Abstract
Recently benzyladenine has been isolated as a natural cytokinin from a number of plants. The natural occurrence of this cytokinin will change the attitude with which physiologists view this hormone. This review attempts to put into context what is known about this cytokinin and its derivatives and to compare and contrast its metabolism and the function and physiological action of its various metabolites. Nothing is known about the biosynthesis of benzyladenine. Its structure would suggest that its biosynthetic pathway may differ considerably from that of zeatin and iso-pentenyladenine.
Similar content being viewed by others
Abbreviations
- Ade:
-
adenine
- Ado:
-
adenosine
- BA:
-
benzyladenine
- [9R]BA:
-
BA ribonucleoside
- [9R-MP]BA:
-
BA nucleotide
- [9R-DP]BA:
-
BA dinucleotide
- [9R-TP]BA:
-
BA trinucleotide
- [3G]BA:
-
BA 3 glucoside
- [7G]BA:
-
BA 7 glucoside
- [9G]BA:
-
BA 9 glucoside
- [9R-G]BA:
-
BA 9-ribosylglucoside
- [9Ala]BA:
-
BA alanine-conjugate
- (2OH)BA:
-
BA ortho-OH
- (2OH)[9R]BA:
-
BA ortho-Oh-riboside
- KN:
-
kinetin
- [9R]KN:
-
KN ribonucleoside
- DHZ:
-
dihydrozeatin
- Z:
-
trans-zeatin
- [9R]Z:
-
zeatin ribonucleoside
- [7G]Z:
-
zeatin-7-glucoside
- [9G]Z:
-
zeatin-9-glucoside
- [9Ala]Z:
-
zeatin alanine-conjugate
- (OG)[9R]Z:
-
O-glucoside of zeatin ribonucleoside
- [9R-MP]Z:
-
zeatin nucleotide
- iP:
-
iso-pentenyladenine
- [9R]iP:
-
iP ribonucleoside
References
Adedipipe NO, Hunt LA and Fletcher RA (1971) Effects of benzyladenine on photosynthesis, growth and senescence of the bean plant. Physiol Plant 25: 151–153
Agrawal KML and Bahl OP (1968) Glycosidases of Phaseolus vulgaris. II. Isolation and general properties. J Biol Chem 243: 103–111
Ainley WM, McNeil KJ, Hill JW, Lingle WL, Simpson RB, Brenner ML, NaGao RT and Key JL (1993) Regulatable endogenous production of cytokinins up to ‘toxic’ levels in transgenic plants and plant tissues. Plant Mol Biol 22: 13–23
Armstrong DJ and Firtel RA (1989) Cytokinin oxidase activity in the cellular slime mold, Dictyostelium discoideum. Dev Biol 136: 491–499
Armstrong DJ, Murai N, Taller BJ and Skoog F (1976) Incorporation of a cytokinin N 6-benzyladenine into tobacco callus transfer ribonucleic acid and ribosomal nucleic acid preparations. Plant Physiol 57: 15–22
Ashford AE (1970) Histochemical localisation of β-glycosidases in roots of Zea mays. I. A simultaneous coupling azo-dye technique for the localisation of β-glycosidase and β-galactosidase. protoplasma 71: 281–293
Ashford AE and McCully ME (1970) Histochemical localisation of β-glycosidases in roots of Zea mays. II. Changes in localisation and activity of β-glucosidase in main root apex. protoplasma 71: 389–402
Ashihara H (1983) Changes in activities of purine salvage and ureide synthesis during germination of black gram (Phaselus mungo) seeds. Z Pflanzenphysiol 113: 47–60
Auer CA and Cohen JD (1993) Identification of a benzyladenine disaccharide conjugate produced during shoot organogenesis in Petunia leaf explants. Plant Physiol 102: 541–545
Auer CA, Cohen JD, Laloue M and Cooke TJ (1992) Comparison of benzyl adenine metabolism in two Petunia hybrida lines differing in shoot organogenesis. Plant Physiol 98: 1035–1041
Auer CA, Laloue M, Cohen JD and Cooke TJ (1992) Benzyladenine uptake and metabolism during Petunia shoot organogenesis. In: Kaminek M, Mok DWS and Zazimalova E (eds) Physiology and Biochemistry of Cytokinins in Plants, pp 69–70. The Hague, The Netherlands: SPB Academic Publishing
Auer CA, Laloue M, Cohen JD and Cooke TJ (1992) Uptake and metabolism of benzyladenine during shoot organogenesis in Petunia leaf explants. Plant Growth Regul 11: 105–114
Bassil NV, Mok DWS and Mok MC (1993) Partial purification of a cis-trans-isomerase of zeatin from immature seed of Phaseolus vulgaris L. Plant Physiol 102: 867–872
Bayley AD, VanStaden J, Mallett JA and Drewes SE (1989) The in vitro metabolism of [8-14C]benzyladenine by excised organs of tomato plants. Plant Growth Regul 8: 193–204
Becker JL and Roussaux J (1981) 6-Benzyladenine as a growth factor for Drosophila melanogaster cells grown in vitro. In: Guern J and Peaud-Lenoël C (eds) Metabolism and Molecular Activities of Cytokinins, pp 319–329 Berlin, Germany: Springer-Verlag
Bezemer-Sybrandy SM and Veldstra H (1971) The metabolism of 6-benzylaminopurinein Lemna minor. Physiol Plant 25: 1–7
Biondi S, Canciani L and Bagnni N (1984) Uptake and translocation of benzyladenine by elm shoots cultured in vitro. Can J Bot 62: 2385–2390
Black MK and Osborne DJ (1965) Polarity of transport of benzyladenine, adenine and indole-3-acetic acid in petiole segments of Phaseolus vulgaris. Plant Physiol 40: 676–680
Blakesley D (1991) Uptake and metabolism of 6-benzyladenine in shoot cultures of Musa and Rhododendron. Plant Cell Tissue Org Cult 25: 69–74
Blakesley D and Constantine D (1992) Uptake and metabolism of 6-benzyladenine in shoot cultures of a range of species. Plant Cell Tissue Org Cult 28: 183–186
Blakesley D, Lenton JR and Horgan R (1990) Benzyladenine ribosylglucoside: a metabolite of benzyladenine in Gerbera jamesonii. Phytochem 30: 387–388
