Boas MH, Egge H, Pohlentz G, Hartmann R, Bergter EB Structural determination of N-2'-hydroxyoctadecenoyl-1-O-beta-D-glucopyranosyl-9-methyl-4,8-sphingadienine from species of Aspergillus Chemistry and Physics of Lipids70(1) (1994)
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The structure was elucidated in this paper NCBI PubMed ID:8013053 Publication DOI:10.1016/0009-3084(94)90043-4 Journal NLM ID:0067206 Institutions: Institut für Physiologische Chemie der Universität Bonn, Bonn, Germany, Departmento de Microbiologia Geral, Instituto de Microbiologia da Universidade Federal de Rio de Janeiro, Rio de Janeiro, Brasil
Ceramide monohexosides from Aspergillus fumigatus 2140 and 2109 strains and Aspergillus versicolor 550 strain, obtained by silica gel 60, and Iatrobeads chromatography were analysed using high-resolution 1D-, 2D-1H-NMR and 13C-NMR spectroscopy and fast atom bombardment mass spectrometry (FAB-MS). The ceramide monohexoside fraction (CMH) from A. fumigatus 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 fungi, including edible ones, this is the first report on their occurrence in species pathogenic in humans.
Methods: 13C NMR, 1H NMR, GLC-MS, NMR-2D, FAB-MS, NMR-1D, methanolysis, HPLC, extraction, HPTLC, CC Comments, role: Aspergillus fumigatus NCPF 2190 glycosphingolipid consists of a mixture of glucosyl and galactosylceramide at a ratio of 1:1; 1H-NMR chemical shifts of the ceramide part from the peracetylated glucosyl- and galactosylceramide differ by <0.02 ppm
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