title: Nigellidine-4-O-sulfite, the first sulfated indazole-type alkaloid from the seeds of Nigella sativa.
abstract: 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.
authors.affiliation: National Center for Natural Products Research, University of Mississippi, Mississippi, USA.
authors.forename: Zulfiqar
authors.initials: Z
authors.lastname: Ali
authors.forename: Daneel
authors.initials: D
authors.lastname: Ferreira
authors.forename: Paulo
authors.initials: P
authors.lastname: Carvalho
authors.forename: Mitchell A
authors.initials: MA
authors.lastname: Avery
authors.forename: Ikhlas A
authors.initials: IA
authors.lastname: Khan
mesh_terms: 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*
chemical_list: D000470:Alkaloids; D007191:Indazoles; D013463:Sulfuric Acid Esters; C531293:nigellidine-4-O-sulfite