Glycosylated N-Acyl Phosphoethanolamines as Bacterial Food-Dependent Signaling Molecules in Caenorhabditis Nematodes

IF 4.3 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY
Siva Bandi, Marie-Désirée Schlemper-Scheidt, Rocío Rivera Sánchez, Sylvain Sutour, Gaétan Glauser, Yojiro Ishida and Stephan H. von Reuß*, 
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引用次数: 0

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.

糖基化n -酰基磷酸乙醇胺在线虫中的细菌食物依赖信号分子
n-酰基乙醇胺是一种保守的亲脂性信号分子,在g蛋白偶联受体、离子通道和核受体上起内源性配体的作用。采用比较超高效液相色谱-电喷雾电离高分辨率串联质谱(UHPLC-ESI-HR-MSE)分析和微反应相结合的方法,对隐杆线虫中n -酰基磷酸乙醇胺的多样性进行了表征。代表性样品经RP-C18色谱富集,核磁共振鉴定。比较代谢组学和同位素结合实验表明,同源n -酰基构建块(大约50种化合物)的生物合成取决于细菌食物来源、食物来源脂肪酸的链延伸和去饱和,或线虫的新生生物合成,而中链n -酰基单元的生物合成取决于通过3-酮酰基- s -辅酶a硫酶daf-22进行的过氧化物酶体β-氧化循环。这些亲脂性n -酰基乙醇胺的糖基化产生两亲性模块化代谢物(大约100种已确定的化合物),这些代谢物被释放到环境中并表现出潜在的信号功能。只有雄性产生的β-sophorosyl n -酰基磷酸乙醇胺,如snap13:1cyclo,保留了wallacei和brenneri Caenorhabditis的雌性,其生物合成需要细菌环脂肪酸17:1cyclo和19:1cyclo,从而将生长阶段依赖性的细菌脂肪生成转化为行为信号。2-(β-葡萄糖基)-甘油三酯n -二十碳五烯烯基磷酸乙醇胺(GGp-NAE-20:5)是秀丽隐线虫代谢组的主要成分,是n -二十碳五烯烯基乙醇胺(NAE 20:5)的水溶性衍生物,可能实现种内和种间内源性大麻素信号传导。
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来源期刊
ACS Bio & Med Chem Au
ACS Bio & Med Chem Au 药物、生物、化学-
CiteScore
4.10
自引率
0.00%
发文量
0
期刊介绍: ACS Bio & Med Chem Au is a broad scope open access journal which publishes short letters comprehensive articles reviews and perspectives in all aspects of biological and medicinal chemistry. Studies providing fundamental insights or describing novel syntheses as well as clinical or other applications-based work are welcomed.This broad scope includes experimental and theoretical studies on the chemical physical mechanistic and/or structural basis of biological or cell function in all domains of life. It encompasses the fields of chemical biology synthetic biology disease biology cell biology agriculture and food natural products research nucleic acid biology neuroscience structural biology and biophysics.The journal publishes studies that pertain to a broad range of medicinal chemistry including compound design and optimization biological evaluation molecular mechanistic understanding of drug delivery and drug delivery systems imaging agents and pharmacology and translational science of both small and large bioactive molecules. Novel computational cheminformatics and structural studies for the identification (or structure-activity relationship analysis) of bioactive molecules ligands and their targets are also welcome. The journal will consider computational studies applying established computational methods but only in combination with novel and original experimental data (e.g. in cases where new compounds have been designed and tested).Also included in the scope of the journal are articles relating to infectious diseases research on pathogens host-pathogen interactions therapeutics diagnostics vaccines drug-delivery systems and other biomedical technology development pertaining to infectious diseases.
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