Glucosylceramide isolation

The amphicerebrosides are probably the first known examples of a-glucosylceramides. Isolated from the species Amphimedon viridis harvested in the Gulf of Eilat (Red Sea) they contain an N-glucosamine in a or P configuration. Unlike the agelasphins, the amphicerebrosides have no particular biological activity (Hirsch and Kashman, 1989). 

Morrison (1970) presented earlier data on the fatty acid composition of these lipids. Morrison and Hay (1970) described the isolation and analyses of milk sphingomyelin, glucosylceramide, and lactosylcera-... 

Glucosylceramides are considered as characteristic compounds of plants but also found in low amounts in animal tissues, such as spleen, nervous tissues, and erythrocytes. In plants, they are abundant in photosynthetic tissues (31). From nonphotosynthetic tissues, monoglycosylceramides that contain a P-D-mannopyranosyl residue have been isolated. 

The stratum corneum intercellular lipids exist as a continuous lipid phase occupying about 20% of the stratum corneum volume and arranged in multiple lamellar structures. They are composed of cholesterol (27 /o) and ceramides (41 /o), together with free fatty acids (9 /o), cholesteryl esters (10 /o) and cholesteryl sulfate (2 /o) (Table 1). Phospholipids, which dominate in the basal layer, are converted to glucosylceramides and subsequently to ceramides and free fatty acids, and are virtually absent in the outer layers of the stratum corneum. Eight classes of ceramides have been isolated and identified in human stratum corneum but the functions of the individual ceramide types are not fully understood. Similarly, the exact function of cholesterol esters within the stratum corneum lamellae is also elusive but it is theoretically possible that cholesterol esters may span adjacent bilayers and serve as additional stabilizing moieties. 

D-Glucosylceramide was isolated from rat intestine and the major sphingoid base was 4D-hydroxysphingamine. ... 

Recently, three homogeneous sphingosine-type glucocerebrosides were isolated from the body walls of the cold water sea cucumber C. frondosa. These glucosylceramides have been previously isolated from the sea cucumbers C. echinata and S. japonicus [34],... 

Both glycosphingolipids and ceramides have been isolated from human and pig epidermal tissue. The least polar of four chromatographically distinct D-glucosylceramides from pig epidermal tissue, and probably from human epidermal tissue due to similar properties, was characterized as l-(3 -0-octadecadienoyl) - j8 - d - glucosyl - N- dihydroxypentatriacontadienoyl - sphingo-sine. ... 

Maier, M.S., Kuriss, A., and Seldes, A.M. (1998) Isolation and structure of glucosylceramides from the starflsh Cosmasterias lurida. Lipids, 33, 825-827. 

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