Bopp M and Ercichsen U (1981) Metabolism of the cytokinins in mosses. In: Guern J and Peaud-Lenoël C (eds) Metabolism and Molecular Activities of Cytokinins, pp 105–114 Berlin, Germany: Springer-Verlag
Brinegar AC, Cooper G, Stevens A, Hauer CR, Shabanowitz J, Hunt DF and Fox JE (1988) Characterisation of a benzyladenine binding-site peptide isolated from a wheat cytokinin-binding protein: sequence analysis and identification of a single affinity-labeled histidine residue by mass spectroscopy. Proc Natl Acad Sci USA 85: 5927–5931
Brownlee BG, Hall RH and Whitty CD (1975) 3-Methyl-2-butenal: an enzymic product of the cytokinin, N6-(Δ2-isopentenyl)adenine. Can J Biochem 53: 37–41
Bui-Dang-Ha D and Nitsch JP (1970) Isolation of zeatin riboside from the chicory root. Planta 95: 119–126
Burch LR and Stuchbury T (1986) Purification and properties of adenosine nucleosidase from tomato (Lycopersicon esculentum) roots and leaves. J Plant Physiol 125: 267–273
Burch LR and Stuchbury T (1987) Activity and distribution of enzymes that interconvert purine bases, ribosides and ribotides in the tomato plant and possible implications for cytokinin metabolism. Physiol Plant 69: 283–288
Caers M, Rudelsheim P, VanOnckelen H and Horemans S (1985) Effect of heat stress on photosynthetic activity and chloroplast ultrastructure in correlation with endogenous cytokinin concentration in maize seedlings. Plant Cell Physiol 26: 47–52
Chatfield JM and Armstrong DJ (1986) Regulation of cytokinin oxidase in callus tissues of Phaseolus vulgaris L. cv. Great Northern. Plant Physiol 80: 493–499
Chatfield JM and Armstrong DJ (1987) Cytokinin oxidase from Phaseolus vulgaris callus tissues. Enhanced in vitro activity of the enzyme in the presence of copper-imidazole complexes. Plant Physiol 84: 726–731
Chatfield JM and Armstrong DJ (1988) Cytokinin oxidase from Phaseolus vulgaris callus tissues. Plant Physiol 88: 245–247
Chen C-M (1981) Biosynthesis and enzymic regulation of the interconversion of cytokinin. In: Guern J and Peaud-Lenoël C (eds) Metabolism and Molecular Activities of Cytokinins, pp 34–43. Berlin, Germany: Springer-Verlag
Chen C-M and Eckert RL (1977) Phosphorylation of cytokinin by adenosine kinase from wheat germ. Plant Physiol 59: 443–447
Chen C-M and Kristopeit SM (1981) Metabolism of cytokinin: deribosylation of cytokinin ribonucleoside by adenine nucleosidase from wheat germ cells. Plant Physiol 68: 1020–1023
Chen C-M and Kristopeit SM (1981) Metanolism of cytokinin: dephosphorylation of cytokinin ribonucleotide by 5′-nucleotidases from wheat germ cytosol. Plant Physiol 67: 494–498
Chen C-M and Leisner SM (1984) Modification of cytokinins by cauliflower microsomal enzymes. Plant Physiol 75: 442–446
Chen C-M, Logan DM, McLennan BD and Hall RH (1968) Studies on the metabolism of a cytokinin, N6-(Δ2-isopentenyl)-adenosine. Plant Physiol 43 (Suppl.): 18
Chen C-M, Melitz DK and Clough FW (1982) Metabolism of cytokinin: phosphoribosylation of cytokinin bases by adenine phosphoribosyltransferase from wheat germ. Arch Biochem Biophys 214: 634–641
Chen C-M and Petschow B (1978) Metabolism of cytokinin: ribosylation of cytokinin base by adenosine phosphorylase from wheat germ. Plant Physiol 62: 871–874
Chism GW, Long AR and Rolle R (1984) Assay of enzymes involved in cytokinin metabolism by means of reversed-phase high performance liquid chromatography. J Chrom 317: 263–270
Cowley DE, Duke CC, Liepa AJ, Macleod JK and Letham DS (1978) The structure and synthesis of cytokinin metabolites. I. The 7- and 9-β-D-glucofuranosides and pyranosides of zeatin and 6-benzylaminopurine. Aust J Chem 31: 1095–1111
Datko AH and Maclachlan GA (1970) Patterns of development of glycosidase activities in the pea epicotyl. Can J Bot 48: 1165–1169
Davey JE and VanStaden J (1976) Cytokinin translocation: changes in zeatin and zeatin riboside levels in the root exudate of tomato plants during their development. Planta 130: 69–72
Dei M (1983) Benzyladenine-induced stimulation of chlorophyll formation in attached cotyledons of etiolated cucumber seedlings. Plant Sci Lett 30: 251–257
Dekhuijzen HM, Bossen ME and Vonk CR (1978) The uptake of cytokinins by protoplasts and root sections of Brassica campestris. Physiol Plant 43: 142–147
Deleuze GG, McChesney JD and Fox JE (1972) Identification of a stable cytokinin metabolite. Biochem Biophys Res Commun 48: 1426–1432
Doree M and Guern J (1973) Short-time metabolism of some exogenous cytokinins in Acer pseudoplatanus cells. Biochim Biophys Acta 304: 611–622
Doree M and Terrine C (1973) Enzymatic synthesis of ribonucleoside-51-phosphate from some N 6-substituted adenosines. Phytochem 12: 1017–1023
Doree M, Terrine C and Guem J (1972) Plant cell permeability to kinetin. In. Hormonal Regulation in Plant Growth Development, pp 221–231. Weinheim, Germany: Verlag Chemie
Duke CC, Letham DS, Parker CW, Macleod JK and Summons RE (1979) The complex of O-glucosylzeatin derivatives formed in Populus species. Phytochem 18: 819–824
Duke CC, Liepa AJ, Macleod JK, Letham DS and Parker CW (1975) Synthesis of raphanatin and its 6-benzylaminopurine analogue. J Chem Soc Chem Commun 1146
Duke CC, Macleod JK, Summons RE, Letham DS and Parker CW (1978) The structure and synthesis of cytokinin metabolites. II. Lupinic acid and O-β-D-glucopyranosyl zeatin from Lupinus angustifolius. Aust J Chem 31: 1291–1301
