Sphingosines sulfate

The first marine examples of sphingosines sulfated at position 4 were observed in this same Korean species, Spirastrella abata (Alam et al, 2002). These derivatives are cytotoxic to five types of human solid tumor, with IC50 values ranging from 0.3 to lOpgml". ... 

A partial synthesis of cerebroside sulfate [ sulfatide, the glycoside of ceramide with galactose 3-sulfate, (90)] was achieved [90] by acylating the sphingosine galactosyl 3-sulfate (89) (obtained by basic hydrolysis of natural sulfatide) with palmitoyl chloride or D-2-acetoxypalmitoyl chloride (and subsequent basic hydrolysis of the... 

In 2006, Rezanka etal44 isolated an antifeedant, syriacin (59), from the freshwater sponge Ephydatia syriaca in the Jordan river. It is an unusual sulfated ceramide glycoside with branched-chain sphingosine and also a branched-chain fatty acid. From the viewpoint of absolute configuration, 59 is very unusual, because it contains both (if)- and (.V)-configured. rcc-butyl terminals in its alkyl chains. It seems to be biosynthesized from precursors with opposite absolute configuration. 

These results are consistent with the hypothesis that the sulfur atom of DCS is derived from cysteine and carbon atoms 1 and 2 are derived from serine. Biosynthesis of DCS would then follow the well known [8]serine palmityol CoA pathway with introduction of the sulfur atom into sphingosine or ceramide by a cystathionine-type reaction with cysteine followed by oxidation of the SH group to a sulfonic acid group The role of cysteic acid is not clear, since it cannot participate in a cystathionine-type reaction, but it may be a more effective donor of sulfur than sulfate for synthesis of cysteine from serine. 

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