New lipoxygenase and cholinesterase inhibitory sphingolipids from Carthamus oxyacantha.
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.
a Department of Chemistry , The Islamia University of Bahawalpur , Bahawalpur , Pakistan.
Muhammad
M
Dilshad
a Department of Chemistry , The Islamia University of Bahawalpur , Bahawalpur , Pakistan.
Naheed
N
Riaz
a Department of Chemistry , The Islamia University of Bahawalpur , Bahawalpur , Pakistan.
Muhammad
M
Saleem
a Department of Chemistry , The Islamia University of Bahawalpur , Bahawalpur , Pakistan.
Nusrat
N
Shafiq
a Department of Chemistry , The Islamia University of Bahawalpur , Bahawalpur , Pakistan.|b Department of Biochemistry and Biotechnology , The Islamia University of Bahawalpur , Bahawalpur , Pakistan.
Muhammad
M
Ashraf
b Department of Biochemistry and Biotechnology , The Islamia University of Bahawalpur , Bahawalpur , Pakistan.
Tayaba
T
Ismail
a Department of Chemistry , The Islamia University of Bahawalpur , Bahawalpur , Pakistan.
Hafiza Mehwish
HM
Rafiq
a Department of Chemistry , The Islamia University of Bahawalpur , Bahawalpur , Pakistan.
Abdul
A
Jabbar
D000110:Acetylcholinesterase / Q000187:drug effects; D002091:Butyrylcholinesterase / Q000187:drug effects; D031178:Carthamus / Q000737:chemistry*; D002800:Cholinesterase Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D008084:Lipoxygenase / Q000378:metabolism; D016859:Lipoxygenase Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015394:Molecular Structure; D013107:Sphingolipids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
D002800:Cholinesterase Inhibitors; D016859:Lipoxygenase Inhibitors; D013107:Sphingolipids; D008084:Lipoxygenase; D000110:Acetylcholinesterase; D002091:Butyrylcholinesterase
Carthamus oxyacantha; cholinesterase inhibition; lipoxygenase inhibition; secondary metabolites; sphingolipids