebrates and even terrestrial plants and animals. Various bioassay systems have also been developed to assess the efficacy of antifouling agents. However, very limited compounds have been developed into products.

This Special Issue will provide extensive reviews on antifouling compounds from all sources, and the challenges we are currently facing and possible ways to move forward.

Prof. Dr. Pei-Yuan Qian
Prof. Dr. Nobuhiro Fusetani
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All papers will be peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Marine Drugs is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 1800 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • antifouling compounds
  • antifouling materials
  • mode-of-the action
  • marine coatings
  • natural products
  • natural and synthetic antifoulants

Published Papers (7 papers)

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Research

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Open AccessArticle New Marine Antifouling Compounds from the Red Alga Laurencia sp.
Mar. Drugs 2017, 15(9), 267; doi:10.3390/md15090267
Received: 31 July 2017 / Revised: 20 August 2017 / Accepted: 23 August 2017 / Published: 28 August 2017
Cited by 1 | PDF Full-text (650 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Six new compounds, omaezol, intricatriol, hachijojimallenes A and B, debromoaplysinal, and 11,12-dihydro-3-hydroxyretinol have been isolated from four collections of Laurencia sp. These structures were determined by MS and NMR analyses. Their antifouling activities were evaluated together with eight previously known compounds isolated from
[...] Read more.
Six new compounds, omaezol, intricatriol, hachijojimallenes A and B, debromoaplysinal, and 11,12-dihydro-3-hydroxyretinol have been isolated from four collections of Laurencia sp. These structures were determined by MS and NMR analyses. Their antifouling activities were evaluated together with eight previously known compounds isolated from the same samples. In particular, omaezol and hachijojimallene A showed potent activities (EC50 = 0.15–0.23 µg/mL) against larvae of the barnacle Amphibalanus amphitrite. Full article
(This article belongs to the Special Issue Antifouling Marine Natural Products)
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Open AccessArticle Design, Synthesis, and Antifouling Activity of Glucosamine-Based Isocyanides
Mar. Drugs 2017, 15(7), 203; doi:10.3390/md15070203
Received: 16 May 2017 / Revised: 12 June 2017 / Accepted: 21 June 2017 / Published: 29 June 2017
PDF Full-text (861 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Biofouling, an undesirable accumulation of organisms on sea-immersed structures such as ship hulls and fishing nets, is a serious economic issue whose effects include oil wastage and clogged nets. Organotin compounds were utilized since the 1960s as an antifouling material; however, the use
[...] Read more.
Biofouling, an undesirable accumulation of organisms on sea-immersed structures such as ship hulls and fishing nets, is a serious economic issue whose effects include oil wastage and clogged nets. Organotin compounds were utilized since the 1960s as an antifouling material; however, the use of such compounds was later banned by the International Maritime Organization (IMO) due to their high toxicity toward marine organisms, resulting in masculinization and imposex. Since the ban, there have been extensive efforts to develop environmentally benign antifoulants. Natural antifouling products obtained from marine creatures have been the subject of considerable attention due to their potent antifouling activity and low toxicity. These antifouling compounds often contain isocyano groups, which are well known to have natural antifouling properties. On the basis of our previous total synthesis of natural isocyanoterpenoids, we envisaged the installation of an isocyano functional group onto glucosamine to produce an environmentally friendly antifouling material. This paper describes an effective synthetic method for various glucosamine-based isocyanides and evaluation of their antifouling activity and toxicity against cypris larvae of the barnacle Amphibalanus amphitrite. Glucosamine isocyanides with an ether functionality at the anomeric position exhibited potent antifouling activity, with EC50 values below 1 μg/mL, without detectable toxicity even at a high concentration of 10 μg/mL. Two isocyanides had EC50 values of 0.23 and 0.25 μg/mL, comparable to that of CuSO4, which is used as a fouling inhibitor (EC50 = 0.27 μg/mL). Full article
(This article belongs to the Special Issue Antifouling Marine Natural Products)
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Review

