Cyanogramide with a new spiro[indolinone-pyrroloimidazole] skeleton from Actinoalloteichus cyanogriseus.

Cyanogramide (1), an unprecedented alkaloid bearing a novel spirocyclic pyrrolo[1,2-c]imidazole skeleton, was identified from the fermentation broth of the marine-derived Actinoalloteichus cyanogriseus WH1-2216-6. The structure was fully determined by spectroscopic analysis, an exciton chirality CD method, and quantum mechanical calculations. Cyanogramide (1) could efficiently reverse the adriamycin-induced resistance of K562/A02 and MCF-7/Adr cells, and the vincristine-induced resistance of KB/VCR cells at a concentration of 5 μM, with the reversal fold values of 15.5, 41.5, and 9.7, respectively.