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

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.

Bioactivity Profiling and Untargeted Metabolomics of Microbiota Associated with Mesopelagic Jellyfish Periphylla Periphylla

“…agaricicola showed activity against Bacillus megaterium and Escherichia coli [ 79 ]. Diverse antimicrobial activities have further been reported for OL [ 80 , 81 ] and, hence, these compounds may contribute to the observed antimicrobial activities in this study. Sulfobacins are a class of sphingosine lipids first isolated from the gram-negative Chryseobacterium sp.…”

Marine natural products

“…12 Chemical investigations of a mangrove soil-sourced Isoptericola chiayiensis identi-ed new 2-furanone 29, sesquiterpenoid 30 and benzenoid 31 derivatives, ve new avonoids 32-36, and four other related metabolites 37-40 that were isolated for the rst time from nature. 13 Two novel lyso-ornithine lipids 41, 42 were isolated from an arctic Lacinutrix sp., 14 whilst an acyl dipeptide named micromonosporamide A 43 was isolated from the fermentation broth of Micromonospora sp. and was shown to display glutaminedependent cytotoxicity.…”

“…Two novel lyso-ornithine lipids 41 , 42 were isolated from an arctic Lacinutrix sp., 14 whilst an acyl dipeptide named micromonosporamide A 43 was isolated from the fermentation broth of Micromonospora sp. and was shown to display glutamine-dependent cytotoxicity.…”

Marine Compounds for Melanoma Treatment and Prevention

“…A certain cytotoxic activity has been observed for one of the two lipids against the melanoma cell line A2058, with a cellular survival of 23% at 50 µM and a cell survival of about 0% at 100 µM and 150 µM, while the other lipid showed no activity against melanoma cells. The isolated compounds were tested on the normal lung-fibroblast MRC-5 cells and neither of them were active against normal cells [ 21 ].…”