Rubreserine (3), a known degradation product of physostigmine (1), and
a new indole derivative, 4, were isolated when 1 was refluxed with NH
4OH. The structure of the rearrangement product of 1, compound 4, was
deduced through the interpretation of NMR data. Rubreserine (3) was ve
ry weakly cytotoxic to KB (human oral epidermoid carcinoma) and LNCaP
(hormone-dependent human prostate cancer) cells and was active in the
ASK (astrocytoma) assay. Compound 4 showed potent cytotoxicity in all
cell lines tested.