Novel dimeric amide alkaloids from Piper chaba Hunter: isolation, cytotoxic activity, and their biomimetic synthesis

Abstract

Chromatographic fractionation of methanol extract from roots of the Piper chaba Hunter resulted in the isolation of four new dimeric alkaloids, chabamide H ( 1), I ( 2), J ( 3), K ( 4) together with 11 known compounds ( 5– 15). Their chemical structures and relative stereochemistry were determined on the basis of the comprehensive spectroscopic techniques (IR, Mass, and NMR) and further confirmed by comparison of the data with those reported in literature. In addition, cytotoxic activities of all the dimeric amides ( 1– 7) along with their monomers ( 8– 10) were evaluated against cervical (HELA), breast (MCF-7), liver (HEPG2), colon (HT-29), and colon (COLO-205) cancer cell lines. Among the tested isolates, 5 and 7 exhibited potent cytotoxic activity against COLO-205 cell line with IC 50 value of 3.10 μg/mL and 0.018 μg/mL, respectively. To prove biogenesis of the newly isolated compounds, biomimetic synthesis has also been carried out via Diels–Alder reaction by using copper(II) salts in aqueous medium.