Nigellidine-4-O-sulfite, the first sulfated indazole-type alkaloid from the seeds of Nigella sativa.
The rare indazole-type alkaloid nigellidine (2) is accompanied by its 4-O-sulfite (4) in the seeds of Nigella sativa. Compound 4 may represent the true natural product leading to nigellidine (2) via hydrolysis of the sulfate functionality during the isolation process. The structure of nigellidine-4-O-sulfite (4) is confirmed by NMR, MS, and X-ray crystallographic data. This is the first report of the natural occurrence of sulfated indazole-type alkaloids.
Ali
Zulfiqar
Z
National Center for Natural Products Research, University of Mississippi, Mississippi, USA.
Ferreira
Daneel
D
Carvalho
Paulo
P
Avery
Mitchell A
MA
Khan
Ikhlas A
IA
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification*; D018360:Crystallography, X-Ray; D007191:Indazoles / Q000737:chemistry / Q000302:isolation & purification*; D008968:Molecular Conformation; D015394:Molecular Structure; D031881:Nigella sativa / Q000737:chemistry*; D012639:Seeds / Q000737:chemistry; D013463:Sulfuric Acid Esters / Q000737:chemistry / Q000302:isolation & purification*
D000470:Alkaloids; D007191:Indazoles; D013463:Sulfuric Acid Esters; C531293:nigellidine-4-O-sulfite