From Natural Xanthones to Synthetic C-1 Aminated 3,4-Dioxygenated Xanthones as Optimized Antifouling Agents

Biofouling, which occurs when certain marine species attach and accumulate in artificial submerged structures, represents a serious economic and environmental issue worldwide. The discovery of new non-toxic and eco-friendly antifouling systems to control or prevent biofouling is, therefore, a practi...

Descripción completa

Guardado en:

Detalles Bibliográficos
Autores principales:	Diana I. S. P. Resende, Joana R. Almeida, Sandra Pereira, Alexandre Campos, Agostinho Lemos, Jeffrey E. Plowman, Ancy Thomas, Stefan Clerens, Vitor Vasconcelos, Madalena Pinto, Marta Correia-da-Silva, Emília Sousa
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	xanthones anti-settlement antifouling molecular targets eco-friendly alternatives Biology (General) QH301-705.5
Acceso en línea:	https://doaj.org/article/00ab613a30dc4b64a8042500bf39ede4
Etiquetas:	Agregar Etiqueta Sin Etiquetas, Sea el primero en etiquetar este registro!

id	oai:doaj.org-article:00ab613a30dc4b64a8042500bf39ede4
record_format	dspace
spelling	oai:doaj.org-article:00ab613a30dc4b64a8042500bf39ede42021-11-25T18:12:59ZFrom Natural Xanthones to Synthetic C-1 Aminated 3,4-Dioxygenated Xanthones as Optimized Antifouling Agents10.3390/md191106381660-3397https://doaj.org/article/00ab613a30dc4b64a8042500bf39ede42021-11-01T00:00:00Zhttps://www.mdpi.com/1660-3397/19/11/638https://doaj.org/toc/1660-3397Biofouling, which occurs when certain marine species attach and accumulate in artificial submerged structures, represents a serious economic and environmental issue worldwide. The discovery of new non-toxic and eco-friendly antifouling systems to control or prevent biofouling is, therefore, a practical and urgent need. In this work, the antifouling activity of a series of 24 xanthones, with chemical similarities to natural products, was exploited. Nine (<b>1</b>, <b>2</b>, <b>4</b>, <b>6</b>, <b>8</b>, <b>16</b>, <b>19</b>, <b>21</b>, and <b>23</b>) of the tested xanthones presented highly significant anti-settlement responses at 50 μM against the settlement of mussel <i>Mytilus galloprovincialis</i> larvae and low toxicity to this macrofouling species. Xanthones <b>21</b> and <b>23</b> emerged as the most effective larval settlement inhibitors (EC<sub>50</sub> = 7.28 and 3.57 µM, respectively). Additionally, xanthone <b>23</b> exhibited a therapeutic ratio (LC<sub>50</sub>/EC<sub>50</sub>) > 15, as required by the US Navy program attesting its suitability as natural antifouling agents. From the nine tested xanthones, none of the compounds were found to significantly inhibit the growth of the marine biofilm-forming bacterial strains tested. Xanthones <b>4</b>, <b>6</b>, <b>8</b>, <b>16</b>, <b>19</b>, <b>21</b>, and <b>23</b> were found to be non-toxic to the marine non-target species <i>Artemia salina</i> (<10% mortality at 50 μM). Insights on the antifouling mode of action of the hit xanthones <b>21</b> and <b>23</b> suggest that these two compounds affected similar molecular targets and cellular processes in mussel larvae, including that related to mussel adhesion capacity. This work exposes for the first time the relevance of C-1 aminated xanthones with a 3,4-dioxygenated pattern of substitution as new non-toxic products to prevent marine biofouling.Diana I. S. P. ResendeJoana R. AlmeidaSandra PereiraAlexandre CamposAgostinho LemosJeffrey E. PlowmanAncy ThomasStefan ClerensVitor VasconcelosMadalena PintoMarta Correia-da-SilvaEmília SousaMDPI AGarticlexanthonesanti-settlementantifoulingmolecular targetseco-friendly alternativesBiology (General)QH301-705.5ENMarine Drugs, Vol 19, Iss 638, p 638 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	xanthones anti-settlement antifouling molecular targets eco-friendly alternatives Biology (General) QH301-705.5
spellingShingle	xanthones anti-settlement antifouling molecular targets eco-friendly alternatives Biology (General) QH301-705.5 Diana I. S. P. Resende Joana R. Almeida Sandra Pereira Alexandre Campos Agostinho Lemos Jeffrey E. Plowman Ancy Thomas Stefan Clerens Vitor Vasconcelos Madalena Pinto Marta Correia-da-Silva Emília Sousa From Natural Xanthones to Synthetic C-1 Aminated 3,4-Dioxygenated Xanthones as Optimized Antifouling Agents