Dybing CD and Lay C (1981) Field evaluations of morphactins and other growth regulators for senescence delay of flax, soybean, wheat and oats. Crop Sci 21: 879–884
Dyson W, Fox JE and McChesney JD (1972) Short term metabolism of urea and purine cytokinins. Plant Physiol 49: 506–513
Elliott DC and Murray AW (1975) Evidence against an involvement of cyclic nucleotides in the induction of betacyanin synthesis by cytokinins. Biochem J 146: 333–337
Elliott DC and Thompson MJ (1982) The identity of the major metabolite of benzylaminopurine in soybean cultures and the inhibition of its formation by aminophylline. Plant Sci Lett 28: 29–38
El-Saidi MT (1971) Transport and metabolism of kinetin-8-14C in Zea mays L. roots. Ann Bot 35: 1073–1083
Entsch B and Letham DS (1979) Enzymic glucosylation of the cytokinin, 6-benzylaminopurine. Plant Sci Lett 14: 205–212
Entsch B, Letham DS, Parker CW, Summons RE and Gollnow BI (1979) Metabolites of cytokinins. In: Skoog F (ed) Plant Growth Substances 1979, pp 109–118, Berlin, Germany: Springer Verlag
Entsch B, Parker CW and Letham DS (1978) Enzymatic glucosylation of the phytohormone, zeatin. Aust Biochem Soc Proc 11: 53
Entsch B, Parker CW and Letham DS (1983) An enzyme from lupin seeds forming alanine derivatives of cytokinins. Phytochem 22: 375–381
Entsch B, Parker CW, Letham DS and Summons RE (1979) Preparation and characterization using high performance liquid chromatography, of an enzyme forming glucosides of cytokinins. Biochim Biophys Acta 570: 124–139
Erichsen U, Knoop B and Bopp M (1978) Uptake, transport and metabolism of cytokinin in moss protonema. Plant Cell Physiol 19: 839–850
Ernst D, Schäfer W and Oesterholt D (1983) Isolation and identification of a new, naturally occurring cytokinin (6-benzyl-aminopyrine riboside) from an anise cell culture (Pimpinella anisum L.). Planta 159: 222–225
Estruch JJ, Chriqui D, Grossmann K, Schell J and Spena A (1991) The plant oncogene rolC is responsible for the release of cytokinins from glucoside conjugates. EMBO J 10: 2889–2895
Fletcher RA (1969) Retardation of leaf senescence by benzyladenine in intact bean plants. Planta 89: 1–8
Forsyth C and VanStaden J (1986) The metabolism and cell division activity of adenine derivatives in soybean callus. J Plant Physiol 124: 275–287
Fox JE (1964) Incorporation of kinins into the RNA of plant tissue cultures. Plant Physiol 39 (Suppl.): 31
Fox JE (1966) Incorporation of a kinin, N,6-benzyladenine, into soluble RNA. Plant Physiol 41: 75–82
Fox JE and Chen C-M (1967) Characterisation of labeled ribonucleic acid from tissue grown on 14C-containing cytokinins. J Biol Chem 242: 4490–4494
Fox JE, Cornette J, Deleuze G, Dyson W, Giersak C, Niu P, Zapata J and McChesney J (1973) The formation isolation, and biological activity of a cytokinin 7-glucoside. Plant Physiol 52: 627–632
Fox JE, Dyson W, Sood C and McChesney JD (1972) Active forms of the cytokinins. In: Carr DJ (ed) Plant Growth Substances 1970, pp 4492–458. Berlin, Germany: Springer-Verlag
Fox JE, Sood CK, Buckwalter B and McChesney JD (1971) The metabolism and biological activity of a 9-substituted cytokinin. Plant Physiol 47: 275–281
Fox JE, Sood CK and McChesney JD (1973) Effect of substituents at the 9-position on cytokinin activity. Phytochem 12: 1531–1533
Fusseder A, Ziegler P, Peters W and Beck E (1989) Tumover of O-glucosides of dihydrozeatin and dihydrozeatin-9-riboside during the cell growth cycle of photoautotrophic cell suspension cultures of Chenopodium rubrum. Bot Acta 102: 335–340
Garrison FR, Brinker AM and Noodén LD (1984) Relative activities of xylem-supplied cytokinins in retarding soybean leaf senescence and sustaining pod development. Plant Cell Physiol 25: 213–224
Gawer M, Laloue M, Terrine C and Guem J (1977) Metabolism and biological significance of benzyladenine-7-glucoside. Plant Sci Lett 8: 267–274
Gilbert ML, Thompson JE and Dumbroff BE (1980) Delayed cotyledon senescence following treatment with a cytokinin: an effect at the level of membranes. Can J Bot 58: 1797–1803
Gordon ME, Letham DS and Parker CW (1974) The metabolism and translocation of zeatin in intact radish seedlings. Ann Bot 38: 809–825
Guern J, Doree M and Sadorge P (1968) Transport, metabolism and biological activity of some cytokinins. In: Wightman F and Setterfield G (eds) Biochemistry and Physiology of Plant Growth Substances, pp 1155–1167. Ottawa, Canada
Guranowski A and Schneider Z (1977) Purification and characterisation of adenosine nucleosidase from barley leaves. Biochim Biophys Acta 482: 145–158
Hamill JD (1993) Alterations in auxin and cytokinin metabolism of higher plants due to expression of specific genes from pathogenic bacteria: A review. Aust J Plant Physiol 20: 405–423
Hecht SM, Bock RM, Schmitz RY, Skoog F, Leonard NJ and Occolowitz J (1971) Question of the ribosyl moiety in the promotion of callus growth by exogenously added cytokinins. Biochem 10: 4224–4228
Hecht SM, Frye RB, Werner D, Hawrelak SD, Skoog F and Schmitz RY (1975) On the ‘activation’ of cytokinins. J Biol Chem 250: 7343–7351
