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Metabolism of indole-3-acetic acid in rice: identification and characterization of N-beta-D-glucopyranosyl indole-3-acetic acid and its conjugates.
Phytochemistry. 2007 Oct; 68(20):2512-22.P

Abstract

A search was made for conjugates of indole-3-acetic acid (IAA) in rice (Oryza sativa) using liquid chromatography-electrospray ionization-tandem mass spectrometry (LC-ESI-MS/MS) in order to elucidate unknown metabolic pathways for IAA. N-beta-d-Glucopyranosyl indole-3-acetic acid (IAA-N-Glc) was found in an alkaline hydrolysate of rice extract. A quantitative analysis of 3-week-old rice demonstrated that the total amount of IAA-N-Glc was equal to that of IAA. A LC-ESI-MS/MS-based analysis established that the major part of IAA-N-Glc was present as bound forms with aspartate and glutamate. Their levels were in good agreement with the total amount of IAA-N-Glc during the vegetative growth of rice. Further detailed analysis showed that both conjugates highly accumulated in the root. The free form of IAA-N-Glc accounted for 60% of the total in seeds but could not be detected in the vegetative tissue. An incorporation study using deuterium-labeled compounds showed that the amino acid conjugates of IAA-N-Glc were biosynthesized from IAA-amino acids. IAA-N-Glc and/or its conjugates were also found in extracts of Arabidopsis, Lotus japonicus, and maize, suggesting that N-glucosylation of indole can be the common metabolic pathway of IAA in plants.

Authors+Show Affiliations

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

Pub Type(s)

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

Language

eng

PubMed ID

17628621

Citation

Kai, Kenji, et al. "Metabolism of Indole-3-acetic Acid in Rice: Identification and Characterization of N-beta-D-glucopyranosyl Indole-3-acetic Acid and Its Conjugates." Phytochemistry, vol. 68, no. 20, 2007, pp. 2512-22.
Kai K, Wakasa K, Miyagawa H. Metabolism of indole-3-acetic acid in rice: identification and characterization of N-beta-D-glucopyranosyl indole-3-acetic acid and its conjugates. Phytochemistry. 2007;68(20):2512-22.
Kai, K., Wakasa, K., & Miyagawa, H. (2007). Metabolism of indole-3-acetic acid in rice: identification and characterization of N-beta-D-glucopyranosyl indole-3-acetic acid and its conjugates. Phytochemistry, 68(20), 2512-22.
Kai K, Wakasa K, Miyagawa H. Metabolism of Indole-3-acetic Acid in Rice: Identification and Characterization of N-beta-D-glucopyranosyl Indole-3-acetic Acid and Its Conjugates. Phytochemistry. 2007;68(20):2512-22. PubMed PMID: 17628621.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Metabolism of indole-3-acetic acid in rice: identification and characterization of N-beta-D-glucopyranosyl indole-3-acetic acid and its conjugates. AU - Kai,Kenji, AU - Wakasa,Kyo, AU - Miyagawa,Hisashi, Y1 - 2007/07/12/ PY - 2006/11/24/received PY - 2007/04/27/revised PY - 2007/05/12/accepted PY - 2007/7/14/pubmed PY - 2008/1/23/medline PY - 2007/7/14/entrez SP - 2512 EP - 22 JF - Phytochemistry JO - Phytochemistry VL - 68 IS - 20 N2 - A search was made for conjugates of indole-3-acetic acid (IAA) in rice (Oryza sativa) using liquid chromatography-electrospray ionization-tandem mass spectrometry (LC-ESI-MS/MS) in order to elucidate unknown metabolic pathways for IAA. N-beta-d-Glucopyranosyl indole-3-acetic acid (IAA-N-Glc) was found in an alkaline hydrolysate of rice extract. A quantitative analysis of 3-week-old rice demonstrated that the total amount of IAA-N-Glc was equal to that of IAA. A LC-ESI-MS/MS-based analysis established that the major part of IAA-N-Glc was present as bound forms with aspartate and glutamate. Their levels were in good agreement with the total amount of IAA-N-Glc during the vegetative growth of rice. Further detailed analysis showed that both conjugates highly accumulated in the root. The free form of IAA-N-Glc accounted for 60% of the total in seeds but could not be detected in the vegetative tissue. An incorporation study using deuterium-labeled compounds showed that the amino acid conjugates of IAA-N-Glc were biosynthesized from IAA-amino acids. IAA-N-Glc and/or its conjugates were also found in extracts of Arabidopsis, Lotus japonicus, and maize, suggesting that N-glucosylation of indole can be the common metabolic pathway of IAA in plants. SN - 0031-9422 UR - https://www.unboundmedicine.com/medline/citation/17628621/Metabolism_of_indole_3_acetic_acid_in_rice:_identification_and_characterization_of_N_beta_D_glucopyranosyl_indole_3_acetic_acid_and_its_conjugates_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0031-9422(07)00344-5 DB - PRIME DP - Unbound Medicine ER -