Cerebrosides with antiproliferative activity from Euphorbia peplis L.
Two new cerebrosides have been isolated from the whole plants of Euphorbia peplis L. The structures were established by FT-IR spectroscopy, FAB MS, EI-MS, ESI-MS, 1D and 2D NMR spectroscopy. The structures of the cerebrosides were characterized as 1-O-beta-d-glycosides of phytosphingosines, which comprised a common long-chain base, (2S, 3S, 4R, 8Z)-2-amino-8 (Z)-octadecene-1,3,4-triol with 2-hydroxy fatty acids of varying chain lengths (C25, C22) linked to the amino group. The isolated compounds were shown to possess significant antiproliferative properties against cultured human tumor cell lines KB and IMR-32.
Cateni
Francesca
F
Department of Pharmaceutical Sciences, University of Trieste, P.zle Europa, 1, 34127 Trieste, Italy. cateni@units.it
Zilic
Jelena
J
Zacchigna
Marina
M
Procida
Giuseppe
G
D000972:Antineoplastic Agents, Phytogenic / Q000302:isolation & purification / Q000494:pharmacology* / Q000627:therapeutic use; D002277:Carcinoma / Q000188:drug therapy*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects*; D002554:Cerebrosides / Q000302:isolation & purification / Q000494:pharmacology* / Q000627:therapeutic use; D028481:Euphorbia / Q000737:chemistry*; D006801:Humans; D015394:Molecular Structure; D009369:Neoplasms / Q000188:drug therapy*; D008517:Phytotherapy; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology* / Q000627:therapeutic use
C550892:(2S,3S,4R,8Z)-1-O-(beta-D-galactopyranosyl)-2N-((2'R)-2'-hydroxypentacosanoilamino)8(Z)-octadecene-1,3,4-triol; C550893:1-O-(beta-D-galactopyranosyl)-(2S,3S,4R,8Z)-2-((2'R)-2'-hydroxydocosanoilamino)-8(Z)-octadecene-1,3,4-triol; D000972:Antineoplastic Agents, Phytogenic; D002554:Cerebrosides; D010936:Plant Extracts