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Regulators of cell division in plant tissues

XXVIII. Metabolites of zeatin in sweet-corn kernels: Purifications and identifications using high-performance liquid chromatography and chemical-ionization mass spectrometry

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Abstract

The cytokinins in certain fractions prepared from extracts of immature sweet-corn (Zea mays L.) kernels using polystyrene ion-exchange resins have been further investigated. Cytokinins active in the radish cotyledon bioassay were purified from these fractions and identified as 9-β-D-glucopyranosylzeatin, 9-β-D-glucopyranosyldihydrozeatin, O-β-D-glucopyranosylzeatin. and O-β-D-glucopyranosyl-9-β-D-ribofuranosylzeatin. In addition, compounds which resemble zeatin and its glycosides in chromatographic behaviour and in ultraviolet absorption characteristics were purified from extracts of the same material by high-performance liquid chromatography. In addition to zeatin and zeatin riboside, the following compounds were identified unambiguously: O-β-D-glucopyranosyl-9-β-D-ribofuranosyldihydrozeatin, O-β-D-glucopyranosyldihydrozeatin, and hihydrozeatin riboside. A further compound was tentatively identified as O-β-D-glucopyranosylzeatin, and at least two unidentified compounds appeared to be new derivatives of zeatin. In identifying the above compounds, chemical-ionization mass spectrometry proved to be an invaluable complementary technique, yielding spectra showing intense protonated-molecular-ion peaks and also prominent structure-related fragmentation that was either not evident or very minor in the electron-impact spectra. An assessment of the relative importance of the various possible mechanisms for cytokinin modification and inactivation in mature sweet-corn kernels was made by supplying [3H]zeatin and [3H]zeatin riboside to such kernels after excision. The principal metabolites of zeatin were adenine nucleotides, adenosine and adenine, while little of the metabolite radioactivity was attributable to known O-glucosides. Adenine nucleotides and adenine were the principal metabolites of zeatin riboside, while lesser metabolites were identified as adenosine, dihydrozeatin, and the O-glucosides of dihydrozeatin and dihydrozeatin riboside. Side-chain cleavage, rather than side-chain modification, appears to be the dominant form of cytokinin metabolism in mature sweet-corn kernels.

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Abbreviations

CI-MS:

chemical-ionization mass spectrum

EIMS:

electron-impact mass spectrum

GC-MS:

combined gas chromatography-mass spectrometry

HPLC:

high performance liquid chromatography

M+ :

molecular ion

MH+ :

protonated molecular ion

TLC:

thin-layer chromatography

TMS:

trimethylsilyl

UV:

ultraviolet

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Authors and Affiliations

  1. Research School of Biological Sciences, Australian National University, P.O. Box 475, 2601, Canberra City, A.C.T., Australia

    B. Entsch, D. S. Letham & B. I. Gollnow

  2. Research School of Chemistry, Australian National University, P.O. Box 475, 2601, Canberra City, A.C.T., Australia

    J. K. MacLeod

Authors
  1. R. E. Summons
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  2. B. Entsch
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  3. D. S. Letham
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  4. B. I. Gollnow
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  5. J. K. MacLeod
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XXVII=Letham et al. (1979)

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Summons, R.E., Entsch, B., Letham, D.S. et al. Regulators of cell division in plant tissues. Planta 147, 422–434 (1980). https://doi.org/10.1007/BF00380183

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  • DOI: https://doi.org/10.1007/BF00380183

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