Hendry NS, VanStaden J and Allan P (1982) Cytokinins in Citrus. II. Fluctuations during growth in juvenile and adult plants. Sci Hort 17: 247–256
Henson IE (1978) Types, formation and metabolism of cytokinins in leaves of Alnus glutinosa (L.) Gaertn. J Exp Bot 29: 935–951
Henson IE and Wareing PF (1977) Cytokinins in Xanthium strumarium L: the metabolism of cytokinins in detached leaves and buds in relation to photoperiod. New Phytol 78: 27–33
Henson IE and Wheeler CT (1977) Hormones in plants bearing nitrogen-fixing root nodules: metabolism of [8-14C]zeatin in root nodules of Alnus Glutinosa (L.) Gaertn. J Exp Bot 28: 1087–1098
Hocart CH, Letham DS and Parker CW (1991) Substituted xanthines and cytokinin analogues as inhibitors of cytokinin N-glucosylation. Phytochem 30: 2477–2486
Hochstadt-Ozer J and Stadtman ER (1971) Adenine phosphoribosyl-transferase in isolated membrane preparations and its role in transport of adenine across the membrane. J Biol Chem 246: 5304–5311
Horgan R (1975) A new cytokinin metabolite. Biochem Biophys Res Commun 65: 358–363
Horgan R (1984) Cytokinins. In: Wilkins MB (ed) Advanced Plant Physiology, pp 53–75. Bath, UK: The Pitman Press
Horgan R (1987) Cytokinin genes. In: Hoad GV, Lenton JR, Jackson MB and Atkin RK (eds) Hormone Action in Plant Development, pp 119–130. London, UK: Butterworths
Horgan R, Hewett EW, Purse JG and Wareing PF (1973) A new cytokinin from Populus robusta. Teth Lett 30: 2827–2828
Hughes MA (1968) Studies on β-glucosidase production in cultured tissue of Trifolium repens L. J Exp Bot 19: 52–63
Hutton MJ and VanStaden J (1984) Transport and metabolism of labelled zeatin applied to the stems of Phaseolus vulgaris at different stages of development. Z Pflanzenphysiol 114: 331–339
Jones LH and Hanke DE (1992) Kinetin-9-glucoside is a major metabolite of kinetin in oil palm cultures. In: Kaminek M, Mok DWS and Zazimalova E (eds) Physiology and Biochemistry of Cytokinins in Plants, pp 65–68. The Hague, The Netherlands: SPB Academic Publishing
Jouanneau J-P and Teyssendier de la Serve B (1981) Covalent insertion of N 6-benzyladenine into rRNA species of tobacco cells. In: Guern J and Peaud-Lenoël C (eds) Metabolism and Molecular Activities of Cytokinins, pp 228–238. Berlin, Germany: Springer-Verlag
Kaminek M (1992) Progress in cytokinin research. Tibtech 10: 159–164
Kaminek M and Armstrong DJ (1990) Genotypic variation in cytokinin oxidase from Phaseolus callus cultures. Plant Physiol 93: 1530–1538
Krenitsky TA, Papioannou R and Elion GB (1969) Human hypoxanthine phosphoribosyltransferase. II. Kinetics and chemical modification. J Biol Chem 244: 1271–1277
Kuiper D, Kuiper PJC, Lambers H, Schuit J and Staal M (1989) Cytokinin concentration in relation to mineral nutrition and benzyladenine treatment in Plantago major ssp. pleiosperma. Physiol Plant 75: 511–517
Laloue M (1977) Cytokinins: 7-glucosylation is not a prerequisite of the expression of their biological activity. Planta 134: 273–275
Laloue M and Pethe C (1982) Dynamics of cytokinin metabolism in tobacco cells. In: Wareing PF (ed) Plant Growth Substances 1982, pp 185–195. New York, USA: Academic Press
Laloue M, Pethe-Terrine C and Guem J (1981) Uptake and metabolism in tobacco cells: studies in relation to the expression of their biological activities. In: Guern J and Peaud-Lenoël C (eds) Metabolism and Molecular Activities of Cytokinins, pp 80–96. Berlin, Germany: Springer-Verlag
Laloue M, Terrine C and Gawer M (1974) Cytokinins: formation of the nucleoside-5′-triphosphate in tobacco and Acer cells. Fed Eur Biochem Soc Lett 46: 45–50
Laloue M, Terrine C and Guern J (1977) Cytokinins: metabolism and biological activity of N 6-(Δ2-isopentenyl) adenosine and N 6-(Δ2-isopentenyl)adenine in tobacco cells and callus. Plant Physiol 59: 478–483
Lampugnani MG, Fantelli R, Longo GP, Longo CP and Rossi G (1981) Uptake of benzyladenine by excised watermelon cotyledons. Plant Physiol 68: 11–14
Lee D and Moffatt BA (1993) Purification and characterisation of adenine phosphoribosyltransferase from Arabidopsis thaliana. Physiol Plant 87: 483–493
Lee YH, Mok MC, Mok DWS, Griffin DA and Shaw G (1985) Cytokinin metabolism in Phaseolus embryos: genetic difference and the occurrence of novel zeatin metabolites. Plant Physiol 77: 635–641
LeFloc' HF, Lafleuriel J and Guillot A (1978) L'ádeninephospho-ribosyltransferase des pousses de topinambour Helianthus tuberosus. Phytochem 17: 643–646
LeFloc' HF, Lafleuriel J and Guillot A (1982) Interconversion of purine nucleotides in Jerusalem artichoke shoots. Plant Sci Lett 27: 309–316
Leonard NJ, Hecht SM, Skoog F and Schmitz RY (1968) Cytokinins: synthesis of 6-(3-methyl-3-butenylamino)-β-D-ribofuranosyl purine (3iPA) and the effect of sidechain unsaturation on the biological activity of isopentylaminopurines and their ribosides. Proc Natl Acad Sci USA 59: 15–21
Leonard NJ, Hecht SM, Skoog F and Schmitz RY (1969) Cytokinins: synthesis, mass spectra, and biological activity of compounds related to zeatin. Proc Natl Acad Sci USA 63: 175–182
Leopold AC and Kawase M (1964) Benzyladenine effects on leaf growth and senescence. Am J Bot 51: 294–298
Leszczynska D, Schneider Z, Tomaszewski M and Mackowiak M (1984) Comparative studies on adenosine nucleosidase occurrence in plants. Ann Bot 54: 847–849
