STRUCTURAL DETERMINATION OF -BETA-D-GLUCOPYRANOSYL-9-METHYL-4,8-SPHINGADIENINE FROM SPECIES OF ASPERGILLUS

Ceramide monohexosides from Aspergillus fumigatus 2140 and 2109 strain s and Aspergillus versicolor 550 strain, obtained by silica gel 60, an d Iatrobeads chromatography were analysed using high-resolution 1D-, 2 D-H-1-NMR and C-13-NMR spectroscopy and fast atom bombardment mass spe ctrometry (FAB-MS). The ceramide monohexoside fraction (CMH) from A. f umigatus 2140 and A. versicolor 550 was identified as glucosylceramide , whereas glucose and galactose were present at a ratio of 1:1 in the CMH of A. fumigatus 2109. The major glycosphingolipid has a particular ceramide composition consisting of 9-methyl-4,8-sphingadienine linked to a 2-hydroxyoctadec-3-enoic acid. Although the structures presently described are similar to those of monohexosylceramides from other fun gi, including edible ones, this is the first report on their occurrenc e in species pathogenic in humans.