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. 1967 Mar;42(3):425–430. doi: 10.1104/pp.42.3.425

Inhibitory Oxidation Products of Indole-3-Acetic Acid: 3-Hydroxymethyloxindole and 3-Methyleneoxindole as Plant Metabolites 1

V Tuli 1, H S Moyed 1
PMCID: PMC1086552  PMID: 16656521

Abstract

Extracts of pea seedlings (Pisum sativum, variety Alaska) oxidize indole-3-acetic acid to a bacteriostatic compound which has been identified as 3-hydroxymethyloxindole. At physiological pH this compound is readily dehydrated to 3-methyleneoxindole, another bacteriostatic agent. The extracts of pea seedlings also contain a reduced triphosphopyridine nucleotide-linked enzyme which reduces 3-methyleneoxindole to 3-methyloxindole, a non-toxic compound.

These enzymatic reactions also take place in intact seedlings; thus, a pathway of indole-3-acetic acid degradation via oxindoles appears to be pertinent to plant metabolism.

The significance of such metabolism lies in the fact that a key intermediate of this pathway, 3-methyleneoxindole, is a sulfhydryl reagent capable of profound effects on metabolism and growth.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. ABRAMOVITCH R. A., AHMED K. S. Oxidative decarboxylation of indole-3-acetic acid by mangani-versene and by wheat leaf enzyme. Nature. 1961 Oct 21;192:259–260. doi: 10.1038/192259a0. [DOI] [PubMed] [Google Scholar]
  2. Dear J., Aronoff S. Relative Kinetics of Chlorogenic and Caffeic Acids During the Onset of Boron Deficiency in Sunflower. Plant Physiol. 1965 May;40(3):458–459. doi: 10.1104/pp.40.3.458. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. FUKUYAMA T. T., MOYED H. S. INHIBITION OF CELL GROWTH BY PHOTOOXIDATION PRODUCTS OF INDOLE-3-ACETIC ACID. J Biol Chem. 1964 Jul;239:2392–2397. [PubMed] [Google Scholar]
  4. GALSTON A. W. Riboflavin, light, and the growth of plants. Science. 1950 Jun 9;111(2893):619–624. doi: 10.1126/science.111.2893.619. [DOI] [PubMed] [Google Scholar]
  5. HINMAN R. L., LANG J. PEROXIDASE-CATALYZED OXIDATION OF INDOLE-3-ACETIC ACID. Biochemistry. 1965 Jan;4:144–158. doi: 10.1021/bi00877a023. [DOI] [PubMed] [Google Scholar]
  6. RAY P. M., CURRY G. M. Intermediates and competing reactions in the photodestruction of indoleacetic acid. Nature. 1958 Mar 29;181(4613):895–896. doi: 10.1038/181895a0. [DOI] [PubMed] [Google Scholar]
  7. STILL C. C., FUKUYAMA T. T., MOYED H. S. INHIBITORY OXIDATION PRODUCTS OF INDOLE-3-ACETIC ACID. MECHANISM OF ACTION AND ROUTE OF DETOXIFICATION. J Biol Chem. 1965 Jun;240:2612–2618. [PubMed] [Google Scholar]
  8. Tuli V., Moyed H. S. Desensitization of regulatory enzymes by a metabolite of plant auxin. J Biol Chem. 1966 Oct 10;241(19):4564–4566. [PubMed] [Google Scholar]

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