Metabolism of indole-3-acetaldoxime in plants

Planta. 1972 Mar;103(1):45-54. doi: 10.1007/BF00394605.

Abstract

Living tissues of diverse plants representing 17 families were infiltrated with indole-3-acetaldoxime (IAAld oxime) in phosphate buffer, pH 6, and incubated for 3 hours at 25°C. Indole compounds were then extracted, separated and identified by paper or thin-layer chromatography (TLC). Indole-3-acetic acid (IAA) was quantitatively determined. Every tissue tested converted the oxime to IAA and tryptophol (T-ol). While accumulation of indole-3-acetonitrile (IAN) was observed in the non-acidic fractions of extracts of tissues of 8 species, indole-3-acetaldehyde (IAAld) accumulated in only a single tissue viz. Amaranthus shoot.IAAld oxime undergoes spontaneous hydrolysis at pH values below 4.7 leading to the formation of IAAld. Ce l-free preparations of etiolated Avena coleoptiles appear to contain an enzyme system capable of hydrolysing the oxime to IAAld. In the presence of such preparations, more IAAld and IAA are formed at all tested durations than the spontaneously formed IAAld. In the presence of bisulfite or semicarbazide, no IAA is formed, suggesting the intermediary formation of IAAld. The compound trapped with sodium bisulfite resembles very closely synthetic IAAld in its IR spectrum.In intact tissues, therefore, IAAld oxime appears to be first hydrolysed to IAAld which is then partly oxidized to IAA and mostly reduced to T-ol. Besides other evidence, formation of T-ol in every instance is believed to indicate the intermediary formation of IAAld. The nitrile pathway is considered to be only of minor importance in normal IAA biogenesis in the majority of higher plants.