Advertisement

Planta

, Volume 172, Issue 1, pp 47–52 | Cite as

Identification of oxindole-3-acetic acid, and metabolic conversion of indole-3-acetic acid to oxindole-3-acetic acid in Pinus sylvestris seeds

  • Arild Ernstsen
  • Göran Sandberg
  • Karin Lundström
Article

Abstract

Oxindole-3-acetic acid (OxIAA) has been identified in germinating seeds of Scots pine (Pinus sylvestris) using gas chromatography-mass spectrometry. Seeds germinated for 5 d contained 2.7 ng OxIAA·g-1 (dry weight) whereas ungerminated seeds contained 0.2 ng·g-1. Isotopically labelled OxIAA was formed in seeds incubated with [1′-14C]-, [2′-14C]- or [2H5]indole-3-acetic acid.

Key words

Auxin catabolism Indole-3-acetic acid catabolism Pinus Seed germination 

Abbreviations

DDC

sodium diethyldithiocarbamate

GC

gas chromatography

HPLC

high-performance liquid chromatography

IAA

indole-3-acetic acid

MS

mass spectrometry

OxIAA

oxindole-3-acetic acid

PVP

polyvinylpyrrolidone

TMS

trimethylsilyl

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Bandurski, R.S., Schulze, A., Reinecke, D.M. (1986) Biosynthetic and metabolic aspects of auxins. In: Plant growth substances 1985, pp. 83–91, Bopp, M., ed. Springer, Berlin Heidelberg New York TokyoGoogle Scholar
  2. Ernstsen, A., Sandberg, G. (1986) Identification of 4-chloroindole-3-acetic acid and indole-3-aldehyde in seeds of Pinus sylvestris. Physiol. Plant. 68, 511–518Google Scholar
  3. Hinman, R.L., Bauman, C.P. (1964) Reactions of N-bromosuccinimide and indoles. A simple synthesis of 3-bromooxindoles. J. Org. Chem. 29, 1206–1215Google Scholar
  4. Kinashi, H., Suzuki, Y., Takeuchi, S., Kawarada, A. (1976) Possible metabolic intermediates from IAA to β-acid in rice bran. Agric. Biol. Chem. 40, 2465–2470Google Scholar
  5. Nonhebel, H.M., Bandurski, R.S. (1984) Oxidation of indole-3-acetic acid and oxindole-3-acetic acid to 2,3-dihydro-7-hydroxy-2-oxo-1H indole-3-acetic acid-7′-O-β-D-glucopyranoside in Zea mays seedlings. Plant Physiol 76, 979–983Google Scholar
  6. Nonhebel, H.M., Kruse, Kruse, L.I., Bandurski, R.S. (1985) Indole-3-acetic acid catabolism in Zea mays seedlings. Metabolic conversion of oxindole-3-acetic acid to 7-hydroxy-2-oxindole-3-acetic acid-7′-O-β-D-glucopyranoside. J. Biol. Chem. 260, 12685–12689Google Scholar
  7. Reinecke, D.M., Bandurski, R.S. (1981) Metabolic conversion of 14C-indole-3-acetic acid to 14C-oxindole-3-acetic acid. Biochem. Biophys. Res. Commun. 103, 429–433Google Scholar
  8. Reinecke, D.M., Bandurski, R.S. (1983) Oxindole-3-acetic acid, an indole-3-acetic acid catabolite in Zea mays. Plant Physiol. 71, 211–213Google Scholar
  9. Sandberg, G., Crozier, A., Jensen, E. (1984) Analysis of 3-indole carboxylic acid in Pinus sylvestris needles. Phytochemistry 23, 99–101Google Scholar
  10. Sembdner, G., Gross, D., Liebisch, H.-W., Schneider, G. (1980) Biosynthesis and metabolism of plant hormones. In: Encyclopedia of plant physiology, N. S., vol. 9: Hormonal regulation of development. I. Molecular aspects of plant hormones, pp. 281–444, MacMillan, J., ed. Springer, Berlin Heidelberg New YorkGoogle Scholar
  11. Sundberg, B., Sandberg, G., Jensen, E. (1985) Identification and quantification of indole-3-methanol in etiolated seedlings of Scots pine (Pinus sylvestris L.). Plant Physiol. 77, 952–955Google Scholar
  12. Tsurumi, S., Wada, S. (1980) Metabolism of indole-3-acetic acid and natural occurrence of dioxindole-3-acetic acid derivatives in Vicia roots. Plant Cell Physiol. 21, 1515–1525Google Scholar
  13. Tsurumi, S., Wada, S. (1985) Identification of 3-(O-β-glucosyl)-2-indolone-3-acetylaspartic acid as a new indole-3-acetic acid metabolite in Vicia seedlings. Plant Physiol. 79, 667–671Google Scholar
  14. Tsurumi, S., Wada, S. (1986) Identification of 3-hydroxy-2-indolone-3-acetylaspartic acid as a new indole-3-acetic acid metabolite in vicia roots. Plant Cell Physiol. 27, 559–562Google Scholar

Copyright information

© Springer-Verlag 1987

Authors and Affiliations

  • Arild Ernstsen
    • 1
  • Göran Sandberg
    • 1
  • Karin Lundström
    • 1
  1. 1.Department of Forest Genetics and Plant PhysiologyThe Swedish University of Agricultural SciencesUmeåSweden

Personalised recommendations