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Isolation and structural characterisation of two antibacterial free fatty acids from the marine diatom, Phaeodactylum tricornutum

  • Applied Microbial and Cell Physiology
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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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Acknowledgements

The authors thank Dr. Mike Walton for assistance during DMDS adducts synthesis and Ms. Caroline Horsburgh (School of Chemistry, University of St. Andrews) and Dr. Catherine Botting (School of Biology, University of St. Andrews) for mass spectrometry. Strains of B. cereus, B. weihenstephanensis, C. glabrata, C. neoformis, MRSA252 and S. cerevisiae were gifted by Dr. Peter Coote (School of Biology, University of St. Andrews) and Prof. Simon Foster (Department of Molecular Biology and Biotechnology, University of Sheffield) gifted the S. aureus strain. This work was funded by a BBSRC studentship (BBS/S/M/2003/10490) with additional financial support from Dr. Andrew Mearns-Spragg (CEO, Aquapharm Bio-Discovery Ltd.).

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  1. Andrew P. Desbois

    Present address: Centre for Biomolecular Sciences, School of Biology, University of St Andrews, Fife, Scotland

Authors and Affiliations

  1. Gatty Marine Laboratory, School of Biology, University of St Andrews, Fife, Scotland

    Andrew P. Desbois & Valerie J. Smith

  2. Purdie Building, School of Chemistry, University of St Andrews, Fife, Scotland

    Tomas Lebl

  3. Aquapharm Bio-Discovery Limited, European Centre for Marine Biotechnology, Dunstaffnage Marine Laboratory, Oban, Argyll, Scotland

    Liming Yan

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  1. Andrew P. Desbois
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  2. Tomas Lebl
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  3. Liming Yan
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  4. Valerie J. Smith
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Correspondence to Valerie J. Smith.

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Desbois, A.P., Lebl, T., Yan, L. et al. Isolation and structural characterisation of two antibacterial free fatty acids from the marine diatom, Phaeodactylum tricornutum . Appl Microbiol Biotechnol 81, 755–764 (2008). https://doi.org/10.1007/s00253-008-1714-9

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  • DOI: https://doi.org/10.1007/s00253-008-1714-9

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