dehydropipernonaline and pellitorine

In this study, via a bioactivity-guided fractionation of MeOH extracts of the fruits of Piper nigrum, alkamide (5) and five previously-identified alkamides were isolated. Their structures were elucidated via spectroscopic analysis ((1)H, (13)C NMR and ESI-MS), as follows: retrofractamide A (1), pipercide (2), piperchabamide D (3), pellitorin (4), dehydroretrofractamide C (5) and dehydropipernonaline (6). The IC(50) values determined for the compounds were 24.5 (1), 3.7 (2), 13.5 (3), 40.5 (4), 60 (5) and 90 microM (6), according to the results of an ACAT enzyme assay system using rat liver microsomes. These compounds all inhibited cholesterol esterification in HepG2 cells.

Topics: Amides; Animals; Benzodioxoles; Cell Line, Tumor; Cholesterol Esters; Dose-Response Relationship, Drug; Enzyme Inhibitors; Fatty Acids, Unsaturated; Fruit; Humans; Magnetic Resonance Spectroscopy; Microsomes, Liver; Molecular Structure; Organic Chemicals; Piper nigrum; Piperidines; Plant Extracts; Polyunsaturated Alkamides; Rats; Spectrometry, Mass, Electrospray Ionization; Sterol O-Acyltransferase