Inhibition Of Photosynthetic Electron Transport Research Articles

Aux/IAA11 Is Required for UV-AB Tolerance and Auxin Sensing in Arabidopsis thaliana

In order to survive, plants have, over the course of their evolution, developed sophisticated acclimation and defense strategies governed by complex molecular and physiological, and cellular and extracellular, signaling pathways. They are also able to respond to various stimuli in the form of tropisms; for example, phototropism or gravitropism. All of these retrograde and anterograde signaling pathways are controlled and regulated by waves of reactive oxygen species (ROS), electrical signals, calcium, and hormones, e.g., auxins. Auxins are key phytohormones involved in the regulation of plant growth and development. Acclimation responses, which include programmed cell death induction, require precise auxin perception. However, our knowledge of these pathways is limited. The Aux/IAA family of transcriptional corepressors inhibits the growth of the plant under stress conditions, in order to maintain the balance between development and acclimation responses. In this work, we demonstrate the Aux/IAA11 involvement in auxin sensing, survival, and acclimation to UV-AB, and in carrying out photosynthesis under inhibitory conditions. The tested iaa11 mutants were more susceptible to UV-AB, photosynthetic electron transport (PET) inhibitor, and synthetic endogenous auxin. Among the tested conditions, Aux/IAA11 was not repressed by excess light stress, exclusively among its phylogenetic clade. Repression of transcription by Aux/IAA11 could be important for the inhibition of ROS formation or efficiency of ROS scavenging. We also hypothesize that the demonstrated differences in the subcellular localization of the two Aux/IAA11 protein variants might indicate their regulation by alternative splicing. Our results suggest that Aux/IAA11 plays a specific role in chloroplast retrograde signaling, since it is not repressed by high (excess) light stress, exclusively among its phylogenetic clade.

Role of guard cell- or mesophyll cell-localized phytochromes in stomatal responses to blue, red, and far-red light.

Guard cell- or mesophyll cell-localized phytochromes do not have a predominant direct light sensory role in red- or blue-light-mediated stomatal opening or far-red-light-mediated stomatal closure of Arabidopsis. The role of phytochromes in blue- and red-light-mediated stomatal opening, and far-red-light- mediated decrease in opening, is still under debate. It is not clear whether reduced stomatal opening in a phytochrome B (phyB) mutant line, is due to phytochrome acting as a direct photosensor or an indirect growth effect. The exact tissue localization of the phytochrome photoreceptor important for stomatal opening is also not known. We studied differences in stomatal opening in an Arabidopsis phyB mutant, and lines showing mesophyll cell-specific or guard cell-specific inactivation of phytochromes. Stomatal conductance (gs) of intact leaves was measured under red, blue, and blue + far-red light. Lines exhibiting guard cell-specific inactivation of phytochrome did not show a change in gs under blue or red light compared to Col-0. phyB consistently exhibited a reduction in gs under both blue and red light. Addition of far-red light did not have a significant impact on the blue- or red-light-mediated stomatal response. Treatment of leaves with DCMU (3-(3,4-dichlorophenyl)-1,1-dimethylurea), a photosynthetic electron transport (PET) inhibitor, eliminated the response to red light in all lines, indicating that stomatal opening under red light is controlled by PET, and not directly by phytochrome. Similar to previous studies, leaves of the phyB mutant line had fewer stomata. Overall, phytochrome does not appear have a predominant direct sensory role in stomatal opening under red or blue light. However, phytochromes likely have an indirect effect on the degree of stomatal opening under light through effects on leaf growth and stomatal development.

Dual Redox Regulation of the DNA-Binding Activity of the Response Regulator RpaB in the Cyanobacterium Synechocystis sp. PCC 6803.

