Isolation, structure elucidation and total synthesis of a cytotoxic dienone from Echinacea pallida.
The isolation and structure characterization of a dienone from the roots of Echinacea pallida, namely (8Z,11Z)-pentadeca-8,11-dien-2-one, are described here. To assess the configuration of this secondary metabolite, the stereoselective total synthesis of the two isomeric forms, (8Z,11Z)- and (8Z,11E)-pentadeca-8,11-dien-2-one, was undertaken and the structure elucidation of the natural compound was unambiguously carried out. The cytotoxic activity of both isomers was also evaluated on a human T cell leukaemia cancer line (Jurkat cells). The results indicated that these compounds exert a dose-dependent cytotoxicity with a medium-level potency on the tested cell line.
Morandi
Stefania
S
Department of Pharmaceutical Sciences, University of Modena and Reggio Emilia, Via G. Campi 183, 41100, Modena, Italy.
Pellati
Federica
F
Ori
Claudia
C
Adinolfi
Barbara
B
Nieri
Paola
P
Benvenuti
Stefania
S
Prati
Fabio
F
D002470:Cell Survival / Q000187:drug effects; D002851:Chromatography, High Pressure Liquid; D003603:Cytotoxins / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification* / Q000633:toxicity; D020900:Echinacea / Q000737:chemistry*; D006801:Humans; D019169:Jurkat Cells; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification* / Q000633:toxicity; D009682:Magnetic Resonance Spectroscopy
D003603:Cytotoxins; D007659:Ketones; C533801:penta-8,11-dien-2-one