論文 - 詳細
| RRC ID | 87971 |
|---|---|
| 著者 | Bandi S, Schlemper-Scheidt MD, Rivera Sánchez R, Sutour S, Glauser G, Ishida Y, von Reuß SH. |
| タイトル | Glycosylated N‑Acyl Phosphoethanolamines as Bacterial Food-Dependent Signaling Molecules in Caenorhabditis Nematodes. |
| ジャーナル | ACS Bio Med Chem Au |
| Abstract |
N-acyl ethanolamines represent conserved lipophilic signaling molecules that function as endogenous ligands at G-protein-coupled receptors, ion channels, and nuclear receptors. Using a combination of comparative ultrahigh-performance liquid chromatography electrospray ionization high-resolution tandem mass spectrometry (UHPLC-ESI-HR-MSE) analysis and microreactions, a diversity of glycosylated N-acyl phosphoethanolamines were characterized in Caenorhabditis nematodes. Representative examples were enriched by RP-C18 chromatography and identified by NMR spectroscopy. Comparative metabolomics and isotope incorporation experiments revealed that the biosynthesis of the homologous N-acyl building blocks (approximately 50 compounds) depends on the bacterial food source, chain elongation and desaturation of food-derived fatty acids, or their de novo biosynthesis by the nematode, whereas the biosynthesis of medium-chain N-acyl units depends on the peroxisomal β-oxidation cycle via the 3-ketoacyl-S-CoA thiolase daf-22. Glycosylation of these lipophilic N-acyl ethanolamines results in amphiphilic modular metabolites (approximately 100 identified compounds) that are released into the environment and exhibit potential signaling functions. Exclusively male-produced β-sophorosyl N-acyl-phosphoethanolamines like SNAP-13:1cyclo retain females of Caenorhabditis wallacei and Caenorhabditis brenneri, and its biosynthesis requires bacterial cyclo fatty acids 17:1cyclo and 19:1cyclo, thereby translating growth phase-dependent bacterial lipogeneses into a behavioral signal. Amphiphilic 2-(β-glucosyl)-glyceryl N-eicosapentaenoyl phosphoethanolamine (GGp-NAE-20:5), a dominating component of the Caenorhabditis elegans metabolome, represents a water-soluble derivative of N-eicosapentaenoyl ethanolamine (NAE 20:5), potentially enabling intra- and interspecies endocannabinoid signaling. |
| 巻・号 | 5(4) |
| ページ | 602-619 |
| 公開日 | 2025-8-20 |
| DOI | 10.1021/acsbiomedchemau.5c00012 |
| PMID | 40860022 |
| PMC | PMC12371488 |
| オルトメトリクス指標 |
オルトメトリクス指標項目
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| 最多言及媒体 | X(Twitter) |
| 各媒体での言及数の合計 | 5 |
| 過去6か月間でのオルトメトリクス指標の変動値 | 0.0 |
| リソース情報 | |
| 線虫 | tm1037 |