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Marine Drugs
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Marine Natural Products with Antifouling Activity, 2nd Edition
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Marine Natural Products with Antifouling Activity, 2nd Edition

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

Deadline for manuscript submissions: closed (30 September 2022) | Viewed by 10993

Special Issue Editors

Dr. Joana Reis Almeida

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Guest Editor
CIIMAR|Interdisciplinary Centre of Marine and Environmental Research, University of Porto, Novo Edifício do Terminal de Cruzeiros do Porto de Leixões, Avenida General Norton de Matos, s/n, 4450-208 Matosinhos, Portugal
Interests: marine biology and ecology; marine environmental health; marine biotechnology; sustainable antifouling strategies; natural bioactive metabolites; bioproducts and biomaterials
Special Issues, Collections and Topics in MDPI journals
Dr. Marta Correia-da-Silva

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Guest Editor
1. Laboratório de Química Orgânica e Farmacêutica, Departamento de Ciências, Químicas, Faculdade de Farmácia, Universidade do Porto, Rua Jorge Viterbo Ferreira 228, 4050-313 Porto, Portugal
2. CIIMAR | Interdisciplinary Centre of Marine and Environmental Research, University of Porto, Novo Edifício do Terminal de Cruzeiros do Porto de Leixões, Avenida General Norton de Matos, s/n, 4450-208 Matosinhos, Portugal
Interests: medicinal chemistry; synthesis of sulfated and glycosylated small-molecule mimetics of heparin; discovery of biological activities for persulfated versus partially sulfated small molecules; antifouling studies of partially sulfated small molecules; antithrombotic studies of persulfated small molecules; structure–activity and structure–property relationship studies of bioactive small molecules
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Marine biofouling is one of the natural phenomena representing a challenge worldwide due to the costly effects on shipping and maritime-related industries, and to the related environmental threats. Intense research is aimed at new methods for preventing, controlling, or reducing fouling development in different submerged marine structures. The most prevalent solution to inhibit fouling is to make surfaces unsuitable for settlers, using coatings with repellent AF properties. Most of the AF agents in use in these coatings have undesirable effects on nontarget species, including commercially important ones. The search for new nontoxic antifouling technologies has become a necessity, particularly after the ban of organotin compounds such as tributyltin (TBT), one of the most efficient and widespread antifouling agents. Alternative organic and metal-based biocides are now used in antifouling paints, but their persistence and toxic effects in the aquatic environment have been reported. A nontoxic alternative for antifouling protection comes from the possibility of adopting natural antifouling compounds that may be found in sessile marine invertebrates like sponges, bryozoans, corals, and tunicates, as well as in marine microorganisms. Such metabolites prevent their producers from being fouled on by other organisms, or are simply products of their secondary metabolism and may act as bioactive compounds to several purposes. As natural marine compounds, they may inhibit settlement through a nontoxic mechanism without posing adverse effects to the marine environment. Such compounds can constitute new harmless ingredients for antifouling coatings. So far, a rather limited number of natural product antifoulants (NPAs) have been isolated from marine organisms, but a huge reservoir of compounds with potential antifouling activity is hidden in marine organisms. This Special Issue on Marine Natural Products with Antifouling Activity, 2nd Edition aims at the discovery of such natural compounds, the use of these compounds as an inspiration for the design of new ones, their activity against biofouling species settlement, the evaluation of environmental fate parameters, and their application in antifouling coatings as novel environmentally friendly agents.

Dr. Joana Reis Almeida
Dr. Marta Correia-da-Silva
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 submissions that pass pre-check are 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 2900 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

  • marine natural compounds
  • antifouling
  • toxicity
  • coatings
  • environment

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Published Papers (5 papers)

