Mesobilirubinogen
Formula: C33H44N4O6 (592.3261)
Chinese Name: 尿胆素原
BioDeep ID: BioDeep_00000003497
( View LC/MS Profile)
SMILES: CCC1=C(C(=O)NC1CC2=C(C(=C(N2)CC3=C(C(=C(N3)CC4C(=C(C(=O)N4)CC)C)C)CCC(=O)O)CCC(=O)O)C)C
Found 15 Sample Hits
m/z | Adducts | Species | Organ | Scanning | Sample | |
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593.329 | [M+H]+PPM:7.3 |
Homo sapiens | Liver | MALDI (DHB) |
20171107_FIT4_DHBpos_p70_s50 - Rappez et al (2021) SpaceM reveals metabolic states of single cellsResolution: 50μm, 70x70
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593.3409 | [M+H]+PPM:12.7 |
Rattus norvegicus | Epididymis | MALDI (DHB) |
epik_dhb_head_ito03_17 - MTBLS58Resolution: 17μm, 208x108
1 male adult wild-type rat was obtained from Inserm U1085 - Irset Research Institute (University of Rennes1, France). Animals were age 60 days and were reared under ad-lib conditions. Care and handling of all animals complied with EU directive 2010/63/EU on the protection of animals used for scientific purposes. The whole epididymis was excised from each animal immediately post-mortem, loosely wrapped rapidly in an aluminum foil and a 2.5% (w/v) carboxymethylcellulose (CMC) solution was poured to embed the epididymis to preserve their morphology. To remove air bubbles, the filled aluminum molds was gently freezed by depositing it on isopentane or dry ice, then on the nitrogen vapors and finally by progressively dipping the CMC/sample coated with aluminum foil into liquid nitrogen (or only flush with liquid nitrogen). Frozen tissues were stored at -80 °C until use to avoid degradation. |
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593.3409 | [M+H]+PPM:12.7 |
Rattus norvegicus | Epididymis | MALDI (DHB) |
epik_dhb_head_ito03_18 - MTBLS58Resolution: 17μm, 208x104
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593.3409 | [M+H]+PPM:12.7 |
Rattus norvegicus | Epididymis | MALDI (DHB) |
epik_dhb_head_ito08_43 - MTBLS58Resolution: 17μm, 298x106
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593.3409 | [M+H]+PPM:12.7 |
Rattus norvegicus | Epididymis | MALDI (DHB) |
epik_dhb_head_ito08_44 - MTBLS58Resolution: 17μm, 299x111
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593.3408 | [M+H]+PPM:12.6 |
Rattus norvegicus | Epididymis | MALDI (DHB) |
epik_dhb_head_ito08_46 - MTBLS58Resolution: 17μm, 298x106
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593.3409 | [M+H]+PPM:12.7 |
Rattus norvegicus | Epididymis | MALDI (DHB) |
epik_dhb_head_ito08_47 - MTBLS58Resolution: 17μm, 301x111
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593.3409 | [M+H]+PPM:12.7 |
Rattus norvegicus | Epididymis | MALDI (DHB) |
epik_dhb_head_ito08_48 - MTBLS58Resolution: 17μm, 294x107
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593.3409 | [M+H]+PPM:12.7 |
Rattus norvegicus | Epididymis | MALDI (DHB) |
epik_dhb_head_ito01_04 - MTBLS58Resolution: 17μm, 178x91
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593.3408 | [M+H]+PPM:12.6 |
Rattus norvegicus | Epididymis | MALDI (DHB) |
epik_dhb_head_ito01_03 - MTBLS58Resolution: 17μm, 159x110
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593.3409 | [M+H]+PPM:12.7 |
Rattus norvegicus | normal | MALDI (DHB) |
epik_dhb_head_ito01_05 - MTBLS58Resolution: 17μm, 183x105
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593.3409 | [M+H]+PPM:12.7 |
Rattus norvegicus | Epididymis | MALDI (DHB) |
epik_dhb_head_ito01_06 - MTBLS58Resolution: 17μm, 183x103
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593.341 | [M+H]+PPM:12.9 |
Rattus norvegicus | Epididymis | MALDI (DHB) |
epik_dhb_head_ito03_14 - MTBLS58Resolution: 17μm, 205x103
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593.3396 | [M+H]+PPM:10.5 |
Homo sapiens | esophagus | DESI () |
LNTO22_1_4 - MTBLS385Resolution: 17μm, 82x80
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593.344 | [M+H]+PPM:18 |
Mus musculus | Liver | MALDI (CHCA) |
Salmonella_final_pos_recal - MTBLS2671Resolution: 17μm, 691x430
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. |