The response regulator RpaB plays a central role in transcriptional regulation of photosynthesis-related genes in cyanobacteria. RpaB is phosphorylated by its cognate histidine kinase Hik33 and functions as both an activator and a repressor under low-light conditions, whereas its phosphorylation level and DNA-binding activity promptly decrease upon the upshift of photon flux density, causing changes in the gene expression profile. In this study, we assessed the possibility of redox regulation of the DNA-binding activity of RpaB in Synechocystis sp. PCC 6803 by the addition of inhibitors of photosynthetic electron transport, 3-(3,4-dichlorophenyl)-1,1-dimethylurea and 2,5-dibromo-3-methyl-6-isopropyl-p-benzoquinone, or the reducing agent dithiothreitol under different photon flux densities. Analysis of the phosphorylation level of RpaB revealed that reduction of QA and increase in the availability of reducing equivalents at the acceptor side of photosystem I (PSI) can independently trigger dephosphorylation. The redox-state-dependent regulation by an unidentified thiol other than Cys59 of RpaB is prerequisite for the phosphorylation-dependent regulation of the DNA-binding activity. Environmental signals, recognized by Hik33, and metabolic signals recognized as the availability of reducing equivalents, must be integrated at the master regulator RpaB, in order to attain the flexible regulation of acclimatory responses.

Arbuscular mycorrhizal fungus regulates cadmium accumulation, migration, transport, and tolerance in Medicago sativa

Cadmium (Cd) pollution in croplands is a global environmental problem. Measures to improve the tolerance of sensitive crops and reduce pollutant absorption and accumulation are needed in contaminated agricultural areas, and inoculation with rhizosphere microorganisms to regulate plant resistance and heavy metal transport can provide an effective solution. A pot experiment was conducted to analyse the impact of arbuscular mycorrhizal fungi (AMF) on alfalfa oxidase activity, heavy metal resistance genes and transport proteins, metabolism, and other biochemical regulation mechanisms that lead to complexation, compartmentalisation, efflux, enrichment, and antioxidant detoxification pathways. The AMF reduced shoot and protoplasm Cd inflow, and promoted organic compound production (e.g., by upregulating HM-Res4 for 1.2 times), to complex with Cd, reducing its biological toxicity. The AMF increased the ROS scavenging efficiency and osmotic regulatory substance content of the alfalfa plants, reduced oxidative stress (ROS dereased), and maintained homeostasis. It also alleviated Cd inhibition of photosynthetic electron transport, tricarboxylic acid circulation, and nitrogen assimilation. These AMF effects improved leaf and root biomass by 43.87% and 59.71% and facilitated recovery of a conservative root economic strategy. It is speculated that AMF induces the resistance signal switch by regulating the negative feedback regulation mode of indole acetic acid upward transport and methyl jasmonate downward transmission in plants.

Effect of 2-[3-(trifluoromethyl)phenyl]-4H-furo[3,2-b]pyrrole-5-carboxhydrazides on photosynthetic processes

A new series of carboxhydrazides 6-8 was synthesized under microwave irradiation by reaction of carboxhydrazide 1 with heterocyclic aldehydes 2-4 in the presence of p-toluenesulfonic acid in ethanol. N-Benzoylcarboxhydrazide 9 was prepared by reaction of 1 with benzoylchlorid 5 in THF at room temperature. The effects of 6-9 on inhibition of photosynthetic electron transport in spinach chloroplasts and chlorophyll content in the antialgal suspensions of Chlorella vulgaris were investigated.

Growth and metabolic responses to methyl viologen (1,1′-dimethyl - 4,4′-bipyridinium dichloride) on Chlorella vulgaris

Aquatic environments are especially susceptible to being contaminated by pesticides used in agricultural fields. Methyl viologen (MV) is an herbicide with high effectiveness for the control of unwanted land plants; however, it also has a high toxicity towards the algae in the aquatic environment. The objective of this work was to describe the effect of MV on photosynthetic metabolism and its relationship with respiration, growth and the content of photosynthetic pigments of Chlorella vulgaris. The cultures of C. vulgaris were exposed for 72 h at different concentrations of methyl viologen. The results show that growth, pigment content and metabolic activity decrease as the concentration of MV increases. Analysis of the photochemical activity indicates that MV produces an inhibition of electron transport between quinone A and quinone B of photosystem II. The inhibition of photosynthetic electron transport is directly related to the reduction of metabolic activity and cell growth. The results found in this research show that methyl viologen can be a toxic pollutant for primary producers in aquatic environments.

