Probing the Structure-Activity Relationship of the Natural Antifouling Agent Polygodial against both Micro- and Macrofoulers by Semisynthetic Modification.
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.
Department of Chemistry, UiT The Arctic University of Norway , Breivika, N-9037, Tromsø, Norway.
Lindon W K
LW
Moodie
Biodimar LEMAR UMR 6539, Université de Bretagne Occidentale , 6 Avenue le Gorgeu, 29200 Brest, France.
Rozenn
R
Trepos
Department of Marine Sciences - Tjärnö, University of Gothenburg , SE-452 96 Strömstad, Sweden.
Gunnar
G
Cervin
Department of Chemistry, University of Otago , P.O. Box 56, Dunedin, New Zealand.
Lesley
L
Larsen
Department of Chemistry, University of Otago , P.O. Box 56, Dunedin, New Zealand.
David S
DS
Larsen
Department of Marine Sciences - Tjärnö, University of Gothenburg , SE-452 96 Strömstad, Sweden.
Henrik
H
Pavia
Biodimar LEMAR UMR 6539, Université de Bretagne Occidentale , 6 Avenue le Gorgeu, 29200 Brest, France.
Claire
C
Hellio
Cawthron Institute , 98 Halifax Street East, Nelson 7010, New Zealand.
Patrick
P
Cahill
Department of Chemistry, UiT The Arctic University of Norway , Breivika, N-9037, Tromsø, Norway.|Department of Chemistry, Material and Surfaces, SP Technical Research Institute of Sweden , Box 857, SE-501 15 Borås, Sweden.
Johan
0000-0002-4729-9359
J
Svenson
D000818:Animals; D001419:Bacteria / Q000187:drug effects; D057219:Biofouling; D007814:Larva / Q000187:drug effects; D015394:Molecular Structure; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D001468:Thoracica / Q000187:drug effects*; D014561:Urochordata / Q000187:drug effects*
D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; C437376:drimane; C034380:polygodial