Letham DS (1973) Regulators of cell division in plant tissues. XV. Cytokinins from Zea mays. Phytochem 12: 245–2455
Letham DS (1978) Cytokinins. In: Letham DS, Goodwin PB and Higgins TJV (eds) Phytohormones and Related Compounds-a Comprehensive Treatise. Volume 1, pp 205–263. Amsterdam, The Netherlands: Elsevier Press
Letham DS and Gollnow BI (1985) Regulators of cell division in plant tissues. XXX. Cytokinin metabolism in relation to radish cotyledon expansion and senescence. Plant Growth Regul 4: 129–145
Letham DS, Gollnow BI and Parker CW (1979) The reported occurrence of 7-glucofuranoside metabolites of cytokinins. Plant Sci Lett 15: 217–223
Letham DS and Palni LMS (1983) The biosynthesis and metabolism of cytokinins. Annu Rev Plant Physiol 34: 163–197
Letham DS, Plani LMS, Tao G-Q, Gollnow BI and Bates CM (1983) Regulators of cell division in plant tissues. XXIX. The activities of cytokinin glucosides and alanine conjugates in cytokinin bioassays. Plant Growth Regul 2: 103–115
Letham DS, Parker CW and Gordon ME (1972) Regulators of cell division in plant tissues. XIV. The cytokinin activities and metabolism of 6-acylaminopurines. Physiol Plant 27: 285–290
Letham DS, Summons RE, Entsch R, Gollnow BI, Parker CW and Macleod JK (1978) Regulators of cell division in plant tissues. XXVI. Glucosylation of cytokinin analogues. Phytochem 17: 2053–2057
Letham DS, Summons RE, Parker CW and Macleod JK (1979) Regulators of cell division in plant tissues. XXVII. Identification of an amino-acid conjugate of 6-benzylaminopurine formed in Phaseolus vulgaris seedlings. Planta 146: 71–74
Letham DS, Tao G-Q and Parker CW (1982) An overview of cytokinin metabolism. In: Wareing PF (ed) Plant Growth substances 1982, pp 143–153. London, UK: Academic Press
Letham DS, Wilson MM, Parker CW, Jenkins ID, Macleod JK and Summons RE (1975) Regulators of cell division in plant tissues. XXIII. The identity of an unusual metabolite of 6-benzylaminopurine. Biochim Biophys Acta 399: 61–70
Lindoo SJ and Noodén LD (1978) Correlations of cytokinins and abscisic acid with monocarpic senescence in soybean. Plant Cell Physiol 19: 997–1006
Macleod JK, Summons RE, Parker CW and Letham DS (1975) Lupinic acid, a purinyl amino acid and a novel metabolite of zeatin. J Chem Soc Commun: 865
Martin JH (1969) A study of cytokinin metabolism. Ph.D. Thesis. Diss Abstr B, Sci Eng 30: 1000–1001
Martin RC, Mok MC, Shaw G and Mok DWS (1989) An enzyme mediating the conversion of zeatin to dihydrozeatin in Phaseolus embryos. Plant Physiol 90: 1630–1635
Matsubara S (1990) Structure-activity relationships of cytokinins. Crit Rev Plant Sci 9: 17–57
Matsubara S, Shiojiri S, Fujii T, Ogawa D, Inamura K, Yamagishi K and Koshimizu K (1977) Synthesis and cytokinin activity of (R)- and (S)- dihydrozeatins and their ribosides. Phytochem 16: 933–937
McCalla DR, Morré DJ and Osborne DJ (1962) The metabolism of a kinin, benzyladenine. Biochim Biophys Acta 55: 522–528
McCreight JD, Pharr DM, Lower RL and Sox HN (1976) Comparative study of β-glucosidase from cotyledons and fruits of cucumber, Cucumis sativus. Physiol Plant 37: 17–22
McGaw BA, Heald JK and Horgan R (1984) Dihydrozeatin metabolism in radish seedlings. Phytochem 23: 1373–1377
McGaw BA and Horgan R (1983) Cytokinin oxidase from Zea mays kernels and Vinca rosea crown gall tissue. planta 159: 30–37
McGaw RA and Horgan R (1985) Cytokinin metabolism and the control of cytokinin activity. Biol Plant 27: 180–187
Miernyk JK and Blaydes DF (1977) Short-term metabolism of radioactive kinetin during lettuce seed germination. Pysiol Plant 39: 4–8
Miller CO (1967) Cytokinins in Zea mays. Ann New York Acad Sci 144: 251–257
Miller CO (1968) Naturally-occurring cytokinins. In: Wightman F and Setterfield G (eds) Biochemistry and Physiology of Plant Growth Substances, pp 33–45. Ottawa, Canada: Runge Press
Miller GW and Evans HJ (1955) Nucleosidase from higher plants. Plant Physiol 30 (Suppl.): 37
Minocha SC and Nissen P (1982) Uptake of benzyladenine by tuber slices of Jerusalem artichoke (Helianthus tuberosus L.) over a wide concentration range. Plant Physiol 70: 528–531
Miura G and Hall RH (1973) Trans-ribosylzeatin. Its biosynthesis in Zea mays endosperm and the mycorrhizal fungus Rhizopogon roseolus. Plant Physiol 51: 563–569
Moffatt B, Pethe C and Laloue M (1991) Metabolism of benzyladenine is impaired in a mutant of Arabidopsis thaliana lacking adenine phosphoribosyltransferase activity. Plant Physiol 95: 900–908
Mok MC, Martin RC, Mok DWS and Shaw G (1992) Cytokinin activity, metabolism and function in Phaseolus. In: Kaminek M, Mok DWS and Zazimalova E (eds) Physiology and Biochemistry of Cytokinins in Plants, pp 41–46. The Hague, The Netherlands: SPB Academic Publishing
Mok DWS and Mok MC (1987) Metabolism of 14C-zeatin in Phaseolus embryos: occurrence of O-xylosyldihydrozeatin and its ribonucleoside. Plant Physiol 84: 596–599
Mok MC, Mok DWS, Dixon SC, Armstrong DJ and Shaw G (1982) Cytokinin structure-activity relationships and the metabolism of N 6-(Δ2-isopentenyl)adenosine-[8-14C] in Phaseolus callus tissues. Plant Physiol 70: 173–178