Isophorone‐induced light‐independent lipid peroxidation and loss of cell membrane integrity

AbstractIsophorone (3,5,5‐trimethylcyclohex‐2‐en‐1‐one) is a plant‐derived volatile compound with strong phytotoxic activity. Here, we aimed to elucidate the mechanism of action of isophorone, and to this end, the effects of isophorone on shoot fresh weight, chlorophyll content, electrolyte leakage, and lipid peroxidation of Lactuca sativa L. and photosynthetic electron transport activity in chloroplast isolated from Spinacia oleracea L. were investigated. Isophorone induced light‐independent decreases in shoot fresh weight and light‐dependent chlorosis. In addition, increased electrolyte leakage and lipid peroxidation occurred under light conditions. However, the inhibitory activity on photosynthetic electron transport was unexpectedly low, and electrolyte leakage and lipid peroxidation were induced even under dark conditions. These results suggest that the inhibition of photosynthetic electron transport is not the main mechanism of action of isophorone and that the phytotoxic effects are mainly due to light‐independent oxidative damage and subsequent loss of cell membrane integrity.

The effect of salinity shock on the growth and rapid light curve of dunaliella salina

To confirm the effect of hypersaline shock on the growth of Dunaliella salina, the rapid light curves and chlorophyll fluorescence in D. salina with a NaCl upshift from 80 to 160, 240 and 320 g·L−1, respectively, were measured. Results showed that the photosynthetical saturated light of Dunaliella salina was downregulated to deal effectively with the severe NaCl increase from 80 to 160, 240 and 320 g·L−1. Dunaliella salina can deal effectively with the cells’ rapid increase in NaCl from 80 to 160 g·L−1 by heat dissipation to dissipate the excess energy. Salinity with 240–320 g·L−1 NaCl led to overproduction of QA− and the destruction of the PSII acceptor side, causing inhibition of photosynthetic electron transport. Dunaliella salina can also manage the abrupt rise in NaCl concentration from 80 to 240 g·L−1 by accumulating the amount of β-carotene and glycerol per cell. However, Dunaliella salina cannot effectively manage the rapid increase in NaCl from 80 to 320 g·L−1 due to the stronger inhibition and impaired of the PSII acceptor side. It is suitable to shade D. salina cells to 500 and 800 μmol·m−2·s−1 when cells are exposed to a severe NaCl shift from 80 to 160 g·L−1 and 80 to 240 g·L−1. NaCl ranged from 80 to 240 g·L−1 favoured the growth and carotenoid content of D. salina; however, the survival rate and photosynthetic activity were lowered by the sudden increase in NaCl.

Chloroplast-derived photo-oxidative stress causes changes in H2O2 and EGSH in other subcellular compartments.

Metabolic fluctuations in chloroplasts and mitochondria can trigger retrograde signals to modify nuclear gene expression. Mobile signals likely to be involved are reactive oxygen species (ROS), which can operate protein redox switches by oxidation of specific cysteine residues. Redox buffers, such as the highly reduced glutathione pool, serve as reservoirs of reducing power for several ROS-scavenging and ROS-induced damage repair pathways. Formation of glutathione disulfide and a shift of the glutathione redox potential (EGSH) toward less negative values is considered as hallmark of several stress conditions. Here we used the herbicide methyl viologen (MV) to generate ROS locally in chloroplasts of intact Arabidopsis (Arabidopsis thaliana) seedlings and recorded dynamic changes in EGSH and H2O2 levels with the genetically encoded biosensors Grx1-roGFP2 (for EGSH) and roGFP2-Orp1 (for H2O2) targeted to chloroplasts, the cytosol, or mitochondria. Treatment of seedlings with MV caused rapid oxidation in chloroplasts and, subsequently, in the cytosol and mitochondria. MV-induced oxidation was significantly boosted by illumination with actinic light, and largely abolished by inhibitors of photosynthetic electron transport. MV also induced autonomous oxidation in the mitochondrial matrix in an electron transport chain activity-dependent manner that was milder than the oxidation triggered in chloroplasts by the combination of MV and light. In vivo redox biosensing resolves the spatiotemporal dynamics of compartmental responses to local ROS generation and provides a basis for understanding how compartment-specific redox dynamics might operate in retrograde signaling and stress acclimation in plants.

