Studies on annonaceous tetrahydrofuranic acetogenins from Annona squamosa L. seeds
2004
Araya, H. (National Inst. of Agrobiological Sciences, Tsukuba, Ibaraki (Japan))
Synopsis The method for structure elucidation of annonaceous tetrahydrofuranic acetogenins, which have attracted much interest in these years because of potent various biological activities, were studied. In the course of the investigation, seven new acetogenins and sixteen known acetogenins were isolated from seeds of Annona squamosa L. (Annonaceae) collected in India. All of their structures were determined by spectroscopic methods. The planar structures of some acetogenins have been elucidated by newly developed method (amine method), namely, the application of precursor ion scanning in mass spectrometry. Thus, these compounds were converted into lactam derivatives on treatment with amines such as N,N-dimethylethylnediamine. Precursor ion scan spectra of the derivatives from a specific fragment ion due to C-N bond cleavage were measured. By use of this method, planar structure of tetrahydrofuranic acetogenins could be determined unambiguously. Absolute configuration of all carbinol centers of the isolated acetogenins were determined by advanced Mosher method and CD spectra. The concern about the amine method, feature of isolated compounds, biosynthesis, biological activity and other remaining problems were also discussed.
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