Mok MC, Mok DWS, Marsden KE and Shaw G (1987) The biological activity and metabolism of a novel cytokinin metabolite, O-xylosylzeatin in callus tissue of P. vulgaris and P. lunatus. Plant Physiol 130: 423–431
Mok MC, Mok DWS and Turner JE (1985) Reversed activities of cytokinin bases and ribonucleosides in callus cultures of Phaseolus lunatus L. J Plant Physiol 121: 273–280
Morris DA (1981) Distribution and metabolism of rootapplied cytokinins in Pisum sativum. Physiol Plant 52: 251–256
Morris JW, Doumas P, Morris OR and Zaerr JB (1990) Cytokinins in vegetative and reproductive buds of Pseudotsuga menziesii. Plant Physiol 93: 67–71
Motyka V and Kaminek M (1990) Regulation of cytokinin catabolism in tobacco callus cultures. In: Nijkamp HJJ, Van derPlas LHW and Aartrijk J (eds) Progress in Plant Cellular and Molecular Biology, pp 492–497. Dordrecht, The Netherlands: Academic Publishers
Murakoshi I, Ikegami F, Ookama N, Haginiwa J and Letham DS (1977) Enzymic synthesis of lupinic acid, a novel metabolite of zeatin in higher plants. Chem Pharm Bull 25: 520–522
Nandi SK, Letham DS, Palni LMS, Wong OC and Summons RE (1989) 6-Benzylaminopurine and its glycosides as naturally occurring cytokinins. Plant Sci 61: 189–196
Nandi SK, Palni LMS, Letham DS and Wong OC (1989) Identification of cytokinins in primary crown gall tumors of tomato. Plant Cell Environ 12: 273–283
Nicholls PB and Murray AW (1968) Adenine phosphoribosyl-transferase in plant tissue: some effects of kinetin on enzymic activity. Plant Physiol 43: 645–648
Niederwieser JG, Vanstaden J, Upfold SJ and Drewes FE (1992) Metabolism of 6-benzyladenine by leaf explants of Lachenalia during adventitious bud formation. S Afr J Bot 58: 236–238
Paces V (1976) Metabolism of cytokinins in barley leaves. Biochem Biophys Res Comm 72: 830–839
Paces V and Kaminek M (1976) Effect of ribosylzeatin isomers on the enzymatic degradation of N 6-(Δ2-isopentenyl) adenosine. Nucleic Acids Res 3: 2309–2314
Paces V, Werstiuk E and Hall RH (1971) Conversion of N 6-(Δ2-isopentenyl) adenosine to adenosine by enzyme activity in tobacco tissue. Plant Physiol 48: 775–778
Palmer MV, Horgan R and Wareing PF (1981) Cytokinin metabolism in Phaseolus vulgaris L. 1: variation in cytokinin levels in leaves of decapitated plants in relation to lateral bud outgrowth. J Exp Bot 32: 1231–1241
Palmer MV, Horgan R and Wareing PF (1981) Cytokinin metabolism in Phaseolus vulgaris L. Identification of endogenous cytokinins and metabolism of (8-14C)dihydrozeatin in stems of decapitated plants. Planta 153: 297–302
Palmer MV, Letham DS and Gunning BES (1984) Cytokinin metabolism in nondividing and auxin-induced dividing explats of Helianthus tuberosus L. tuber tissue. Plant Growth Regul 2: 289–298
Palmer MV and Palni LMS (1986) Substrate effects on cytokinin metabolism in soybean callus tissue. J Plant Physiol 126: 365–371
Palmer MV, Scott IM and Horgan R (1981) Cytokinin metabolism in Phaseolus vulgaris L. II. Comparative metabolism of exogenous cytokinins by detached leaves. Plant Sci Lett 22: 187–195
Palni LMS, Burch L and Horgan R (1988) The effect of auxin concentration on cytokinin stability and metabolism. Planta 174: 231–234
Palni LMS, Palmer MV and Lethan DS (1984) The stability and biological activity of cytokinin metabolites in soybean callus tissue. Planta 160: 242–249
Parker CW, Entsch B and Letham DS (1986) Inhibition of two enzymes which metabolise cytokinins. Phytochem 25: 303–310
Parker CW and Letham DS (1973) Regulators of cell divisions in plant tissues. XVI. Metabolism of zeatin by radish cotyledons and hypocotyls. Planta 114: 199–218
Parker CW and Letham DS (1974) Regulators of cell division in plant tissues. XVIII. Metabolism of zeatin in Zea mays seedlings. Planta 115: 337–344
Parker CW, Letham DS, Cowley DE and Macleod JK (1972) Raphanatin, an unusual purine derivative and a metabolite of zeatin. Biochem Biophys Res Commun 49: 460–466
Parker CW, Letham DS, Gollnow BI, Summons RE, Duke CC and Macleod JK (1978) Regulators of cell division in plant tissues. XXV. Metabolism of zeatin by lupin seedlings. Planta 142: 239–251
Parker CW, Letham DS, Wilson MM, Jenkins ID, Macleod JK and Summons RE (1975) The identity of two new cytokinin metabolites. Ann Bot 39: 375–376
Parker CW, Wilson M, Letham DS, Cowley DE and Macleod JK (1973) The glucosylation of cytokinins. Biochem Biophys Res Commun 55: 1370–1376
Peters W and Beck E (1992)_Endogenous cytokinins in suspension cultured cells of Chenopodium rubrum at different growth stages. In: Kaminek M, Mok DWS and Zazimalova E (eds) Physiology and Biochemistry of Cytokinins in Plants, pp 71–73. The Hague, The Netherlands: SPB Academic Publishing
Pietraface WJ and Blaydes DF (1981) Activity and metabolism of 9-substituted cytokinins during lettuce seed germination. Physiol Plant 53: 249–254
Poulton JE and Butt VS (1976) Partial purification and properties of adenosine nucleosidase from elves of spinach beet (Beta vulgaris L.). Planta 131: 179–185
Ramina A (1979) Aspects of [8-14C]benzylaminopurine metabolism in Phaseolus vulgaris. Plant Physiol 63: 298–300
Rolle RS and Chism GW (1989) Kinetic comparison of cytokinin nucleosidase activity isolated from normally ripening and mutant tomato varieties. Plant Physiol 91: 148–150