A Systematic Survey of the Light/Dark-dependent Protein Degradation Events in a Model Cyanobacterium

Light is essential for photosynthetic organisms and is involved in the regulation of protein synthesis and degradation. The significance of light-regulated protein degradation is exemplified by the well-established light-induced degradation and repair of the photosystem II reaction center D1 protein in higher plants and cyanobacteria. However, systematic studies of light-regulated protein degradation events in photosynthetic organisms are lacking. Thus, we conducted a large-scale survey of protein degradation under light or dark conditions in the model cyanobacterium Synechocystis sp. PCC 6803 (hereafter referred to as Synechocystis) using the isobaric labeling-based quantitative proteomics technique. The results revealed that 79 proteins showed light-regulated degradation, including proteins involved in photosystem II structure or function, quinone binding, and NADH dehydrogenase. Among these, 25 proteins were strongly dependent on light for degradation. Moreover, the light-dependent degradation of several proteins was sensitive to photosynthetic electron transport inhibitors (DCMU and DBMIB), suggesting that they are influenced by the redox state of the plastoquinone (PQ) pool. Together, our study comprehensively cataloged light-regulated protein degradation events, and the results serve as an important resource for future studies aimed at understanding light-regulated processes and protein quality control mechanisms in cyanobacteria.

In Planta Monitoring of Cold-Responsive Promoter Activity Reveals a Distinctive Photoperiodic Response in Cold Acclimation.

Plant cold acclimation involves complicated pathways that integrate signals from temperature changes and light conditions. To understand plant responses to environmental signals in detail, molecular events that are regulated by temperature and light must be investigated at the whole-plant level in a nondestructive way. Using the promoter of COR15A connected to the luciferase reporter gene as a cold-responsive indicator, we developed an in planta monitoring system for gene expression under controlled temperature and photoperiod conditions. COR15A promoter activity was intensified by day-night cycles at 2�C, while its induction was abruptly suppressed in the dark at 8�C or higher, indicating a difference in responsiveness to photocycle between these two acclimation conditions. Freeze-thawing tests of whole plants proved that lower acclimation temperature resulted in higher tolerance to freezing, consistent with the temperature-dependent induction of COR15A. Inhibition of photosynthetic electron transport by 3-(3,4-dichlorophenyl)-1,1-dimethylurea eliminated the responsiveness to the day-night cycles at 2�C, indicating a possibility that the photosynthetic redox and/or the accumulation of photosynthates modulate COR15A responsiveness to photoperiod during cold acclimation, in addition to the well-known regulation by CBF (C-repeat binding factor) genes. These findings indicate that the cold-responsive promoter is regulated by distinctive mechanisms dependent on temperature and simultaneously affected by photocycle and photosynthesis.

Nutrient deficiency stimulates the production of superoxide in the noxious red-tide-forming raphidophyte Chattonella antiqua

The raphidophyte Chattonella antiqua is a single-celled alga that forms ‘red tides’ in coastal areas. C. antiqua produces superoxide anions (O2−), the excessive production of which has been associated with fish mortality. It is suggested that putative NADPH oxidase in the outer membrane oxidizes intracellular NADPH to produce O2− and secrete it externally. Earlier studies revealed that photosynthetic electron transport, a major producer of NADPH in photosynthetic organisms, is involved in the production of O2− in C. antiqua but the details of the O2− production mechanism have yet to be elucidated. Since nutrient deficiency adversely affects the formation of blooms of C. antiqua, in this study, we examined the effects of nutrient deficiency on O2− production in C. antiqua. When cells were grown under nitrogen (N)- or phosphorus (P)-deficient conditions, the production of O2− was stimulated. In particular, the extracellular levels of O2− under N- or P-deficient conditions were high during the dark period when photosynthetic activities in terms of actual quantum efficiency and photochemical quenching were low. The extracellular levels of O2− under the nutrient-deficient conditions were unaffected by the presence of 3-(3,4-dichlorophenyl)-1,1‑dimethylurea (DCMU), an inhibitor of photosynthetic electron transport, but decreased when the nutrients were present. Furthermore, the intracellular ratio of NADPH to NADP+ under N- or P-deficient conditions was higher than that under nutrient-replete conditions. These observations suggest that another metabolic pathway, independent of photosynthesis, provides NADPH for the production of O2− under nutrient deficiency.

