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Phidianidine A and synthetic analogues as naturally inspired marine antifoulants
UiT The Arctic University of Norway, Norway.
UiT The Arctic University of Norway, Norway.
UiT The Arctic University of Norway, Norway.
University of Gothenburg, Sweden.
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2020 (English)In: Journal of Natural Products, ISSN 0163-3864, E-ISSN 1520-6025, Vol. 83, no 11, p. 3413-3423Article in journal (Refereed) Published
Abstract [en]

Stationary and slow-moving marine organisms regularly employ a natural product chemical defense to prevent being colonized by marine micro- and macroorganisms. While these natural antifoulants can be structurally diverse, they often display highly conserved chemistries and physicochemical properties, suggesting a natural marine antifouling pharmacophore. In our current report, we investigate the marine natural product phidianidine A, which displays several chemical properties found in highly potent marine antifoulants. Phidianidine A and synthetic analogues were screened against the settlement and metamorphosis of Amphibalanus improvisus cyprids, and several of the compounds displayed inhibitory activities at low micromolar concentrations with IC50 values down to 0.7 μg/mL observed. The settlement study highlights that phidianidine A is a potent natural antifoulant and that the scaffold can be tuned to generate simpler and improved synthetic analogues. The bioactivity is closely linked to the size of the compound and to its basicity. The study also illustrates that active analogues can be prepared in the absence of the natural constrained 1,2,4-oxadiazole ring. A synthetic lead analogue of phidianidine A was incorporated in a coating and included in antifouling field trials, where it was shown that the coating induced potent inhibition of marine bacteria and microalgae settlement.

Place, publisher, year, edition, pages
American Chemical Society , 2020. Vol. 83, no 11, p. 3413-3423
National Category
Engineering and Technology
Identifiers
URN: urn:nbn:se:ri:diva-50996DOI: 10.1021/acs.jnatprod.0c00881Scopus ID: 2-s2.0-85096227269OAI: oai:DiVA.org:ri-50996DiVA, id: diva2:1508278
Note

Funding details: Göteborgs Universitet; Funding details: Norges Forskningsråd, ES508288, 275043; Funding text 1: For C.L., J.H.H., J.S., and V.E., this work was partly supported with grants from the Norwegian Research Council (ES508288 and 275043 CasCat). L.W.K.M. acknowledges the Uppsala Antibiotic Centre for support. 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. Finally, the authors are grateful to V. Bhave (TOC) for providing the image of Phidiana militaris.

Available from: 2020-12-10 Created: 2020-12-10 Last updated: 2021-03-26Bibliographically approved

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