Abstract
The cytokinin activities of cis and trans ribosylzeatin isomers and that of N6-(Δ2-isopentenyl)adenosine were compared in four bioassays. The trans isomer was found to be more active than the cis isomer in stimulation of cucumber cotyledon expansion (100x), retention of chlorophyll in detached leaf pieces (7x), induction and stimulation of chlorophyll synthesis in cucumber cotyledons (20x) and of betacyanin synthesis in Amaranthus caudatus seedlings grown in the dark (60x). The N6-(Δ2-isopentenyl)adenosine adenosine was less active than the trans ribosylzeatin in all four bioassays and more active than the cis ribosylzeatin in induction and stimulation of betacyanin and chlorophyll synthesis. These results show that the hydroxylation of the trans methyl group in the N6 side chain of N6-(Δ2-isopentenyl)adenosine increases the biological activity and that this activity is either decreased or not significantly changed when the cis methyl group is hydroxylated.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
Abbreviations
- i6Ado:
-
N6-(Δ2-isopentenyl)adenosine or 6-(3-methyl-2-butenylamino)-9-β-D-ribofuranosylpurine
- t-to6Ado:
-
trans-ribosylzeatin or 6-(4-hydroxy-3-methyl-trans-2-butenylamino)-9-β-D-ribofuranosylpurine
- c-io6Ado:
-
cis-ribosylzeatin or 6-(4-hydroxy-3-methyl-cis-2-butenylamino)-9-β-D-ribofuranosylpurine
- HPLC:
-
high pressure liquid chromatography
References
Challice, J.S.: Separation of cytokinins by high pressure liquid chromatography. Planta 122, 203–207 (1975)
Challice, J.S., Williams, A.H.: A spectrophotometric study of the ionization of p-coumaric acid. Spectrochim. Acta 21, 1869–1880 (1965)
Challice, J.S., Williams, A.H.: Paper chromatographic separation and behaviour of the cis-and trans-isomers of cinnamic acid derivatives. J. Chromatogr. 21, 357–362 (1966)
Conrad, K.: Zur Specifität des Amaranthus Cytokinintests. V. Adenin-und Adenosinderivate. Biochem. Physiol. Pflanzen 162, 327–333 (1971)
Conrad, K.: Ein sensibilisierter Amaranthus-Cytokinintest(AT 74). Biochem. Physiol. Pflanzen 165, 531–535 (1974)
Farineau, N., Roussaux, J.: Influence de la 6-benzylaminopurine sur la différenciation plastidiale dans les cotylédon de concombre. Physiol. Plant. 33, 194–202 (1975)
Feng, K.A.: Effects of kinetin on the permeability of Allium cepa cells. Plant Physiol. 51, 868–870 (1973)
Fletcher, R.A., McCullagh, D.: Cytokinin-induced chlorophyll formation in cucumber cotyledons. Planta 101, 88–90 (1971)
Göring, H., Mardanov, A.A.: Beziehungen zwischen dem K+/Ca++-Verhältnis im Gewebe und Wirkung von Zytokininen in höheren Pflanzen. Biol. Rundschau 14, 177–189 (1976)
Kamínek, M.: Evolution of tRNA and origin of the two positional isomers of zeatin. J. Theor. Biol. 48, 489–492 (1974)
Kamínek, M.: Die Zytokinine und ihre Beziehungen zu den Transfer-Ribonucleinsäuren. Biol. Rundschau 13, 137–151 (1975)
Kamínek, M., Luštinec, J.: Sensitivity of oat leaf senescence bioassay to natural and synthesis cytokinins. Biol. Plant 20, 377–382 (1978)
Kuhnle, J.A., Fuller, G., Corse, J., Mackey, B.E.: Antisenescent activity of natural cytokinins. Physiol. Plant. 41, 14–21 (1977)
Leonard, N.J., Playtis, A.J., Skoog, F., Schmitz, R.Y.: Stereoselective synthesis of cis-zeatin. J. Am. Chem. Soc. 93, 3056–3058 (1971)
Letham, D.S.: Regulators of cell division in plant tissues: V. A comparison of the activities of zeatin and other cytokinins in five bioassays. Planta 74, 228–242 (1967)
Miura, G.A., Hall, R.H.: trans-Ribosylzeatin. Its biosynthesis in Zea mays endosperm and the mycorrhizal fungus Rhizopogon roseolus. Plant Physiol. 51, 563–569 (1973)
Narain, A., Laloraya, M.M.: Cucumber cotyledon expansion as a bioassay for cytokinins. Z. Pflanzenphysiol. 71, 313–322 (1974)
Pačes, V., Kaminek, M.: Effect of ribosylzeatin isomers on the enzymtic degradation of N6-(Δ 2-Isopentenyl)adenosine. Nucleic Acid Res. 3, 2309–2314 (1976)
Schmitz, R.Y., Skoog, F., Playtis, A.J., Leonard, N.J.: Cytokinins: Synthesis and biological activity of geometric and positional isomers of zeatin. Plant Physiol. 50, 702–705 (1972)
Thimann, K.V., Sachs, T.: The role of cytokinins in the fasciation disease caused by Corynebacterium fascians. Am. J. Bot 83, 731–739 (1966)
Varga, A., Bruinsma, J.: Effects of different cytokinins on the senescence of detached oat leaves. Planta 111, 91–93 (1973)
Vreman, H.J., Schmitz, R.Y., Skoog, F., Playtis, A.J., Frihart, C.R., Leonard, N.J.: Synthesis of 2-methylthio-cis-and trans-ribosylzeatin and their isolation from Pisum tRNA. Phytochemistry 13, 31–37 (1974)
Whitty, C.D., Hall, R.H.: A cytokinin oxidase in Zea mays. Can. J. Biochem. 52, 789–799 (1974)
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Kamínek, M., Pačes, V., Corse, J. et al. Effect of stereospecific hydroxylation of N6-(Δ 2-Isopentenyl)adenosine on cytokinin activity. Planta 145, 239–243 (1979). https://doi.org/10.1007/BF00454447
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00454447