Isolation and structure determination of sulfonoquinovosyl dipalmitoyl glyceride, a P-selectin receptor inhibitor from the alga Dictyochloris fragrans

J Nat Prod. 1997 Apr;60(4):387-9. doi: 10.1021/np9606761.

Abstract

Bioassay-guided fractionation of the marine alga Dictyochloris fragrans led to the isolation and identification of sulfonoquinovosyl dipalmitoyl glyceride (1). The structure of 1 was determined by a combination of spectroscopic methods. On the basis of P-selectin inhibition assays (i.e., P-selectin-IgG ELISA, cell binding assay of receptor globulin, and platelet:HL60 adhesion, it was demonstrated that 1 selectively blocks the P-selectin-ligand interaction in vitro and could be considered a lead compound for synthetic modification in order to design more potent inhibitors of cell adhesion processes that play important roles in development of inflammatory-mediated disease states.

MeSH terms

  • Cell Adhesion / drug effects
  • Enzyme-Linked Immunosorbent Assay
  • Eukaryota / chemistry
  • Glycolipids / chemistry
  • Glycolipids / isolation & purification*
  • Glycolipids / pharmacology
  • HL-60 Cells
  • Humans
  • Immunoglobulin E / chemistry
  • P-Selectin / metabolism*
  • Receptors, Antigen / metabolism
  • Spectrometry, Mass, Fast Atom Bombardment

Substances

  • Glycolipids
  • P-Selectin
  • Receptors, Antigen
  • sulfoquinovosyl dipalmitoyl glyceride
  • Immunoglobulin E