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.
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Departamento de Farmacia, Facultad de Química, Universidad Nacional Autónoma de México, D.F. 04510, México.
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D000972:Antineoplastic Agents, Phytogenic / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D005663:Furans / Q000302:isolation & purification* / Q000494:pharmacology; D008401:Gas Chromatography-Mass Spectrometry; D006801:Humans; D006868:Hydrolysis; D007783:Lactones / Q000302:isolation & purification* / Q000494:pharmacology; D008800:Mexico; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology; D010946:Plants, Medicinal / Q000737:chemistry*; D012639:Seeds / Q000737:chemistry; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013056:Spectrophotometry, Ultraviolet; D014363:Tryptamines / Q000302:isolation & purification* / Q000494:pharmacology; D014407:Tumor Cells, Cultured
D000972:Antineoplastic Agents, Phytogenic; D005663:Furans; D007783:Lactones; D010936:Plant Extracts; D014363:Tryptamines; C112079:isomurisolenin