Next Article in Journal
Effects of Traditional and Modern Post-Harvest Withering Processes on the Composition of the Vitis v. Corvina Grape and the Sensory Profile of Amarone Wines
Next Article in Special Issue
Efficacy of Precocene I from Desmosstachya bipinnata as an Effective Bioactive Molecules against the Spodoptera litura Fab. and Its Impact on Eisenia fetida Savigny
Previous Article in Journal
Positive Charges in the Brace Region Facilitate the Membrane Disruption of MLKL-NTR in Necroptosis
Previous Article in Special Issue
Saponin Stabilization via Progressive Freeze Concentration and Sterilization Treatment
 
 
Article

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

1
Fraunhofer Institute for Molecular Biology and Applied Ecology (IME), Branch for Bioresources, 35392 Giessen, Germany
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
*
Authors to whom correspondence should be addressed.
These authors contributed equally to this work.
Academic Editor: Natalizia Miceli
Molecules 2021, 26(17), 5195; https://doi.org/10.3390/molecules26175195
Received: 31 July 2021 / Revised: 22 August 2021 / Accepted: 25 August 2021 / Published: 27 August 2021
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, 511) 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 (13) 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. View Full-Text
Keywords: linear lipoamino acid; lipid 430; lipid 654; N-acyl amino acid; lysophosphatidylethanolamine; bacteroidetes; Chitinophaga; Olivibacter; LC-MS/MS; antimicrobial lipids linear lipoamino acid; lipid 430; lipid 654; N-acyl amino acid; lysophosphatidylethanolamine; bacteroidetes; Chitinophaga; Olivibacter; LC-MS/MS; antimicrobial lipids
Show Figures

Graphical abstract

MDPI and ACS Style

Bill, M.-K.; Brinkmann, S.; Oberpaul, M.; Patras, M.A.; Leis, B.; Marner, M.; Maitre, M.-P.; Hammann, P.E.; Vilcinskas, A.; Schuler, S.M.M.; Schäberle, T.F. Novel Glycerophospholipid, Lipo- and N-acyl Amino Acids from Bacteroidetes: Isolation, Structure Elucidation and Bioactivity. Molecules 2021, 26, 5195. https://doi.org/10.3390/molecules26175195

AMA Style

Bill M-K, Brinkmann S, Oberpaul M, Patras MA, Leis B, Marner M, Maitre M-P, Hammann PE, Vilcinskas A, Schuler SMM, Schäberle TF. Novel Glycerophospholipid, Lipo- and N-acyl Amino Acids from Bacteroidetes: Isolation, Structure Elucidation and Bioactivity. Molecules. 2021; 26(17):5195. https://doi.org/10.3390/molecules26175195

Chicago/Turabian Style

Bill, Mona-Katharina, Stephan Brinkmann, Markus Oberpaul, Maria A. Patras, Benedikt Leis, Michael Marner, Marc-Philippe Maitre, Peter E. Hammann, Andreas Vilcinskas, Sören M. M. Schuler, and Till F. Schäberle. 2021. "Novel Glycerophospholipid, Lipo- and N-acyl Amino Acids from Bacteroidetes: Isolation, Structure Elucidation and Bioactivity" Molecules 26, no. 17: 5195. https://doi.org/10.3390/molecules26175195

Find Other Styles
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Back to TopTop