Cargando…
Antifouling phenyl ethers and other compounds from the invertebrates and their symbiotic fungi collected from the South China Sea
Marine organism-derived secondary metabolites are promising potential sources for discovering environmentally safe antifouling agents. In present study, 55 marine secondary metabolites and their synthesized derivatives were tested and evaluated for their antifouling activities and security. These co...
Autores principales: | , , , , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Springer Berlin Heidelberg
2016
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5081312/ https://www.ncbi.nlm.nih.gov/pubmed/27785778 http://dx.doi.org/10.1186/s13568-016-0272-2 |
_version_ | 1782462863414132736 |
---|---|
author | Wang, Chao-Yi Wang, Kai-Ling Qian, Pei-Yuan Xu, Ying Chen, Min Zheng, Juan-Juan Liu, Min Shao, Chang-Lun Wang, Chang-Yun |
author_facet | Wang, Chao-Yi Wang, Kai-Ling Qian, Pei-Yuan Xu, Ying Chen, Min Zheng, Juan-Juan Liu, Min Shao, Chang-Lun Wang, Chang-Yun |
author_sort | Wang, Chao-Yi |
collection | PubMed |
description | Marine organism-derived secondary metabolites are promising potential sources for discovering environmentally safe antifouling agents. In present study, 55 marine secondary metabolites and their synthesized derivatives were tested and evaluated for their antifouling activities and security. These compounds include 44 natural products isolated from marine invertebrates and their symbiotic microorganisms collected from the South China Sea and 11 structural modified products derived from the isolated compounds. The natural secondary metabolites, covering phenyl ether derivatives, terpenoids, 9, 11-secosteroids, anthraquinones, alkaloids, nucleoside derivatives and peptides, were isolated from two corals, one sponge and five symbiotic fungi. All of the isolated and synthesized compounds were tested for their antifouling activities against the cyprids of barnacle Balanus (Amphibalanus) amphitrite Darwin. Noticeably, five phenyl ether derivatives (9, 11, 13–15) exhibited potent anti-larval settlement activity with the EC(50) values lower than 3.05 μM and the LC(50)/EC(50) ratios higher than 15. The study of structure–activity relationship (SAR) revealed that the introduction of acetoxy groups and bromine atoms to phenyl ether derivatives could significantly improve their antifouling activities. This is the first report on the SAR of phenyl ether derivatives on antifouling activity against barnacle B. amphitrite. The polybrominated diphenyl ether derivative, 2, 4, 6, 2′, 4′, 6′-hexabromo-diorcinol (13), which displayed excellent antifouling activity, was considered as a promising candidate of environmentally friendly antifouling agents. ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (doi:10.1186/s13568-016-0272-2) contains supplementary material, which is available to authorized users. |
format | Online Article Text |
id | pubmed-5081312 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | Springer Berlin Heidelberg |
record_format | MEDLINE/PubMed |
spelling | pubmed-50813122016-11-10 Antifouling phenyl ethers and other compounds from the invertebrates and their symbiotic fungi collected from the South China Sea Wang, Chao-Yi Wang, Kai-Ling Qian, Pei-Yuan Xu, Ying Chen, Min Zheng, Juan-Juan Liu, Min Shao, Chang-Lun Wang, Chang-Yun AMB Express Original Article Marine organism-derived secondary metabolites are promising potential sources for discovering environmentally safe antifouling agents. In present study, 55 marine secondary metabolites and their synthesized derivatives were tested and evaluated for their antifouling activities and security. These compounds include 44 natural products isolated from marine invertebrates and their symbiotic microorganisms collected from the South China Sea and 11 structural modified products derived from the isolated compounds. The natural secondary metabolites, covering phenyl ether