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Research

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8 pages, 273 KiB  
Article
Quantification of a Sulfated Marine-Inspired Antifouling Compound in Several Aqueous Matrices: Biodegradation Studies and Leaching Assays from Polydimethylsiloxane Coatings
by Cátia Vilas-Boas, Virgínia Gonçalves, Paolo De Marco, Emília Sousa, Madalena Pinto, Elisabete R. Silva, Maria Elizabeth Tiritan and Marta Correia-da-Silva
Mar. Drugs 2022, 20(9), 548; https://doi.org/10.3390/md20090548 - 25 Aug 2022
Cited by 1 | Viewed by 1852
Abstract
The development of marine-inspired compounds as non-toxic antifouling (AF) agents has been pursued in the last years. Sulfur is the third most common element in seawater. Sulfur is present in oxygenated seawater as sulfate anion (SO42−), which is the most [...] Read more.
The development of marine-inspired compounds as non-toxic antifouling (AF) agents has been pursued in the last years. Sulfur is the third most common element in seawater. Sulfur is present in oxygenated seawater as sulfate anion (SO42−), which is the most stable combination of sulfur in seawater, and several promising AF secondary metabolites with sulfate groups have been described. However, sulfated compounds proved to be an analytical challenge to quantify by HPLC. Taking these facts into consideration, this work presents the development and validation of a method for the quantification of gallic acid persulfate (GAP) in seawater and ultrapure water matrix, based on hydrophilic interaction liquid chromatography (HILIC). This method was used to evaluate GAP stability following several abiotic and biotic degradation assays, and to quantify its release in seawater from room-temperature-vulcanizing polydimethylsiloxane commercial coating. GAP was very stable in several water matrices, even at different pH values and in the presence/absence of marine microorganisms and presented a leaching value lower than 0.5%. This work discloses HILIC as an analytical method to overcome the difficulties in quantifying sulfated compounds in water matrices and highlights the potential of GAP as a promising long-lasting coating. Full article
(This article belongs to the Special Issue Marine Natural Products with Antifouling Activity, 2nd Edition)
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12 pages, 2155 KiB  
Article
Antifouling Marine Coatings with a Potentially Safer and Sustainable Synthetic Polyphenolic Derivative
by Ana R. Neves, Luciana C. Gomes, Sara I. Faria, João Sousa, Raquel Ruivo, Inês Páscoa, Madalena Pinto, Emília Sousa, Miguel M. Santos, Elisabete R. Silva, Marta Correia-da-Silva and Filipe Mergulhão
Mar. Drugs 2022, 20(8), 507; https://doi.org/10.3390/md20080507 - 5 Aug 2022
Cited by 8 | Viewed by 3046
Abstract
The development of harmless substances to replace biocide-based coatings used to prevent or manage marine biofouling and its unwanted consequences is urgent. The formation of biofilms on submerged marine surfaces is one of the first steps in the marine biofouling process, which facilitates [...] Read more.
The development of harmless substances to replace biocide-based coatings used to prevent or manage marine biofouling and its unwanted consequences is urgent. The formation of biofilms on submerged marine surfaces is one of the first steps in the marine biofouling process, which facilitates the further settlement of macrofoulers. Anti-biofilm properties of a synthetic polyphenolic compound, with previously described anti-settlement activity against macrofoulers, were explored in this work. In solution this new compound was able to prevent biofilm formation and reduce a pre-formed biofilm produced by the marine bacterium, Pseudoalteromonas tunicata. Then, this compound was applied to a marine coating and the formation of P. tunicata biofilms was assessed under hydrodynamic conditions to mimic the marine environment. For this purpose, polyurethane (PU)-based coating formulations containing 1 and 2 wt.% of the compound were prepared based on a prior developed methodology. The most effective formulation in reducing the biofilm cell number, biovolume, and thickness was the PU-based coating containing an aziridine-based crosslinker and 2 wt.% of the compound. To assess the marine ecotoxicity impact of this compound, its potential to disrupt endocrine processes was evaluated through the modulation of two nuclear receptors (NRs), peroxisome proliferator-activated receptor γ (PPARγ), and pregnane X receptor (PXR). Transcriptional activation of the selected NRs upon exposure to the polyphenolic compound (10 µM) was not observed, thus highlighting the eco-friendliness towards the addressed NRs of this new dual-acting anti-macro- and anti-microfouling agent towards the addressed NRs. Full article
(This article belongs to the Special Issue Marine Natural Products with Antifouling Activity, 2nd Edition)
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14 pages, 2778 KiB  
Article
Effective Synthesis and Antifouling Activity of Dolastatin 16 Derivatives
by Loida O. Casalme, Keisuke Katayama, Yoshiki Hayakawa, Kensuke Nakamura, Arisa Yamauchi, Yasuyuki Nogata, Erina Yoshimura, Fuyuhiko Matsuda and Taiki Umezawa
Mar. Drugs 2022, 20(2), 124; https://doi.org/10.3390/md20020124 - 4 Feb 2022
Cited by 6 | Viewed by 2572
Abstract
Some derivatives of dolastatin 16, a depsipeptide natural product first obtained from the sea hare Dolabella auricularia, were synthesized through second-generation synthesis of two unusual amino acids, dolaphenvaline and dolamethylleuine. The second-generation synthesis enabled derivatizations such as functionalization of the aromatic ring [...] Read more.
Some derivatives of dolastatin 16, a depsipeptide natural product first obtained from the sea hare Dolabella auricularia, were synthesized through second-generation synthesis of two unusual amino acids, dolaphenvaline and dolamethylleuine. The second-generation synthesis enabled derivatizations such as functionalization of the aromatic ring in dolaphenvaline. The derivatives of fragments and whole structures were evaluated for antifouling activity against the cypris larvae of Amphibalanus amphitrite. Small fragments inhibited the settlement of the cypris larvae at potent to moderate concentrations (EC50 = 0.60-4.62 μg/mL), although dolastatin 16 with a substituent on the aromatic ring (24) was much less potent than dolastatin 16. Full article
(This article belongs to the Special Issue Marine Natural Products with Antifouling Activity, 2nd Edition)
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16 pages, 1320 KiB  
Article
Antifouling Activity of Halogenated Compounds Derived from the Red Alga Sphaerococcus coronopifolius: Potential for the Development of Environmentally Friendly Solutions
by Maxence Quémener, Stefanos Kikionis, Marilyne Fauchon, Yannick Toueix, Fanny Aulanier, Antonios M. Makris, Vassilios Roussis, Efstathia Ioannou and Claire Hellio
Mar. Drugs 2022, 20(1), 32; https://doi.org/10.3390/md20010032 - 28 Dec 2021
Cited by 12 | Viewed by 2778
Abstract
Nowadays, biofouling is responsible for enormous economic losses in the maritime sector, and its treatment with conventional antifouling paints is causing significant problems to the environment. Biomimetism and green chemistry approaches are very promising research strategies for the discovery of new antifouling compounds. [...] Read more.
Nowadays, biofouling is responsible for enormous economic losses in the maritime sector, and its treatment with conventional antifouling paints is causing significant problems to the environment. Biomimetism and green chemistry approaches are very promising research strategies for the discovery of new antifouling compounds. This study focused on the red alga Sphaerococcus coronopifolius, which is known as a producer of bioactive secondary metabolites. Fifteen compounds, including bromosphaerol (1), were tested against key marine biofoulers (five marine bacteria and three microalgae) and two enzymes associated with the adhesion process in macroalgae and invertebrates. Each metabolite presented antifouling activity against at least one organism/enzyme. This investigation also revealed that two compounds, sphaerococcinol A (4) and 14R-hydroxy-13,14-dihydro-sphaerococcinol A (5), were the most potent compounds without toxicity towards oyster larvae used as non-target organisms. These compounds are of high potential as they are active towards key biofoulers and could be produced by a cultivable alga, a fact that is important from the green chemistry point of view. Full article
(This article belongs to the Special Issue Marine Natural Products with Antifouling Activity, 2nd Edition)
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Review