Light-Dependent Activation of the GCN2 Kinase Under Cold and Salt Stress Is Mediated by the Photosynthetic Status of the Chloroplast.

Regulation of cytosolic mRNA translation is a key node for rapid adaptation to environmental stress conditions. In yeast and animals, phosphorylation of the α-subunit of eukaryotic translation initiation factor eIF2 is the most thoroughly characterized event for regulating global translation under stress. In plants, the GCN2 kinase (General Control Nonderepressible-2) is the only known kinase for eIF2α. GCN2 is activated under a variety of stresses including reactive oxygen species (ROS). Here, we provide new evidence that the GCN2 kinase in Arabidopsis is also activated rapidly and in a light-dependent manner by cold and salt treatments. These treatments alone did not repress global mRNA ribosome loading in a major way. The activation of GCN2 was accompanied by a more oxidative environment and was attenuated by inhibitors of photosynthetic electron transport, suggesting that it is gated by the redox poise or the reactive oxygen status of the chloroplast. In keeping with these results, gcn2 mutant seedlings were more sensitive than wild type to both cold and salt in a root elongation assay. These data suggest that cold and salt stress may both affect the status of the cytosolic translation apparatus via the conserved GCN2-eIF2α module. The potential role of the GCN2 kinase pathway in the global repression of translation under abiotic stress is discussed.

Extracellular secretion of superoxide is regulated by photosynthetic electron transport in the noxious red-tide-forming raphidophyte Chattonella antiqua

The raphidophyte Chattonella antiqua is a noxious red-tide-forming alga that harms fish culture and the aquatic environment. Chattonella antiqua produces and secretes superoxide anions (O2−), and excessive secretion of O2– into the water has been associated with fish mortality. It is known that strong light stimulates the production of O2– in Chattonella spp. but the mechanism of the light-induced production of O2– remains to be clarified. In the present study, we examined the effects of light on extracellular levels of O2– and photosynthesis in C. antiqua. Extracellular levels of O2– rose during growth under high-intensity light, and the level of O2– was correlated with the photosynthetic parameter qP, which reflects the rate of transport of electrons downstream of photosystem II. The production of O2– was inhibited in the presence of 3-(3,4-dichlorophenyl)-1,1-dimethylurea, an inhibitor of photosynthetic electron transport, suggesting that reducing power derived from electron transport might be required for the production of O2−. By contrast, the production of O2– was enhanced in the presence of glycolaldehyde, an inhibitor of the Calvin-Benson cycle, suggesting that the accumulation of NADPH might stimulate the production of O2−. Thus, it is likely that the production of O2– is regulated by photosynthesis in C. antiqua.

Electrochemistry of ring-substituted 1-hydroxynaphthalene-2-carboxanilides: Relation to structure and biological activity

Twenty-two novel antimycobacterial agents, 1-hydroxynaphthalene-2-carboxanilides, were studied by cyclic voltammetry on a glassy carbon electrode in a phosphate buffer pH 7.2 – dimethyl sulfoxide (DMSO) mixed medium (9:1; v/v). All compounds exhibited similar voltammetric behavior with one irreversible anodic signal in the range 100–300 mV corresponding to the oxidation of hydroxyl group on the naphthalene moiety. A shift of the oxidation potential was caused solely by electron donating or withdrawing effects of substituents and their position on the benzene moiety. Mechanism of oxidation in the studied medium was briefly outlined. Values of oxidation potentials exhibited very good linear correlation with calculated Hammett σ substituent constants. For all active compounds, a relationship between oxidation potentials and MIC or IC50 values obtained from in vitro screening was investigated in detail. Primary in vitro screening of synthesized compounds was previously performed against three species of Mycobacterium pathogens. Additionally, their activity related to the inhibition of photosynthetic electron transport (PET) in spinach chloroplasts was tested in previous publications. In vitro screening against Mycobacterium tuberculosis was performed here for the first time with 1-hydroxy-N-(3-trifluoromethylphenyl)naphthalene-2-carboxamide being the most effective (MIC = 11.7 μmol L−1). Furthermore, several other compounds showed higher antimycobacterial activity than the standard isoniazid. Relation of biological activities and oxidation potentials was successfully found in some cases; however, final correlations must also be considered with other physical and chemical factors contributing to the biological activity. Relation of structure, biological activity and electrochemical potential was also studied by cyclic voltammetry in cathodic area for three compounds containing reducible nitro moiety.

