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Chemical Compound Review

Zeatin     (E)-2-methyl-4-(7H-purin-6- ylamino)but-2...

Synonyms: Zeatine, t-zeatin, trans-Zeatin, PubChem9588, SureCN49689, ...
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Disease relevance of Zeatin


High impact information on Zeatin


Chemical compound and disease context of Zeatin


Biological context of Zeatin

  • Out of eight different aminopurines and a synthetic auxin tested for their ability to override lovastatin inhibition of mitosis, only zeatin was active [11].
  • As ectopic morphogenesis proceeded, HtKNOT1 transcripts and zeatin co-localized and showed different patterns in ectopic shoot compared with embryo-like structures, consistent with the differential role of both cytokinin and knox genes in the two morphogenetic events [12].
  • Photosynthetic rate and zeatin + zeatin riboside concentrations in the flag leaves declined faster in WS plants than in WW plants, and they decreased more slowly with HN than with NN when soil water potential was the same, indicating that the water deficit enhanced, whereas HN delayed, senescence [13].
  • In contrast, there were sharp peaks in the levels of specific cytokinins (zeatin- and dihydrozeatin-type) at the end of the S phase and during mitosis [14].
  • The SE were obtained by a simple somatic embryogenesis protocol: leaf explants from two adult plants (QsG0, QsG5) and from two juvenile plants (QsGM1, QsGM2) were inoculated on Murashige and Skoog (MS) medium with 2,4-dichlorophenoxyacetic acid and zeatin [15].

Anatomical context of Zeatin


Associations of Zeatin with other chemical compounds

  • Cytokinins (CKs), a group of phytohormones, are adenine derivatives that carry either an isoprene-derived or an aromatic side chain at the N(6) terminus. trans-Zeatin (tZ), an isoprenoid CK, is assumed to play a central physiological role because of its general occurrence and high activity in bioassays [21].
  • Indole-3-acetic acid (IAA) and combined zeatin riboside (ZR) and zeatin riboside-5'-monophosphate (ZRMP) contents were analysed by mass spectrometry in young, developing leaves from the cross, the parental lines and the wild type [22].
  • O-Glucosylation is stereo-specific: the O-glucosyltransferase encoded by the Phaseolus lunatus ZOG1 gene has high affinity for trans-zeatin as the substrate, whereas the enzyme encoded by the maize (Zea mays) cisZOG1 gene prefers cis-zeatin [23].
  • Using a zeatin affinity column a 40 kDa protein was isolated from tobacco Bright Yellow 2 (TBY-2) and identified by mass spectrometry as adenosine kinase [24].
  • In high light (300 mumol PPFD m-2 s-1), ipt mRNA was detected and zeatin/zeatin glucoside levels were 10-fold higher than in control plants or when transformants were grown in low light (30 mumol PPFD m-2 s-1) [25].

Gene context of Zeatin

  • Direct measurements demonstrate that AtPUP1 is capable of mediating uptake of radiolabeled trans-zeatin [26].
  • In contrast to their high activity in bioassays, the BAP derivatives were recognised with much lower sensitivity than trans-zeatin in both Arabidopsis thaliana AHK3 and AHK4 receptor assays [27].
  • Two enzymes catalyzing the formation of O-glycosyl derivatives of zeatin have been characterized, O-glucosyltransferase and O-xylosyltransferase, occurring in seeds of lima bean (Phaseolus lunatus) and bean (Phaseolus vulgaris), respectively [28].
  • Tobacco chloroplasts from dark-treated leaves contained zeatin riboside-O-glucoside and dihydrozeatin riboside-O-glucoside, as well as a relatively high CK oxidase activity [29].
  • In higher plants, trans-zeatin (tZ), a major CK, is formed by subsequent hydroxylation, which is catalyzed by a cytochrome P450 monooxygenase (P450), CYP735A1 or CYP735A2 [2].

Analytical, diagnostic and therapeutic context of Zeatin

  • Using recombinant protein and isothermal titration calorimetry as well as fluorescence measurements coupled with ligand displacement, we have reexamined the K(d) values and show them to range from approximately 10(-6) M (for 4PU30) to 10(-4) M (for zeatin) for 1:1 stoichiometry complexes [5].
  • Mutant exconjugants, confirmed by PCR, did not contain zeatin in their tRNAs and did not secrete zeatin into the medium, findings which are consistent with the hypothesis that all zeatin is tRNA derived rather than synthesized de novo [4].
  • Using immunoaffinity and high-performance liquid chromatography (HPLC) purification, we obtained 22 to 111 ng of trans-zeatin per liter from culture filtrates of four PPFM leaf isolates (from Arabidopsis, barley, maize, and soybean) and of a Methylobacterium extorquens type culture originally recovered as a soil isolate [4].
  • Embryos were analyzed by ELISA for abscisic acid (ABA), abscisic acid-glucose ester, 2,4-D, indole-3-acetic acid (IAA), indole-3-aspartate (IAAsp), zeatin (Z), zeatin riboside (ZR), isopentenyladenine (iP) and isopentenyladenosine (iPA) [30].
  • Double-solvent extraction followed by fractionation with both normal and reverse phase column chromatographies and analysis by liquid chromatography/tandem mass spectrometry identified trans-zeatin riboside (ZR) as the primary suppressor of adventitious root formation [31].


