Glycophosphoceramides from plants. Purification and characterization of a novel tetrasaccharide derived from tobacco leaf glycolipids.
A glycophosphoceramide concentrate prepared from tobacco leaves was shown to contain a mixture of related lipids (Kaul, K., and Lester, R. L. (1975) Plant Physiol. 55, 120-129; Kaul, K., and Lester, R. L. (1978) Biochemistry 17, 3569-3575) with the simplest and most abundant components having the structure GlcN(+/- Ac)(alpha 1 leads to 4)GlcUA(alpha 1 leads to 2)myoinositol-1-O-phosphorylceramide (Hsieh, T. C.-Y., Kaul, K., Laine, R. A., and Lester, R. L. (1978) Biochemistry 17, 3575-3579). To determine the structure of the more complex members of this series, a mixture of oligosaccharides was prepared from a carboxyl-reduced glycophosphoceramide concentrate by alkali-catalyzed hydrolysis and alkaline phosphatase treatment. A combination of reverse-phase high pressure liquid chromatography (Wells, G. B., and Lester, R. L. (1979) Anal. Biochem. 97, 184-190), normal-phase high pressure liquid chromatography, and thin layer chromatography were used to resolve several oligosaccharides as acetylated derivatives. Products of methylation analysis, CrO3 oxidation, and deacetylation-deamination were identified using chemical ionization mass spectrometry to give the following novel structures. A major tetrasaccharide was completely characterized as Gal(alpha 1 leads to 4)GlcNAc(alpha 1 leads to 4)GlcUA(alpha 1 leads to 2)myoinositol. An additional structure of a minor tetrasaccharide was partially characterized as GlcNAc(alpha 1 leads to 4)GlcUA(alpha 1 leads to ?)myoinositol(O leads from 1 alpha)Man. These are representatives of a class of acidic glycolipids from plants, possibly analogous to the acidic gangliosides found in animal cell membranes.
Publication Source (Journal or Book title)
Journal of Biological Chemistry
Hsieh, T., Lester, R., & Laine, R. (1981). Glycophosphoceramides from plants. Purification and characterization of a novel tetrasaccharide derived from tobacco leaf glycolipids.. Journal of Biological Chemistry, 256 (15), 7747-7755. Retrieved from https://digitalcommons.lsu.edu/biosci_pubs/2235