A Storable Mediatorless Electrochemical Biosensor for Herbicide Detection.

A novel mediatorless photo-bioelectrochemical sensor operated with a biofilm of the cyanobacterium Synechocystis PCC6803 wt. for herbicide detection with long term stability (>20 days) was successfully developed and tested. Photoanodic current generation was obtained in the absence of artificial mediators. The inhibitory effect on photocurrent of three commonly used herbicides (i.e., atrazine, diuron, and paraquat) was used as a means of measuring their concentrations in aqueous solution. The injection of atrazine and diuron into the algal medium caused an immediate photocurrent drop due to the inhibition of photosynthetic electron transport. The detected concentrations were suitable for environmental analysis, as revealed by a comparison with the freshwater quality benchmarks set by the Environmental Protection Agency of the United States (US EPA). In contrast, paraquat caused an initial increase (~2 h) of the photocurrent effect of about 200%, as this compound can act as a redox mediator between the cells and the anode. A relatively long-term stability of the biosensor was demonstrated, by keeping anodes colonized with cyanobacterial biofilm in the dark at 4 °C. After 22 days of storage, the performance in terms of the photocurrent was comparable with the freshly prepared biosensor. This result was confirmed by the measurement of chlorophyll content, which demonstrated preservation of the cyanobacterial biofilm. The capacity of this biosensor to recover after a cold season or other prolonged environmental stresses could be a key advantage in field applications, such as in water bodies and agriculture. This study is a step forward in the biotechnological development and implementation of storable mediatorless electrochemical biosensors for herbicide detection.

Significant inhibition of photosynthesis and respiration in leaves of Cucumis sativus L. by oxybenzone, an active ingredient in sunscreen

Oxybenzone (OBZ), an active ingredient in most sunscreens, was recently shown to be toxic to humans, corals and other animals. This study is the first to demonstrate that OBZ can significantly inhibit photosynthesis and respiration in the leaves of a higher plant, cucumber. An OBZ suspension content as low as 0.228 mg/L obviously inhibited the photosynthesis and respiration of cucumber. OBZ instantly inhibits the electron transport of chloroplasts and mitochondria in cucumber leaves. Probit analysis demonstrated that the effective content for 20% inhibition of photosynthetic electron transport was 11.7 mg/L (95% confidence level). The inhibition of photosynthesis and respiration restricts carbohydrate synthesis and ATP regeneration, respectively, limiting the energy available for metabolic processes including the synthesis of vital organic macromolecules such as proteins and nucleic acids in plant cells. The inhibition of photosynthesis also enhanced the excess excitation energy in chloroplasts, resulting in overproduction of reactive oxygen species (ROS), and the inhibition of respiration aggravated this process. ROS accumulation adversely affects the structure and function of proteins, DNA and membrane lipids in plant cells, interfering with normal metabolism and even leading to plant death. Therefore, reducing the use of OBZ is important for protecting global ecological security.

Red Light-Induced Phosphorylation of Plasma Membrane H+-ATPase in Stomatal Guard Cells.

