CONSTITUENTS OF EUPHORBIACEAE .13. COMM - ISOLATION AND STRUCTURE ELUCIDATION OF 5 CEREBROSIDES FROM EUPHORBIA-CHARACIAS L

Five cerebrosides B-1-B-4 were isolated from the fraction B, obtained from the latex of Euphorbia characias L. On the basis of spectral evid ences and chemical reactions they were characterized as (2 S, 3 S, 4 R , 8 Z)-1-O-(beta-D-glucopyranosyl)-2 N-[(2'R)-2' hydroxytetracosenoyl] -8 (Z)-octadecene-1,3,4-triol-2-amino (B-1), (2S, 3S, 4R, 8Z)-1-O-(bet a-D-glucopyranosyl)-2 N-[(2'R)-2'-hydroxyhexacosenoyl]-8 (Z)-octadecen e-1,3,4-triol-2-amino (B 2), (2 S, 3 S, 4 R, 8 Z)-l-O-(beta-D-glucopyr anosyl)-2 N-[(2'R)-2'-hydroxyoctacosenoyl]-8 (Z)-octadecene-1,3 ,4-tri ol-2-amino (B-3), (2 S, 3 S, 4 R, 8 Z)-1 -O-(beta-D-glucopyranosyl)-2 N-[(2'R)-2-'hydroxyhexacosanoyl]-8 (Z)-octadecene-1,3,4-triol-2-amino (B-3a), (2S, 3 S, 4R, 8 Z)-1-0(beta-D-glucopyranosyl)-2 N-[(2'R)-2' -h ydroxyheptacosanoyl]-8 (Z)-octadecene-1,3,4-triol-2-amino (B-4). Rever sed phase column flash chromatography was effective for the isolation of the cerebrosides. FAB-MS spectrometry, H-1 NMR,C-13 NMR analyses an d DQF-COSY and H-1-detected HMQC (single bond and multiple bond) exper iments and chemical reactions were useful in providing informations fo r the structure elucidation.