Isolation and Structure-Activity Relationship of Subergorgic Acid and Synthesis of Its Derivatives as Antifouling Agent
In this study, as part of our continuous search for environmentally-friendly antifoulants from natural resources, subergorgic acid (SA) was identified from the gorgonian coral <i>Subergorgia suberosa</i>, demonstrating non-toxic, significant inhibitory effects (EC<sub>50</sub>...
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doaj-f7417e4c840141e99c11ceac226ec87a2020-11-24T21:16:11ZengMDPI AGMarine Drugs1660-33972019-02-0117210110.3390/md17020101md17020101Isolation and Structure-Activity Relationship of Subergorgic Acid and Synthesis of Its Derivatives as Antifouling AgentJun Zhang0Wei Ling1Zhiqiang Yang2Yan Liang3Linyan Zhang4Can Guo5Kailing Wang6Balian Zhong7Shihai Xu8Ying Xu9National Engineering Research Center of Navel Orange, Gannan Normal University, Ganzhou 341000, ChinaNational Engineering Research Center of Navel Orange, Gannan Normal University, Ganzhou 341000, ChinaNational Engineering Research Center of Navel Orange, Gannan Normal University, Ganzhou 341000, ChinaNational Engineering Research Center of Navel Orange, Gannan Normal University, Ganzhou 341000, ChinaNational Engineering Research Center of Navel Orange, Gannan Normal University, Ganzhou 341000, ChinaNational Engineering Research Center of Navel Orange, Gannan Normal University, Ganzhou 341000, ChinaCollege of Life Science and Oceanography, Shenzhen University, Shenzhen 518000, ChinaNational Engineering Research Center of Navel Orange, Gannan Normal University, Ganzhou 341000, ChinaDepartment of Chemistry, Jinan University, Guangzhou 510000, ChinaCollege of Life Science and Oceanography, Shenzhen University, Shenzhen 518000, ChinaIn this study, as part of our continuous search for environmentally-friendly antifoulants from natural resources, subergorgic acid (SA) was identified from the gorgonian coral <i>Subergorgia suberosa</i>, demonstrating non-toxic, significant inhibitory effects (EC<sub>50</sub> 1.25 μg/mL, LC<sub>50</sub> > 25 μg/mL) against the settlement of <i>Balanus amphitrite</i>. To further explore the bioactive functional groups of SA and synthesize more potent antifouling compounds based on the lead SA, the structure-activity relationships of SA were studied, followed by rational design and synthesis of two series of SA derivatives (one being benzyl esters of SA and another being SA derivatives containing methylene chains of various lengths). Our results indicated that (1) both the double bond and ketone carbonyl are essential elements responsible for the antifouling effect of SA, while the acid group is not absolutely necessary for maintaining the antifouling effect; (2) all benzyl esters of SA displayed good antifouling effects (EC<sub>50</sub> ranged from 0.30 to 2.50 μg/mL) with the most potent compound being <b>5</b> (EC<sub>50</sub> 0.30 μg/mL, LC<sub>50</sub> > 25 μg/mL), which was over four-fold more potent than SA; and (3) the introduction of a methylene chain into SA reduces the antifouling potency while the length of the methylene chain may differently influence the antifouling effect, depending on the functional group at the opposite site of the methylene chain. Not only has this study successfully revealed the bioactive functional groups of SA, contributing to the mechanism of SA against the settlement of <i>B. amphitrite</i>, but it has also resulted in the identification of a more potent compound <b>5</b>, which might represent a non-toxic, high-efficiency antifoulant.https://www.mdpi.com/1660-3397/17/2/101subergorgic acidantifouling<i>Balanus amphitrite</i>structure-activity relationship |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Jun Zhang Wei Ling Zhiqiang Yang Yan Liang Linyan Zhang Can Guo Kailing Wang Balian Zhong Shihai Xu Ying Xu |
spellingShingle |
Jun Zhang Wei Ling Zhiqiang Yang Yan Liang Linyan Zhang Can Guo Kailing Wang Balian Zhong Shihai Xu Ying Xu Isolation and Structure-Activity Relationship of Subergorgic Acid and Synthesis of Its Derivatives as Antifouling Agent Marine Drugs subergorgic acid antifouling <i>Balanus amphitrite</i> structure-activity relationship |
author_facet |
Jun Zhang Wei Ling Zhiqiang Yang Yan Liang Linyan Zhang Can Guo Kailing Wang Balian Zhong Shihai Xu Ying Xu |
author_sort |
Jun Zhang |
title |
Isolation and Structure-Activity Relationship of Subergorgic Acid and Synthesis of Its Derivatives as Antifouling Agent |
title_short |
Isolation and Structure-Activity Relationship of Subergorgic Acid and Synthesis of Its Derivatives as Antifouling Agent |
title_full |
Isolation and Structure-Activity Relationship of Subergorgic Acid and Synthesis of Its Derivatives as Antifouling Agent |
title_fullStr |
Isolation and Structure-Activity Relationship of Subergorgic Acid and Synthesis of Its Derivatives as Antifouling Agent |
title_full_unstemmed |
Isolation and Structure-Activity Relationship of Subergorgic Acid and Synthesis of Its Derivatives as Antifouling Agent |
title_sort |
isolation and structure-activity relationship of subergorgic acid and synthesis of its derivatives as antifouling agent |
publisher |
MDPI AG |
series |
Marine Drugs |
issn |
1660-3397 |
publishDate |
2019-02-01 |
description |
In this study, as part of our continuous search for environmentally-friendly antifoulants from natural resources, subergorgic acid (SA) was identified from the gorgonian coral <i>Subergorgia suberosa</i>, demonstrating non-toxic, significant inhibitory effects (EC<sub>50</sub> 1.25 μg/mL, LC<sub>50</sub> > 25 μg/mL) against the settlement of <i>Balanus amphitrite</i>. To further explore the bioactive functional groups of SA and synthesize more potent antifouling compounds based on the lead SA, the structure-activity relationships of SA were studied, followed by rational design and synthesis of two series of SA derivatives (one being benzyl esters of SA and another being SA derivatives containing methylene chains of various lengths). Our results indicated that (1) both the double bond and ketone carbonyl are essential elements responsible for the antifouling effect of SA, while the acid group is not absolutely necessary for maintaining the antifouling effect; (2) all benzyl esters of SA displayed good antifouling effects (EC<sub>50</sub> ranged from 0.30 to 2.50 μg/mL) with the most potent compound being <b>5</b> (EC<sub>50</sub> 0.30 μg/mL, LC<sub>50</sub> > 25 μg/mL), which was over four-fold more potent than SA; and (3) the introduction of a methylene chain into SA reduces the antifouling potency while the length of the methylene chain may differently influence the antifouling effect, depending on the functional group at the opposite site of the methylene chain. Not only has this study successfully revealed the bioactive functional groups of SA, contributing to the mechanism of SA against the settlement of <i>B. amphitrite</i>, but it has also resulted in the identification of a more potent compound <b>5</b>, which might represent a non-toxic, high-efficiency antifoulant. |
topic |
subergorgic acid antifouling <i>Balanus amphitrite</i> structure-activity relationship |
url |
https://www.mdpi.com/1660-3397/17/2/101 |
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