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
- 1 December 1984
- journal article
- research article
- Published by Oxford University Press (OUP) in Plant Physiology
- Vol. 76 (4), 979-983
- https://doi.org/10.1104/pp.76.4.979
Abstract
Radiolabeled oxindole-3-acetic acid was metabolized by roots, shoots, and caryopses of dark grown Zea mays seedlings to 2,3-dihydro-7-hydroxy-2-oxo-1H indole-3-acetic acid-7′-O-β-d-glycopyranoside with the simpler name of 7-hydroxyoxindole-3-acetic acid-glucoside. This compound was also formed from labeled indole-3-acetic acid supplied to intact seedlings and root segments. The glucoside of 7-hydroxyoxindole-3-acetic acid was also isolated as an endogenous compound in the caryopses and shoots of 4-day-old seedlings. It accumulates to a level of 4.8 nanomoles per plant in the kernel, more than 10 times the amount of oxindole-3-acetic acid. In the shoot it is present at levels comparable to that of oxindole-3-acetic acid and indole-3-acetic acid (62 picomoles per shoot). We conclude that 7-hydroxyoxindole-3-acetic acid-glucoside is a natural metabolite of indole-3-acetic acid in Z. mays seedlings. From the data presented in this paper and in previous work, we propose the following route as the principal catabolic pathway for indole-3-acetic acid in Zea seedlings: Indole-3-acetic acid → Oxindole-3-acetic acid → 7-Hydroxyoxindole-3-acetic acid → 7-Hydroxyoxindole-3-acetic acid-glucoside.This publication has 11 references indexed in Scilit:
- Myo-Inositol Esters of Indole-3-acetic Acid Are Endogenous Components of Zea mays L. Shoot TissuePlant Physiology, 1984
- Oxindole-3-acetic Acid, an Indole-3-acetic Acid Catabolite in Zea maysPlant Physiology, 1983
- Characterization of Dihydrophaseic Acid 4′-O- β -D-Glucopyranoside as a Major Metabolite of Abscisic AcidFunctional Plant Biology, 1982
- Enzymatic synthesis of 5‐3H‐indole‐3‐acetic acid and 5‐3H‐indole‐3‐acetyl‐myo‐inositol from 5‐3H‐L‐tryptophanJournal of Labelled Compounds and Radiopharmaceuticals, 1982
- Metabolic conversion of 14C-indole-3-acetic acid to 14C-oxindole-3-acetic acidBiochemical and Biophysical Research Communications, 1981
- Double-standard isotope dilution assayAnalytical Biochemistry, 1981
- Metabolism of indole-3-acetic acid and natural occurrence of dioxindole-3-acetic acid derivatives in Vicia rootsPlant and Cell Physiology, 1980
- Concentration and Metabolic Turnover of Indoles in Germinating Kernels of Zea mays L.Plant Physiology, 1980
- Possible Metabolic Intermediates from IAA toβ-Acid in Rice BranAgricultural and Biological Chemistry, 1976
- Effect of Oxindoles on the Growth of Tobacco Tissue CulturesNature, 1966