Novel myelin penta- and hexa-acetyl-galactosyl-ceramides: structural characterization and immunoreactivity in cerebrospinal fluid[S]
Fast migrating cerebrosides (FMC) are derivatives of galactosylceramide (GalCer). The structures of the most hydrophobic FMC-5, FMC-6, and FMC-7 were determined by electrospray ionization linear ion-trap mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopy complementing previous...
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Elsevier
2010-06-01
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| Series: | Journal of Lipid Research |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S0022227520410132 |
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| author | Maria Podbielska Somsankar Dasgupta Steven B. Levery Wallace W. Tourtellotte Heidi Annuk Anthony P. Moran Edward L. Hogan |
| author_facet | Maria Podbielska Somsankar Dasgupta Steven B. Levery Wallace W. Tourtellotte Heidi Annuk Anthony P. Moran Edward L. Hogan |
| author_sort | Maria Podbielska |
| collection | DOAJ |
| description | Fast migrating cerebrosides (FMC) are derivatives of galactosylceramide (GalCer). The structures of the most hydrophobic FMC-5, FMC-6, and FMC-7 were determined by electrospray ionization linear ion-trap mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopy complementing previous NMR spectroscopy and gas chromatography-mass spectrometry to be 3-O-acetyl-sphingosine-GalCer derivatives with galactose O-acetyl modifications. FMC-5 and FMC-6 are 3-O-acetyl-sphingosine-2,3,4,6-tetra-O-acetyl-GalCer with nonhydroxy and hydroxy-N-fatty-acids, while FMC-7 has an additional O-acetylation of the 2-hydroxy-fatty acid. The immuno-reactivity in human cerebrospinal fluid (CSF) to these acetylated glycolipids was examined in central nervous system (CNS) infectious disease, noninflammatory disorders, and multiple sclerosis (MS). Screening for lipid binding in MS and other neurological disease groups revealed that the greatest anti-hydrophobic FMC reactivity was observed in the inflammatory CNS diseases (meningitis, meningo-encephalitis, and subacute sclerosing panencephalitis). Some MS patients had increased reactivity with the hydrophobic FMCs and with glycoglycerophospholipid MfGL-II from Mycoplasma fermentans. The cross-reactivity of highly acetylated GalCer with microbial acyl-glycolipid raises the possibility that myelin-O-acetyl-cerebrosides, bacterial infection, and neurological disease are linked. |
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| format | Article |
| id | doaj.art-ca6d46f7e2514f21b2cef603a820c3cc |
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| issn | 0022-2275 |
| language | English |
| last_indexed | 2024-12-17T07:24:04Z |
| publishDate | 2010-06-01 |
| publisher | Elsevier |
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| series | Journal of Lipid Research |
| spelling | doaj.art-ca6d46f7e2514f21b2cef603a820c3cc2022-12-21T21:58:41ZengElsevierJournal of Lipid Research0022-22752010-06-0151613941406Novel myelin penta- and hexa-acetyl-galactosyl-ceramides: structural characterization and immunoreactivity in cerebrospinal fluid[S]Maria Podbielska0Somsankar Dasgupta1Steven B. Levery2Wallace W. Tourtellotte3Heidi Annuk4Anthony P. Moran5Edward L. Hogan6Department of Neurology, Institute of Molecular Medicine and Genetics, Medical College of Georgia, Augusta, GA; Department of Immunochemistry, Ludwik Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Wroclaw, PolandDepartment of Neurology, Institute of Molecular Medicine and Genetics, Medical College of Georgia, Augusta, GADepartment of Cellular and Molecular Medicine, Faculty of Health Sciences, University of Copenhagen, Copenhagen N, DenmarkHuman Brain and Spinal Fluid Resource Center, Veterans Affairs West Los Angeles Healthcare Center, Los Angeles, CADepartment of Microbiology, School of Natural Sciences, National University of Ireland Galway, Galway, IrelandDepartment of Microbiology, School of Natural Sciences, National University of Ireland Galway, Galway, IrelandDepartment of Neurology, Institute of Molecular Medicine and Genetics, Medical College of Georgia, Augusta, GA; Department of Microbiology, School of Natural Sciences, National University of Ireland Galway, Galway, IrelandFast migrating cerebrosides (FMC) are derivatives of galactosylceramide (GalCer). The structures of the most hydrophobic FMC-5, FMC-6, and FMC-7 were determined by electrospray ionization linear ion-trap mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopy complementing previous NMR spectroscopy and gas chromatography-mass spectrometry to be 3-O-acetyl-sphingosine-GalCer derivatives with galactose O-acetyl modifications. FMC-5 and FMC-6 are 3-O-acetyl-sphingosine-2,3,4,6-tetra-O-acetyl-GalCer with nonhydroxy and hydroxy-N-fatty-acids, while FMC-7 has an additional O-acetylation of the 2-hydroxy-fatty acid. The immuno-reactivity in human cerebrospinal fluid (CSF) to these acetylated glycolipids was examined in central nervous system (CNS) infectious disease, noninflammatory disorders, and multiple sclerosis (MS). Screening for lipid binding in MS and other neurological disease groups revealed that the greatest anti-hydrophobic FMC reactivity was observed in the inflammatory CNS diseases (meningitis, meningo-encephalitis, and subacute sclerosing panencephalitis). Some MS patients had increased reactivity with the hydrophobic FMCs and with glycoglycerophospholipid MfGL-II from Mycoplasma fermentans. The cross-reactivity of highly acetylated GalCer with microbial acyl-glycolipid raises the possibility that myelin-O-acetyl-cerebrosides, bacterial infection, and neurological disease are linked.http://www.sciencedirect.com/science/article/pii/S0022227520410132acetyl-cerebrosidecross-reactivityelectrospray ionizationEscherichia colifast migrating cerebrosidesglycosphingolipids |
| spellingShingle | Maria Podbielska Somsankar Dasgupta Steven B. Levery Wallace W. Tourtellotte Heidi Annuk Anthony P. Moran Edward L. Hogan Novel myelin penta- and hexa-acetyl-galactosyl-ceramides: structural characterization and immunoreactivity in cerebrospinal fluid[S] Journal of Lipid Research acetyl-cerebroside cross-reactivity electrospray ionization Escherichia coli fast migrating cerebrosides glycosphingolipids |
| title | Novel myelin penta- and hexa-acetyl-galactosyl-ceramides: structural characterization and immunoreactivity in cerebrospinal fluid[S] |
| title_full | Novel myelin penta- and hexa-acetyl-galactosyl-ceramides: structural characterization and immunoreactivity in cerebrospinal fluid[S] |
| title_fullStr | Novel myelin penta- and hexa-acetyl-galactosyl-ceramides: structural characterization and immunoreactivity in cerebrospinal fluid[S] |
| title_full_unstemmed | Novel myelin penta- and hexa-acetyl-galactosyl-ceramides: structural characterization and immunoreactivity in cerebrospinal fluid[S] |
| title_short | Novel myelin penta- and hexa-acetyl-galactosyl-ceramides: structural characterization and immunoreactivity in cerebrospinal fluid[S] |
| title_sort | novel myelin penta and hexa acetyl galactosyl ceramides structural characterization and immunoreactivity in cerebrospinal fluid s |
| topic | acetyl-cerebroside cross-reactivity electrospray ionization Escherichia coli fast migrating cerebrosides glycosphingolipids |
| url | http://www.sciencedirect.com/science/article/pii/S0022227520410132 |
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