Tomato Seed Coat Permeability: Optimal Seed Treatment Chemical Properties for Targeting the Embryo with Implications for Internal Seed-Borne Pathogen Control

Seed treatments are frequently applied for the management of early-season pests, including seed-borne pathogens. However, to be effective against internal pathogens, the active ingredient must be able to penetrate the seed coat. Tomato seeds were the focus of this study, and the objectives were to (1) evaluate three coumarin fluorescent tracers in terms of uptake and (2) quantify seed coat permeability in relation to lipophilicity to better elucidate chemical movement in seed tissue. Uptake in seeds treated with coumarin 1, 120, and 151 was assessed by fluorescence microscopy. For quantitative studies, a series of 11 n-alkyl piperonyl amides with log Kow in the range of 0.02–5.66 were applied, and two portions, namely, the embryo, and the endosperm + seed coat, were analyzed by high-performance liquid chromatography (HPLC). Coumarin 120 with the lowest log Kow of 1.3 displayed greater seed uptake than coumarin 1 with a log Kow of 2.9. In contrast, the optimal log Kow for embryo uptake ranged from 2.9 to 3.3 derived from the amide series. Therefore, heterogeneous coumarin tracers were not suitable to determine optimal log Kow for uptake. Three tomato varieties were investigated with the amide series, and the maximum percent recovered in the embryonic tissue ranged from only 1.2% to 5%. These data suggest that the application of active ingredients as seed treatments could result in suboptimal concentrations in the embryo being efficacious.

Acidic Ionic Liquid-catalyzed Synthesis of Pyrano[4,3-b]pyran-5(4H)-ones using 4,4,4-trifluoro-1-phenylbutane-1,3-dione as a Building Block

Aims: synthesis of pyrano[c-2,3]chromens with Ionic Liquid catalyst with simple method. Background: Synthesis of pyrano[c]coumarins has a special place in the structure due to two bioactive compounds in its structure and attracts a great deal of attention in this research work, it has been attempted to attach chromatically valuable skeletons to them and synthesize the pyrano [c] coumarines, which can potentially have high biological properties. For this purpose, electrophilic β-ketoester ringing in the presence of ionic liquid catalysts was used. While optimizing the catalyst recovery, it is possible to synthesize several coumarine pyrano[ c]derivatives with high yield. Objective: This paper describes an efficient procedure for the multi-component reaction of aromatic aldehydes, 4,4,4-Trifluoro-1-phenyl-1,3-butanedione and 4-hydroxycoumarinwhich catalyzed by Ioniq liquid (OlmDSA), at room temperature. This catalyst was synthesized with new simple procedure. This protocol has advantages of simplicity, mild condition and high yield. Materials and Methods: After formation of a new stain corresponding to the alkene intermediate, 4-hydroxy coumarin (1 mM) was added. The reaction was progressed by thin layer chromatography in a 1: 2 ratio solvent containing ethyl acetate and hexane. The reaction mixture was then stirred for one hour. After the reaction was complete, the catalyst was first removed by washing. Ethanol was then added to the reaction residue and washed and finally filtered. The residual solid on the filter paper after drying was considered as the product and was taken to confirm. its structure, melting point and spectra. The following is a general overview of the reaction. Results and Discussion: In addition to the advantages mentioned for this tri-component reaction, the conservation of the coumarin ring is very important in this research design because it is formed in many of the reported open reactions and phenolic ring. Conclusion: The benefits of this work include simple reaction steps, review of reaction progress by TLC chromatography, simple separation of the catalyst by washing and reuse for three times without any reduction in yield and high reaction yield.

