title: Biomimetic cyclization of cnicin to malacitanolide, a cytotoxic eudesmanolide from Centaurea malacitana.
abstract: Malacitanolide (2), a new eudesmanolide isolated from the aerial parts of Centaurea malacitana, was characterized spectroscopically. The synthesis of 2 from cnicin (1), via the epoxide 3, confirmed the structure and stereochemistry of malacitanolide, as well as its biogenetic relationship with 1. Cytotoxic activity values for 2 are significantly higher than for 1.
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Granada, Spain. afbarre@goliat.ugr.es
authors.forename: A F
authors.initials: AF
authors.lastname: Barrero
authors.forename: J E
authors.initials: JE
authors.lastname: Oltra
authors.forename: V
authors.initials: V
authors.lastname: Morales
authors.forename: M
authors.initials: M
authors.lastname: Alvarez
authors.forename: I
authors.initials: I
authors.lastname: Rodríguez-García
mesh_terms: D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000302:isolation & purification* / Q000494:pharmacology; D003500:Cyclization; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007941:Leukemia P388 / Q000188:drug therapy; D051379:Mice; D018515:Plant Leaves / Q000737:chemistry*; D012717:Sesquiterpenes / Q000302:isolation & purification* / Q000378:metabolism* / Q000494:pharmacology; D014407:Tumor Cells, Cultured
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D012717:Sesquiterpenes; C109394:malacitanolide; C012849:cnicin