PS(20:0/PGF2alpha)

(2S)-2-amino-3-({[(2R)-2-{[(5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoyl]oxy}-3-(icosanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid

Formula: C46H84NO13P (889.568)
Chinese Name:
BioDeep ID: BioDeep_00000207071 ( View LC/MS Profile)
SMILES: CCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCC\C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)CCCCC



Found 19 Sample Hits

m/z Adducts Species Organ Scanning Sample
890.5588 [M+H]+
PPM:18.5
Mus musculus Lung MALDI (DHB)
image1 - MTBLS2075
Resolution: 40μm, 187x165

Description

Fig. 2 MALDI-MSI data from the same mouse lung tissue analyzed in Fig. 1. A: Optical image of the post-MSI, H&E-stained tissue section. B–D, F–G: Ion images of (B) m/z 796.6855 ([U13C-DPPC+Na]+), (C) m/z 756.5514 ([PC32:0+Na]+), (D) m/z 765.6079 ([D9-PC32:0+Na]+), (F) m/z 754.5359 ([PC32:1+Na]+), and (G) m/z 763.5923 ([D9-PC32:1+Na]+). E, H: Ratio images of (E) [D9-PC32:0+Na]+:[PC32:0+Na]+ and (H) [D9-PC32:1+Na]+:[PC32:1+Na]+. Part-per-million (ppm) mass errors are indicated in parentheses. All images were visualized using total-ion-current normalization and using hotspot removal (high quantile = 99%). DPPC = PC16:0/16:0. U13C-DPPC, universally 13C-labeled dipalmitoyl PC; PC, phosphatidylcholine; MSI, mass spectrometry imaging; H&E, hematoxylin and eosin. Fig 1-3, Fig S1-S3, S5

890.5737 [M+H]+
PPM:1.8
Homo sapiens esophagus DESI ()
LNTO22_1_3 - MTBLS385
Resolution: 75μm, 121x68

Description

889.5827 [M-H2O+NH4]+
PPM:9.6
Homo sapiens colorectal adenocarcinoma DESI ()
80TopL, 50TopR, 70BottomL, 60BottomR-profile - MTBLS415
Resolution: 17μm, 137x136

Description

The human colorectal adenocarcinoma sample was excised during a surgical operation performed at the Imperial College Healthcare NHS Trust. The sample and procedures were carried out in accordance with ethical approval (14/EE/0024).

889.584 [M-H2O+NH4]+
PPM:8.2
Homo sapiens colorectal adenocarcinoma DESI ()
520TopL, 490TopR, 510BottomL, 500BottomR-profile - MTBLS415
Resolution: 17μm, 147x131

Description

The human colorectal adenocarcinoma sample was excised during a surgical operation performed at the Imperial College Healthcare NHS Trust. The sample and procedures were carried out in accordance with ethical approval (14/EE/0024).

889.5822 [M-H2O+NH4]+
PPM:10.2
Homo sapiens NA DESI ()
160TopL,130TopR,150BottomL,140BottomR-profile - MTBLS415
Resolution: 17μm, 142x136

Description

889.5873 [M-H2O+NH4]+
PPM:4.5
Homo sapiens esophagus DESI ()
TO29T - MTBLS385
Resolution: 75μm, 56x48

Description

889.5894 [M-H2O+NH4]+
PPM:2.1
Homo sapiens esophagus DESI ()
LNTO22_1_7 - MTBLS385
Resolution: 75μm, 69x54

Description

890.5738 [M+H]+
PPM:1.7
Homo sapiens esophagus DESI ()
LNTO22_1_7 - MTBLS385
Resolution: 75μm, 69x54

Description

889.5886 [M-H2O+NH4]+
PPM:3
Homo sapiens esophagus DESI ()
LNTO22_2_1 - MTBLS385
Resolution: 75μm, 89x88

Description

890.5734 [M+H]+
PPM:2.1
Homo sapiens esophagus DESI ()
LNTO22_2_1 - MTBLS385
Resolution: 75μm, 89x88

Description

889.5899 [M-H2O+NH4]+
PPM:1.5
Homo sapiens esophagus DESI ()
LNTO22_2_2 - MTBLS385
Resolution: 75μm, 135x94

Description

890.5747 [M+H]+
PPM:0.6
Homo sapiens esophagus DESI ()
LNTO22_2_2 - MTBLS385
Resolution: 75μm, 135x94

Description

889.5868 [M-H2O+NH4]+
PPM:5
Homo sapiens esophagus DESI ()
LNTO29_18_2 - MTBLS385
Resolution: 75μm, 62x68

Description

889.5891 [M-H2O+NH4]+
PPM:2.4
Homo sapiens colorectal adenocarcinoma DESI ()
240TopL, 210TopR, 230BottomL, 220BottomR-centroid - MTBLS176
Resolution: 50μm, 142x141

Description

890.5731 [M+H]+
PPM:2.4
Homo sapiens colorectal adenocarcinoma DESI ()
240TopL, 210TopR, 230BottomL, 220BottomR-centroid - MTBLS176
Resolution: 50μm, 142x141

Description

889.5885 [M-H2O+NH4]+
PPM:3.1
Homo sapiens colorectal adenocarcinoma DESI ()
200TopL, 170TopR, 190BottomL, 180BottomR-centroid - MTBLS176
Resolution: 50μm, 132x126

Description

890.5736 [M+H]+
PPM:1.9
Homo sapiens colorectal adenocarcinoma DESI ()
200TopL, 170TopR, 190BottomL, 180BottomR-centroid - MTBLS176
Resolution: 50μm, 132x126

Description

890.5727 [M+H]+
PPM:2.9
Homo sapiens colorectal adenocarcinoma DESI ()
160TopL,130TopR,150BottomL,140BottomR-centroid - MTBLS176
Resolution: 50μm, 142x136

Description

890.5798 [M+H]+
PPM:5.1
Drosophila melanogaster brain MALDI (DHB)
Drosophila18 - 2019-10-16_14h26m34s
Resolution: 5μm, 686x685

Description

Sample information Organism: Drosophila melanogaster Organism part: Brain Condition: Healthy Sample preparation Sample stabilisation: Frozen Tissue modification: Frozen MALDI matrix: 2,5-dihydroxybenzoic acid (DHB) MALDI matrix application: TM sprayer Solvent: Aceton/water MS analysis Polarity: Positive Ionisation source: Prototype Analyzer: Orbitrap Pixel size: 5μm × 5μm Annotation settings m/z tolerance (ppm): 3 Analysis version: Original MSM Pixel count: 469910 Imzml file size: 696.23 MB Ibd file size: 814.11 MB


PS(20:0/PGF2alpha) is an oxidized phosphatidylserine (PS). Oxidized phosphatidylserines are glycerophospholipids in which a phosphorylserine moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidylserines belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396). As is the case with diacylglycerols, phosphatidylserines can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PS(20:0/PGF2alpha), in particular, consists of one chain of one eicosanoyl at the C-1 position and one chain of Prostaglandin F2alpha at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PSs can be synthesized via three different routes. In one route, the oxidized PS is synthetized de novo following the same mechanisms as for PSs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PS backbone, mainly through the action of LOX (PMID: 33329396).