Suppression of Elongation and Growth of Tomato Seedlings by Auxin Biosynthesis Inhibitors and Modeling of the Growth and Environmental Response

Higashide, Tadahisa; Narukawa, Megumi; Shimada, Yukihisa; Soeno, Kazuo

doi:10.1038/srep04556

Cited by 18 publications

(16 citation statements)

References 16 publications

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“…We studied auxin biosynthesis inhibitors in our previous investigations (Ishii et al ., ; Soeno et al ., ; Higashide et al ., ; Ishida et al ., ), during which we collected about 600 compounds. We synthesized 160 ourselves and others were obtained from commercial sources.…”

Section: Methodsmentioning

confidence: 99%

Small‐molecule auxin inhibitors that target YUCCA are powerful tools for studying auxin function

et al. 2015

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Summary Auxin is essential for plant growth and development, this makes it difficult to study the biological function of auxin using auxin‐deficient mutants. Chemical genetics have the potential to overcome this difficulty by temporally reducing the auxin function using inhibitors. Recently, the indole‐3‐pyruvate (IPyA) pathway was suggested to be a major biosynthesis pathway in Arabidopsis thaliana L. for indole‐3‐acetic acid (IAA), the most common member of the auxin family. In this pathway, YUCCA, a flavin‐containing monooxygenase (YUC), catalyzes the last step of conversion from IPyA to IAA. In this study, we screened effective inhibitors, 4‐biphenylboronic acid (BBo) and 4‐phenoxyphenylboronic acid (PPBo), which target YUC. These compounds inhibited the activity of recombinant YUC in vitro, reduced endogenous IAA content, and inhibited primary root elongation and lateral root formation in wild‐type Arabidopsis seedlings. Co‐treatment with IAA reduced the inhibitory effects. Kinetic studies of BBo and PPBo showed that they are competitive inhibitors of the substrate IPyA. Inhibition constants (Ki) of BBo and PPBo were 67 and 56 nm, respectively. In addition, PPBo did not interfere with the auxin response of auxin‐marker genes when it was co‐treated with IAA, suggesting that PPBo is not an inhibitor of auxin sensing or signaling. We propose that these compounds are a class of auxin biosynthesis inhibitors that target YUC. These small molecules are powerful tools for the chemical genetic analysis of auxin function.

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Section: Methodsmentioning

confidence: 99%

Small‐molecule auxin inhibitors that target YUCCA are powerful tools for studying auxin function

et al. 2015

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“…Higashide et al . () recently showed that KOK1101, which is an AOPP derivative and has both a methylated carboxyl group and a phthaloyl group instead of the aminooxy group, effectively inhibited the accumulation of IAA in tomato and Arabidopsis seedlings. Based this finding, we further modified Type II compounds by adding a protection group of the aminooxy moiety; these were classified as Type III compounds (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…l ‐α‐(2‐aminoethoxyvinyl)glycine (AVG) and l ‐α‐aminooxyphenylpropionic acid (AOPP) may inhibit IAA biosynthesis by targeting Trp aminotransferase. AOPP decreases the levels of IAA in seedlings of several plant species (Soeno et al ., ), and seedlings treated with AOPP or its derivatives show an auxin‐deficient phenotype in Arabidopsis (Soeno et al ., ) and tomato (Higashide et al ., ). Another small molecule, l ‐kynurenine (Kyn), is an alternative substrate and competitive inhibitor of TAA1 (He et al ., ).…”

Section: Introductionmentioning

confidence: 97%

Aminooxy‐naphthylpropionic acid and its derivatives are inhibitors of auxin biosynthesis targeting l‐tryptophan aminotransferase: structure–activity relationships

