Identification of skatolyl hydroperoxide and its role in the peroxidase-catalysed oxidation of indol-3-yl acetic acid

Irina G. Gazarian, L. Mark Lagrimini, Fred A. Mellon, Michael J. Naldrett, Gillian A. Ashby, Roger N.F. Thorneley

Research output: Contribution to journalArticle

Abstract

Indol-3-yl acetic acid (IAA, auxin) is a plant hormone whose degradation is a key determinant of plant growth and development. The first evidence for skatolyl hydroperoxide formation during the plant peroxidase-catalysed degradation of IAA has been obtained by electrospray MS. Skatolyl hydroperoxide degrades predominantly non-enzymically to oxindol-3-yl carbinol but in part enzymically into indol-3-yl methanol via a peroxidase cycle in which IAA acts as an electron donor. Skatolyl hydroperoxide is degradable by catalase. Horseradish peroxidase isoenzyme C (HRP-C) and anionic tobacco per-oxidase (TOP) exhibit differences in their mechanisms of reaction. The insensitivity of the HRP-C-catalysed reaction to catalase is ascribed to the formation of HRP-C Compound III at the initiation step and its subsequent role in radical propagation. This is in contrast with the TOP-catalysed process in which skatolyl hydroperoxide has a key role. Indol-3-yl aldehyde is produced not via the peroxidase cycle but by catalysis involving ferrous peroxidase, Because indol-3-yl aldehyde is one of the main IAA-derived products identified in planta, we conclude that ferrous peroxidases participate in IAA catalytic transformations in vivo. A general scheme for peroxidase-catalysed IAA oxidation is presented.

Original languageEnglish (US)
Pages (from-to)223-232
Number of pages10
JournalBiochemical Journal
Volume333
Issue number1
DOIs
StatePublished - Jul 1 1998

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Acetic Acid
Peroxidase
Horseradish Peroxidase
Isoenzymes
Aldehydes
Catalase
Tobacco
Methanol
Oxidoreductases
Peroxidases
Indoleacetic Acids
Plant Growth Regulators
Plant Development
Catalysis
Growth and Development
skatolyl hydroperoxide
Electrons

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Cell Biology

Cite this

Identification of skatolyl hydroperoxide and its role in the peroxidase-catalysed oxidation of indol-3-yl acetic acid. / Gazarian, Irina G.; Lagrimini, L. Mark; Mellon, Fred A.; Naldrett, Michael J.; Ashby, Gillian A.; Thorneley, Roger N.F.

In: Biochemical Journal, Vol. 333, No. 1, 01.07.1998, p. 223-232.

Research output: Contribution to journalArticle

Gazarian, Irina G. ; Lagrimini, L. Mark ; Mellon, Fred A. ; Naldrett, Michael J. ; Ashby, Gillian A. ; Thorneley, Roger N.F. / Identification of skatolyl hydroperoxide and its role in the peroxidase-catalysed oxidation of indol-3-yl acetic acid. In: Biochemical Journal. 1998 ; Vol. 333, No. 1. pp. 223-232.
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