The Structural Diversity of Natural Glycosphingolipids (GSLs).

Glycosphingolipids (GSLs) are a subclass of glycolipids made of a glycan and a ceramide that, in turn, is composed of a sphingoid base moiety and a fatty acyl group. GSLs represent the vast majority of glycolipids in eukaryotes, and as an essential component of the cell membrane, they play an important role in many biological and pathological processes. Therefore, they are useful targets for the development of novel diagnostic and therapeutic methods for human diseases. Since sphingosine was first described by J. L. Thudichum in 1884, several hundred GSL species, not including their diverse lipid forms that can further amplify the number of individual GSLs by many folds, have been isolated from natural sources and structurally characterized. This review tries to provide a comprehensive survey of the major GSL species, especially those with distinct glycan structures and modification patterns, and the ceramides with unique modifications of the lipid chains, that have been discovered to date. In particular, this review is focused on GSLs from eukaryotic species. This review has listed 251 GSL glycans with different linkages, 127 glycans with unique modifications, 46 sphingoids, and 43 fatty acyl groups. It should be helpful for scientists who are interested in GSLs, from isolation and structural analyses to chemical and enzymatic syntheses, as well as their biological studies and applications.