Two Novel Lyso-Ornithine Lipids Isolated from an Arctic Marine Lacinutrix sp. Bacterium

Kristoffersen, Venke; Jenssen, Marte; Jawad, Heba Raid; Isaksson, Johan; Hansen, Espen H.; Rämä, Teppo; Hansen, Kine Ø.; Andersen, Jeanette Hammer

doi:10.3390/molecules26175295

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Two Novel Lyso-Ornithine Lipids Isolated from an Arctic Marine Lacinutrix sp. Bacterium

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Jeanette Hammer Andersen

Marbio, Faculty for Fisheries, Biosciences and Economy, UiT-The Arctic University of Norway, Breivika, N-9037 Tromsø, Norway

Department of Chemistry, Faculty of Natural Sciences, UiT-The Arctic University of Norway, Breivika, N-9037 Tromsø, Norway

Author to whom correspondence should be addressed.

Academic Editors: Magdalena Ligor and Aleksandra Szydłowska-Czerniak

Molecules 2021, 26(17), 5295; https://doi.org/10.3390/molecules26175295

Received: 2 July 2021 / Revised: 27 August 2021 / Accepted: 27 August 2021 / Published: 31 August 2021

(This article belongs to the Special Issue Isolation and Structure Determination of Bioactive Natural Products)

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Abstract

The Lacinutrix genus was discovered in 2005 and includes 12 Gram-negative bacterial species. To the best of our knowledge, the secondary metabolite production potential of this genus has not been explored before, and examination of Lacinutrix species may reveal novel chemistry. As part of a screening project of Arctic marine bacteria, the Lacinutrix sp. strain M09B143 was cultivated, extracted, fractionated and tested for antibacterial and cytotoxic activities. One fraction had antibacterial activity and was subjected to mass spectrometry analysis, which revealed two compounds with elemental composition that did not match any known compounds in databases. This resulted in the identification and isolation of two novel isobranched lyso-ornithine lipids, whose structures were elucidated by mass spectrometry and NMR spectroscopy. Lyso-ornithine lipids consist of a 3-hydroxy fatty acid linked to the alpha amino group of an ornithine amino acid through an amide bond. The fatty acid chains were determined to be iso-C15:0 (1) and iso-C16:0 (2). Compound 1 was active against the Gram-positive S. agalactiae, while 2 showed cytotoxic activity against A2058 human melanoma cells. View Full-Text

Keywords: marine bacteria; lipoamino acid; secondary metabolites; amphiphilic compounds; antibacterial; cytotoxic; anti-cancer

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MDPI and ACS Style

Kristoffersen, V.; Jenssen, M.; Jawad, H.R.; Isaksson, J.; Hansen, E.H.; Rämä, T.; Hansen, K.Ø.; Andersen, J.H. Two Novel Lyso-Ornithine Lipids Isolated from an Arctic Marine Lacinutrix sp. Bacterium. Molecules 2021, 26, 5295. https://doi.org/10.3390/molecules26175295

AMA Style

Kristoffersen V, Jenssen M, Jawad HR, Isaksson J, Hansen EH, Rämä T, Hansen KØ, Andersen JH. Two Novel Lyso-Ornithine Lipids Isolated from an Arctic Marine Lacinutrix sp. Bacterium. Molecules. 2021; 26(17):5295. https://doi.org/10.3390/molecules26175295

Chicago/Turabian Style

Kristoffersen, Venke, Marte Jenssen, Heba Raid Jawad, Johan Isaksson, Espen H. Hansen, Teppo Rämä, Kine Ø. Hansen, and Jeanette Hammer Andersen. 2021. "Two Novel Lyso-Ornithine Lipids Isolated from an Arctic Marine Lacinutrix sp. Bacterium" Molecules 26, no. 17: 5295. https://doi.org/10.3390/molecules26175295

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Two Novel Lyso-Ornithine Lipids Isolated from an Arctic Marine Lacinutrix sp. Bacterium

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