Synthetic studies on glycosphingolipids from Protostomia phyla: syntheses and biological activities of amphoteric glycolipids containing a phosphocholine residue from the earthworm Pheretima hilgendorfi

Two types of amphoteric glycosphingolipid found in the earthworm Pheretima hilgendorfi, PC(→6)-β-d-Galp-(1→6)-β-d-Galp-(1→1)Cer (1) and PC(→6)-β-d-Galp-(1→6)-β-d-Galp-(1→6)-β-d-Galp-(1→1)Cer (2), and their derivatives (4, 5) were synthesized. These were examined for their ability to enhance production of interleukin-8 (IL-8), a potent inflammatory cytokine involved in neutrophil chemotaxis, in a TNFα-stimulated granulocytic HL-60 cells. Compounds 1 and 2 were found to be potent enhancers of IL-8 production.

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