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

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Isolation and structural characterisation of two antibacterial free fatty acids from the marine diatom, Phaeodactylum tricornutum. / Desbois, Andrew P.; Lebl, Tomas; Yan, Liming; Smith, Valerie J.

In: Applied Microbiology and Biotechnology, Vol. 81, 12.2008, p. 755-764.

Research output: Contribution to journalArticle

Harvard

Desbois, AP, Lebl, T, Yan, L & Smith, VJ 2008, 'Isolation and structural characterisation of two antibacterial free fatty acids from the marine diatom, Phaeodactylum tricornutum' Applied Microbiology and Biotechnology, vol. 81, pp. 755-764. https://doi.org/10.1007/s00253-008-1714-9

APA

Desbois, A. P., Lebl, T., Yan, L., & Smith, V. J. (2008). Isolation and structural characterisation of two antibacterial free fatty acids from the marine diatom, Phaeodactylum tricornutum. Applied Microbiology and Biotechnology, 81, 755-764. https://doi.org/10.1007/s00253-008-1714-9

Vancouver

Desbois AP, Lebl T, Yan L, Smith VJ. Isolation and structural characterisation of two antibacterial free fatty acids from the marine diatom, Phaeodactylum tricornutum. Applied Microbiology and Biotechnology. 2008 Dec;81:755-764. https://doi.org/10.1007/s00253-008-1714-9

Author

Desbois, Andrew P. ; Lebl, Tomas ; Yan, Liming ; Smith, Valerie J. / Isolation and structural characterisation of two antibacterial free fatty acids from the marine diatom, Phaeodactylum tricornutum. In: Applied Microbiology and Biotechnology. 2008 ; Vol. 81. pp. 755-764.

Bibtex - Download

@article{f315d51b62354f2c95834b51aa163196,
title = "Isolation and structural characterisation of two antibacterial free fatty acids from the marine diatom, Phaeodactylum tricornutum",
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.",
keywords = "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",
author = "Desbois, {Andrew P.} and Tomas Lebl and Liming Yan and Smith, {Valerie J.}",
year = "2008",
month = "12",
doi = "10.1007/s00253-008-1714-9",
language = "English",
volume = "81",
pages = "755--764",
journal = "Applied Microbiology and Biotechnology",
issn = "0175-7598",
publisher = "Springer-Verlag",

}

RIS (suitable for import to EndNote) - Download

TY - JOUR

T1 - Isolation and structural characterisation of two antibacterial free fatty acids from the marine diatom, Phaeodactylum tricornutum

AU - Desbois, Andrew P.

AU - Lebl, Tomas

AU - Yan, Liming

AU - Smith, Valerie J.

PY - 2008/12

Y1 - 2008/12

N2 - 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.

AB - 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.

KW - Antimicrobial

KW - (6Z

KW - 9Z

KW - 12Z)-hexadecatrienoic acid

KW - Palmitoleic acid

KW - Micro-alga

KW - Phaeodactylum tricornutum

KW - MRSA

KW - NATURAL-PRODUCTS

KW - THALASSIOSIRA-ROTULA

KW - DIALYSIS CULTURE

KW - MONOGLYCERIDES

KW - LIPIDS

KW - IDENTIFICATION

KW - STAPHYLOCOCCI

KW - INACTIVATION

KW - METABOLITES

KW - MICROALGAE

UR - http://www.scopus.com/inward/record.url?scp=57249094297&partnerID=8YFLogxK

U2 - 10.1007/s00253-008-1714-9

DO - 10.1007/s00253-008-1714-9

M3 - Article

VL - 81

SP - 755

EP - 764

JO - Applied Microbiology and Biotechnology

T2 - Applied Microbiology and Biotechnology

JF - Applied Microbiology and Biotechnology

SN - 0175-7598

ER -

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ID: 595431