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Antifouling activity of portimine, select semisynthetic analogues, and other microalga-derived spirocyclic imines
Cawthron Institute, New Zealand.
University of Gothenburg, Sweden.
Cawthron Institute, New Zealand.
Cawthron Institute, New Zealand.
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2018 (Engelska)Ingår i: Biofouling (Print), ISSN 0892-7014, E-ISSN 1029-2454, Vol. 34, nr 8, s. 950-961Artikel i tidskrift (Refereegranskat) Published
Abstract [en]

A range of natural products from marine invertebrates, bacteria and fungi have been assessed as leads for nature-inspired antifouling (AF) biocides, but little attention has been paid to microalgal-derived compounds. This study assessed the AF activity of the spirocyclic imine portimine (1), which is produced by the benthic mat-forming dinoflagellate Vulcanodinium rugosum. Portimine displayed potent AF activity in a panel of four macrofouling bioassays (EC50 0.06–62.5 ng ml−1), and this activity was distinct from that of the related compounds gymnodimine-A (2), 13-desmethyl spirolide C (3), and pinnatoxin-F (4). The proposed mechanism of action for portimine is induction of apoptosis, based on the observation that portimine inhibited macrofouling organisms at developmental stages known to involve apoptotic processes. Semisynthetic modification of select portions of the portimine molecule was subsequently undertaken. Observed changes in bioactivity of the resulting semisynthetic analogues of portimine were consistent with portimine’s unprecedented 5-membered imine ring structure playing a central role in its AF activity.

Ort, förlag, år, upplaga, sidor
2018. Vol. 34, nr 8, s. 950-961
Nyckelord [en]
Bioassay, biofouling, microalgae, natural product, portimine
Nationell ämneskategori
Kemiteknik
Identifikatorer
URN: urn:nbn:se:ri:diva-37308DOI: 10.1080/08927014.2018.1514461Scopus ID: 2-s2.0-85058480982OAI: oai:DiVA.org:ri-37308DiVA, id: diva2:1280188
Tillgänglig från: 2019-01-18 Skapad: 2019-01-18 Senast uppdaterad: 2019-03-29Bibliografiskt granskad

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