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Probing the Structure-Activity Relationship of the Natural Antifouling Agent Polygodial against both Micro- and Macrofoulers by Semisynthetic Modification

Journal article
Authors L. W. K. Moodie
R. Trepos
Gunnar Cervin
L. Larsen
D. S. Larsen
Henrik Pavia
C. Hellio
P. Cahill
J. Svenson
Published in Journal of Natural Products
Volume 80
Issue 2
Pages 515-525
ISSN 0163-3864
Publication year 2017
Published at Department of marine sciences
Pages 515-525
Language en
Keywords barnacle balanus-improvisus, resistant cancer-cells, drimane, sesquiterpenoids, saccharomyces-cerevisiae, ciona-intestinalis, antimicrobial peptides, bacterial attachment, nordrimane compounds, antifeedant activity, synthetic analogs, Plant Sciences, Pharmacology & Pharmacy, icago, il, v13, p6742
Subject categories Zoology

Abstract

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.

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Utskriftsdatum: 2020-07-05