- Metabolism of N-alkyldiamines and N-alkylnortropinones by transformed root cultures of Nicotiana and Brugmansia
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A range of analogues of N-methylputrescine and tropinone were fed to transformed root cultures of Nicotiana rustica and/or a Brugmansia candida x aurea hybrid. These cultures were made by the transformation of the relevant plant species with Agrobacterium rhizogenes. A number of the metabolites, notably those showing a relatively modest alteration in the N-alkyl substituent, were metabolized in vivo to form homologues of the normal alkaloids biosynthesized by these roots. These products were identified by GC/MS and comparison with some synthetic reference materials. Analogues with major alterations in the size of the N-alkyl substituent were not metabolized at all. In the N. rustica cultures, the analogues fed at 1 mM significantly affected the profile of normal alkaloids, with up to a 4-fold diminution in nicotine being found in the presence of N-n-propylputrescine. The ratio between alkaloids of the pyrrolidine series and the piperideine series was also affected. In contrast, the presence of the analogues in the B. candida x aurea hybrid culture at 1 mM did not inhibit or substantially interfere with the accumulation of the normal spectrum of alkaloids. The potential for using these cultures to make complex novel products from simple precursors is discussed.
- Boswell, Henry D.,Draeger, Birgit,Eagles, John,McClintock, Carol,Parr, Adrian,Portsteffen, Andreas,Robins, David J.,Robins, Richard J.,Walton, Nicholas J.,Wong, Chi
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p. 855 - 869
(2007/10/03)
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- ALKALOIDS OF SOME EUROPEAN AND MACARONESIAN SEDOIDEAE AND SEMPERVIVOIDEAE (CRASSULACEAE)
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Some 22 pyrrolidine and piperidine alkaloids were detected in the leafy parts of Sedum acre, S. aetnense, S. anglicum, S. brissemoreti, S. farinosum, S. fusiforme, S. lancerottense, S. melanantherum, and S. nudum.In addition to the alkaloids known from S. acre, 1-(2-pyrrolidyl)-propan-2-one and 2-monosubstituted piperidine alkaloids bearing butan-2-one, butan-2-ol, pentan-2-one and pentan-2-ol sidechains were identified.Phenylethylamine was isolated from the vegetative parts of S. album.In S. lydium, S. meyeri-johannis, and 16 species of S. series Rupestria, Aeonium, Greenovia, Jovibarba and Sempervivum no alkaloids could be detected.The results indicate a correlation between the presence of alkaloids and the major evolutionary trends in the European and Macaronesian Crassulaceae. Key Word Index: Sedum; Aeonium; Greenovia; Jovibarba; Sempervivum; Crassulaceae; pyrrolidine and piperidine alkaloids; chemotaxonomy; evolution.
- Stevens, Jan F.,Hart, Henk 't,Hendriks, Henk,Malingre, Theo M.
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p. 3917 - 3924
(2007/10/02)
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- Alkynylation of Thiolactams. New Synthesis of α-Substituted Pyrrolidine and Piperidine Alkaloids
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Alkynylation of S-alkylthioamidium salts of thiolactams with lithium acetylides followed by reduction with LiAlH4 provided α-alkynylazacycloalkanes, which on reduction, or hydroboration followed by oxidation, gave α-substituted pyrrolidine and piperidine alkaloids.
- Takahata, Hiroki,Takahashi, Koichi,Wang, Eng-Chi,Yamazaki, Takao
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p. 1211 - 1214
(2007/10/02)
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