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25 pages, 3251 KiB  
Review
Anti-Larval and Anti-Algal Natural Products from Marine Microorganisms as Sources of Anti-Biofilm Agents
by Kai-Ling Wang, Zheng-Rong Dou, Gao-Fen Gong, Hai-Feng Li, Bei Jiang and Ying Xu
Mar. Drugs 2022, 20(2), 90; https://doi.org/10.3390/md20020090 - 21 Jan 2022
Cited by 20 | Viewed by 5172
Abstract
Bacteria growing inside biofilms are more resistant to hostile environments, conventional antibiotics, and mechanical stresses than their planktonic counterparts. It is estimated that more than 80% of microbial infections in human patients are biofilm-based, and biofouling induced by the biofilms of some bacteria [...] Read more.
Bacteria growing inside biofilms are more resistant to hostile environments, conventional antibiotics, and mechanical stresses than their planktonic counterparts. It is estimated that more than 80% of microbial infections in human patients are biofilm-based, and biofouling induced by the biofilms of some bacteria causes serious ecological and economic problems throughout the world. Therefore, exploring highly effective anti-biofilm compounds has become an urgent demand for the medical and marine industries. Marine microorganisms, a well-documented and prolific source of natural products, provide an array of structurally distinct secondary metabolites with diverse biological activities. However, up to date, only a handful of anti-biofilm natural products derived from marine microorganisms have been reported. Meanwhile, it is worth noting that some promising antifouling (AF) compounds from marine microbes, particularly those that inhibit settlement of fouling invertebrate larvae and algal spores, can be considered as potential anti-biofilm agents owing to the well-known knowledge of the correlations between biofilm formation and the biofouling process of fouling organisms. In this review, a total of 112 anti-biofilm, anti-larval, and anti-algal natural products from marine microbes and 26 of their synthetic analogues are highlighted from 2000 to 2021. These compounds are introduced based on their microbial origins, and then categorized into the following different structural groups: fatty acids, butenolides, terpenoids, steroids, phenols, phenyl ethers, polyketides, alkaloids, flavonoids, amines, nucleosides, and peptides. The preliminary structure-activity relationships (SAR) of some important compounds are also briefly discussed. Finally, current challenges and future research perspectives are proposed based on opinions from many previous reviews. Full article
(This article belongs to the Special Issue Marine Natural Products with Antifouling Activity, 2nd Edition)
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