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Antifouling activity of portimine, select semisynthetic analogues, and other microalga-derived spirocyclic imines

Journal article
Authors Darby G. Brooke
Gunnar Cervin
Olivier Champeau
D. Tim Harwood
Henrik Pavia
Andrew I. Selwood
Johan Svenson
Louis A. Tremblay
Patrick L. Cahill
Published in Biofouling
Volume 34
Pages 950-961
ISSN 08927014
Publication year 2018
Published at Department of marine sciences
Pages 950-961
Language en
Keywords Bioassay, biofouling, microalgae, natural product, portimine
Subject categories Marine ecology, Chemical Engineering

Abstract

© 2018, © 2018 Informa UK Limited, trading as Taylor & Francis Group. 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 (EC 50 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.

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