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Probing the Structure-Activity Relationship of the Natural Antifouling Agent Polygodial against both Micro- and Macrofoulers by Semisynthetic Modification
Umeå University, Faculty of Science and Technology, Department of Chemistry. Department of Chemistry, UiT The Arctic University of Norway, Breivika, N-9037, Tromsø, Norway.
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2017 (English)In: Journal of natural products (Print), ISSN 0163-3864, E-ISSN 1520-6025, Vol. 80, no 2, 515-525 p.Article in journal (Refereed) Published
Abstract [en]

The current study represents the first comprehensive investigation into the general antifouling activities of the natural drimane sesquiterpene polygodial. Previous studies have highlighted a high antifouling effect toward macrofoulers, such as ascidians, tubeworms, and mussels, but no reports about the general antifouling effect of polygodial have been communicated before. To probe the structural and chemical basis for antifouling activity, a library of 11 polygodial analogues was prepared by semisynthesis. The library was designed to yield derivatives with ranging polarities and the ability to engage in both covalent and noncovalent interactions, while still remaining within the drimane sesquiterpene scaffold. The prepared compounds were screened against 14 relevant marine micro- and macrofouling species. Several of the polygodial analogues displayed inhibitory activities at sub-microgram/mL concentrations. These antifouling effects were most pronounced against the macrofouling ascidian Ciona savignyi and the barnacle Balanus improvisus, with inhibitory activities observed for selected compounds comparable or superior to several commercial antifouling products. The inhibitory activity against the microfouling bacteria and microalgae was reversible and significantly less pronounced than for the macrofoulers. This study illustrates that the macro- and microfoulers are targeted by the compounds via different mechanisms.

Place, publisher, year, edition, pages
AMER CHEMICAL SOC , 2017. Vol. 80, no 2, 515-525 p.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:umu:diva-132819DOI: 10.1021/acs.jnatprod.6b01056ISI: 000395046900033PubMedID: 28170258OAI: oai:DiVA.org:umu-132819DiVA: diva2:1092927
Available from: 2017-05-04 Created: 2017-05-04 Last updated: 2017-05-04Bibliographically approved

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Moodie, Lindon W. K.
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CiteExportLink to record
Permanent link

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Cite
Citation style
  • apa
  • harvard1
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
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  • de-DE
  • en-GB
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More languages
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