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Open AccessReview Mini-Review: Antifouling Natural Products from Marine Microorganisms and Their Synthetic Analogs
Mar. Drugs 2017, 15(9), 266; doi:10.3390/md15090266
Received: 19 May 2017 / Revised: 2 July 2017 / Accepted: 12 July 2017 / Published: 28 August 2017
PDF Full-text (3084 KB) | HTML Full-text | XML Full-text
Abstract
Biofouling causes huge economic loss and generates serious ecological issues worldwide. Marine coatings incorporated with antifouling (AF) compounds are the most common practices to prevent biofouling. With a ban of organotins and an increase in the restrictions regarding the use of other AF
[...] Read more.
Biofouling causes huge economic loss and generates serious ecological issues worldwide. Marine coatings incorporated with antifouling (AF) compounds are the most common practices to prevent biofouling. With a ban of organotins and an increase in the restrictions regarding the use of other AF alternatives, exploring effective and environmentally friendly AF compounds has become an urgent demand for marine coating industries. Marine microorganisms, which have the largest biodiversity, represent a rich and important source of bioactive compounds and have many medical and industrial applications. This review summarizes 89 natural products from marine microorganisms and 13 of their synthetic analogs with AF EC50 values ≤ 25 μg/mL from 1995 (the first report about marine microorganism-derived AF compounds) to April 2017. Some compounds with the EC50 values < 5 μg/mL and LC50/EC50 ratios > 50 are highlighted as potential AF compounds, and the preliminary analysis of structure-relationship (SAR) of these compounds is also discussed briefly. In the last part, current challenges and future research perspectives are proposed based on opinions from many previous reviews. To provide clear guidance for the readers, the AF compounds from microorganisms and their synthetic analogs in this review are categorized into ten types, including fatty acids, lactones, terpenes, steroids, benzenoids, phenyl ethers, polyketides, alkaloids, nucleosides and peptides. In addition to the major AF compounds which targets macro-foulers, this review also includes compounds with antibiofilm activity since micro-foulers also contribute significantly to the biofouling communities. Full article
(This article belongs to the Special Issue Antifouling Marine Natural Products)
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Open AccessReview Antifouling Compounds from Marine Macroalgae
Mar. Drugs 2017, 15(9), 265; doi:10.3390/md15090265
Received: 30 March 2017 / Revised: 29 June 2017 / Accepted: 12 July 2017 / Published: 28 August 2017
PDF Full-text (3190 KB) | HTML Full-text | XML Full-text
Abstract
Marine macroalgae produce a wide variety of biologically-active metabolites that have been developed into commercial products, such as antibiotics, immunosuppressive, anti-inflammatory, cytotoxic agents, and cosmetic products. Many marine algae remain clean over longer periods of time, suggesting their strong antifouling potential. Isolation of
[...] Read more.
Marine macroalgae produce a wide variety of biologically-active metabolites that have been developed into commercial products, such as antibiotics, immunosuppressive, anti-inflammatory, cytotoxic agents, and cosmetic products. Many marine algae remain clean over longer periods of time, suggesting their strong antifouling potential. Isolation of biogenic compounds and the determination of their structure could provide leads for the development of environmentally-friendly antifouling paints. Isolated substances with potent antifouling activity belong to fatty acids, lipopeptides, amides, alkaloids, lactones, steroids, terpenoids, and pyrroles. It is unclear as yet to what extent symbiotic microorganisms are involved in the synthesis of these compounds. Algal secondary metabolites have the potential to be produced commercially using genetic and metabolic engineering techniques. This review provides an overview of publications from 2010 to February 2017 about antifouling activity of green, brown, and red algae. Some researchers were focusing on antifouling compounds of brown macroalgae, while metabolites of green algae received less attention. Several studies tested antifouling activity against bacteria, microalgae and invertebrates, but in only a few studies was the quorum sensing inhibitory activity of marine macroalgae tested. Rarely, antifouling compounds from macroalgae were isolated and tested in an ecologically-relevant way. Full article
(This article belongs to the Special Issue Antifouling Marine Natural Products)
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Open AccessReview Review on Molecular Mechanisms of Antifouling Compounds: An Update since 2012
Mar. Drugs 2017, 15(9), 264; doi:10.3390/md15090264
Received: 23 June 2017 / Revised: 23 July 2017 / Accepted: 26 July 2017 / Published: 28 August 2017
PDF Full-text (557 KB) | HTML Full-text | XML Full-text
Abstract
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
[...] Read more.
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. Full article
(This article belongs to the Special Issue Antifouling Marine Natural Products)
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Open AccessReview Antifouling Compounds from Marine Invertebrates
Mar. Drugs 2017, 15(9), 263; doi:10.3390/md15090263
Received: 30 April 2017 / Revised: 10 July 2017 / Accepted: 10 July 2017 / Published: 28 August 2017
PDF Full-text (3701 KB) | HTML Full-text | XML Full-text
Abstract
In this review, a comprehensive overview about the antifouling compounds from marine invertebrates is described. In total, more than 198 antifouling compounds have been obtained from marine invertebrates, specifically, sponges, gorgonian and soft corals. Full article
(This article belongs to the Special Issue Antifouling Marine Natural Products)
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Open AccessReview Off the Shelf Fouling Management
Mar. Drugs 2017, 15(6), 176; doi:10.3390/md15060176
Received: 6 May 2017 / Revised: 31 May 2017 / Accepted: 8 June 2017 / Published: 14 June 2017
PDF Full-text (1385 KB) | HTML Full-text | XML Full-text
Abstract
This chapter tells the story of a research thread that identified and modified a pharmaceutical that could be a component of environmentally benign fouling management coatings. First, I present the background context of biofouling and how fouling is managed. The major target of
[...] Read more.
This chapter tells the story of a research thread that identified and modified a pharmaceutical that could be a component of environmentally benign fouling management coatings. First, I present the background context of biofouling and how fouling is managed. The major target of the research is disrupting transduction of a complex process in all macrofouling organisms: metamorphosis. Using a bioassay directed approach we first identified a pharmaceutical candidate. Then, based on structure function studies coupled with laboratory and field bioassays, we simplified the molecule, eliminating halogens and aromatic rings to a pharmacophore that could be readily broken down by bacteria. Next, we did further structure function studies coupled to lab and field bioassays of modifications that enabled delivery of the molecule in a variety of coatings. The outcome is a different way of thinking about managing fouling and concepts in which molecules are designed to perform a function and then degrade. This work is discussed in the context of existing fouling management approaches and business models which use long-lived broad-spectrum biocides which have consequences for human, environmental health, and food security. Full article
(This article belongs to the Special Issue Antifouling Marine Natural Products)
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