Stomatal opening is stimulated by red and blue light. Blue light activates plasma membrane (PM) H+-ATPase by phosphorylating its penultimate residue, threonine, via a blue light photoreceptor phototropin-mediated signaling pathway in guard cells. Blue light-activated PM H+-ATPase promotes the accumulation of osmolytes and, thus, the osmotic influx of water into guard cells, driving stomatal opening. Red light-induced stomatal opening is thought to be dependent on photosynthesis in both guard cell chloroplasts and mesophyll cells; however, how red light induces stomatal opening and whether PM H+-ATPase is involved in this process have remained unclear. In this study, we established an immunohistochemical technique to detect the phosphorylation level of PM H+-ATPase in guard cells using whole leaves of Arabidopsis (Arabidopsis thaliana) and unexpectedly found that red light induces PM H+-ATPase phosphorylation in whole leaves. Red light-induced PM H+-ATPase phosphorylation in whole leaves was correlated with stomatal opening under red light and was inhibited by the plant hormone abscisic acid. In aha1-9, a knockout mutant of one of the major isoforms of PM H+-ATPase in guard cells, red light-dependent stomatal opening was delayed in whole leaves. Furthermore, the photosynthetic electron transport inhibitor 3-(3,4-dichlorophenyl)-1,1-dimethylurea inhibited red light-induced PM H+-ATPase phosphorylation as well as red light-induced stomatal opening in whole leaves. Our results indicate that red light-induced PM H+-ATPase phosphorylation in guard cells promotes stomatal opening in whole leaves, providing insight into the photosynthetic regulation of stomatal opening.

Synthesis and Spectrum of Biological Activities of Novel N-arylcinnamamides.

A series of sixteen ring-substituted N-arylcinnamamides was prepared and characterized. Primary in vitro screening of all the synthesized compounds was performed against Staphylococcus aureus, three methicillin-resistant S. aureus strains, Mycobacterium tuberculosis H37Ra, Fusarium avenaceum, and Bipolaris sorokiniana. Several of the tested compounds showed antistaphylococcal, antitubercular, and antifungal activities comparable with or higher than those of ampicillin, isoniazid, and benomyl. (2E)-N-[3,5-bis(trifluoromethyl)phenyl]-3-phenylprop-2-enamide and (2E)-3-phenyl-N-[3-(trifluoromethyl)phenyl]prop-2-enamide showed the highest activities (MICs = 22.27 and 27.47 µM, respectively) against all four staphylococcal strains and against M. tuberculosis. These compounds showed an activity against biofilm formation of S. aureus ATCC 29213 in concentrations close to MICs and an ability to increase the activity of clinically used antibiotics with different mechanisms of action (vancomycin, ciprofloxacin, and tetracycline). In time-kill studies, a decrease of CFU/mL of >99% after 8 h from the beginning of incubation was observed. (2E)-N-(3,5-Dichlorophenyl)- and (2E)-N-(3,4-dichlorophenyl)-3-phenylprop-2-enamide had a MIC = 27.38 µM against M. tuberculosis, while a significant decrease (22.65%) of mycobacterial cell metabolism determined by the MTT assay was observed for the 3,5-dichlorophenyl derivative. (2E)-N-(3-Fluorophenyl)- and (2E)-N-(3-methylphenyl)-3-phenylprop-2-enamide exhibited MICs = 16.58 and 33.71 µM, respectively, against B. sorokiniana. The screening of the cytotoxicity of the most effective antimicrobial compounds was performed using THP-1 cells, and these chosen compounds did not shown any significant lethal effect. The compounds were also evaluated for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. (2E)-N-(3,5-dichlorophenyl)-3-phenylprop-2-enamide (IC50 = 5.1 µM) was the most active PET inhibitor. Compounds with fungicide potency did not show any in vivo toxicity against Nicotiana tabacum var. Samsun. The structure–activity relationships are discussed.

In silico study toward the identification of new and safe potential inhibitors of photosynthetic electron transport

To address the rising global demand for food, it is necessary to search for new herbicides that can control resistant weeds. We performed a 2D-quantitative structure-activity relationship (QSAR) study to predict compounds with photosynthesis-inhibitory activity. A data set of 44 compounds (quinolines and naphthalenes), which are described as photosynthetic electron transport (PET) inhibitors, was used. The obtained model was approved in internal and external validation tests. 2D Similarity-based virtual screening was performed and 64 compounds were selected from the ZINC database. By using the VEGA QSAR software, 48 compounds were shown to have potential toxic effects (mutagenicity and carcinogenicity). Therefore, the model was also tested using a set of 16 molecules obtained by a similarity search of the ZINC database. Six compounds showed good predicted inhibition of PET. The obtained model shows potential utility in the design of new PET inhibitors, and the hit compounds found by virtual screening are novel bicyclic scaffolds of this class.