Chemistry of costunolide and biological activity of the derived lactones

Article abstract of DOI:10.1016/S0031-9422(00)80816-X

Costunolide and its derived C-16 germacranolides on oxidation with selenium dioxide-t-butyl hydroperoxide afforded two melampolides, an aldehydolactone and the corresponding hydroxylactone, in each case. Structures were assigned to these melampolides on the basis of spectral data and chemical correlation. The aldehydolactones were significantly more active root promotors than their parent lactones. Costunolide and related germacranolides underwent cyclization on treatment with iodine and pyridinium chlorochromate to afford interesting products. (-)-β-Frullanolide has been synthesized and shown to be biologically more active when compared with its parent trans-lactone.