et al. 2016

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SUMMARYWe previously reported L-a-aminooxy-phenylpropionic acid (AOPP) to be an inhibitor of auxin biosynthesis, but its precise molecular target was not identified. In this study we found that AOPP targets TRYPTOPHAN AMINOTRANSFERASE of ARABIDOPSIS 1 (TAA1). We then synthesized 14 novel compounds derived from AOPP to study the structure-activity relationships of TAA1 inhibitors in vitro. The aminooxy and carboxy groups of the compounds were essential for inhibition of TAA1 in vitro. Docking simulation analysis revealed that the inhibitory activity of the compounds was correlated with their binding energy with TAA1. These active compounds reduced the endogenous indole-3-acetic acid (IAA) content upon application to Arabidopsis seedlings. Among the compounds, we selected 2-(aminooxy)-3-(naphthalen-2-yl)propanoic acid (KOK1169/AONP) and analyzed its activities in vitro and in vivo. Arabidopsis seedlings treated with KOK1169 showed typical auxin-deficient phenotypes, which were reversed by exogenous IAA. In vitro and in vivo experiments indicated that KOK1169 is more specific for TAA1 than other enzymes, such as phenylalanine ammonia-lyase. We further tested 41 novel compounds with aminooxy and carboxy groups to which we added protection groups to increase their calculated hydrophobicity. Most of these compounds decreased the endogenous auxin level to a greater degree than the original compounds, and resulted in a maximum reduction of about 90% in the endogenous IAA level in Arabidopsis seedlings. We conclude that the newly developed compounds constitute a class of inhibitors of TAA1. We designated them 'pyruvamine'.

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“…Growth analysis and modelling are useful tools for investigating plant growth under different conditions. We showed that when l-α-aminooxy-β-phenyl propionic acid, an auxin biosynthesis inhibitor, was supplied to tomato seedlings, elongation growth was suppressed, but the net assimilation rate was not affected (Higashide et al, 2014). Both observation and growth modelling showed that the effect of the inhibitor depended on the environmental conditions, even if there was no difference in photosynthetic ability per unit leaf area.…”

Section: Introductionmentioning

confidence: 93%

“…Both observation and growth modelling showed that the effect of the inhibitor depended on the environmental conditions, even if there was no difference in photosynthetic ability per unit leaf area. In this study, we therefore sought to clarify the effects of UFB treatment on growth and dry matter (DM) production of tomato seedlings using growth analysis and modelling as described by Higashide et al (2014) Using this model, we tried to predict the growth of seedlings grown with or without UFB treatment under different day length conditions. We then validated the model by comparing its predictions with data from a second, independent experiment.…”

Section: Introductionmentioning

confidence: 99%

Application of a Growth Model to Validate the Effects of an Ultrafine-bubble Nutrient Solution on Dry Matter Production and Elongation of Tomato Seedlings

et al. 2019

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To clarify the effect of ultrafine bubbles (UFBs) on the growth of tomato seedlings, we investigated elongation growth and dry matter production by analysing growth under different assimilation conditions and by modelling. The leaf area enlargement rate of plants grown with UFB nutrient solution increased and the specific leaf area (SLA) decreased at 18 days after sowing (DAS) relative to those grown without UFB solution. Thus, UFBs increased both leaf area and leaf thickness. UFB significantly increased the relative growth rate (RGR) and net assimilation rate (NAR) at 18 DAS, but there was no significant difference in SLA, RGR, and NAR between treatments at 25 DAS. These results were used to model plant growth with and without UFB treatment. In a second experiment, UFB treatment increased aboveground dry weight under a lowassimilation condition, but had no significant effect under a high-assimilation condition. Our model supported these results. It was also implied that UFB treatment affected leaf area expansion, but not dry matter production. Although the values predicted by the model were slightly lower than observed, it was possible to predict the effect of UFB treatment on plant growth with high accuracy.

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Suppression of Elongation and Growth of Tomato Seedlings by Auxin Biosynthesis Inhibitors and Modeling of the Growth and Environmental Response

Cited by 18 publications

References 16 publications

Small‐molecule auxin inhibitors that target YUCCA are powerful tools for studying auxin function

Small‐molecule auxin inhibitors that target YUCCA are powerful tools for studying auxin function

Aminooxy‐naphthylpropionic acid and its derivatives are inhibitors of auxin biosynthesis targeting l‐tryptophan aminotransferase: structure–activity relationships

Application of a Growth Model to Validate the Effects of an Ultrafine-bubble Nutrient Solution on Dry Matter Production and Elongation of Tomato Seedlings

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