Abstract
The phytohormone auxin is involved in almost every process of a plant’s life, from germination to plant development. Nowadays, auxin research connects synthetic chemistry, plant biology and computational chemistry in order to develop innovative and safe compounds to be used in sustainable agricultural practice. In this framework, we developed new fluorescent compounds, ethanolammonium p-aminobenzoate (HEA-pABA) and p-nitrobenzoate (HEA-pNBA), and investigated their auxin-like behavior on two main commercial vegetables cultivated in Europe, cucumber (Cucumis sativus) and tomato (Solanum lycopersicum), in comparison to the model plant Arabidopsis (Arabidopsis thaliana). Moreover, the binding modes and affinities of two organic salts in relation to the natural auxin indole-3-acetic acid (IAA) into TIR1 auxin receptor were investigated by computational approaches (homology modeling and molecular docking). Both experimental and theoretical results highlight HEA-pABA as a fluorescent compound with auxin-like activity both in Arabidopsis and the commercial cucumber and tomato. Therefore, alkanolammonium benzoates have a great potential as promising sustainable plant growth stimulators to be efficiently used in vegetable crops.
Highlights
Since its discovery nearly a century ago, deciphering the complexity of auxin action has been an open question in plant hormone research [1]
The response of seed germination and root growth development to HEA-pABA, HEA-pNBA and natural auxin indole-3-acetic acid (IAA) used as reference was investigated in Arabidopsis, cucumber and tomato
The results indicate that cucumber modification of auxin-like in Arabidopsis the two main commercial vegetables, and tomato, properties which should be considered for future design of new fluorescent orescence property in the case of studied organic salts was generated by the pre plant growth regulators. groups on the benzene ring
Summary
Since its discovery nearly a century ago, deciphering the complexity of auxin action has been an open question in plant hormone research [1]. Small biologically active molecules, such as benzoic acid and its derivatives, which are important structural elements for many drugs and natural products, drew attention in the last years due to their involvement in various plant physiological processes [10]. We report the development of new fluorescent compounds, ethanolammonium p-aminobenzoate (HEA-pABA) and p-nitrobenzoate (HEA-pNBA), and investigate their auxin-like plant growth regulatory activity on two main commercial vegetables cultivated in Europe, cucumber and tomato. Ethanolamine (EA) is an important metabolite in plants and is a precursor of choline and membrane lipids [32] Computational approaches such as homology modeling and molecular docking were used to explain the auxin-like behavior of these compounds against TIR1 in cucumber and tomato
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