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Chlorinated Auxins-How Does Arabidopsis Thaliana Deal with Them?
Int J Mol Sci. 2020 Apr 07; 21(7)IJ

Abstract

Plant hormones have various functions in plants and play crucial roles in all developmental and differentiation stages. Auxins constitute one of the most important groups with the major representative indole-3-acetic acid (IAA). A halogenated derivate of IAA, 4-chloro-indole-3-acetic acid (4-Cl-IAA), has previously been identified in Pisum sativum and other legumes. While the enzymes responsible for the halogenation of compounds in bacteria and fungi are well studied, the metabolic pathways leading to the production of 4-Cl-IAA in plants, especially the halogenating reaction, are still unknown. Therefore, bacterial flavin-dependent tryptophan-halogenase genes were transformed into the model organism Arabidopsis thaliana. The type of chlorinated indole derivatives that could be expected was determined by incubating wild type A. thaliana with different Cl-tryptophan derivatives. We showed that, in addition to chlorinated IAA, chlorinated IAA conjugates were synthesized. Concomitantly, we found that an auxin conjugate synthetase (GH3.3 protein) from A. thaliana was able to convert chlorinated IAAs to amino acid conjugates in vitro. In addition, we showed that the production of halogenated tryptophan (Trp), indole-3-acetonitrile (IAN) and IAA is possible in transgenic A. thaliana in planta with the help of the bacterial halogenating enzymes. Furthermore, it was investigated if there is an effect (i) of exogenously applied Cl-IAA and Cl-Trp and (ii) of endogenously chlorinated substances on the growth phenotype of the plants.

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Authors+Show Affiliations

Walter A
Institute of Botany, Technische Universität Dresden, 01062 Dresden, Germany.
Caputi L
Department of Natural Product Synthesis, Max Planck Institute for Chemical Ecology, 07745 Jena, Germany.
O'Connor S
Department of Natural Product Synthesis, Max Planck Institute for Chemical Ecology, 07745 Jena, Germany.
van Pée KH
Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, 01062 Dresden, Germany.
Ludwig-Müller J
Institute of Botany, Technische Universität Dresden, 01062 Dresden, Germany.

MeSH

Amino AcidsArabidopsisArabidopsis ProteinsFabaceaeGene Expression Regulation, PlantHalogenationIndoleacetic AcidsIndolesPeasPlant Growth RegulatorsPlant RootsTryptophan

Pub Type(s)

Journal Article

Language

eng

PubMed ID

32272759

Citation

Walter, Antje, et al. "Chlorinated Auxins-How Does Arabidopsis Thaliana Deal With Them?" International Journal of Molecular Sciences, vol. 21, no. 7, 2020.
Walter A, Caputi L, O'Connor S, et al. Chlorinated Auxins-How Does Arabidopsis Thaliana Deal with Them? Int J Mol Sci. 2020;21(7).
Walter, A., Caputi, L., O'Connor, S., van Pée, K. H., & Ludwig-Müller, J. (2020). Chlorinated Auxins-How Does Arabidopsis Thaliana Deal with Them? International Journal of Molecular Sciences, 21(7). https://doi.org/10.3390/ijms21072567
Walter A, et al. Chlorinated Auxins-How Does Arabidopsis Thaliana Deal With Them. Int J Mol Sci. 2020 Apr 7;21(7) PubMed PMID: 32272759.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Chlorinated Auxins-How Does Arabidopsis Thaliana Deal with Them? AU - Walter,Antje, AU - Caputi,Lorenzo, AU - O'Connor,Sarah, AU - van Pée,Karl-Heinz, AU - Ludwig-Müller,Jutta, Y1 - 2020/04/07/ PY - 2020/03/25/received PY - 2020/04/03/accepted PY - 2020/4/11/entrez PY - 2020/4/11/pubmed PY - 2021/1/5/medline KW - Arabidopsis thaliana KW - auxin KW - bacterial halogenase KW - chloro-tryptophan, chloro-indole acetic acid, chloro-indole acetonitrile, plant natural products, plant metabolic engineering JF - International journal of molecular sciences JO - Int J Mol Sci VL - 21 IS - 7 N2 - Plant hormones have various functions in plants and play crucial roles in all developmental and differentiation stages. Auxins constitute one of the most important groups with the major representative indole-3-acetic acid (IAA). A halogenated derivate of IAA, 4-chloro-indole-3-acetic acid (4-Cl-IAA), has previously been identified in Pisum sativum and other legumes. While the enzymes responsible for the halogenation of compounds in bacteria and fungi are well studied, the metabolic pathways leading to the production of 4-Cl-IAA in plants, especially the halogenating reaction, are still unknown. Therefore, bacterial flavin-dependent tryptophan-halogenase genes were transformed into the model organism Arabidopsis thaliana. The type of chlorinated indole derivatives that could be expected was determined by incubating wild type A. thaliana with different Cl-tryptophan derivatives. We showed that, in addition to chlorinated IAA, chlorinated IAA conjugates were synthesized. Concomitantly, we found that an auxin conjugate synthetase (GH3.3 protein) from A. thaliana was able to convert chlorinated IAAs to amino acid conjugates in vitro. In addition, we showed that the production of halogenated tryptophan (Trp), indole-3-acetonitrile (IAN) and IAA is possible in transgenic A. thaliana in planta with the help of the bacterial halogenating enzymes. Furthermore, it was investigated if there is an effect (i) of exogenously applied Cl-IAA and Cl-Trp and (ii) of endogenously chlorinated substances on the growth phenotype of the plants. SN - 1422-0067 UR - https://www.unboundmedicine.com/medline/citation/32272759/Chlorinated_Auxins_How_Does_Arabidopsis_Thaliana_Deal_with_Them DB - PRIME DP - Unbound Medicine ER -