title: Lipid metabolites with free-radical scavenging activity from Euphorbia helioscopia L.
abstract: 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.
authors.affiliation: Department of Chemical and Pharmaceutical Sciences, University of Trieste, P.zle Europa 1, 34127 Trieste, Italy. Electronic address: cateni@units.it.
authors.forename: F
authors.initials: F
authors.lastname: Cateni
authors.affiliation: Department of Chemical and Pharmaceutical Sciences, University of Trieste, P.zle Europa 1, 34127 Trieste, Italy.
authors.forename: J
authors.initials: J
authors.lastname: Zilic
authors.affiliation: Department of Chemical and Pharmaceutical Sciences, University of Trieste, P.zle Europa 1, 34127 Trieste, Italy.
authors.forename: T
authors.initials: T
authors.lastname: Altieri
authors.affiliation: Department of Chemical and Pharmaceutical Sciences, University of Trieste, P.zle Europa 1, 34127 Trieste, Italy.
authors.forename: M
authors.initials: M
authors.lastname: Zacchigna
authors.affiliation: Department of Chemical and Pharmaceutical Sciences, University of Trieste, P.zle Europa 1, 34127 Trieste, Italy.
authors.forename: G
authors.initials: G
authors.lastname: Procida
authors.affiliation: Department of Drug Sciences, University of Pavia, Via Taramelli 12, Pavia, Italy.
authors.forename: R
authors.initials: R
authors.lastname: Gaggeri
authors.affiliation: Department of Drug Sciences, University of Pavia, Via Taramelli 12, Pavia, Italy.
authors.forename: D
authors.initials: D
authors.lastname: Rossi
authors.affiliation: Department of Drug Sciences, University of Pavia, Via Taramelli 12, Pavia, Italy; Center for Studies and Researches in Ethno Pharmacy (C.I.St.R.E.), University of Pavia, Via Taramelli 12, 27100 Pavia, Italy.
authors.forename: S
authors.initials: S
authors.lastname: Collina
mesh_terms: D028481:Euphorbia / Q000737:chemistry / Q000378:metabolism*; D016166:Free Radical Scavengers / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism*; D050356:Lipid Metabolism; D008055:Lipids / Q000737:chemistry* / Q000302:isolation & purification; D000432:Methanol / Q000737:chemistry; D010936:Plant Extracts / Q000737:chemistry*
chemical_list: D016166:Free Radical Scavengers; D008055:Lipids; D010936:Plant Extracts; D000432:Methanol
keywords: Cerebrosides; Diacyldigalactosylglycerol; Diacylmonogalactosylglycerol; Euphorbia helioscopia L.; Free-radical scavenging activity