Biomimetic cyclization of cnicin to malacitanolide, a cytotoxic eudesmanolide from Centaurea malacitana.
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.
Barrero
A F
AF
Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Granada, Spain. afbarre@goliat.ugr.es
Oltra
J E
JE
Morales
V
V
Alvarez
M
M
Rodríguez-García
I
I
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
D000972:Antineoplastic Agents, Phytogenic; D012717:Sesquiterpenes; C109394:malacitanolide; C012849:cnicin