  1. Nucleotide sequence and expression of a Pseudomonas savastanoi cytokinin biosynthetic gene: homology with Agrobacterium tumefaciens tmr and tzs loci. Powell, G.K., Morris, R.O. Nucleic Acids Res. (1986) [Pubmed]
  2. Cytokinin biosynthesis and regulation. Sakakibara, H. Vitam. Horm. (2005) [Pubmed]
  3. Abscisic acid and cytokinins in the root exudates and leaves and their relationship to senescence and remobilization of carbon reserves in rice subjected to water stress during grain filling. Yang, J., Zhang, J., Wang, Z., Zhu, Q., Liu, L. Planta (2002) [Pubmed]
  4. tRNA is the source of low-level trans-zeatin production in Methylobacterium spp. Koenig, R.L., Morris, R.O., Polacco, J.C. J. Bacteriol. (2002) [Pubmed]
  5. Crystal Structure of Vigna radiata Cytokinin-Specific Binding Protein in Complex with Zeatin. Pasternak, O., Bujacz, G.D., Fujimoto, Y., Hashimoto, Y., Jelen, F., Otlewski, J., Sikorski, M.M., Jaskolski, M. Plant Cell (2006) [Pubmed]
  6. Agrobacterium tumefaciens increases cytokinin production in plastids by modifying the biosynthetic pathway in the host plant. Sakakibara, H., Kasahara, H., Ueda, N., Kojima, M., Takei, K., Hishiyama, S., Asami, T., Okada, K., Kamiya, Y., Yamaya, T., Yamaguchi, S. Proc. Natl. Acad. Sci. U.S.A. (2005) [Pubmed]
  7. An alternative cytokinin biosynthesis pathway. Astot, C., Dolezal, K., Nordström, A., Wang, Q., Kunkel, T., Moritz, T., Chua, N.H., Sandberg, G. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  8. N-glucosylation of cytokinins by glycosyltransferases of Arabidopsis thaliana. Hou, B., Lim, E.K., Higgins, G.S., Bowles, D.J. J. Biol. Chem. (2004) [Pubmed]
  9. Molecular characterization of cytokinin-responsive histidine kinases in maize. Differential ligand preferences and response to cis-zeatin. Yonekura-Sakakibara, K., Kojima, M., Yamaya, T., Sakakibara, H. Plant Physiol. (2004) [Pubmed]
  10. Secretion of trans-zeatin by Agrobacterium tumefaciens: a function determined by the nopaline Ti plasmid. Regier, D.A., Morris, R.O. Biochem. Biophys. Res. Commun. (1982) [Pubmed]
  11. Zeatin is indispensable for the G2-M transition in tobacco BY-2 cells. Laureys, F., Dewitte, W., Witters, E., Van Montagu, M., Inzé, D., Van Onckelen, H. FEBS Lett. (1998) [Pubmed]
  12. Zeatin accumulation and misexpression of a class I knox gene are intimately linked in the epiphyllous response of the interspecific hybrid EMB-2 (Helianthus annuus x H. tuberosus). Chiappetta, A., Michelotti, V., Fambrini, M., Bruno, L., Salvini, M., Petrarulo, M., Azmi, A., Van Onckelen, H., Pugliesi, C., Bitonti, M.B. Planta (2006) [Pubmed]
  13. Activities of fructan- and sucrose-metabolizing enzymes in wheat stems subjected to water stress during grain filling. Yang, J., Zhang, J., Wang, Z., Zhu, Q., Liu, L. Planta (2004) [Pubmed]
  14. Levels of endogenous cytokinins, indole-3-acetic acid and abscisic acid during the cell cycle of synchronized tobacco BY-2 cells. Redig, P., Shaul, O., Inze, D., Van Montagu, M., Van Onckelen, H. FEBS Lett. (1996) [Pubmed]
  15. Determination of genetic stability in long-term somatic embryogenic cultures and derived plantlets of cork oak using microsatellite markers. Lopes, T., Pinto, G., Loureiro, J., Costa, A., Santos, C. Tree Physiol. (2006) [Pubmed]
  16. Receptor of trans-zeatin involved in transcription activation by cytokinin. Kulaeva, O.N., Karavaiko, N.N., Selivankina SYu, n.u.l.l., Zemlyachenko YaV, n.u.l.l., Shipilova, S.V. FEBS Lett. (1995) [Pubmed]
