PS(18:0/20:3(8Z,11Z,14Z))

(2S)-2-amino-3-({hydroxy[(2R)-2-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]-3-(octadecanoyloxy)propoxy]phosphoryl}oxy)propanoic acid

Formula: C44H80NO10P (813.552)
Chinese Name:
BioDeep ID: BioDeep_00000032603 ( View LC/MS Profile)
SMILES: [H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/CCCCC)C(O)=O



Found 43 Sample Hits

m/z Adducts Species Organ Scanning Sample
852.6541 [M+K]+
PPM:5.2
Rattus norvegicus Brain MALDI (CHCA)
Spectroswiss - sol_2x_br_2 - 2016-09-29_07h40m45s
Resolution: 17μm, 488x193

Description

814.5573 [M+H]+
PPM:2.4
Homo sapiens Liver MALDI (DHB)
20171107_FIT4_DHBpos_p70_s50 - Rappez et al (2021) SpaceM reveals metabolic states of single cells
Resolution: 50μm, 70x70

Description

796.5366 [M+H-H2O]+
PPM:15.1
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito08_47 - MTBLS58
Resolution: 17μm, 301x111

Description

814.5653 [M+H]+
PPM:7.5
Mus musculus Lung MALDI (DHB)
image4 - MTBLS2075
Resolution: 40μm, 162x156

Description

Fig 6c Fig. 6 MALDI-MSI of U13C-PC16:0/16:0 acyl chain remodeling. A: Averaged MALDI mass spectrum from lung tissue collected from mice euthanized 12 h after administration of D9-choline and U13C-DPPC–containing Poractant alfa surfactant. The ion at m/z 828.6321 is assigned as the [M+Na]+ ion of 13C24-PC16:0_20:4 formed by acyl remodeling of U13C-PC16:0/16:0. The “NL” value refers to the intensity of the base peak in the full range MS1 spectrum. B: MS/MS spectrum of precursor ions at m/z 828.5 ± 0.5 with fragment ions originating from [13C24-PC16:0_20:4+Na]+ annotated. Part-per-million (ppm) mass errors are provided in parentheses. C, D: MALDI-MSI data of [U13C-DPPC+Na]+ (blue), [PC36:4+Na]+ (green) and [13C24-PC16:0_20:4+Na]+ (red) in lung tissue collected from mice (C) 12 h and (D) 18 h after label administration. All images were visualized using total-ion-current normalization and hotspot removal (high quantile = 99%). MS/MS, tandem mass spectrometry; MSI, mass spectrometry imaging; PC, phosphatidylcholine; U13C-DPPC, universally 13C-labeled dipalmitoyl PC.

852.6481 [M+K]+
PPM:1.9
Mus musculus Lung MALDI (DHB)
image2 - MTBLS2075
Resolution: 40μm, 550x256

Description

Supplementary Figure S6. Ion distribution images for (a) [PC36:4+Na]+ (m/z 804.5514) and (b) [PC38:6+Na]+ (m/z 828.5515) obtained from mouse lung tissue collected 6 h after administration of D9- choline and U13C-DPPC–containing CHF5633. Parts-per-million (ppm) mass errors are indicated in parentheses. (c) Magnification of the boxed region in (a) with selected bronchiolar regions outlined in white boxes. (d) The corresponding H&E-stained tissue section with the same selected bronchiolar regions outlined in black boxes. These data demonstrate the co-localisation of the polyunsaturated lipids PC36:4 and PC38:6 with the bronchiolar regions of the lung. All MSI images were visualised using total ion current normalisation and hotspot removal (high quantile = 99%).

813.5586 [M]+
PPM:8.8
Macropus giganteus Brain MALDI (BPYN)
170321_kangaroobrain-dan3-pos_maxof50.0_med1 - 170321_kangaroobrain-dan3-pos_maxof50.0_med1
Resolution: 50μm, 81x50

Description

Sample information Organism: Macropus giganteus (kangaroo) Organism part: Brain Condition: Wildtype Sample growth conditions: Wild

814.5496 [M+H]+
PPM:11.8
Macropus giganteus Brain MALDI (BPYN)
170321_kangaroobrain-dan3-pos_maxof50.0_med1 - 170321_kangaroobrain-dan3-pos_maxof50.0_med1
Resolution: 50μm, 81x50

Description

Sample information Organism: Macropus giganteus (kangaroo) Organism part: Brain Condition: Wildtype Sample growth conditions: Wild

814.5593 [M+H]+
PPM:0.1
Homo sapiens esophagus DESI ()
LNTO22_1_4 - MTBLS385
Resolution: 17μm, 82x80

Description

813.5891 [M-H2O+NH4]+
PPM:17.1
Homo sapiens esophagus DESI ()
LNTO29_16_2 - MTBLS385
Resolution: 17μm, 95x101

Description

813.5479 [M]+
PPM:4.3
Homo sapiens esophagus DESI ()
TO42T - MTBLS385
Resolution: 17μm, 69x81

