Isolation and structural characterisation of two antibacterial free fatty acids from the marine diatom, <Emphasis Type="Italic">Phaeodactylum tricornutum</Emphasis> |
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Authors: | Andrew P Desbois Tomas Lebl Liming Yan Valerie J Smith |
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Institution: | (1) Gatty Marine Laboratory, School of Biology, University of St Andrews, Fife, Scotland;(2) Purdie Building, School of Chemistry, University of St Andrews, Fife, Scotland;(3) Aquapharm Bio-Discovery Limited, European Centre for Marine Biotechnology, Dunstaffnage Marine Laboratory, Oban, Argyll, Scotland;(4) Present address: Centre for Biomolecular Sciences, School of Biology, University of St Andrews, Fife, Scotland |
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Abstract: | One solution to the global crisis of antibiotic resistance is the discovery of novel antimicrobial compounds for clinical
application. Marine organisms are an attractive and, as yet, relatively untapped resource of new natural products. Cell extracts
from the marine diatom, Phaeodactylum tricornutum, have antibacterial activity and the fatty acid, eicosapentaenoic acid (EPA), has been identified as one compound responsible
for this activity. During the isolation of EPA, it became apparent that the extracts contained further antibacterial compounds.
The present study was undertaken to isolate these additional antibacterial factors using silica column chromatography and
reverse-phase high-performance liquid chromatography. Two antibacterial fractions, each containing a pure compound, were isolated
and their chemical structures were investigated by mass spectrometry and nuclear magnetic resonance spectroscopy. The antibacterial
compounds were identified as the monounsaturated fatty acid (9Z)-hexadecenoic acid (palmitoleic acid; C16:1 n-7) and the relatively unusual polyunsaturated fatty acid (6Z, 9Z, 12Z)-hexadecatrienoic acid (HTA; C16:3 n-4). Both are active against Gram-positive bacteria with HTA further inhibitory to the
growth of the Gram-negative marine pathogen, Listonella anguillarum. Palmitoleic acid is active at micro-molar concentrations, kills bacteria rapidly, and is highly active against multidrug-resistant
Staphylococcus aureus. These free fatty acids warrant further investigation as a new potential therapy for drug-resistant infections. |
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Keywords: | Antimicrobial (6Z 9Z 12Z)-hexadecatrienoic acid Palmitoleic acid Micro-alga Phaeodactylum tricornutum MRSA |
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