Abstract
An intensive accumulation of thiophene derivatives occurs during the first days of development in Tagetes seedlings. After that, the thiophene content (related to dry weight) decreases to reach low values until the twelfth day of growth. High performance liquid chromatography analyses performed on cotyledons, on hypocotyls, and on roots of normal-grown and of partly-etiolated seedlings showed that bithienylbutinen, the major compound in hypocotyls and roots, is accumulated earlier than the other thiophene derivatives. The synthesis of acetoxybutinylbithiophene seems to be light-induced. This compound is not found in cotyledons. Hydroxybutinylbithiophene is synthesized specifically in the roots, α-terthiophene in cotyledons. The results obtained indicate a high intensity of thiophene metabolism in these particular organs during seedling development.
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Bohlmann, F., Burkhardt, T., Zdero, C. (1973) Naturally occurring acetylenes. Academic Press, London New York
Bohlmann, F., Zdero, C. (1979) Über dimere Terpenketone aus Tagetes gracilis. Phytochemistry 18, 341–343
Chan, G.F.Q., Towers, G.H.N., Mitchell, J.C. (1975) UV-mediated antibiotic activity of thiophene compounds of Tagetes. Phytochemistry 14, 2295–2296
Conn, E.E. (1981) The biochemistry of plants. A comprehensive treatise, vol. 7, Stumpf, P.K., Conn, E.E., eds. Academic Press, New York London Toronto Sydney San Francisco
Gommers, F.F., Bakker, J., Smits, L. (1980) Effect of singlet oxygen generated by the nematicidal compound α-terthienyl from Tagetes on the nematode Aphelenchus avenae. Nematologica 26, 369–375
Hahlbrock, K., Grisebach, H. (1975) Biosynthesis of flavonoids. In: The flavonoids. pp. 866–915, Harborne, J.B., Mabry, T.J., Mabry, H., eds. Chapman and Hall, London
Jente, R., Olatunji, G.A., Bosold, F. (1981) Formation of natural thiophene derivatives from acetylenes by Tagetes patula. Phytochemistry 20, 2169–2175
MacRae, W.D., Chan, G.F.R., Wat, C.-K., Towers, G.H.N., Lam, J. (1980) Examination of naturally occurring polyacetylenes and α-terthienyl for their ability to induce cytogenetic damage. Experimentia 36, 1096–1097
Setia, B. (1978) Polyacetylene von Tagetes erecta und Tagetes patula nana: Biosynthese der Thiophen-Derivate und Polyacetylene von Tagetes erecta durch Zellkulturen. Dissertation, Münster, FRG
Sørensen, N.A. (1977) Polyacetylenes and conservation of chemical characters in the Compositae. In: The biology and chemistry of the Compositae, vol. 1, pp. 385–409, Heywood, V.H., Harborne, J.B., Turner, B.L., eds. Academic Press, London New York San Francisco
Sütfeld, R., Towers, G.H.N. (1982) 5-(4-Acetoxy-1-butinyl)-2.2′-bithiophene: acetate esterase from Tagetes patula. Phytochemistry 21, 277–279
Towers, G.H.N. (1980) Photosensitizers in plants and their photodynamic action (a review). Prog. Phytochem. 6, 183–202
Towers, G.H.N., Arnason, T., Wat, C.-K., Graham, E.A., Lam, J., Mitchell, J.C. (1979) Phototoxic polyacetylenes and their thiophene derivatives (effects on human skin). Contact Dermatitis 5, 140–144
Wat, C.-K., MacRae, W.D., Yamamoto, E., Towers, G.H.N., Lam, J. (1980) Phototoxic effects of naturally occurring polyacetylenes and α-terthienyl on human erythrocytes. Photochem. Photobiol. 32, 167–172
Wiermann, R. (1981) Secondary plant products and cell and tissue differentation. In: The biochemistry of plants. A comprehensive treatise, vol. 7, pp. 86–116, Stumpf, P.K., Conn, E.E., eds. Academic Press, New York London Toronto Sydney San Francisco
Zenk, M.H. (1980) Enzymatic synthesis of ajmalicine and related indole alkaloids. J. Nat. Prod. 43, 483–451
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Sütfeld, R. Distribution of thiophene derivatives in different organs of Tagetes patula seedlings grown under various conditions. Planta 156, 536–540 (1982). https://doi.org/10.1007/BF00392777
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DOI: https://doi.org/10.1007/BF00392777