- Three oxidative metabolites of indole-3-acetic acid from Arabidopsis thaliana
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Three metabolites of indole-3-acetic acid (IAA), N-(6-hydroxyindol-3-ylacetyl)-phenylalanine (6-OH-IAA-Phe), N-(6-hydroxyindol-3-ylacetyl)-valine (6-OH-IAA-Val), and 1-O-(2-oxoindol-3-ylacetyl)-β-d-glucopyranose (OxIAA-Glc), were found by a liquid chromatography-electrospray ionization-tandem mass spectrometry (LC-ESI-MS/MS)-based search for oxidative IAA metabolites during the vegetative growth of Arabidopsis. Their structures were confirmed by making a comparison of chromatographic characteristics and mass spectra between naturally occurring compounds and synthetic standards. An incorporation study using deuterium-labeled compounds showed that 6-OH-IAA-Phe and 6-OH-IAA-Val were biosynthesized from IAA-Phe and IAA-Val, respectively, which strongly suggested the formation of these amino acid conjugates of IAA in plants. Both 6-OH-IAA-Phe and 6-OH-IAA-Val were inactive as auxins, as indicated by no significant root growth inhibition in Arabidopsis. Quantitative analysis demonstrated that OxIAA-Glc was present in the largest amount among the metabolites of IAA in Arabidopsis, suggesting that the conversion into OxIAA-Glc represents the main metabolic process regarding IAA in Arabidopsis.
- Kai, Kenji,Horita, Junko,Wakasa, Kyo,Miyagawa, Hisashi
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p. 1651 - 1663
(2008/02/05)
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- Tandem Michael Addition-Sigmatropic Rearrangement Processes. Part 2. Construction of Cyclopropapyrroloindol-4-one (CPI) Unit of Antitumour Antibiotic CC-1065
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Development of an alternative strategy for preparing 3-acetoxymethyl-2,3-dihydro-1-methylsulfonyl-6-methoxyindole 25 has been completed.Since 25 was an intermediate in a previous synthesis of the CPI unit 5 of the antitumour antibiotic CC-1065 1, this ach
- Toyota, Masahiro,Fukumoto, Keiichiro
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p. 547 - 552
(2007/10/02)
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