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  • 1.
    Carstens, Bodil B.
    et al.
    University of Queensland, Australia.
    Rosengren, K. Johan
    University of Queensland, Australia.
    Gunasekera, Sunithi
    Uppsala University, Sweden.
    Schempp, Stefanie
    Uppsala University, Sweden.
    Bohlin, Lars
    Uppsala University, Sweden.
    Dahlström, Mia
    RISE, SP – Sveriges Tekniska Forskningsinstitut, SP Kemi Material och Ytor, Material och ytteknik.
    Clark, Richard J.
    University of Queensland, Australia.
    Göransson, Ulf
    Uppsala University, Sweden.
    Isolation, characterization, and synthesis of the Barrettides: disulfide-containing peptides from the marine sponge Geodia barretti2015In: Journal of Natural Products, ISSN 0163-3864, E-ISSN 1520-6025, Vol. 78, no 8, p. 1886-1893Article in journal (Refereed)
    Abstract [en]

    Two disulfide-containing peptides, barrettides A (1) and B (2), from the cold-water marine sponge Geodia barretti are described. Those 31 amino acid residue long peptides were sequenced using mass spectrometry methods and structurally characterized using NMR spectroscopy. The structure of 1 was confirmed by total synthesis using the solid-phase peptide synthesis approach that was developed. The two peptides were found to differ only at a single position in their sequence. The three-dimensional structure of 1 revealed that these peptides possess a unique fold consisting of a long β-hairpin structure that is cross-braced by two disulfide bonds in a ladder-like arrangement. The peptides are amphipathic in nature with the hydrophobic and charged residues clustered on separate faces of the molecule. The barrettides were found not to inhibit the growth of either Escherichia coli or Staphylococcus aureus but displayed antifouling activity against barnacle larvae (Balanus improvisus) without lethal effects in the concentrations tested. (Figure Presented).

  • 2.
    Moodie, Lindon W. K.
    et al.
    UiT The Arctic University of Norway, Norway.
    Trepos, Rozenn
    Université de Bretagne Occidentale, France.
    Cervin, Gunnar
    University of Gothenburg, Sweden.
    Brathen, Kari Anne
    UiT The Arctic University of Norway, Norway.
    Lindgard, Bente
    UiT The Arctic University of Norway, Norway.
    Reiersen, Rigmor
    UiT The Arctic University of Norway, Norway.
    Cahill, Patrick
    Cawthron Institute, New Zealand.
    Pavia, Henrik
    University of Gothenburg, Sweden.
    Hellio, Clair
    Université de Bretagne Occidentale, France.
    Svenson, Johan
    RISE - Research Institutes of Sweden, Bioscience and Materials, Chemistry and Materials. UiT The Arctic University of Norway, Norway.
    Prevention of Marine Biofouling Using the Natural Allelopathic Compound Batatasin-III and Synthetic Analogues2017In: Journal of Natural Products, ISSN 0163-3864, E-ISSN 1520-6025, Vol. 80, no 7, p. 2001-2011Article in journal (Refereed)
    Abstract [en]

    The current study reports the first comprehensive evaluation of a class of allelopathic terrestrial natural products as antifoulants in a marine setting. To investigate the antifouling potential of the natural dihydrostilbene scaffold, a library of 22 synthetic dihydrostilbenes with varying substitution patterns, many of which occur naturally in terrestrial plants, were prepared and assessed for their antifouling capacity. The compounds were evaluated in an extensive screen against 16 fouling marine organisms. The dihydrostilbene scaffold was shown to possess powerful general antifouling effects against both marine microfoulers and macrofoulers with inhibitory activities at low concentrations. The species of microalgae examined displayed a particular sensitivity toward the evaluated compounds at low ng/mL concentrations. It was shown that several of the natural and synthetic compounds exerted their repelling activities via nontoxic and reversible mechanisms. The activities of the most active compounds such as 3,5-dimethoxybibenzyl (5), 3,4-dimethoxybibenzyl (9), and 3-hydroxy-3′,4,5′-trimethoxybibenzyl (20) were comparable to the commercial antifouling booster biocide Sea-nine, which was employed as a positive control. The investigation of terrestrial allelopathic natural products to counter marine fouling represents a novel strategy for the design of "green" antifouling technologies, and these compounds offer a potential alternative to traditional biocidal antifoulants.

  • 3.
    Moodie, Lindon W. K.
    et al.
    UiT The Arctic University of Norway, Norway.
    Trepos, Rozenn
    Université de Bretagne Occidentale, France.
    Cervin, Gunnar
    University of Gothenburg, Sweden.
    Larsen, Lesley
    University of Otago, New Zealand.
    Larsen, David S.
    University of Otago, New Zealand.
    Pavia, Henrik
    University of Gothenburg, Sweden.
    Hellio, Claire
    Université de Bretagne Occidentale, France.
    Cahill, Patrick
    Cawthron Institute, New Zealand.
    Svenson, Johan
    RISE - Research Institutes of Sweden, Bioscience and Materials, Chemistry, Materials and Surfaces. UiT The Arctic University of Norway, Norway.
    Probing the Structure-Activity Relationship of the Natural Antifouling Agent Polygodial against both Micro- and Macrofoulers by Semisynthetic Modification2017In: Journal of natural products (Print), ISSN 0163-3864, E-ISSN 1520-6025, Vol. 80, no 2, p. 515-525Article in journal (Refereed)
    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.

  • 4. Tadesse, M
    et al.
    Svenson, J
    RISE, SP – Sveriges Tekniska Forskningsinstitut, SP Kemi Material och Ytor.
    Sepčić, K
    Trembleau, L
    Engqvist, M
    Andersen, J H
    Isolation and synthesis of pulmonarin A and B, acetylcholinesterase inhibitors from the colonial ascidian Synoicum pulmonaria2014In: Journal of natural products (Print), ISSN 0163-3864, E-ISSN 1520-6025, Vol. 77, no 2, p. 364-369Article in journal (Refereed)
    Abstract [en]

    Pulmonarins A and B are two new dibrominated marine acetylcholinesterase inhibitors that were isolated and characterized from the sub-Arctic ascidian Synoicum pulmonaria collected off the Norwegian coast. The structures of natural pulmonarins A and B were tentatively elucidated by spectroscopic methods and later verified by comparison with synthetically prepared material. Both pulmonarins A and B displayed reversible, noncompetitive acetylcholinesterase inhibition comparable to several known natural acetylcholinesterase inhibitiors. Pulmonarin B was the strongest inhibitor, with an inhibition constant (Ki) of 20 μM. In addition to reversible, noncompetitive acetylcholinesterase inhibition, the compounds displayed weak antibacterial activity but no cytotoxicity or other investigated bioactivities.

1 - 4 of 4
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