Cytolipin H

Literature References: A glycosphingolipid containing lactose and a ceramide (N-acyl fatty acid deriv of a sphingosine). Fatty acid composition is variable but is primarily palmitic, behenic and lignoceric acids. First isolated from human epidermoid carcinoma cells, later found to be one of the major neutrophil glycolipids serving as a neutrophil-differentiation marker. Isoln: M. M. Rapport et al., Cancer 12, 438 (1959). Simplified prepn from ox spleen: M. M. Rapport et al., J. Biol. Chem. 237, 1056 (1962). Structure elucidation: A. C. Schram et al., Nature 197, 1074 (1963). Synthesis: D. Shapiro, E. S. Rachaman, ibid. 201, 878 (1964); K. C. Nicolaou et al., J. Am. Chem. Soc. 110, 7910 (1988). Serological activity: M. M. Rapport, L. Graf, Nature 201, 879 (1964); and effect of fatty acid chain length: L. Graf, M. M. Rapport, Chem. Phys. Lipids 13, 367 (1974). Characterization and distribution of glycolipids in leukemic and nonleukemic blood cells: J. Hildebrand et al., J. Lipid Res. 12, 361 (1971); in neutrophils: B. A. Macher, J. C. Klock, J. Biol. Chem. 255, 2092 (1980). Role as neutrophil cell surface marker: F. W. Symington et al., J. Immunol. 134, 2498 (1985). Intracellular localization: eidem, J. Biol. Chem. 262, 11356 (1987). TLC determn: K. Ogawa et al., J. Chromatogr. 426, 188 (1988). Clinical implications in inflammatory bowel disease: C. R. Stevens et al., Gut 29, 580 (1988). Review of structure, organization and role of glycolipids in the cell surface membrane: S. Hakomori, Annu. Rev. Biochem. 50, 733-764 (1981).

Properties: Coral-like clusters from pyridine + acetone, mp 230-240° with sintering at 180-190°. [a]D24 -10.8° (c = 2 in pyridine). Practically insol in water, cold methanol, acetone, cold acetic acid, ether, acetonitrile. Soluble in pyridine, chloroform, hot methanol, hot acetic acid. Dissolves readily in chloroform + methanol mixtures of high chloroform content.