Novel Glycerophospholipid,Lipo- and N-acyl Amino Acids from Bacteroidetes: Isolation,Structure Elucidation and Bioactivity |
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Authors: | Mona-Katharina Bill Stephan Brinkmann Markus Oberpaul Maria A Patras Benedikt Leis Michael Marner Marc-Philippe Maitre Peter E Hammann Andreas Vilcinskas Sren M M Schuler Till F Schberle |
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Institution: | 1.Fraunhofer Institute for Molecular Biology and Applied Ecology (IME), Branch for Bioresources, 35392 Giessen, Germany; (M.-K.B.); (S.B.); (M.O.); (M.A.P.); (B.L.); (M.M.); (A.V.);2.Sanofi Pasteur, R&D, 69280 Marcy L’Etoile, France;3.Sanofi-Aventis Deutschland GmbH, R&D, 65926 Frankfurt am Main, Germany;4.Evotec International GmbH, 37079 Göttingen, Germany;5.Institute for Insect Biotechnology, Justus-Liebig-University of Giessen, 35392 Giessen, Germany |
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Abstract: | 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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Keywords: | linear lipoamino acid lipid 430 lipid 654 N-acyl amino acid lysophosphatidylethanolamine bacteroidetes Chitinophaga Olivibacter LC-MS/MS antimicrobial lipids |
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