Lipoxygenase inhibitory sphingolipids from Launaea nudicaulis

J Asian Nat Prod Res. 2012;14(6):545-54. doi: 10.1080/10286020.2012.680440.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Asteraceae / chemistry*
  • Dose-Response Relationship, Drug
  • Inhibitory Concentration 50
  • Lipoxygenase Inhibitors / chemistry
  • Lipoxygenase Inhibitors / isolation & purification*
  • Lipoxygenase Inhibitors / pharmacology*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Pakistan
  • Sphingolipids / chemistry
  • Sphingolipids / isolation & purification*
  • Sphingolipids / pharmacology*
  • Stereoisomerism

Substances

  • Lipoxygenase Inhibitors
  • Sphingolipids