Ceramide structure

A model for the structural relationship of /V-butyl-1 -deoxynojirimycin (131, Scheme 33) with ceramide, the substrate of ceramide glucosyltransferase, was suggested by Butters and coworkers. They conducted a comparative investigation on a range of 14 derivatives of 1-deoxynojirimycin substituted at the ring nitrogen and/or C-l, as well as 5 pyrrolidine-type inhibitors selected by superpositioning of the iminoalditol with a portion of the ceramide structure.364... 

Figure 21-6 Pathways of synthesis and metabolism of sphingolipids. Gray arrows indicate catabolic pathways. See also Fig. 20-11. The green extension on the ceramide structure is that of a long-chain co-hydroxyceramide that is covalently bound to protein in human skin.

Wuhrer, M., Dennis, R.D., Doenhoff, M.J. and Geyer, R. (2000b) Stage-associated expression of ceramide structures in glycosphingolipids from the human trematode parasite Schistosoma mansoni. Biochimica et Biophysica Acta 1524, 1 55-1 61. 

S. B. Levery, M. S. Toledo, R. L. Doong, A. H. Straus, and H. K. Takahashi, Comparative analysis of ceramide structural modification found in fungal cerebrosides by electrospray tandem mass spectrometry with low energy collision-induced dissociation of Li + adduct ions, Rapid Commun. Mass Spectrom., 14 (2000) 551-563. 

The literature is replete with the use of chromatographic fraction numbers to indicate ceramide structural types. This can be very confusing because different laboratories have achieved different degrees of separation and because, even with the best resolution achieved, there is at least one fraction... 

Bouhours,). F., and Bouhours, D. (1981). Ceramide structure of sphingomyelin from human milk fat globule membrane. Lipids 16,721-711. 

Fig. 1 Schematic representation of ceramide species separation into groups differing in position and number of hydroxyls, after migration onto silica gel or onto an arsenite-impregnated silica gel TLC plate. The plate is developed in chloroform-methanol 50 3.5, (v/v) as the solvent system. The ceramide structure is shown and the numbers refer to those reported close to the ceramide spot on the TLC plates. NFA normal (nonhydroxy) fatty acid HFA hydroxy fatty acid DHS di-hydrosphingosine SPH sphingosine PHS phytosphingosine.

Ghering AB, Davidson WS. Ceramide structural features required to stimulate ABCAl-mediated cholesterol efflux to apolipoprotein A-I. J Lipid Res 47(2006) 2781-2788. 

Chagasic sera did not differentiate between glycolipids with terminal p glucosyl or p galactosyl non-reducing units. They however discriminated between glucosylceramides with differences in the ceramide structure. These results suggest that antibody... 

The results show that the major GSL from species of Aspergillus has a distinctive ceramide structure, consisting of 9-methyl-4,8-sphingadienine linked to a 2-hydroxyoctadec-3-enoic acid (Figure 19). While the structure described here is similar to those from A. oryzae (19), F. amygdali (73) and some Basidiomycetes (77), it is the first report of this occurrence in species pathogenic to humans. 

Kawasaki Y, Quan D, Sakamoto K, Maibach HI (1997) Electron resonance studies on the influence of anionic surfactants on human skin. Dermatology 194 238-242 Kerscher M, Korting HC, Schafer-Korting M (1991) Skin ceramides structure and function. Eur J Dermatol 1 39-43 Lehmann P, Holze E, Melnik B, Plewig G (1991) Effects of ultraviolet A and B on the skin barrier a functional, electron microscopic and lipid biochemical study. Photodermatol Photoimmunol Photomed 8 129-134 Leyden J, Lavker R, Grove G, Kaidbey K (1995) Alpha hydroxy acids are more than moisturizers. J Geriatr Dermatol [Suppl A3] 33-37... 

Once you are familiar with ceramide structure, we can go further and use ceramide as a new starting block for more complex sphingolipids. Such sphingolipids fall into two categories. If ceramide is condensed with phosphorylcholine (not to be confounded with phosphatidylcholine, PC), it forms a sphingomyelin (SM, Fig. 1.22). 

Watersipora cucullata (Cheilostomata) harvested in Japan, contains a sulfated ceramide formed from haria-mide, isolated in 1997 from a cnidarian of the genus Zoanthus (Hexacoralha) (see Chapter 20). A second sulfated ceramide, structurally similar to the one just mentioned, is also present in this bryozoan both ceramides are... 

---