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

The ‘core’ metabolome of the Bacteroidetes genus Chitinophaga 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 s...

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Autores principales: 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.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8433624/
https://www.ncbi.nlm.nih.gov/pubmed/34500631
http://dx.doi.org/10.3390/molecules26175195
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author 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.
author_facet 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.
author_sort Bill, Mona-Katharina
collection PubMed
description The ‘core’ metabolome of the Bacteroidetes genus Chitinophaga 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 N-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 (2) and 654. Most of the here characterized LAAs (1, 5–11) are members of a so far undescribed glycine-serine-ornithine tripeptide lipid family. Moreover, this study reports three novel NAAAs (N-(5-methyl)hexanoyl tyrosine (14) and N-(7-methyl)octanoyl tyrosine (15) or phenylalanine (16)) from Olivibacter sp. FHG000416, another Bacteroidetes strain initially selected as best in-house producer for isolation of lipid 430. Antimicrobial profiling revealed most isolated LAAs (1–3) and the two LPE ‘core’ metabolites (12, 13) active against the Gram-negative pathogen M. catarrhalis ATCC 25238 and the Gram-positive bacterium M. luteus DSM 20030. For LAA 1, additional growth inhibition activity against B. subtilis DSM 10 was observed.
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spelling pubmed-84336242021-09-12 Novel Glycerophospholipid, Lipo- and N-acyl Amino Acids from Bacteroidetes: Isolation, Structure Elucidation and Bioactivity 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. Molecules Article The ‘core’ metabolome of the Bacteroidetes genus Chitinophaga 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 N-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 (2) and 654. Most of the here characterized LAAs (1, 5–11) are members of a so far undescribed glycine-serine-ornithine tripeptide lipid family. Moreover, this study reports three novel NAAAs (N-(5-methyl)hexanoyl tyrosine (14) and N-(7-methyl)octanoyl tyrosine (15) or phenylalanine (16)) from Olivibacter sp. FHG000416, another Bacteroidetes strain initially selected as best in-house producer for isolation of lipid 430. Antimicrobial profiling revealed most isolated LAAs (1–3) and the two LPE ‘core’ metabolites (12, 13) active against the Gram-negative pathogen M. catarrhalis ATCC 25238 and the Gram-positive bacterium M. luteus DSM 20030. For LAA 1, additional growth inhibition activity against B. subtilis DSM 10 was observed. MDPI 2021-08-27 /pmc/articles/PMC8433624/ /pubmed/34500631 http://dx.doi.org/10.3390/molecules26175195 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
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.
Novel Glycerophospholipid, Lipo- and N-acyl Amino Acids from Bacteroidetes: Isolation, Structure Elucidation and Bioactivity
title Novel Glycerophospholipid, Lipo- and N-acyl Amino Acids from Bacteroidetes: Isolation, Structure Elucidation and Bioactivity
title_full Novel Glycerophospholipid, Lipo- and N-acyl Amino Acids from Bacteroidetes: Isolation, Structure Elucidation and Bioactivity
title_fullStr Novel Glycerophospholipid, Lipo- and N-acyl Amino Acids from Bacteroidetes: Isolation, Structure Elucidation and Bioactivity
title_full_unstemmed Novel Glycerophospholipid, Lipo- and N-acyl Amino Acids from Bacteroidetes: Isolation, Structure Elucidation and Bioactivity
title_short Novel Glycerophospholipid, Lipo- and N-acyl Amino Acids from Bacteroidetes: Isolation, Structure Elucidation and Bioactivity
title_sort novel glycerophospholipid, lipo- and n-acyl amino acids from bacteroidetes: isolation, structure elucidation and bioactivity
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8433624/
https://www.ncbi.nlm.nih.gov/pubmed/34500631
http://dx.doi.org/10.3390/molecules26175195
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