Description

814.5639 [M+H]+
PPM:5.7
Homo sapiens esophagus DESI ()
LNTO22_1_9 - MTBLS385
Resolution: 75μm, 89x74

Description

814.5557 [M+H]+
PPM:4.3
Mus musculus Liver MALDI (CHCA)
Salmonella_final_pos_recal - MTBLS2671
Resolution: 17μm, 691x430

Description

A more complete and holistic view on host–microbe interactions is needed to understand the physiological and cellular barriers that affect the efficacy of drug treatments and allow the discovery and development of new therapeutics. Here, we developed a multimodal imaging approach combining histopathology with mass spectrometry imaging (MSI) and same section imaging mass cytometry (IMC) to study the effects of Salmonella Typhimurium infection in the liver of a mouse model using the S. Typhimurium strains SL3261 and SL1344. This approach enables correlation of tissue morphology and specific cell phenotypes with molecular images of tissue metabolism. IMC revealed a marked increase in immune cell markers and localization in immune aggregates in infected tissues. A correlative computational method (network analysis) was deployed to find metabolic features associated with infection and revealed metabolic clusters of acetyl carnitines, as well as phosphatidylcholine and phosphatidylethanolamine plasmalogen species, which could be associated with pro-inflammatory immune cell types. By developing an IMC marker for the detection of Salmonella LPS, we were further able to identify and characterize those cell types which contained S. Typhimurium. [dataset] Nicole Strittmatter. Holistic Characterization of a Salmonella Typhimurium Infection Model Using Integrated Molecular Imaging, metabolights_dataset, V1; 2022. https://www.ebi.ac.uk/metabolights/MTBLS2671.

813.5487 [M]+
PPM:3.3
Homo sapiens esophagus DESI ()
LNTO30_8M_1 - MTBLS385
Resolution: 17μm, 69x54

Description

814.5621 [M+H]+
PPM:3.5
Homo sapiens esophagus DESI ()
LNTO30_8M_1 - MTBLS385
Resolution: 17μm, 69x54

Description

813.5482 [M]+
PPM:3.9
Homo sapiens esophagus DESI ()
TO39T - MTBLS385
Resolution: 17μm, 69x81

Description

813.576 [M-H2O+NH4]+
PPM:1
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).

814.5601 [M+H]+
PPM:1.1
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).

813.5739 [M-H2O+NH4]+
PPM:1.6
Homo sapiens NA DESI ()
160TopL,130TopR,150BottomL,140BottomR-profile - MTBLS415
Resolution: 17μm, 142x136

Description

814.5638 [M+H]+
PPM:5.6
Homo sapiens esophagus DESI ()
LNTO26_7_1 - MTBLS385
Resolution: 17μm, 75x74

Description

814.5647 [M+H]+
PPM:6.7
Homo sapiens esophagus DESI ()
LNTO26_7_2 - MTBLS385
Resolution: 17μm, 135x101

Description

814.5634 [M+H]+
PPM:5.1
Homo sapiens esophagus DESI ()
LNTO26_7_3 - MTBLS385
Resolution: 75μm, 82x88

Description

814.5609 [M+H]+
PPM:2
Homo sapiens esophagus DESI ()
TO31T - MTBLS385
Resolution: 75μm, 56x54

Description

814.5634 [M+H]+
PPM:5.1
Homo sapiens esophagus DESI ()
TO29T - MTBLS385
Resolution: 75μm, 56x48

Description

813.5489 [M]+
PPM:3.1
Homo sapiens esophagus DESI ()
LNTO30_8M_2 - MTBLS385
Resolution: 75μm, 108x68

Description

814.5616 [M+H]+
PPM:2.9
Homo sapiens esophagus DESI ()
LNTO30_8M_2 - MTBLS385
Resolution: 75μm, 108x68

Description

813.5487 [M]+
PPM:3.3
Homo sapiens esophagus DESI ()
LNTO30_8M_3 - MTBLS385
Resolution: 75μm, 69x54

Description

814.5616 [M+H]+
PPM:2.9
Homo sapiens esophagus DESI ()
LNTO30_8M_3 - MTBLS385
Resolution: 75μm, 69x54

Description

814.5615 [M+H]+
PPM:2.8
Homo sapiens esophagus DESI ()
LNTO30_8M_4 - MTBLS385
Resolution: 75μm, 62x48

Description

813.549 [M]+
PPM:3
Homo sapiens esophagus DESI ()
LNTO30_8M_5 - MTBLS385
Resolution: 75μm, 56x54

Description

814.5619 [M+H]+
PPM:3.3
Homo sapiens esophagus DESI ()
LNTO30_8M_5 - MTBLS385
Resolution: 75μm, 56x54

Description

814.562 [M+H]+
PPM:3.4
Homo sapiens esophagus DESI ()
LNTO30_17_2 - MTBLS385
Resolution: 75μm, 82x54

