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Probing the Structure-Activity Relationship of the Natural Antifouling Agent Polygodial against both Micro- and Macrofoulers by Semisynthetic Modification
UiT The Arctic University of Norway, Norway.
Université de Bretagne Occidentale, France.
University of Gothenburg, Sweden.
University of Otago, New Zealand.
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2017 (English)In: Journal of natural products (Print), ISSN 0163-3864, E-ISSN 1520-6025, Vol. 80, no 2, p. 515-525Article 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
2017. Vol. 80, no 2, p. 515-525
Keywords [en]
drimane, polygodial, sesquiterpene, animal, bacterium, barnacle, biofouling, chemical structure, chemistry, drug effects, larva, structure activity relation, Urochordata, Animals, Bacteria, Molecular Structure, Sesquiterpenes, Structure-Activity Relationship, Thoracica
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Natural Sciences
Identifiers
URN: urn:nbn:se:ri:diva-31029DOI: 10.1021/acs.jnatprod.6b01056Scopus ID: 2-s2.0-85013796739OAI: oai:DiVA.org:ri-31029DiVA, id: diva2:1138210
Note

 Funding details: MBIE, Ministry of Business, Innovation and Employment; Funding text: This work was partly supported with grants from the Norwegian Research Council (ES508288), and J.S. and L.W.K.M. are grateful for stipend support. J.S. was supported further by a VINNMER M.C. incoming grant from VINNOVA (Grant 2014-01435). H.P. and G.C. were supported by the Centre for Marine Chemical Ecology (http://www.cemace.science.gu.se) at the University of Gothenburg. The authors are grateful to the New Zealand Ministry of Business, Innovation and Employment (MBIE) for funding the Biocide Tool Box research program (UOAX1410), which supported the involvement of P.C. in this research project.

Available from: 2017-09-04 Created: 2017-09-04 Last updated: 2017-09-04Bibliographically approved

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