<i>Arabidopsis thaliana</i>seed germination and early seedling growth are inhibited by monoethanolamine salts of<i>para</i>-halogenated benzoic acids

Crişan, Manuela; Grozav, Mata; Bertea, Cinzia M.

doi:10.1080/17429140903063072

Cited by 16 publications

(13 citation statements)

References 34 publications

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“…The salt and IAA were dissolved in 5 mM MES (2-[ N ′-morpholino] ethanesulfonic acid) buffer, while p ABA, which is slightly soluble in water, was dissolved in MES buffer – EtOH solution, with a final EtOH concentration of 0.2% (v/v). Our previous research on Arabidopsis thaliana (Col 0) [28] and Cucumis sativus L. [27] seeds show that 0.2% (v/v) ethanol concentration in culture media does not alter germination rate of seeds, but inhibit slowly primary root length and lateral root formation, as it is confirmed by some studies reported in the literature [47], [48]. For clarity, control corresponding to p ABA was noted CONTROL 0.2% EtOH and for HEA- p ABA and HEA, CONTROL.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Crystal Structure and Biological Activity of 2-Hydroxyethylammonium Salt of p-Aminobenzoic Acid

et al. 2014

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p-Aminobenzoic acid (pABA) plays important roles in a wide variety of metabolic processes. Herein we report the synthesis, theoretical calculations, crystallographic investigation, and in vitro determination of the biological activity and phytotoxicity of the pABA salt, 2-hydroxyethylammonium p-aminobenzoate (HEA-pABA). The ability of neutral and anionic forms of pABA to interact with TIR1 pocket was investigated by calculation of molecular electrostatic potential maps on the accessible surface area, docking experiments, Molecular Dynamics and Quantum Mechanics/Molecular Mechanics calculations. The docking study of the folate precursor pABA, its anionic form and natural auxin (indole-3-acetic acid, IAA) with the auxin receptor TIR1 revealed a similar binding mode in the active site. The phytotoxic evaluation of HEA-pABA, pABA and 2-hydroxyethylamine (HEA) was performed on the model plant Arabidopsis thaliana ecotype Col 0 at five different concentrations. HEA-pABA and pABA acted as potential auxin-like regulators of root development in Arabidopsis thaliana (0.1 and 0.2 mM) and displayed an agravitropic root response at high concentration (2 mM). This study suggests that HEA-pABA and pABA might be considered as potential new regulators of plant growth.

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Section: Methodsmentioning

confidence: 99%

Synthesis, Crystal Structure and Biological Activity of 2-Hydroxyethylammonium Salt of p-Aminobenzoic Acid

et al. 2014

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“…It is well known that benzoic acid and its different derivatives reduce or inhibit seed germination and growth in various plants like Betula platy phylla var. japonica [12], Pennisetum americanum [14], and Arabidopsis thaliana [15]. BA induces disruption in cellular membrane integrity by lowering sulfhydryl group contents in cells, which ultimately causes lipid peroxidation [16].…”

Section: Resultsmentioning

confidence: 99%

Seed Germination-Influencing Bioactive Secondary Metabolites Secreted by the Endophyte Cladosporium cladosporioides LWL5

et al. 2013

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The present study was aimed to isolate bioactive metabolites produced by a fungal endophyte from Helianthus annuus, Capsicum annuum, and Cucumis sativus and to assess their role in seed germination. Culture filtrate of the endophyte HA-3B from H. annuus was significantly inhibitory towards the germination and growth of lettuce seeds. HA-3B was identified as Cladosporium cladosporioides LWL5 through molecular techniques. Different concentrations (100, 500 and 1000 ppm) of the ethyl acetate extract obtained from the culture inhibited the lettuce seed germination. The extract was subjected to column chromatography and a bioassay-guided isolation method, which yielded compounds 1, 2 and an oily fraction. The oily fraction, subjected to fractionation and spectroscopic techniques, resulted in the identification of 31 different constituents. Compounds 1 and 2 were identified and characterized through MS and NMR spectroscopic techniques as benzoic acid. The bioassay results showed that this compound significantly inhibited the growth and germination of lettuce seeds. In conclusion, assessing the role of

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“…Alkanolammonium benzoates exhibit plant growth regulatory behavior in different plants [16][17][18][19][20]. Beside the presence of carboxylate and planar aromatic ring, the substituent on the benzene ring exhibits an essential role in biological activity establishment.…”

Section: Bioactivity Assaysmentioning

confidence: 99%

“…Small biological 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 [9]. Our previous studies revealed the important role of benzoic acids in the synthesis of stable acid-base systems with supramolecular architectures guided by hydrogen bonding interactions [10][11][12][13][14], low-toxicity [15] and promising plant growth regulatory activity on the model plant Arabidopsis (Arabidopsis thaliana) [16,17] and the vegetable crops cucumber (Cucumis sativus) [18] and tomato (Solanum lycopersicum) [19,20].…”

Section: Introductionmentioning

confidence: 99%

Bioprospecting Fluorescent Plant Growth Regulators from Arabidopsis to Vegetable Crops

Halip¹,

Maffei²,

Croitor³

et al. 2021

Preprint

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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 environmentally-friendly 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.

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Arabidopsis thalianaseed germination and early seedling growth are inhibited by monoethanolamine salts ofpara-halogenated benzoic acids

Cited by 16 publications

References 34 publications

Synthesis, Crystal Structure and Biological Activity of 2-Hydroxyethylammonium Salt of p-Aminobenzoic Acid

Synthesis, Crystal Structure and Biological Activity of 2-Hydroxyethylammonium Salt of p-Aminobenzoic Acid

Seed Germination-Influencing Bioactive Secondary Metabolites Secreted by the Endophyte Cladosporium cladosporioides LWL5

Bioprospecting Fluorescent Plant Growth Regulators from Arabidopsis to Vegetable Crops

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