Novel Glycerophospholipid, Lipo- and -acyl Amino Acids from Bacteroidetes: Isolation, Structure Elucidation and Bioactivity.

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ID: 275181
2021
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Abstract
The 'core' metabolome of the Bacteroidetes genus was recently discovered to consist of only seven metabolites. A structural relationship in terms of shared lipid moieties among four of them was postulated. Here, structure elucidation and characterization via ultra-high resolution mass spectrometry (UHR-MS) and nuclear magnetic resonance (NMR) spectroscopy of those four lipids (two lipoamino acids (LAAs), two lysophosphatidylethanolamines (LPEs)), as well as several other undescribed LAAs and -acyl amino acids (NAAAs), identified during isolation were carried out. The LAAs represent closely related analogs of the literature-known LAAs, such as the glycine-serine dipeptide lipids 430 () and 654. Most of the here characterized LAAs (, -) are members of a so far undescribed glycine-serine-ornithine tripeptide lipid family. Moreover, this study reports three novel NAAAs (-(5-methyl)hexanoyl tyrosine () and -(7-methyl)octanoyl tyrosine () or phenylalanine ()) from sp. FHG000416, another Bacteroidetes strain initially selected as best in-house producer for isolation of lipid 430. Antimicrobial profiling revealed most isolated LAAs (-) and the two LPE 'core' metabolites (, ) active against the Gram-negative pathogen ATCC 25238 and the Gram-positive bacterium DSM 20030. For LAA , additional growth inhibition activity against DSM 10 was observed.
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Authors Bill, Mona-Katharina;Brinkmann, Stephan;Oberpaul, Markus;Patras, Maria A;Leis, Benedikt;Marner, Michael;Maitre, Marc-Philippe;Hammann, Peter E;Vilcinskas, Andreas;Schuler, Sören M M;Schäberle, Till F;
Journal Molecules (Basel, Switzerland)
Year 2021
DOI 5195
URL
Keywords
lc-ms/ms bacteroidetes chitinophaga n-acyl amino acid olivibacter antimicrobial lipids linear lipoamino acid lipid 430 lipid 654 lysophosphatidylethanolamine

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