3-O-acetyl-sphingosine-series myelin glycolipids
Several glycosphingolipids, less polar than galactosylceramide (GalCer), have been purified from rat brain and designated as fast migrating cerebrosides (FMCs). They co-appear with GalCer during myelinogenesis, reach a peak concentration at postnatal day 25–30 and are derivatives of GalCer. Extensiv...
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| Format: | Article |
| Language: | English |
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Elsevier
2002-05-01
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| Series: | Journal of Lipid Research |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S0022227520301176 |
| _version_ | 1818715726807040000 |
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| author | Somsankar Dasgupta Steven B. Levery Edward L. Hogan |
| author_facet | Somsankar Dasgupta Steven B. Levery Edward L. Hogan |
| author_sort | Somsankar Dasgupta |
| collection | DOAJ |
| description | Several glycosphingolipids, less polar than galactosylceramide (GalCer), have been purified from rat brain and designated as fast migrating cerebrosides (FMCs). They co-appear with GalCer during myelinogenesis, reach a peak concentration at postnatal day 25–30 and are derivatives of GalCer. Extensive structural analysis of the partially methylated alditol acetates, mass-spectrometry, and 1H- and 13C-nuclear magnetic resonance (NMR) spectroscopy unequivocally established the structure of two of these FMCs as 3-O-acetyl-sphingosine GalCer with non-hydroxy and hydroxy fatty N-acylation respectively. That is, an acetyl group is linked at the C3-OH of the sphingosine base of GalCer. In addition, NMR spectroscopy of all of the purified FMCs indicates that they contain a 3-O-acetyl group linked with sphingosine and thus delineates a novel series. Several lines of evidence indicate that FMCs are myelin constituents. FMCs, enriched in both central nervous system (CNS) and peripheral nervous system (PNS) myelin, are concentrated in spinal cord and white matter that are composed of myelinated nerve fibers. There is N-acylation with α-hydroxy and C18 and C24 fatty acids, all characteristic of myelin components. They disappear along with GalCer in the murine genetic dysmyelinating disorders, jimpy and quaking, and in a knockout mutant which is devoid of GalCer. In addition, a decrease in FMC and GalCer concentration has been found in Krabbé's disease, a human genetic dysmyelinating disorder.—Dasgupta, S., S. B. Levery, and E. L. Hogan. 3-O-acetyl-sphingosine-series myelin glycolipids: characterization of novel 3-O-acetyl-sphingosine galactosylceramide. J. Lipid Res. 2002. 43: 751–761. |
| first_indexed | 2024-12-17T19:07:57Z |
| format | Article |
| id | doaj.art-00effa522a474576a69e34cc3bfe25eb |
| institution | Directory Open Access Journal |
| issn | 0022-2275 |
| language | English |
| last_indexed | 2024-12-17T19:07:57Z |
| publishDate | 2002-05-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Journal of Lipid Research |
| spelling | doaj.art-00effa522a474576a69e34cc3bfe25eb2022-12-21T21:35:56ZengElsevierJournal of Lipid Research0022-22752002-05-014357517613-O-acetyl-sphingosine-series myelin glycolipidsSomsankar Dasgupta0Steven B. Levery1Edward L. Hogan2Department of Neurology, Medical University of South Carolina, 96 Jonathan Lucas Street, P.O. Box 250606, Charleston, SC 29425; To whom correspondence should be addressed.Complex Carbohydrate Research Center and Department of Biochemistry and Molecular Biology, University of Georgia, 220 Riverbend Road, Athens, GA 30602Department of Neurology, Medical University of South Carolina, 96 Jonathan Lucas Street, P.O. Box 250606, Charleston, SC 29425Several glycosphingolipids, less polar than galactosylceramide (GalCer), have been purified from rat brain and designated as fast migrating cerebrosides (FMCs). They co-appear with GalCer during myelinogenesis, reach a peak concentration at postnatal day 25–30 and are derivatives of GalCer. Extensive structural analysis of the partially methylated alditol acetates, mass-spectrometry, and 1H- and 13C-nuclear magnetic resonance (NMR) spectroscopy unequivocally established the structure of two of these FMCs as 3-O-acetyl-sphingosine GalCer with non-hydroxy and hydroxy fatty N-acylation respectively. That is, an acetyl group is linked at the C3-OH of the sphingosine base of GalCer. In addition, NMR spectroscopy of all of the purified FMCs indicates that they contain a 3-O-acetyl group linked with sphingosine and thus delineates a novel series. Several lines of evidence indicate that FMCs are myelin constituents. FMCs, enriched in both central nervous system (CNS) and peripheral nervous system (PNS) myelin, are concentrated in spinal cord and white matter that are composed of myelinated nerve fibers. There is N-acylation with α-hydroxy and C18 and C24 fatty acids, all characteristic of myelin components. They disappear along with GalCer in the murine genetic dysmyelinating disorders, jimpy and quaking, and in a knockout mutant which is devoid of GalCer. In addition, a decrease in FMC and GalCer concentration has been found in Krabbé's disease, a human genetic dysmyelinating disorder.—Dasgupta, S., S. B. Levery, and E. L. Hogan. 3-O-acetyl-sphingosine-series myelin glycolipids: characterization of novel 3-O-acetyl-sphingosine galactosylceramide. J. Lipid Res. 2002. 43: 751–761.http://www.sciencedirect.com/science/article/pii/S0022227520301176dysmyelinating disordermass spectrometrymonoglycosylceramidenuclear magnetic resonance spectroscopyvertebrate brain |
| spellingShingle | Somsankar Dasgupta Steven B. Levery Edward L. Hogan 3-O-acetyl-sphingosine-series myelin glycolipids Journal of Lipid Research dysmyelinating disorder mass spectrometry monoglycosylceramide nuclear magnetic resonance spectroscopy vertebrate brain |
| title | 3-O-acetyl-sphingosine-series myelin glycolipids |
| title_full | 3-O-acetyl-sphingosine-series myelin glycolipids |
| title_fullStr | 3-O-acetyl-sphingosine-series myelin glycolipids |
| title_full_unstemmed | 3-O-acetyl-sphingosine-series myelin glycolipids |
| title_short | 3-O-acetyl-sphingosine-series myelin glycolipids |
| title_sort | 3 o acetyl sphingosine series myelin glycolipids |
| topic | dysmyelinating disorder mass spectrometry monoglycosylceramide nuclear magnetic resonance spectroscopy vertebrate brain |
| url | http://www.sciencedirect.com/science/article/pii/S0022227520301176 |
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