Constituents of Euphorbiaceae, 13. Comm. [1] Isolation and Structure Elucidation of Five Cerebrosides from Euphorbia characias L

H. Wagner, O. Seligmann Institut für Pharmazeutische Biologie der Universität München, Karlstraße 29, D-80330 München Z. Naturforsch. 49 b, 135-140 (1994); received August 30,1993 Euphorbiaceae, Cerebrosides, Structure Five cerebrosides B-l -B-4 were isolated from the fraction B, obtained from the latex of Euphorbia characias L. On the basis of spectral evidences and chemical reactions they were characterized as (2S, 3S, 4R, 8Z)-l-0-(/?-D-glucopyranosyl)-2N-[(2'R)-2'-hydroxytetracosenoyl]-8 (Z)-octadecene-l,3,4-triol-2-amino (B-l), (2S, 3S, 4R, 8Z)-l-0-(/?-D-glucopyranosyl)-2 N-[(2'R)-2'-hydroxyhexacosenoyl]-8(Z)-octadecene-l,3,4-triol-2-amino(B-2), (2 S, 3 S,4 R, 8 Z)-l-0-(/J-D-glucopyranosyl)-2N-[(2'R)-2'-hydroxyoctacosenoyl]-8 (Z)-octadecene-1,3,4-triol-2-amino (B-3), (2 S, 3 S, 4R, 8Z)-l-0-(/?-D-glucopyranosyl)-2N-[(2'R)-2'hydroxyhexacosanoyl]-8 (Z)-octadecene-l,3,4-triol-2-amino (B-3a), (2S, 3S, 4R, 8Z)-l-0(/3-D-glucopyranosyl)-2 N-[(2'R)-2'-hydroxyheptacosanoyl]-8 (Z)-octadecene-l,3,4-triol-2amino (B-4). Reversed phase column flash chromatography was effective for the isolation of the cere­ brosides. FAB-MS spectrometry, *H NMR, 13C NMR analyses and DQF-COSY and ^ -d e ­ tected HMQC (single bond and multiple bond) experiments and chemical reactions were useful in providing informations for the structure elucidation.