The chemical synthesis of phosphorothioate and phosphorodithioate analogues of lysophosphatidic acid (LPA) and cyclic phosphatidic acid (CPA)

Rytczak, Przemysław Piotr; Koziołkiewicz, Maria; Okruszek, And̀rzej

doi:10.1039/b9nj00704k

Cited by 12 publications

(6 citation statements)

References 49 publications

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“…Metabolomic analysis revealed that chenodeoxycholate and glycocholic acid up-regulated the KEGG pathway of primary bile acid biosynthesis in the cecal contents of PEO group, Primary bile acids are also critical to the digestion and absorption of fat 41 . In the blood of chickens of PEO group, six lipid metabolites (such as LysoPC (18:1(9Z)) and LysoPE (16:0/0:0)) enriched fatty acid biosynthesus, Lyso PCs perform essential functions in the lipid metabolism of organisms 9,42 ; 1-Palmitoylglycerol is the biosynthetic precursor of phosphatidic acid: the major component of lysophosphatidic acid, which is a pluripotent lipid mediator which controls growth, motility, and differentiation 43 . In addition, D-Mannose up-regulated KEGG pathway of fructose and mannose metabolism and ABC transporters in serum of the PEO group.…”

Section: Discussionmentioning

confidence: 99%

Microbiota and metabolome responses in the cecum and serum of broiler chickens fed with plant essential oils or virginiamycin

Chen

Wang

et al. 2020

Sci Rep

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This study investigated the cecal microbiota and serum metabolite profile of chickens fed with plant essential oils (PEO) or virginiamycin (VIRG) using high-throughput 16S rRNA gene sequencing and untargeted metabolomics approach. the main aim of this work was to explore the biochemical mechanisms involved in the improved growth performance of antibiotics and their alternatives in animal production. The results showed that both PEO and VIRG treatment significantly increased the relative abundance of phyla Bacteroidetes and decreased the abundance of phyla firmicutes and genus of Lactobacillus in cecal microbiota of chickens. compared to the control group (ct group), the relative abundance of genus of Alistipes, unclassified Rikenellaceae, Roseburia, and Anaeroplasma was enriched in the peo group; that of genus Bacteroides, Lachnospiraceae, and unclassified Enterobacteriaceae was enriched in the cecal microbiota of the ViRG group. Untargeted metabolomics analyses revealed that the PEO treatment modified 102 metabolites and 3 KEGG pathways (primary bile acid biosynthesis and phenylalanine metabolism) in the cecal microbiota, and 81 metabolites and relevant KEGG pathways (fructose and mannose metabolism, biosynthesis of unsaturated fatty acids, and linoleic acid.) in the serum of the chicken. Compared to the CT group, VIRG treatment group differed 217 metabolites and 10 KEGG pathways in cecal contents and 142 metabolites and 7 KEGG pathways in serum of chickens. pearson's correlation analysis showed that phyla Bacteroidetes and genus of Bacteroides, Alistipes, and unclassified Rikenellaceae (in the VIRG and PE group) were positively correlated with many lipid metabolites. However, phyla firmicutes and genera Lactobacillus (higher in the ct group) were negatively correlated with the lipid and thymine metabolism, and positively correlated with hydroxyisocaproic acid, cytosine, and taurine. this study shows that dietary supplementation with peo and VIRG altered the composition and metabolism profile of the cecal microbiota, modified the serum metabolism profile. The intestinal microbiota, the population of microorganisms that inhabit the intestine, plays an important role in the intestinal morphology, immunity, nutrient digestion and absorption, and host health 1-3. Many studies have demonstrated that intestinal microbiota participates in many metabolic pathways, such as lipid metabolism and amino acid synthesis 4,5. The mechanism by which PEO promote growth of may be alter gut microflora and hence improved absorption of nutrients 6 , increase absorption of micronutrients in the small intestine 7 and reducing the deleterious effects of the microbial metabolites 8-10. There are many alternatives to antibiotics, such as acidifiers, probiotics, oligosaccharides, and plant extracts, which play a growth promoting role by regulating gut microbes in pig and poultry 11. Plant essential oils (PEO), which can be extracted from plants by steam distillation, extrusion, or solvent extraction 12,13 , serve as alternatives for antibi...

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Section: Discussionmentioning

confidence: 99%

Microbiota and metabolome responses in the cecum and serum of broiler chickens fed with plant essential oils or virginiamycin

Chen

Wang

et al. 2020

Sci Rep

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“…The last steps for the preparation of the target compounds 1a-2c were performed accordingly to the reported synthetic procedures. Yields and purity were higher with respect to any reported data (Appendix A) [39,42,43,45,50,55]. We also produced GVs made of (R)-POPC, rac-POPC and a scalemic mixture (scal-POPC) made of (R:S = 2:1) POPC enantiomers (Figures 2 and 3).…”

Section: Discussionmentioning

confidence: 78%

Racemic Phospholipids for Origin of Life Studies

et al. 2020

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Although prebiotic condensations of glycerol, phosphate and fatty acids produce phospholipid esters with a racemic backbone, most experimental studies on vesicles intended as protocell models have been carried out by employing commercial enantiopure phospholipids. Current experimental research on realistic protocell models urgently requires racemic phospholipids and efficient synthetic routes for their production. Here we propose three synthetic pathways starting from glycerol or from racemic solketal (α,β-isopropylidene-dl-glycerol) for the gram-scale production (up to 4 g) of racemic phospholipid ester precursors. We describe and compare these synthetic pathways with literature data. Racemic phosphatidylcholines and phosphatidylethanolamines were obtained in good yields and high purity from 1,2-diacylglycerols. Racemic POPC (rac-POPC, (R,S)-1-palmitoyl-2-oleoyl-3-phosphocholine), was used as a model compound for the preparation of giant vesicles (GVs). Confocal laser scanning fluorescence microscopy was used to compare GVs prepared from enantiopure (R)-POPC), racemic POPC (rac-POPC) and a scalemic mixture (scal-POPC) of (R)-POPC enriched with rac-POPC. Vesicle morphology and size distribution were similar among the different (R)-POPC, rac-POPC and scal-POPC, while calcein entrapments in (R)-POPC and in scal-POPC were significantly distinct by about 10%.

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“…For example, glycidol was reacted with stearic acid anhydride at 85 C for 5 h to synthesize GMS at a yield of 62%. 15 The yield of GMS can be improved by using glycidol, but the industrialization of this process is restricted by the high cost of glycidol. The reaction of glycerol acetonide with stearic acid ester to produce GMS had also been reported.…”

Section: Introductionmentioning

confidence: 99%