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Biological activity of gibberellin analogues

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Abstract

In order to determine the significance of the C-6 carboxyl group for the biological activity gibberellin A3, 6-epigibberellin A3, 7-norgibberellin A3, 6β-methyl-7-norgibberellin A3, and 7-homogibberellin A3 were studied using dwarf pea, dwarf maize, dwarf rice, dwarf barley and α-amylase bioassays. All gibberellin A3(GA3)derivatives tested were considerably less active than GA3. In all biossays, 6-epi-GA3 showed a low activity of the same order, whereas 6β-methyl-7-nor-GA3 was inactive. Surprisingly, 7-nor-GA3 had some activity in the dwarf rice (root application), dwarf barley, and α-amylase bioassay, in contrary to its low potency in the dwarf pea, dwarf maize, and dwarf rice (micro drop) bioassay. 7-Homo-GA3 was primarily active in the dwarf maize, dwarf barley and dwarf rice bioassay. It also caused antigibberellin effects in dwarf rice. The results demonstrate that the C-6 carboxyl group is not absolutely essential for biological activity of gibberellins. The different activities of 7-nor-GA3 observed in the various test systems may indicate that the C-6 carboxyl group is a structural requirement more for uptake and/or transport processes than for receptor affinity.

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Abbreviations

GA3 :

gibberellic acid

References

  • Adam, G., Lischewski, M., Voigt, B., Meyer, A., Bergner, Chr., Sembdner, G. (1980) Modifizierung von Struktur und biologischer Wirkung bei Gibberellinen. In: Wirkungsmechanismen von Herbiziden und synthetischen Wachstumsregulatoren, pp. 69–75, Schütte, H.R., ed. Fischer, Jena

    Google Scholar 

  • Bearder, J.R. (1980) Plant hormones and other growth substances — their background, structures and occurrence. In: Encyclopedia of Plant Physiology, N.S., vol. 9: Hormonal regulation of development I. Molecular aspects of plant hormones, pp. 9–112, MacMillan, J., ed. Springer, Berlin Heidelberg New York

    Google Scholar 

  • Brian, P.W., Grove, J.F., Mulholland, T.P.C. (1967) Relationship between structure and growth promoting activity of the gibberellins and some allied compounds in four test systems. Phytochemistry 6, 1475–1499

    Google Scholar 

  • Gräbner, R., Schneider, G., Sembdner, G. (1975) Fraktionierung von Gibberellinen, Gibberellinkonjugaten und anderen Phytohormonen durch DEAE-Sephadex Chromatographic. J. Chromatogr. 121, 110

    Google Scholar 

  • Heyns, W., de Moor, V. (1974) 3, 17β-Hydroxysteroid dehydrogenases in rat erythrocytes. Biochem. Biophys. Acta 358, 1–13

    Google Scholar 

  • Hiraga, K., Yamane, H., Takahashi, N. (1974) Biological activity of some synthetic gibberellin glucosyl esters. Phytochemistry 13, 2371–2376

    Google Scholar 

  • Hoad, G.V., Pharis, R.P., Railton, J.D., Durley, R.C. (1976) Activity of the aldehyde and alcohol of gibberellins A12 and A14, two derivatives of gibberellin A15 and four decomposition products of gibberellin A2 in 13 plant bioassays. Planta 130, 113–120

    Google Scholar 

  • Iwamura, H., Murakami, S., Koga, J., Matsubara, S., Koshimizu, K. (1979) Quantitative analysis of anticytokinin activity of 4-substituted-2-methylthiopyrido/2,3-d/pyrimidines. Phytochemistry 18, 1265–1268

    Google Scholar 

  • Jacob, F. (1981) Transport and distribution of xenobiotic plant growth regulators. Symp. on “Mechanism of the assimilate distribution and plant growth regulators” Piestany (CSSR) 1981, (Proc, in press)

  • Jacob, F., Neumann, S., Strobel, U. (1973) Studies on mobility of exogen applied substances in plant. Proc. Res. Inst. of Pomology, Skiernewice, Poland, Series E Nr. 3, pp. 315–330

  • Jacobson, A., Corcoran, M.R. (1977) Tannins as gibberellin antagonists in the synthesis of α-amylase and acid phosphatase by barley seeds. Plant Physiol. 59, 129–133

    Google Scholar 

  • Lischewski, M. (1982) Synthesis of 7-nor-gibberellin-A3. Z. Chem. (in press)

  • Lischewski, M., Adam, G. (1980a) Partialsynthese von 6-Epigibberellin-A3. Tetrahedron Lett. 1627

  • Lischewski, M., Adam, G. (1980b) Synthese von 7-desoxygenierten Gibberellin-A3-Verbindungen. Tetrahedron 36, 1237

    Google Scholar 

  • Meyer, A., Liebisch, H.W., Sembdner, G. (1982) Biologische Aktivität C-7 abgewandelter GA3-Analoga; Verteilung und Stoffwechsel von GA3 und GA3-7-aldehyd in Zwergerbsen. Biochem. Physiol. Pflanzen 177, 75–82

    Google Scholar 

  • McRae, D.H., Bonner, J. (1953) Chemical structure and antiauxin activity. Physiol. Plant. 6, 485–510

    Google Scholar 

  • Murakami, Y. (1968) A new rice seedling test for gibberellins “micro-drop method’ and its use for testing extracts of rice and morning glory. Bot. Mag. Tokyo 81, 33–43

    Google Scholar 

  • Nash, L.J., Jones, R.I., Stoddart, J.L. (1978) Gibberellin metabolism in excised lettuce hypocotyls: response to GA9 and the conversion of [3H]-GA9. Planta 140, 143–150

    Google Scholar 

  • Reeve, D.R., Croizer, A. (1975) Gibberellin bioassays. In: Gibberellins and plant growth, Krishnamoorthy, N.H., ed. Wiley Eastern Limited, New Delhi

    Google Scholar 

  • Sembdner, G., Schneider, G., Schreiber, K. (1965) Über die biologische Wirksamkeit einiger Gibberellinsäure-Abbauprodukte (VIII. Mitt. Gibberelline). Planta 66, 65–74

    Google Scholar 

  • Sembdner, G., Borgmann, E., Schneider, G., Liebisch, H.W., Miersch, O., Adam, G., Lischewski, M., Schreiber, K. (1976) Biological activity of some conjugated gibberellins. Planta 132, 249–257

    Google Scholar 

  • Serebryakov, E.P., Lischewski, M., Adam, G. (1978) Partial synthesis of 7-homo-gibberellin-A3. Izy. AN SSSSR Ser. Chim. 2

  • SToddart, J.L., Venis, M.A. (1980) Molecular and subcellular aspects of hormone action. In: Encyclopedia of Plant Physiology, N.S. vol. 9: Hormonal regulation of development. I. Molecular aspects of plant hormones, pp. 445–501, MacMillan, J., ed. Springer, Berlin Heidelberg New York

    Google Scholar 

  • Yokota, T., Takahashi, N. (1981) Gibberellin A59: A new gibberellin from Canavalia gladiata. Agric. Biol. Chem. 45, 1251–1254

    Google Scholar 

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Bergner, C., Lischewski, M., Adam, G. et al. Biological activity of gibberellin analogues. Planta 155, 231–237 (1982). https://doi.org/10.1007/BF00392721

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