Constituents of Euphorbiaceae, 10. Comm. / New Cerebrosides from Euphorbia characias L.

Abstract

Four new cerebrosides C-1 – C-4 were isolated from the latex of Euphorbia characias L. On the basis of spectral evidences and chemical reactions they were characterized as (2S, 3S, 4R, 5R, 6Z)-1-O-(β-D-glucopyranosyl)-2N-[(2'R)-2′-hydroxy-(15′Z)-tetracosenoyl]-6(Z)-octadecene-1,3,4,5-tetraol-2-amino (C-1), (2 S, 3 S, 4 R, 5 R, 6 Z)-1-O-(β-D-glucopyranosyl)-2N-[(2′ R)-2′hydroxy-(17′ Z)-hexacosenoyl]-6(Z)-octadecene-1,3,4,5-tetraol- 2-amino (C-2), (2S, 3S, 4R, 5R, 6Z)-1-O-(β-D-glucopyranosyl)-2N-[(2′R)-2′-hydroxy-(19′Z)-octacosenoyl]-6-(Z)-octadecene-1,3,4,5-tetraol-2-amino (C-3) and (2 S, 3 S, 4 R, 5 R, 6 Z)-1-O-(β-D-glucopyranosyl)-2N-[(2′R)-2′-hydroxy-octacosanoyl]-6-(Z)-octadecene-1,3,4,5-tetraol-2-amino (C-4). Reversed phase column flash chromatography was effective for the isolation of the cerebrosides. FAB-MS spectrometry, 1H NMR, 13C NMR analysis and chemical reactions were useful in providing information for the structure elucidation.