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Synthesis and Antifouling Activity Evaluation of Analogs of Bromosphaerol, a Brominated Diterpene Isolated from the Red Alga Sphaerococcus coronopifolius

Marine biofouling is an epibiotic biological process that affects almost any kind of submerged surface, causing globally significant economic problems mainly for the shipping industry and aquaculture companies, and its prevention so far has been associated with adverse environmental effects for non-...

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Autores principales: Prousis, Kyriakos C., Kikionis, Stefanos, Ioannou, Efstathia, Morgana, Silvia, Faimali, Marco, Piazza, Veronica, Calogeropoulou, Theodora, Roussis, Vassilios
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8781426/
https://www.ncbi.nlm.nih.gov/pubmed/35049862
http://dx.doi.org/10.3390/md20010007
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author Prousis, Kyriakos C.
Kikionis, Stefanos
Ioannou, Efstathia
Morgana, Silvia
Faimali, Marco
Piazza, Veronica
Calogeropoulou, Theodora
Roussis, Vassilios
author_facet Prousis, Kyriakos C.
Kikionis, Stefanos
Ioannou, Efstathia
Morgana, Silvia
Faimali, Marco
Piazza, Veronica
Calogeropoulou, Theodora
Roussis, Vassilios
author_sort Prousis, Kyriakos C.
collection PubMed
description Marine biofouling is an epibiotic biological process that affects almost any kind of submerged surface, causing globally significant economic problems mainly for the shipping industry and aquaculture companies, and its prevention so far has been associated with adverse environmental effects for non-target organisms. Previously, we have identified bromosphaerol (1), a brominated diterpene isolated from the red alga Sphaerococcus coronopifolius, as a promising agent with significant antifouling activity, exerting strong anti-settlement activity against larvae of Amphibalanus (Balanus) amphitrite and very low toxicity. The significant antifouling activity and low toxicity of bromosphaerol (1) motivated us to explore its chemistry, aiming to optimize its antifouling potential through the preparation of a number of analogs. Following different synthetic routes, we successfully synthesized 15 structural analogs (2–16) of bromosphaerol (1), decorated with different functional groups. The anti-settlement activity (EC(50)) and the degree of toxicity (LC(50)) of the bromosphaerol derivatives were evaluated using cyprids and nauplii of the cirriped crustacean A. amphitrite as a model organism. Derivatives 2, 4, and 6–16 showed diverse levels of antifouling activity. Among them, compounds 9 and 13 can be considered as well-performing antifoulants, exerting their activity through a non-toxic mechanism.
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spelling pubmed-87814262022-01-22 Synthesis and Antifouling Activity Evaluation of Analogs of Bromosphaerol, a Brominated Diterpene Isolated from the Red Alga Sphaerococcus coronopifolius Prousis, Kyriakos C. Kikionis, Stefanos Ioannou, Efstathia Morgana, Silvia Faimali, Marco Piazza, Veronica Calogeropoulou, Theodora Roussis, Vassilios Mar Drugs Article Marine biofouling is an epibiotic biological process that affects almost any kind of submerged surface, causing globally significant economic problems mainly for the shipping industry and aquaculture companies, and its prevention so far has been associated with adverse environmental effects for non-target organisms. Previously, we have identified bromosphaerol (1), a brominated diterpene isolated from the red alga Sphaerococcus coronopifolius, as a promising agent with significant antifouling activity, exerting strong anti-settlement activity against larvae of Amphibalanus (Balanus) amphitrite and very low toxicity. The significant antifouling activity and low toxicity of bromosphaerol (1) motivated us to explore its chemistry, aiming to optimize its antifouling potential through the preparation of a number of analogs. Following different synthetic routes, we successfully synthesized 15 structural analogs (2–16) of bromosphaerol (1), decorated with different functional groups. The anti-settlement activity (EC(50)) and the degree of toxicity (LC(50)) of the bromosphaerol derivatives were evaluated using cyprids and nauplii of the cirriped crustacean A. amphitrite as a model organism. Derivatives 2, 4, and 6–16 showed diverse levels of antifouling activity. Among them, compounds 9 and 13 can be considered as well-performing antifoulants, exerting their activity through a non-toxic mechanism. MDPI 2021-12-22 /pmc/articles/PMC8781426/ /pubmed/35049862 http://dx.doi.org/10.3390/md20010007 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Prousis, Kyriakos C.
Kikionis, Stefanos
Ioannou, Efstathia
Morgana, Silvia
Faimali, Marco
Piazza, Veronica
Calogeropoulou, Theodora
Roussis, Vassilios
Synthesis and Antifouling Activity Evaluation of Analogs of Bromosphaerol, a Brominated Diterpene Isolated from the Red Alga Sphaerococcus coronopifolius
title Synthesis and Antifouling Activity Evaluation of Analogs of Bromosphaerol, a Brominated Diterpene Isolated from the Red Alga Sphaerococcus coronopifolius
title_full Synthesis and Antifouling Activity Evaluation of Analogs of Bromosphaerol, a Brominated Diterpene Isolated from the Red Alga Sphaerococcus coronopifolius
title_fullStr Synthesis and Antifouling Activity Evaluation of Analogs of Bromosphaerol, a Brominated Diterpene Isolated from the Red Alga Sphaerococcus coronopifolius
title_full_unstemmed Synthesis and Antifouling Activity Evaluation of Analogs of Bromosphaerol, a Brominated Diterpene Isolated from the Red Alga Sphaerococcus coronopifolius
title_short Synthesis and Antifouling Activity Evaluation of Analogs of Bromosphaerol, a Brominated Diterpene Isolated from the Red Alga Sphaerococcus coronopifolius
title_sort synthesis and antifouling activity evaluation of analogs of bromosphaerol, a brominated diterpene isolated from the red alga sphaerococcus coronopifolius
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8781426/
https://www.ncbi.nlm.nih.gov/pubmed/35049862
http://dx.doi.org/10.3390/md20010007
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