Amphidinol C,a major polyketide from an Irish strain of the dinoflagellate Amphidinium carterae |
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Affiliation: | 1. School of Biological and Chemical Sciences, Ryan Institute, National University of Ireland Galway (NUI Galway), University Road, H91 TK33 Galway, Ireland;2. School of Science, Department of Environmental Science, Centre for Environmental Research, Sustainability and Innovation, Institute of Technology Sligo, Ash Ln, Ballytivnan, F91 YW50 Sligo, Ireland;3. Microbiology Section, Department of Biomedical and Biotechnological Sciences, University of Catania, Torre Biologica, Via Santa Sofia n. 97, 95123 Catania, Italy |
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Abstract: | An Irish strain of the dinoflagellate Amphidinium carterae was previously shown to produce antibacterial amphidinol derivatives of unknown masses. Inspection of the major metabolites present in a bulk culture of this strain led to the isolation and structure elucidation of a new amphidinol derivative named amphidinol C featuring an unprecedented tetrahydropyran ring between the positions C-7 and C-11. The structure was determined using extensive analyses of NMR and MS data and comparison with data of analogues. The new ring was proposed to stem from a nucleophilic substitution of the sulphate present on the side chain of Amphidinol B. The major metabolites isolated were tested for their antibacterial and antifungal activities and Amphidinol C showed moderate fungicidal activity against yeast and filamentous fungi at 8–16 µg mL−1. |
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Keywords: | Amphidinol Fungicidal Polyketide |
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