Rushing JW (1990) Cytokinins affect respiration, ethylene production, and chlorophyll retention of packaged broccoli florets. HortSci 25: 88–90
Schmitz RY, Skoog F, Hecht SM, Bock RM and Leonard NJ (1972) Comparison of cytokinin activities of naturally occurring ribonucleosides and corresponding bases. Phytochem 11: 1603–1610
Schmitz RY, Skoog F, Vincze A, Walker GC, Kirkegaard LH and Leonard NJ (1975) Comparison of cytokinin activities of the base, ribonucleoside and 5′-and cyclic-3′,5′-monophosphate ribonucleotides of N 6-isopentenyl-, N 6-benzyl or 8-bromo-adenine. Phytochem 14: 1479–1484
Scott IM and Horgan R (1984) Mass-spectrometric quantification of cytokinin nucleotides and glycosides in tobacco crown-gall tissue. Planta 161: 345–354
Scott IM, Martin GC, Horgan R and Heald JK (1982) Mass spectrometric measurement of zeatin glycoside levels in Vinca rosea L. crown gall tissue. Planta 154: 273–276
Scott IM, McGaw BA, Horgan R and Williams PE (1982) Biochemical studies on cytokinins in Vinca rosea crown gall tissue. In: Wareing PF (ed) Plant Growth Substances 1982, pp 165–174. London, UK: Press
Scott RA and Liverman JL (1956) Promotion of leaf expansion by kinetin and benzylaminopurine. Plant Physiol 31: 321–322
Senesi S, Falcone G, Mura U, Scarrella F and Ipata PL (1976) A specific adenosine phosphorylase, distinct from purine nucleoside phosphorylase. Fed Eur Biochem Soc 64: 353–356
Shaw G, Smallwood BM and Steward FC (1968) Synthesis and cytokinin activity of the 3-, 7-, and 9-methyl derivatives of zeatin. Experientia 24: 1089–1090
Singh S, Palni LMS and Letham DS (1992) Cytokinin biochemistry in relation to leaf senescence. V Endogenous cytokinin levels and metabolism of zeatin riboside in leaf discs from green and senescent tobacco (Nicotiana rustica) leaves. J Plant Physiol 139: 279–283
Skoog F and Armstrong DJ (1970) Cytokinins. Annu Rev Plant Physiol 21: 359–384
Skoog F, Hamzi HQ, Szweykowska AM, Leonard NJ, Carraway KC, Fujii T, Helgeson JP and Loeppky RN (1967) Cytokinins: structure/activity relationships. Phytochem 6: 1169–1192
Skoog F and Schmitz RY (1979) Biochemistry and physiology of cytokinins. In: Lutwack F (ed) Biochemical Actions of Hormones. Volume VI, pp 335–355. New York, USA: Academic Press
Smith AR and VanStaden J (1978) Changes in endogenous cytokinin levels in kernels of Zea mays L. during imbibition and germination. J Exp Bot 29: 1067–1075
Sondheimer E and Tzou D-S (1971) The metabolism of hormones during seed germination and dormancy. II. the metabolism of 8-14C zeatin in bean axes. Plant Physiol 47: 516–520
Spiess LD (1975) Comparative activity of isomers of zeatin and ribosylzeatin on Funaria hygrometrica. Plant Physiol 55: 583–585
Strnad M, Peters W, Beck E and Kaminek M (1992) Immunodetection and identification of N 6-(o-hydroxybenzylamino)purine as a naturally occurring cytokinin in Populus × canadensis Moench cv. Robusta leaves. Plant Physiol 99: 74–80
Summons RE, Entsch B, Letham DS, Gollnow BI and Macleod JK (1980) Regulators of cell division in plant tissues. XXVIII. Metabolites of zeatin in sweet-corn kernels: purification and identification using high performance liquid chromatography and chemical ionisation mass spectrometry. Planta 147: 422–434
Szweykowska A, Gwozdz E and Spychala M (1981) The cytokinin control of protein synthesis in plants. In: Guem J and Peaud-Lenoël D (eds) Metabolism and Molecular Activities of Cytokinins, pp 211–217. Berlin, Germany: Springer-Verlag
Tao G-Q, Letham DS, Hocart CH and Summons RE (1991) Inhibitors of cytokinin metabolism. III. The inhibition of cytokinin N-glucosylation in radish cotyledons. Plant Growth Regul 10: 179–185
Taya Y, Tanaka Y and Nishimura S (1978) 51-AMP is a direct precursor of cytokinin in Dictylostelium discoideum. Nature 271: 545–547
Taylor JS, Koshioka M, Pharis RP and Sweet GB (1984) Changes in cytokinin and gibberellin-like substances in Pinus radiata buds during lateral shoot initiation and the characterisation of ribosyl zeatin and a novel ribosyl zeatin glycoside. Plant Physiol 74: 626–631
Terrine C and Laloue M (1980) Kinetics of N 6−(Δ2−isopentenyl) adenosine degradation in tobacco cells. Evidence of a regulatory mechanism under the control of cytokinins. Plant Physiol 65: 1090–1095
Thomas TH and Blakesley D (1987) Practical and potential uses of cytokinins in agriculture and horticulture. Brit Plant Growth Regul Group Mono 14: 69–83
Turner JE, Mok DWS, Mok MC and Shaw G (1987) Isolation and partial purification of the enzyme catalysing the formation of novel zeatin metabolites in Phaseolus vulgaris embryos. Proc Natl Acad Sci USA 84: 3714–3717
Tzou D-S, Galston EC and Sondheimer E (1973) The metabolism of hormones during seed germination and release from dormancy. III. The effects and metabolism of zeatin in dormant and nondormant ash embryos. Plant Physiol 51: 894–897
Van derKrieken WM, Croes AF, Barendse GWM and Wullems GJ (1988) Uptake and metabolism of benzyladenine in the early stage of flower bud development in vitro in tobacco. Physiol Plant 74: 113–118
VanStaden J (1973) Changes in endogenous cytokinins of lettuce seed during germination. Physiol Plant 28: 222–227
