New nitro-benzo[c]phenanthridine and indolopyridoquinazoline alkaloids from Zanthoxylum atchoum

Abstract The first phytochemical investigation of the roots of Zanthoxylum atchoum has led to the isolation of two new nitro-benzo[ c ]phenanthridine alkaloids 6-nitronitidine ( 1 ) and 6-nitro-8-methoxy-7,8-dihydronitidine ( 2 ), two new salts of indolopyridoquinazoline alkaloids 3-hydroxy-8,13-dihydro-14-methyl-5-oxo-7 H -indolo[2’,3’:3,4]pyrido[2,1- b ]quinazolin-14-ium ( 3 ) and its zwitterionic form 3-phenolate-8,13-dihydro-14-methyl-5-oxo-7 H -indolo[2’,3’:3,4]pyrido[2,1- b ]quinazolin-14-ium ( 4 ) along with 18 ( 5 – 22 ) known compounds. Their chemical structures were elucidated by spectroscopic analysis including 1D and 2D NMR and MS techniques. This is the first report of the nitro group on the biosynthesis of the natural benzo[ c ]phenantridine alkaloids. Compound 2 exhibited potent antibacterial activity against Staphylococcus aureus of MIC 50  = 4 μg·mL −1 .