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Mesobilirubinogen (also known as I-urobilinogen) is a tetrapyrrole chemical compound that is closely related to two other compounds: urobilinogen (also known as D-urobilinogen) and stercobilinogen (also known as L-urobilinogen). Specifically, urobilinogen can be reduced to form mesobilirubinogen, and mesobilirubinogen can be further reduced to form stercobilinogen. Confusingly, all three of these compounds are frequently collectively referred to as "urobilinogens". Urobilinogen is the parent compound of both stercobilin (the pigment that is responsible for the brown colour of feces) and urobilin (the pigment that is responsible for the yellow colour of urine). Urobilinogen is formed through the microbial degradation of its parent compound bilirubin. Urobilinogen is actually generated through the degradation of heme, the red pigment in hemoglobin and red blood cells (RBCs). RBCs have a life span of about 120 days. When the RBCs have reached the end of their useful lifespan, the cells are engulfed by macrophages and their constituents recycled or disposed of. Heme is broken down when the heme ring is opened by the enzyme known as heme oxygenase, which is found in the endoplasmic reticulum of the macrophages. The oxidation process produces the linear tetrapyrrole known as biliverdin along with ferric iron (Fe3+), and carbon monoxide (CO). In the next reaction, a second methylene group (located between rings III and IV of the porphyrin ring) is reduced by the enzyme known as biliverdin reductase, producing bilirubin. Bilirubin is significantly less extensively conjugated than biliverdin. This reduction causes a change in the colour of the biliverdin molecule from blue-green (vert or verd for green) to yellow-red, which is the colour of bilirubin (ruby or rubi for red). In plasma, virtually all the bilirubin is tightly bound to plasma proteins, largely albumin, because it is only sparingly soluble in aqueous solutions at physiological pH. In the sinusoids, unconjugated bilirubin dissociates from albumin, enters the liver cells across the cell membrane through non-ionic diffusion to the smooth endoplasmatic reticulum. In hepatocytes, bilirubin-UDP-glucuronyltransferase (bilirubin-UGT) adds 2 additional glucuronic acid molecules to bilirubin to produce the more water-soluble version of the molecule known as bilirubin diglucuronide. The bilirubin diglucuronide is transferred rapidly across the canalicular membrane into the bile canaliculi where it is then excreted as bile into the large intestine. The bilirubin is further degraded (reduced) by microbes present in the large intestine to form a colourless product known as urobilinogen. Urobilinogen that remains in the colon can either be reduced to stercobilinogen and finally oxidized to stercobilin, or it can be directly reduced to stercobilin. Some of the urobilinogen produced by the gut bacteria is reabsorbed and re-enters the enterohepatic circulation. This reabsorbed urobilinogen is oxidized and converted to urobilin. The urobilin is processed through the kidneys and then excreted in the urine, which causes the yellowish colour in urine. Urobilinogen is an uribiniloid, the product of bilirubin reduction in multiple sequential reactions. Urobilinogens are colorless chromogens that may in turn be oxidized to respective yellow oxidation products, urobilins. Under normal conditions only small amounts of bilirubin can be found in stools of adults while urobilinoids are predominant bile pigments (50-250 mg/day). Only negligible amounts of fecal urobilinoids are present in the intestinal lumen of infants during the first months of their life, due to undeveloped intestinal microflora capable of reducing bilirubin. This presumably contributes importantly to the pathogenesis of neonatal jaundice. In adults, the urobilinoid production is highly efficient. At times, it is re-excreted in the urine, where it may be later oxidized to urobilin. (PMID: 16504607) [HMDB]