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Four amides, namely, piperine ( 1 ), pellitorine ( 2 ), piperiline ( 5 ) and  N - trans-p -coumaroyltyramine ( 7 ), and three aristolactams, i.e., piperolactams D ( 3 ), B ( 4 ) and A ( 6 ), were isolated from the methanol extract of  Piper wallichii  stems. Piperiline, piperolactams B and D were obtained from this plant for the first time. Compounds  1 ,  3 ,  5 ,  6  and  7  were evaluated for their antioxidant, antimicrobial and cytotoxic activities. Piperine ( 1 ) displayed the highest antioxidant activity in scavenging DPPH radicals with an IC 50  value of 94.51 ± 11.91 μM. Piperolactams D ( 3 ) and A ( 6 ) showed antibacterial activity against Gram-positive bacteria ( B. subtilis  and  S. aureus ) with MICs of between 500-1000 μM. All test compounds were cytotoxic to breast cancer (MCF-7) cells, while the aristolactams were more toxic to colon cancer (Caco-2) cells than the amides. Compounds  1 ,  3 ,  6  and  7  were moderately cytotoxic to the doxorubicin-resistant MCF-7 subline (MCF-7/DOX). All compounds were non-toxic to normal human fibroblast (NIH/3T3) cells.

Antioxidant, Antimicrobial and Cytotoxic Activities of Amides and Aristolactams from Piper wallichii (Miq.) Hand.-Mazz. Stems