title: Lipoxygenase inhibitory sphingolipids from Launaea nudicaulis.
abstract: Four new sphingolipids: nudicaulin A [(2S,3S,4R,14E)-2-{[octadecanoyl]amino}tetraeicos-14-ene-1,3,4-triol; 1], nudicaulin B [(2S,3S,4R,14E)-2-{[(2R)-2-hydroxyoctadecanoyl]amino}tetraeicos-14-ene-1,3,4-triol; 2], nudicaulin C [(2S,3S,4R,14E)-2-{[(2R)-2-hydroxyoctadecanoyl]amino}tetraeicos-14-ene-1,3,4-triol-1-O-β-D-glucopyranoside; 3], and nudicaulin D [(2S,3S,4R)-2-{[(2R,3S,12E)-2,3-dihydroxyeicos-12-enoyl]amino}octadecane-1,3,4-triol; 4] together with 1-hexatriacontanol, β-sitosterol, octadecyl 4-hydroxycinnamate, elaidic acid, cholesta-5,22-diene-3,7-diol, oleanolic acid, apigenin, and β-sitosterol 3-O-β-D-glucopyranoside were isolated from the methanolic extract of the whole plant of Launaea nudicaulis. Their structures were elucidated using ¹H and ¹³C NMR spectra and 2D NMR analyses (HMQC, HMBC, and COSY) in combination with mass spectrometry (EI-MS, HR-EI-MS, FAB-MS, and HR-FAB-MS) experiments and comparison with literature data of related compounds. Compounds 1-4 displayed moderate inhibitory potential against enzyme lipoxygenase in concentration-dependent manner with IC₅₀ value ranges 103-193 μM.
authors.affiliation: Department of Chemistry, Baghdad-ul-Jadeed Campus, The Islamia University of Bahawalpur, 63100 Bahawalpur, Pakistan.
authors.forename: Naheed
authors.initials: N
authors.lastname: Riaz
authors.forename: Shehla
authors.initials: S
authors.lastname: Parveen
authors.forename: Muhammad
authors.initials: M
authors.lastname: Saleem
authors.forename: Muhammad Shaiq
authors.initials: MS
authors.lastname: Ali
authors.forename: Abdul
authors.initials: A
authors.lastname: Malik
authors.forename: Muhammad
authors.initials: M
authors.lastname: Ashraf
authors.forename: Iftikhar
authors.initials: I
authors.lastname: Afzal
authors.forename: Abdul
authors.initials: A
authors.lastname: Jabbar
mesh_terms: D019659:Asteraceae / Q000737:chemistry*; D004305:Dose-Response Relationship, Drug; D020128:Inhibitory Concentration 50; D016859:Lipoxygenase Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010154:Pakistan; D013107:Sphingolipids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D013237:Stereoisomerism
chemical_list: D016859:Lipoxygenase Inhibitors; D013107:Sphingolipids