Skip to content

Research at St Andrews

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

Research output: Contribution to journalArticle

Author(s)

Andrew P. Desbois, Tomas Lebl, Liming Yan, Valerie J. Smith

School/Research organisations

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.

Close

Details

Original languageEnglish
Pages (from-to)755-764
Number of pages10
JournalApplied Microbiology and Biotechnology
Volume81
DOIs
Publication statusPublished - Dec 2008

    Research areas

  • Antimicrobial, (6Z, 9Z, 12Z)-hexadecatrienoic acid, Palmitoleic acid, Micro-alga, Phaeodactylum tricornutum, MRSA, NATURAL-PRODUCTS, THALASSIOSIRA-ROTULA, DIALYSIS CULTURE, MONOGLYCERIDES, LIPIDS, IDENTIFICATION, STAPHYLOCOCCI, INACTIVATION, METABOLITES, MICROALGAE

Discover related content
Find related publications, people, projects and more using interactive charts.

View graph of relations

Related by author

  1. Conjugated, rigidified bibenzimidazole ancillary ligands for enhanced photoluminescence quantum yields of orange/red-emitting iridium(III) complexes

    Henwood, A. F., Antón-García, D., Morin, M., Rota Martir, D., Cordes, D. B., Casey, C., Slawin, A. M. Z., Lebl, T., Buehl, M. & Zysman-Colman, E., 14 Jul 2019, In : Dalton Transactions. 48, 26

    Research output: Contribution to journalArticle

  2. Using fractionation and diffusion ordered spectroscopy to study lignin molecular weight

    Montgomery, J., Bazley, P., Lebl, T. & Westwood, N. J., May 2019, In : ChemistryOpen. 8, 5, p. 601-605 5 p.

    Research output: Contribution to journalArticle

  3. Preparation and reactivity of biomass-derived dihydro-dioxins

    Montgomery, J., Kempf, K., Miles-Barrett, D. M., Kempf, O., Lebl, T. & Westwood, N. J., 10 Jan 2019, In : CHEMSUSCHEM. 12, 1, p. 190-193 4 p.

    Research output: Contribution to journalArticle

  4. Polycyclic ethers and an unexpected dearomatisation reaction during studies towards the bioactive alkaloid, perophoramidine

    Johnston, C. A., Wilkie, R. P., Krauss, H., Neal, A. R., Slawin, A. M. Z., Lebl, T. & Westwood, N. J., 28 Jun 2018, In : Tetrahedron. 74, 26, p. 3339-3347

    Research output: Contribution to journalArticle

Related by journal

  1. Antibacterial free fatty acids: activities, mechanisms of action and biotechnological potential

    Desbois, A. P. & Smith, V. J., Feb 2010, In : Applied Microbiology and Biotechnology. 85, 6, p. 1629 – 1642

    Research output: Contribution to journalArticle

ID: 595431

Top