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.
Highlights
IntroductionLipids are a diverse group of natural biomolecules
The corresponding ion formula of C17 H31 O+ indicated a fatty acyl group based on the molecular composition and apparent carbon-to-hydrogen ratio (Figure 1A)
The metabolomics data generated in our previous study was examined for the presence of both dipeptide lipids
Summary
Lipids are a diverse group of natural biomolecules. Thousands of distinct lipids, such as glycerolipids, sterol lipids, sphingolipids, lipoamino acids (LAAs), and phospholipids, are ubiquitous in all organisms. Each of them is chemically unique, and they exhibit different biological functions. Given the diversity in both the chemical and physical properties of lipids and the fact that each lipid type is involved at various stages of cellular processes, the definition of lipid function besides their primary biological role, i.e., the formation of cell membrane matrixes, is challenging. Described functions in cellular signaling, energy storage, or an implication as substrate for metabolite or protein lipidation are only examples [1]
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