Description

814.5651 [M+H]+
PPM:7.2
Homo sapiens esophagus DESI ()
LNTO22_1_5 - MTBLS385
Resolution: 75μm, 135x94

Description

814.5638 [M+H]+
PPM:5.6
Homo sapiens esophagus DESI ()
LNTO22_2_1 - MTBLS385
Resolution: 75μm, 89x88

Description

814.5644 [M+H]+
PPM:6.3
Homo sapiens esophagus DESI ()
LNTO22_2_2 - MTBLS385
Resolution: 75μm, 135x94

Description

814.564 [M+H]+
PPM:5.9
Homo sapiens esophagus DESI ()
LNTO26_16_1 - MTBLS385
Resolution: 75μm, 95x88

Description

814.5625 [M+H]+
PPM:4
Homo sapiens esophagus DESI ()
LNTO29_18_2 - MTBLS385
Resolution: 75μm, 62x68

Description

813.549 [M]+
PPM:3
Homo sapiens esophagus DESI ()
LNTO30_7_1 - MTBLS385
Resolution: 75μm, 69x68

Description

814.5622 [M+H]+
PPM:3.6
Homo sapiens esophagus DESI ()
LNTO30_7_1 - MTBLS385
Resolution: 75μm, 69x68

Description

814.5617 [M+H]+
PPM:3
Homo sapiens esophagus DESI ()
LNTO30_7_2 - MTBLS385
Resolution: 75μm, 82x68

Description

796.5388 [M+H-H2O]+
PPM:12.4
Mus musculus brain MALDI (DHB)
Brain01_Bregma1-42_02_centroid - MTBLS313
Resolution: 17μm, 434x258

Description

814.5475 [M+H]+
PPM:14.4
Mus musculus brain MALDI (DHB)
Brain01_Bregma1-42_02_centroid - MTBLS313
Resolution: 17μm, 434x258

Description

813.5744 [M-H2O+NH4]+
PPM:1
Mus musculus brain MALDI (DHB)
Brain02_Bregma-3-88 - MTBLS313
Resolution: 17μm, 288x282

Description

814.5613 [M+H]+
PPM:2.5
Homo sapiens colorectal adenocarcinoma DESI ()
160TopL,130TopR,150BottomL,140BottomR-centroid - MTBLS176
Resolution: 50μm, 142x136

Description


PS(18:0/20:3(8Z,11Z,14Z)) is a phosphatidylserine (PS or GPSer). It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoserines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PS(18:0/20:3(8Z,11Z,14Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of homo-g-linolenic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the homo-g-linolenic acid moiety is derived from fish oils, liver and kidney. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. It is usually less than 10\\% of the total phospholipids, the greatest concentration being in myelin from brain tissue. However, it may comprise 10 to 20 mol\\% of the total phospholipid in the plasma membrane and endoplasmic reticulum of the cell. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine, especially during bone formation for example. As phosphatidylserine is located entirely on the inner monolayer surface of the plasma membrane (and of other cellular membranes) and it is the most abundant anionic phospholipids. Therefore phosphatidylseriine may make the largest contribution to interfacial effects in membranes involving non-specific electrostatic interactions. This normal distribution is disturbed during platelet activation and cellular apoptosis. In human plasma, 1-stearoyl-2-oleoyl and 1-stearoyl-2-arachidonoyl species predominate, but in brain (especially grey matter), retina and many other tissues 1-stearoyl-2-docosahexaenoyl species are very abundant. Indeed, the ratio of n-3 to n-6 fatty acids in brain phosphatidylserine is very much higher than in most other lipids. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Phosphatidylserines typically carry a net charge of -1 at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE. PS(18:0/20:3(8Z,11Z,14Z)) is a phosphatidylserine (PS or GPSer). It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoserines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PS(18:0/20:3(8Z,11Z,14Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of homo-g-linolenic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the homo-g-linolenic acid moiety is derived from fish oils, liver and kidney. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. It is usually less than 10\\% of the total phospholipids, the greatest concentration being in myelin from brain tissue. However, it may comprise 10 to 20 mol\\% of the total phospholipid in the plasma membrane and endoplasmic reticulum of the cell. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine, especially during bone formation for example. As phosphatidylserine is located entirely on the inner monolayer surface of the plasma membrane (and of other cellular membranes) and it is the most abundant anionic phospholipids. Therefore phosphatidylseriine may make the largest contribution to interfacial effects in membranes involving non-specific electrostatic interactions. This normal distribution is disturbed during platelet activation and cellular apoptosis. In human plasma, 1-stearoyl-2-oleoyl and 1-stearoyl-2-arachidonoyl species predominate, but in brain (especially grey matter), retina and many other tissues 1-stearoyl-2-docosahexaenoyl species are very abundant. Indeed, the ratio of n-3 to n-6 fatty acids in brain phosphatidylserine is very much higher than in most other lipids.