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Three oxidative metabolites of indole-3-acetic acid from Arabidopsis thaliana.
Phytochemistry. 2007 Jun; 68(12):1651-63.P

Abstract

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)-beta-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.

Authors+Show Affiliations

Division of Applied Life Science, Graduate School of Agriculture, Kitashirakawa, Kyoto University, Kyoto 606-8502, Japan.No affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

17548096

Citation

Kai, Kenji, et al. "Three Oxidative Metabolites of Indole-3-acetic Acid From Arabidopsis Thaliana." Phytochemistry, vol. 68, no. 12, 2007, pp. 1651-63.
Kai K, Horita J, Wakasa K, et al. Three oxidative metabolites of indole-3-acetic acid from Arabidopsis thaliana. Phytochemistry. 2007;68(12):1651-63.
Kai, K., Horita, J., Wakasa, K., & Miyagawa, H. (2007). Three oxidative metabolites of indole-3-acetic acid from Arabidopsis thaliana. Phytochemistry, 68(12), 1651-63.
Kai K, et al. Three Oxidative Metabolites of Indole-3-acetic Acid From Arabidopsis Thaliana. Phytochemistry. 2007;68(12):1651-63. PubMed PMID: 17548096.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Three oxidative metabolites of indole-3-acetic acid from Arabidopsis thaliana. AU - Kai,Kenji, AU - Horita,Junko, AU - Wakasa,Kyo, AU - Miyagawa,Hisashi, Y1 - 2007/06/04/ PY - 2006/11/02/received PY - 2007/04/16/revised PY - 2007/04/23/accepted PY - 2007/6/6/pubmed PY - 2007/10/10/medline PY - 2007/6/6/entrez SP - 1651 EP - 63 JF - Phytochemistry JO - Phytochemistry VL - 68 IS - 12 N2 - 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)-beta-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. SN - 0031-9422 UR - https://www.unboundmedicine.com/medline/citation/17548096/Three_oxidative_metabolites_of_indole_3_acetic_acid_from_Arabidopsis_thaliana_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0031-9422(07)00284-1 DB - PRIME DP - Unbound Medicine ER -