derivatives, terpenoids, 9, 11-secosteroids, anthraquinones, alkaloids, nucleoside derivatives and peptides, were isolated from two corals, one sponge and five symbiotic fungi. All of the isolated and synthesized compounds were tested for their antifouling activities against the cyprids of barnacle Balanus (Amphibalanus) amphitrite Darwin. Noticeably, five phenyl ether derivatives (9, 11, 13–15) exhibited potent anti-larval settlement activity with the EC(50) values lower than 3.05 μM and the LC(50)/EC(50) ratios higher than 15. The study of structure–activity relationship (SAR) revealed that the introduction of acetoxy groups and bromine atoms to phenyl ether derivatives could significantly improve their antifouling activities. This is the first report on the SAR of phenyl ether derivatives on antifouling activity against barnacle B. amphitrite. The polybrominated diphenyl ether derivative, 2, 4, 6, 2′, 4′, 6′-hexabromo-diorcinol (13), which displayed excellent antifouling activity, was considered as a promising candidate of environmentally friendly antifouling agents. ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (doi:10.1186/s13568-016-0272-2) contains supplementary material, which is available to authorized users. Springer Berlin Heidelberg 2016-10-26 /pmc/articles/PMC5081312/ /pubmed/27785778 http://dx.doi.org/10.1186/s13568-016-0272-2 Text en © The Author(s) 2016 Open AccessThis article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. |
spellingShingle | Original Article Wang, Chao-Yi Wang, Kai-Ling Qian, Pei-Yuan Xu, Ying Chen, Min Zheng, Juan-Juan Liu, Min Shao, Chang-Lun Wang, Chang-Yun Antifouling phenyl ethers and other compounds from the invertebrates and their symbiotic fungi collected from the South China Sea |
title | Antifouling phenyl ethers and other compounds from the invertebrates and their symbiotic fungi collected from the South China Sea |
title_full | Antifouling phenyl ethers and other compounds from the invertebrates and their symbiotic fungi collected from the South China Sea |
title_fullStr | Antifouling phenyl ethers and other compounds from the invertebrates and their symbiotic fungi collected from the South China Sea |
title_full_unstemmed | Antifouling phenyl ethers and other compounds from the invertebrates and their symbiotic fungi collected from the South China Sea |
title_short | Antifouling phenyl ethers and other compounds from the invertebrates and their symbiotic fungi collected from the South China Sea |
title_sort | antifouling phenyl ethers and other compounds from the invertebrates and their symbiotic fungi collected from the south china sea |
topic | Original Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5081312/ https://www.ncbi.nlm.nih.gov/pubmed/27785778 http://dx.doi.org/10.1186/s13568-016-0272-2 |
work_keys_str_mv | AT wangchaoyi antifoulingphenylethersandothercompoundsfromtheinvertebratesandtheirsymbioticfungicollectedfromthesouthchinasea AT wangkailing antifoulingphenylethersandothercompoundsfromtheinvertebratesandtheirsymbioticfungicollectedfromthesouthchinasea AT qianpeiyuan antifoulingphenylethersandothercompoundsfromtheinvertebratesandtheirsymbioticfungicollectedfromthesouthchinasea AT xuying antifoulingphenylethersandothercompoundsfromtheinvertebratesandtheirsymbioticfungicollectedfromthesouthchinasea AT chenmin antifoulingphenylethersandothercompoundsfromtheinvertebratesandtheirsymbioticfungicollectedfromthesouthchinasea AT zhengjuanjuan antifoulingphenylethersandothercompoundsfromtheinvertebratesandtheirsymbioticfungicollectedfromthesouthchinasea AT liumin antifoulingphenylethersandothercompoundsfromtheinvertebratesandtheirsymbioticfungicollectedfromthesouthchinasea AT shaochanglun antifoulingphenylethersandothercompoundsfromtheinvertebratesandtheirsymbioticfungicollectedfromthesouthchinasea AT wangchangyun antifoulingphenylethersandothercompoundsfromtheinvertebratesandtheirsymbioticfungicollectedfromthesouthchinasea |