Lipid metabolites with free-radical scavenging activity from Euphorbia helioscopia L.

•Bioassay oriented fractionation of methanolic extract of Euphorbia helioscopia L.•Identification by spectroscopic data and chemical reactions of lipid metabolites.•Identification of one active fraction from E. helioscopia L.•FRS due to compound 10 with an Emax of 69% at 15 μg/mL (EC50 = 5.2 μg/mL).

The methanolic extract of the plant Euphorbia helioscopia L. exhibited an interesting free-radical scavenging activity.From the aerial parts of Euphorbia helioscopia L. (Euphorbiaceae), a complex mixture of seven cerebrosides together with glucoclionasterol, a digalactosyldiacylglycerol and a diacylmonogalactosylglycerol were identified. The structures of the cerebrosides were characterized as 1-O-β-d-glucosides of phytosphingosines, which comprised (2S, 3S, 4E, 8E)-2-amino-4(E),8(E)-octadecadiene-1,3-diol, (2S, 3S, 4E, 8Z)-2-amino-4(E),8(Z)-octadecadiene-1,3-diol, (2S, 3S, 4R, 8Z)-2-amino-8(Z)-octadecene-1,3,4-triol as long chain bases with seven 2-hydroxy fatty acids of varying chain lengths (C16, C24:1, C26:1, C24, C26, C28:1) linked to the amino group.The glycosylglycerides were characterized as (2S)-2,3-O-di-(9,12,15-octadecatrienoyl)-glyceryl-6-O-(α-d-galactopyranosyl)-β-d-galactopyranoside and (2S)-2,3-O-di-(9,12,15-octadecatrienoyl)-glyceryl-1-O-β-d-galactopyranoside. The structures were established on the basis of spectroscopic data and chemical reactions.