Tryptamine derived amides and acetogenins from the seeds of Rollinia mucosa

Bioactivity-directed fractionation of a CHCl(3)-MeOH (1:1) extract prepared from the seeds of Rollinia mucosa led to the isolation of a mixture of eight novel tryptamine amides. Extensive HPLC allowed the isolation of the major component of the mixture, which was characterized as N-lignoceroyltryptamine (6) using a combination of spectroscopic and chemical methods. The minor amides were identified by GC-MS analysis as N-palmitoyltryptamine (1), N-stearoyltryptamine (2), N-arachidoyltryptamine (3), N-behenoyltryptamine (4), N-tricosanoyltryptamine (5), N-pentacosanoyltryptamine (7), and N-cerotoyltryptamine (8). Two lignans (pinoresinol dimethyl ether and magnolin) and six acetogenins [membranacin (9), desacetyluvaricin (10), rolliniastatin 1, bullatacin, squamocin, and motrilin] were also isolated. The cytotoxicity of membranacin (9) and desacetyluvaricin (10) against six human solid tumor cell lines was determined. The absolute configuration of the former is reported.