Lipoxygenase inhibitory sphingolipids from Launaea nudicaulis.

Riaz, Naheed; Parveen, Shehla; Saleem, Muhammad; Ali, MuhammadShaiq; Malik, Abdul; Ashraf, Muhammad; Afzal, Iftikhar; Jabbar, Abdul

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.

CHROMATOGRAPHIC analysis; LIPID analysis; BIOLOGICAL assay; LIPIDS; MASS spectrometry; MOLECULAR structure; NUCLEAR magnetic resonance spectroscopy; OXIDOREDUCTASES; PHARMACEUTICAL chemistry; RESEARCH funding; PLANT extracts; DATA analysis software; DESCRIPTIVE statistics; IN vitro studies; CHEMICAL inhibitors

Journal of Asian Natural Products Research, 2012, Vol 14, Issue 6, p545

1028-6020

Academic Journal

10.1080/10286020.2012.680440