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In kidney MDCK and intestinal Caco-2 epithelial cells, glucosylceramide (GlcCer) and sphingomyelin (SPH) synthesized from the short-chain sphingolipid analogue N-6-[7-nitro-2,1,3-benzoxadiazol-4-yl]aminodecanoyl (C6-NBD)-ceramide are delivered to the cell surface with apical/basolateral polarities of 2-4 and 0.6-0.9 respectively. We have tested how variations in the lipid backbone affect these polarities. First, the C6-NBD moiety was replaced by a bare [14C]octanoyl chain or by the even more bulky fluorophores 8-bimanoylthio-octanoyl (C8-bimane) and 8-diethylaminocoumarin-octanoyl (C8-DECA). In addition, the sphingosine in C6-NBD-ceramide was changed in stereoconfiguration (L-threo) or saturation (dihydro). In all cases, GlcCer and SPH were produced and appeared on the cell surface at 37 degrees C, as assayed by back-exchange. The apical/basolateral polarity of the delivery of GlcCer was variable, but always exceeded 1. GlcCer was apically enriched over SPH (2-6 times for MDCK and 3-9 times for Caco-2). Even GlcCer synthesized from a highly water-soluble truncated ceramide (octanoyl-D-erythro-sphingosine analogue with C8 backbone) was enriched apically by a factor of greater than or equal to 2 both in absolute polarity and compared with SPH. Sphingolipid sorting was quantitatively but not qualitatively affected by dramatic changes in the lipid backbone.

Epithelial sphingolipid sorting allows for extensive variation of the fatty acyl chain and the sphingosine backbone