  17. Overexpression of farnesyl diphosphate synthase in Arabidopsis mitochondria triggers light-dependent lesion formation and alters cytokinin homeostasis. Manzano, D., Busquets, A., Closa, M., Hoyerová, K., Schaller, H., Kamínek, M., Arró, M., Ferrer, A. Plant Mol. Biol. (2006) [Pubmed]
  18. Characterization of high-frequency deletions in the iaa-containing plasmid, pIAA2, of Pseudomonas syringae pv. savastanoi. Soby, S., Kirkpatrick, B., Kosuge, T. Plasmid (1994) [Pubmed]
  19. Gerontomodulatory and youth-preserving effects of zeatin on human skin fibroblasts undergoing aging in vitro. Rattan, S.I., Sodagam, L. Rejuvenation research. (2005) [Pubmed]
  20. Inhibitory effect of zeatin, isolated from Fiatoua villosa, on acetylcholinesterase activity from PC12 cells. Heo, H.J., Hong, S.C., Cho, H.Y., Hong, B., Kim, H.K., Kim, E.K., Shin, D.H. Mol. Cells (2002) [Pubmed]
  21. Arabidopsis CYP735A1 and CYP735A2 encode cytokinin hydroxylases that catalyze the biosynthesis of trans-Zeatin. Takei, K., Yamaya, T., Sakakibara, H. J. Biol. Chem. (2004) [Pubmed]
  22. Transgenic tobacco plants co-expressing Agrobacterium iaa and ipt genes have wild-type hormone levels but display both auxin- and cytokinin-overproducing phenotypes. Eklöf, S., Astot, C., Sitbon, F., Moritz, T., Olsson, O., Sandberg, G. Plant J. (2000) [Pubmed]
  23. Topolins and hydroxylated thidiazuron derivatives are substrates of cytokinin O-glucosyltransferase with position specificity related to receptor recognition. Mok, M.C., Martin, R.C., Dobrev, P.I., Vanková, R., Ho, P.S., Yonekura-Sakakibara, K., Sakakibara, H., Mok, D.W. Plant Physiol. (2005) [Pubmed]
  24. Cytokinin affinity purification and identification of a tobacco BY-2 adenosine kinase. Laukens, K., Lenobel, R., Strnad, M., Van Onckelen, H., Witters, E. FEBS Lett. (2003) [Pubmed]
  25. Light-induced expression of ipt from Agrobacterium tumefaciens results in cytokinin accumulation and osmotic stress symptoms in transgenic tobacco. Thomas, J.C., Smigocki, A.C., Bohnert, H.J. Plant Mol. Biol. (1995) [Pubmed]
  26. Transport of cytokinins mediated by purine transporters of the PUP family expressed in phloem, hydathodes, and pollen of Arabidopsis. Bürkle, L., Cedzich, A., Döpke, C., Stransky, H., Okumoto, S., Gillissen, B., Kühn, C., Frommer, W.B. Plant J. (2003) [Pubmed]
  27. Preparation and biological activity of 6-benzylaminopurine derivatives in plants and human cancer cells. Dolezal, K., Popa, I., Krystof, V., Spíchal, L., Fojtíková, M., Holub, J., Lenobel, R., Schmülling, T., Strnad, M. Bioorg. Med. Chem. (2006) [Pubmed]
  28. A gene encoding the cytokinin enzyme zeatin O-xylosyltransferase of Phaseolus vulgaris. Martin, R.C., Mok, M.C., Mok, D.W. Plant Physiol. (1999) [Pubmed]
  29. Cytokinins in tobacco and wheat chloroplasts. Occurrence and changes due to light/dark treatment. Benková, E., Witters, E., Van Dongen, W., Kolár, J., Motyka, V., Brzobohatý, B., Van Onckelen, H.A., Machácková, I. Plant Physiol. (1999) [Pubmed]
  30. Charcoal affects early development and hormonal concentrations of somatic embryos of hybrid larch. von Aderkas, P., Label, P., Lelu, M.A. Tree Physiol. (2002) [Pubmed]
  31. A trans-zeatin riboside in root xylem sap negatively regulates adventitious root formation on cucumber hypocotyls. Kuroha, T., Kato, H., Asami, T., Yoshida, S., Kamada, H., Satoh, S. J. Exp. Bot. (2002) [Pubmed]
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