3-O-acetyl-sphingosine-series myelin glycolipids

Dasgupta, Somsankar; Levery, Steven B.; Hogan, Edward L.

doi:10.1016/s0022-2275(20)30117-6

Cited by 25 publications

References 43 publications

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Organization of gangliosides into membrane nanodomains

et al. 2020

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Gangliosides are glycosphingolipids consisting of a ceramide base and a bulky sugar chain that contains one or more sialic acids. This unique structure endows gangliosides with a strong tendency to self-aggregate in solution, as well as in cellular membranes, where they can form nanoscopic assemblies called ganglioside nanodomains. As gangliosides are important biological molecules involved in a number of physiological processes, characterization of their lateral organization in membranes is essential. This review aims at providing comprehensive information about the nanoscale organization of gangliosides in various synthetic models. To this end, the impact of the hydrophobic backbone and the headgroup on the segregation of gangliosides into nanodomains are discussed in detail, as well as the way in which the properties of nanodomains are affected by ligand binding. Small size makes the characterization of ganglioside nanodomains challenging, and we thus highlight the biophysical methods that have advanced this research, such as Monte Carlo F€ orster resonance energy transfer, atomic force microscopy and approaches based on molecular diffusion.

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Organization of gangliosides into membrane nanodomains

et al. 2020

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Characterization of novel myelin components 3‐O‐acetyl‐sphingosine galactosylceramides by electrospray ionization Q‐TOF MS and MS/CID‐MS of Li⁺ adducts

et al. 2007

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Glycosphingolipids with R(f) values higher than those of monoglycosylceramides (MGCs) in normal phase HPTLC appear to be normal components of myelin. A series of such low polarity components, referred to as 'fast moving cerebrosides' (FMCs), have been isolated from rat brain, and two of these fractions (FMC-1 and FMC-2) were found to be novel derivatives of galactosylceramide (GalCer) exhibiting O-acetylation at the 3-hydroxy group of the sphingoid moiety, and incorporating either non-hydroxy or 2-hydroxy fatty-N-acylation (Dasgupta S, Levery SB, Hogan EL. J. Lipid Res. 2002; 43: 751-761). Similar to the parent compounds, the 3-O-acetyl-sphingoid derivatives exhibit considerable diversity with respect to fatty-N-acyl chain length, manifested by heterogeneous molecular ion (Li(+) adduct) profiles. However, a detailed analysis of the individual molecular variants ('lipoforms'), e.g. by tandem MS/CID-MS analysis, was not carried out. In addition, several other FMCs distinguished by even lower polarity (higher HPTLC R(f) values) were isolated but have remained uncharacterized. For this study, analysis of both the known and unknown FMC components was carried out by positive ion ESI-MS and MS/CID-MS of their Li(+) adducts on a Q-TOF mass spectrometer. Since a Q-TOF instrument has not yet been applied to MS of lithiated cerebrosides and FMCs, MS/CID-MS spectra of bovine brain GalCer (both types) and the previously characterized rat brain FMCs (FMC-1 and FMC-2), having 3-O-acetylation of the sphingoid, were systematically acquired and their fragmentation behavior compared. This was followed by systematic analysis of previously uncharacterized FMC fractions (FMC-3 through FMC-5/6/7). The GalCer and FMC components proved to be amenable to analysis by this technique, and the data confirm that the latter are all related 3-O-acetyl-sphingoid derivatives, with the higher R(f) components carrying additional O-acetyl modifications on the galactosyl residue, which further reduce their polarity. The utility of the technique, the structures of unknown FMCs, and their characteristic fragmentation patterns are described.

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Cell‐specific expression of neutral glycosphingolipids in vertebrate brain: Immunochemical localization of 3‐O‐acetyl‐sphingosine‐series glycolipid(s) in myelin and oligodendrocytes

Dasgupta

Bhat

Spicer

et al. 2007

J of Neuroscience Research

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The tissue- and cell-specific expression of three neutral glycosphingolipids, gangliotetraosylceramide (GA1), gangliopentaosylceramide (GalNAc-GA1), and the novel 3-O-acetyl-sphingosine-series glycolipid (FMC-5), were examined with monospecific polyclonal antibodies. Immunohistochemical studies of rodent brain cross-sections indicated that both GA1 and FMC-5 antibodies stained myelin. In contrast, GalNAc-GA1 antibody distinctly stained neurons in cerebral cortex, but only partially delineated Purkinje cells and other neurons in cerebellum. Preliminary studies of mixed glial cultures suggested the following: 1) both FMC-5 and GA1 antibodies stained oligodendrocytes and oligo progenitors, and 2) GalNAc-GA1 antibody did not stain any cells in the culture. Because the GalNAc-GA1 was associated with neurons, we examined the immunoreactivity of GalNAc-GA1 antibody in primary neuronal cultures. Further studies using primary cultures of rat brain oligodendrocytes, and dissociated cerebellar neuronal cultures indicated that both GA1 and FMC-5 are specifically expressed by oligodendrocytes, whereas GalNAc-GA1 is primarily localized in interneurons and to some extent in Purkinje neurons.

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3-O-acetyl-sphingosine-series myelin glycolipids

Cited by 25 publications

References 43 publications

Organization of gangliosides into membrane nanodomains

Organization of gangliosides into membrane nanodomains

Characterization of novel myelin components 3‐O‐acetyl‐sphingosine galactosylceramides by electrospray ionization Q‐TOF MS and MS/CID‐MS of Li⁺ adducts

Cell‐specific expression of neutral glycosphingolipids in vertebrate brain: Immunochemical localization of 3‐O‐acetyl‐sphingosine‐series glycolipid(s) in myelin and oligodendrocytes

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3-O-acetyl-sphingosine-series myelin glycolipids

Cited by 25 publications

References 43 publications

Organization of gangliosides into membrane nanodomains

Organization of gangliosides into membrane nanodomains

Characterization of novel myelin components 3‐O‐acetyl‐sphingosine galactosylceramides by electrospray ionization Q‐TOF MS and MS/CID‐MS of Li+ adducts

Cell‐specific expression of neutral glycosphingolipids in vertebrate brain: Immunochemical localization of 3‐O‐acetyl‐sphingosine‐series glycolipid(s) in myelin and oligodendrocytes

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Characterization of novel myelin components 3‐O‐acetyl‐sphingosine galactosylceramides by electrospray ionization Q‐TOF MS and MS/CID‐MS of Li⁺ adducts