Natural occurrence of ganglioside lactones. Isolation and characterization of G(D1b) inner ester from adult human brain

L. Riboni, S. Sonnino, D. Acquotti, A. Malesci, R. Ghidoni, H. Egge, S. Mingrino, G. Tettamanti

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Abstract

A new ganglioside containing an inner ester linkage was extracted from adult brain specimens, obtained at the time of surgery on 51-70-year-old subjects, purified, and analyzed. It contains glucose, galactose, N-acetylgalactosamine, an N-acetylneuraminic acid in the molar ratio 1:2:1:2, but, on ion-exchange chromatography, behaves as a monosialoganglioside. Structural analyses showed its basic neutral glycosphingolipid core to be ganglio-N-tetraose ceramide, carrying a disialosyl residue on the 3-position of internal galactose. Sialidase degradation and chemical analysis of the products obtained after alkaline treatments suggested one sialic acid residue to be involved in an ester linkage. Fast atom bombardment-mass spectrometry indicated the presence of an inner ester linkage between the carboxyl group of the external sialic acid residue and a hydroxyl group of the internal one. On these bases, the new ganglioside can be assumed to be a G(D1b) in lactonic form. This ganglioside is present only in trace amounts in the brain of infants, but its content increases with age, reaching a value of 3.5% of total sialic acid in 51-70-year-old subjects.

Original languageEnglish
Pages (from-to)8514-8519
Number of pages6
JournalJournal of Biological Chemistry
Volume261
Issue number18
Publication statusPublished - 1986

ASJC Scopus subject areas

  • Biochemistry

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    Riboni, L., Sonnino, S., Acquotti, D., Malesci, A., Ghidoni, R., Egge, H., Mingrino, S., & Tettamanti, G. (1986). Natural occurrence of ganglioside lactones. Isolation and characterization of G(D1b) inner ester from adult human brain. Journal of Biological Chemistry, 261(18), 8514-8519.