description	Biofouling, which occurs when certain marine species attach and accumulate in artificial submerged structures, represents a serious economic and environmental issue worldwide. The discovery of new non-toxic and eco-friendly antifouling systems to control or prevent biofouling is, therefore, a practical and urgent need. In this work, the antifouling activity of a series of 24 xanthones, with chemical similarities to natural products, was exploited. Nine (<b>1</b>, <b>2</b>, <b>4</b>, <b>6</b>, <b>8</b>, <b>16</b>, <b>19</b>, <b>21</b>, and <b>23</b>) of the tested xanthones presented highly significant anti-settlement responses at 50 μM against the settlement of mussel <i>Mytilus galloprovincialis</i> larvae and low toxicity to this macrofouling species. Xanthones <b>21</b> and <b>23</b> emerged as the most effective larval settlement inhibitors (EC<sub>50</sub> = 7.28 and 3.57 µM, respectively). Additionally, xanthone <b>23</b> exhibited a therapeutic ratio (LC<sub>50</sub>/EC<sub>50</sub>) > 15, as required by the US Navy program attesting its suitability as natural antifouling agents. From the nine tested xanthones, none of the compounds were found to significantly inhibit the growth of the marine biofilm-forming bacterial strains tested. Xanthones <b>4</b>, <b>6</b>, <b>8</b>, <b>16</b>, <b>19</b>, <b>21</b>, and <b>23</b> were found to be non-toxic to the marine non-target species <i>Artemia salina</i> (<10% mortality at 50 μM). Insights on the antifouling mode of action of the hit xanthones <b>21</b> and <b>23</b> suggest that these two compounds affected similar molecular targets and cellular processes in mussel larvae, including that related to mussel adhesion capacity. This work exposes for the first time the relevance of C-1 aminated xanthones with a 3,4-dioxygenated pattern of substitution as new non-toxic products to prevent marine biofouling.
format	article
author	Diana I. S. P. Resende Joana R. Almeida Sandra Pereira Alexandre Campos Agostinho Lemos Jeffrey E. Plowman Ancy Thomas Stefan Clerens Vitor Vasconcelos Madalena Pinto Marta Correia-da-Silva Emília Sousa
author_facet	Diana I. S. P. Resende Joana R. Almeida Sandra Pereira Alexandre Campos Agostinho Lemos Jeffrey E. Plowman Ancy Thomas Stefan Clerens Vitor Vasconcelos Madalena Pinto Marta Correia-da-Silva Emília Sousa
author_sort	Diana I. S. P. Resende
title	From Natural Xanthones to Synthetic C-1 Aminated 3,4-Dioxygenated Xanthones as Optimized Antifouling Agents
title_short	From Natural Xanthones to Synthetic C-1 Aminated 3,4-Dioxygenated Xanthones as Optimized Antifouling Agents
title_full	From Natural Xanthones to Synthetic C-1 Aminated 3,4-Dioxygenated Xanthones as Optimized Antifouling Agents
title_fullStr	From Natural Xanthones to Synthetic C-1 Aminated 3,4-Dioxygenated Xanthones as Optimized Antifouling Agents
title_full_unstemmed	From Natural Xanthones to Synthetic C-1 Aminated 3,4-Dioxygenated Xanthones as Optimized Antifouling Agents
title_sort	from natural xanthones to synthetic c-1 aminated 3,4-dioxygenated xanthones as optimized antifouling agents
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/00ab613a30dc4b64a8042500bf39ede4
work_keys_str_mv	AT dianaispresende fromnaturalxanthonestosyntheticc1aminated34dioxygenatedxanthonesasoptimizedantifoulingagents AT joanaralmeida fromnaturalxanthonestosyntheticc1aminated34dioxygenatedxanthonesasoptimizedantifoulingagents AT sandrapereira fromnaturalxanthonestosyntheticc1aminated34dioxygenatedxanthonesasoptimizedantifoulingagents AT alexandrecampos fromnaturalxanthonestosyntheticc1aminated34dioxygenatedxanthonesasoptimizedantifoulingagents AT agostinholemos fromnaturalxanthonestosyntheticc1aminated34dioxygenatedxanthonesasoptimizedantifoulingagents AT jeffreyeplowman fromnaturalxanthonestosyntheticc1aminated34dioxygenatedxanthonesasoptimizedantifoulingagents AT ancythomas fromnaturalxanthonestosyntheticc1aminated34dioxygenatedxanthonesasoptimizedantifoulingagents AT stefanclerens fromnaturalxanthonestosyntheticc1aminated34dioxygenatedxanthonesasoptimizedantifoulingagents AT vitorvasconcelos fromnaturalxanthonestosyntheticc1aminated34dioxygenatedxanthonesasoptimizedantifoulingagents AT madalenapinto fromnaturalxanthonestosyntheticc1aminated34dioxygenatedxanthonesasoptimizedantifoulingagents AT martacorreiadasilva fromnaturalxanthonestosyntheticc1aminated34dioxygenatedxanthonesasoptimizedantifoulingagents AT emiliasousa fromnaturalxanthonestosyntheticc1aminated34dioxygenatedxanthonesasoptimizedantifoulingagents
_version_	1718411479056646144

From Natural Xanthones to Synthetic C-1 Aminated 3,4-Dioxygenated Xanthones as Optimized Antifouling Agents

Ejemplares similares