VanStaden J (1973) A comparison of the effect of 6-benzylaminopurine derivatives on some aspects of plant growth. Physiol Plant 29: 137–139
VanStaden J (1976) Seasonal changes in the cytokinin content of Ginkgo biloba leaves. Physiol Plant 38: 1–5
VanStaden J (1976) The identification of zeatin glucoside from coconut milk. Physiol Plant 36: 123–126
VanStaden J (1979) The metabolism of zeatin by cell-free plant extracts. Z Pflanzenphysiol 92: 399–405
VanStaden J (1983) Short term metabolism of different concentrations of zeatin applied to soybean callus. Z Pflanzenphysiol 109: 163–169
VanStaden J (1983a) Long term metabolism of zeatin supplied to soybean callus. Z Pflanzenphysiol 111: 423–428
VanStaden J and Bayley AD (1991) Fate of benzyladenine metabolites extracted from tomato shoots in biological systems. Plant Growth Regul 10: 117–124
VanStaden J, Bayley AD, Upfold SJ and Drewes FE (1990) Cytokinins in cut carnation flowers. VIII. Uptake, transport and metabolism of benzyladenine and the effect of benzyladenine derivatives on flower longevity. J Plant Physiol 135: 703–707
VanStaden J and Davey JE (1981) Cytokinin activity in Lupinus albus. VI. Translocation and metabolism of (8-14C)zeatin applied to the leaves and fruits of fruiting plants. Physiol Plant 51: 49–52
VanStaden J and Dimalla GG (1978) Endogenous cytokinins and the breaking of dormancy and apical dominance in potato tubers. J Exp Bot 29: 1077–1084
VanStaden J and Drewes FE (1991) The biological activity of cytokinin derivatives in the soybean callus bioassay. Plant Growth Regul 10: 109–115
VanStaden J and Drewes FE (1992) The stability and metabolism of benzyladenine glucosides in soybean callus. J Plant Physiol 140: 92–95
VanStaden J and Drewes FE (1992a) Metabolism of ribosylzeatin-51-monophosphate by soybean callus. Plant Growth Regul 11: 189–191
VanStaden J and Hutton MJ (1982) Metabolism of 8[14C]t-zeatin in soybean callus. Z Pflanzenphysiol 106: 355–365
VanStaden J and Mallett JA (1988) Metabolism and transport of [8-14C]benzyladenine applied to rootless shoots and the roots of intact tomato plants. Plant Physiol Biochem 26: 47–54
VanStaden J and Mooney PA (1987) The effect of IAA on the metabolism of kinetin by Catharanthus roseus crown-gall callus. J Plant Physiol 131: 297–303
VanStaden J and Papaphilippou AP (1977) Biological activity of O-β-D-glucopyranosylzeatin. Plant Physiol 60: 649–650
Venis M (1985) Hormone Binding Sites in Plants. London, UK: Longman Press
Vogelmann TC, Bornman CH and Nissen P (1984) Uptake of benzyladenine in explants of Picea abies and Pinus sylvestris. Physiol Plant 61: 513–517
Vonk CR and Davelaar E (1981) 8-14C-Zeatin metabolites and their transport from leaf to phloem exudate of Yucca. Physiol Plant 52: 101–107
Wagner BM and Beck E (1993) Cytokinins in the perennial herb Urtica dioica L. as influenced by its nitrogen status. Planta 190: 511–518
Wang TL, Thompson AG and Horgan R (1977) A cytokinin glucoside from the leaves of Phaseolus vulgaris L. Planta 0 135: 285–288
Wang TP (1955) Hydrolytic nucleosidases. Methods Enzymol 2: 456–464
Wareing PF, Horgan R, Henson IE and Davis W (1977) Cytokinin relations in the whole plant. In: Pilet PE (ed) Plant Growth Regulation, pp 147–153, Berlin, Germany: Springer-Verlag
Whitacker BD and Kende H (1974) Bud formation in Funaria hygrometrica. A comparison of the activities of three cytokinins with their ribosides. Planta 121: 93–96
Whitty CD and Hall RH (1974) A cytokinin oxidase in Zea mays. Can J Biochem 52: 789–799
Wilson MM, Gordon ME, Letham DS and Parker CW (1974) Regulators of cell division in plant tissues (XIX). The metabolism of 6-benzylaminopurine in radish cotyledons and seedlings. J Exp Bot 25: 725–732
Woolley DJ and Wareing PF (1972) The role of roots, cytokinins and apical dominance in the control of lateral shoot form in Solanum andigena. Planta 105: 33–42
Yoshida R and Oritani T (1972) Cytokinin glucoside in roots of the rice plant. Plant Cell Physiol 13: 337–343
Zhang R, Hocart CH and Letham DS (1989) Inhibitors of cytokinin metabolism. II. Inhibition of cytokinin-alanine conjugation in soybean leaves and associated effects on senescence. Plant Growth Regul 8: 327–330
Zhang R and Letham DS (1989) Cytokinin biochemistry in relation to leaf senescence. III. The senescence retarding activity and metabolism of 9-substituted 6-benzylaminopurines in soybean leaves. Plant Growth Regul 8: 181–197
Zhang R, Letham DS, Parker CW, Schroeder H and Higgins TJV (1987) Retardation of soybean leaf senescence and associated effects on seed composition. Plant Growth Regul 6: 15–21
Zhang R, Letham DS, Wong OC, Noodén LD and Parker CW (1987) The metabolism of 6-benzylaminopurine in soybean leaves and the inhibition of its conjugation. Plant Physiol 83: 334–340
Zimmerman TP, Gersten NB, Ross AF and Miech RP (1971) Adenine as a substrate for purine nucleoside phosphorylase. Can J Biochem 49: 1050–1054
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
van Staden, J., Crouch, N. Benzyladenine and derivatives-their significance and interconversion in plants. Plant Growth Regul 19, 153–175 (1996). https://doi.org/10.1007/BF00024582
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00024582