Abstract
Calystegines are a new group of polyhydroxy alkaloids with a nortropane skeleton. They were detected in Atropa belladonna root cultures by chromatographic methods (TLC, GC) and identified by NMR and mass spectroscopy. Their occurrence was examined in several species of the Solanaceae. The biosynthesis of these compounds is suggested to proceed via the tropane alkaloid pathway, the first metabolite being pseudotropine. A pseudotropine-forming tropinone reductase was isolated and characterized from Atropa belladonna root cultures. Further evidence is given for the significance of tropinone and pseudotropine in calystegine formation by feeding experiments that increased calystegine formation. 15N-tropinone was shown to be incorporated into calystegines.
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Abbreviations
- GC:
-
gas chromatography
- TBON:
-
8-thiabicyclo[3.2.1]octan-3-one
- TLC:
-
thin-layer chromatography
References
Boyer FD, Ducrot PH, Henryon V, Soulié & Lallemand JY (1992) Studies on the synthesis of the 1-hydroxynortropane system; part II. Synthesis of calystegine A3 and physoperuvine. Synlett 357–359
Cronquist A (1988) The evolution and classification of flowering plants. The new Botanical Garden. Bronx NY, pp 420
Dräger B, Hashimoto T & Yamada Y (1988) Purification and characterization of pseudotropine forming tropinone reductase from Hyoscyamus niger root cultures. Agric. Biol. Chem. 52: 2663–2667
Dräger B, Portsteffen A, Schaal A, McCabe PH, Peerless ACJ & Robins RJ (1992) Levels of tropinone reductase activities influence the spectrum of tropane esters found in transformed root cultures of Datura stramonium. L. Planta 188: 581–586
Dräger B & Schaal A (1994) Tropinone reduction in Atropa belladonna root cultures. Phytochemistry 35: 1441–1447
Duclos O, Mondange M, Duréault A & Depezay JC (1992) Polyhydroxylated nortropanes starting from D-glucose: Synthesis of homochiral (+) and (-)-calystegines B2. Tetrahedron Lett. 33: 8061–8064
Goldmann A, Milat ML, Ducrot PH, Lallamand JY, Maille M, Lepingle A, Charpin I & Tepfer D (1990) Tropane derivatives from Calystegia sepium. Phytochemistry 29: 2125–2127
Hashimoto T, Nakajima K, Ongena G & Yamada Y (1992) Two tropinone reductases with distinct stereospecificities from cultured roots of Hyoscyamus niger. Plant Physiol. 100: 836–845
Parr AJ, Walton NJ, Bensalem S, McCabe P & Routledge W (1991) 8-Thiabicyclo[3.2.1]octan-3-one as a biochemical tool in the study of tropane alkaloid biosynthesis. Phytochemistry 30: 2607–2609
Portsteffen A, Dräger B & Nahrstedt A (1992) Two tropinone reducing enzymes from Datura stramonium transformed root cultures. Phytochemistry 31: 1135–1138
Tepfer D, Goldmann A, Pamboukdjian N, Maille M, Lepingle A, Chevalier D, Dénarié J & Rosenberg C (1988) A plasmid of Rhizobium meliloti 41 encodes catabolism of two compounds from root exudate of Calystegia sepium. J. Bacteriol. 170: 1153–1161
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Dräger, B., Funck, C., Höhler, A. et al. Calystegines as a new group of tropane alkaloids in Solanaceae. Plant Cell Tiss Organ Cult 38, 235–240 (1994). https://doi.org/10.1007/BF00033882
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DOI: https://doi.org/10.1007/BF00033882