New lipoxygenase and cholinesterase inhibitory sphingolipids from Carthamus oxyacantha

Nat Prod Res. 2016 Aug;30(16):1787-95. doi: 10.1080/14786419.2015.1075524. Epub 2015 Aug 19.

Abstract

Two new sphingolipids: oxyacanthin A [(2S,3S,4R)-2-{[(2R,5E)-2-hydroxyoctadec-5-enoyl]amino}hexaeicosane-1,3,4-triol; 1] and B [(2S,3S,4R)-2-{[(2R,5E)-2-hydroxyoctadec-5-enoyl]amino}hexaeicosane-1,3,4-triol-1-O-β-D-glucopyranoside; 2], together with 1-octacosanol, β-sitosterol, β-sitosterol 3-O-β-D-glucopyranoside and luteolin 7-O-β-glucopyranoside were isolated from the methanolic extract of the whole plant of Carthamus oxyacantha. Their structures were elucidated using (1)H and (13)C 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 in comparison with the literature data of the related compounds. Both the compounds 1 and 2 showed inhibitory potential against lipoxygenase (LOX) in a concentration-dependent manner with IC50 values 83.3 ± 1.3 and 245.7 ± 1.1 µM, whereas compound 2 showed inhibition against enzymes acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) with IC50 values 65.3 ± 0.1 and 93.6 ± 0.1 µM, respectively.

Keywords: Carthamus oxyacantha; cholinesterase inhibition; lipoxygenase inhibition; secondary metabolites; sphingolipids.

MeSH terms

  • Acetylcholinesterase / drug effects
  • Butyrylcholinesterase / drug effects
  • Carthamus / chemistry*
  • Cholinesterase Inhibitors / chemistry
  • Cholinesterase Inhibitors / isolation & purification*
  • Cholinesterase Inhibitors / pharmacology
  • Inhibitory Concentration 50
  • Lipoxygenase / metabolism
  • Lipoxygenase Inhibitors / chemistry
  • Lipoxygenase Inhibitors / isolation & purification*
  • Lipoxygenase Inhibitors / pharmacology
  • Molecular Structure
  • Sphingolipids / chemistry
  • Sphingolipids / isolation & purification*
  • Sphingolipids / pharmacology

Substances

  • Cholinesterase Inhibitors
  • Lipoxygenase Inhibitors
  • Sphingolipids
  • Lipoxygenase
  • Acetylcholinesterase
  • Butyrylcholinesterase