Antimicrobial Activity and Interactions of Toddalia asiatica Isolated Coumarins with Two Known Drugs

Five coumarins namely, 5, 7-dimethoxy-6-(3'-hydroxy-3'-methylbutan-2-oxo) coumarin coumarin (1), Toddalolactone (2), Coumurrenol (3), gleinadiene (4) and Toddaculin (5) were isolated from either the stem and/or root bark of Toddalia asiatica , with compound 1 being reported for the first time. These were obtained using chromatographic methods and identified using spectroscopic techniques, as well as comparison of their physical data with already published results. Combinations of compound 3 and fluconazole displayed additive effect in inhibiting the growth of Penicillium digitatum with reduced MIC to 125 μg/mL compared to that of fluconazole alone at 250 μg /mL. Combination of compounds 1 and 3 also showed additive effect in inhibiting Rhizopus stolonifer lowering the MIC from 500 μg/mL (for both molecules) to 250 μg /mL. Interaction in antibacterial activity between two isolated compounds 1 and 3 was also evident. These lowered the MIC in action against Staphylococcus aureus to 250 μg/mL compared to individual compounds with MIC of 500 μg/mL while showing additive effect. All the crude extracts apart from that of stem bark hexane and the individual isolated compounds showed considerable activity against all the organisms tested.

Synthesis of Novel Stilbene–Coumarin Derivatives and Antifungal Screening of Monotes kerstingii-Specialized Metabolites Against Fusarium oxysporum

Fusarium is one of the most toxigenic phytopathogens causing diseases and reduced agricultural productivity worldwide. Current chemical fungicides exhibit toxicity against non-target organisms, triggering negative environmental impact, and are a danger to consumers. In order to explore the chemical diversity of plants for potential antifungal applications, crude extract and fractions from Monotes kerstingii were screened for their activity against two multi-resistant Fusarium oxysporum strains: Fo32931 and Fo4287. Antifungal activity was evaluated by the determination of minimum inhibitory concentration (MIC) by broth dilution of fermentative yeasts using kinetic OD600 nm reading by a spectrophotometer. The n-butanol fraction showed the best activity against Fo4287. We screened eleven previously reported natural compounds isolated from different fractions, and a stilbene–coumarin 5-[(1E)-2-(4-hydroxyphenyl)ethenyl]-4,7-dimethoxy-3-methyl-2H-1-benzopyran-2-one (1) was the most active compound against both strains. Compound 1 was employed as a nucleophile with a selection of electrophilic derivatizing agents to synthesize five novel stilbene–coumarin analogues. These semisynthetic derivatives showed moderate activity against Fo32931 with only prenylated derivative exhibiting activity comparable to the natural stilbene–coumarin (1), demonstrating the key role of the phenolic group.

Anti-Inflammatory and Cytotoxic Potential of New Phenanthrenoids from Luzula sylvatica

Phenanthrenoids have been widely described, in the Juncaceae family, for their biological properties such as antitumor, anxiolytic, anti-microbial, spasmolytic, and anti-inflammatory activities. The Juncaceae family is known to contain a large variety of phenanthrenoids possessing especially anti-inflammatory and cytotoxic properties. Luzula sylvatica, a Juncaceae species, is widely present in the Auvergne region of France, but has never been studied neither for its phytochemical profile nor for its biological properties. We investigated the phytochemical profile and evaluated the potential anti-inflammatory activities of L. sylvatica aerial parts extracts. A bioassay-guided fractionation was carried out to identify the most active fractions. Nine compounds were isolated, one coumarin 1 and eight phenanthrene derivatives (2–9), including four new compounds (4, 5, 8 and 9), from n-hexane and CH2Cl2, fractions. Their structures were established by HRESIMS, 1D and 2D NMR experiments. The biological properties, especially the anti-inflammatory/antioxidant activities (ROS production) and antiproliferative activity on THP-1, a monocytic leukemia cell line, of each compound, were evaluated. Three phenanthrene derivatives 4, 6, and 7 showed very promising antiproliferative activities.

Applicability of 1,6-Diphenylquinolin-2-one Derivatives as Fluorescent Sensors for Monitoring the Progress of Photopolymerisation Processes and as Photosensitisers for Bimolecular Photoinitiating Systems

The applicability of new 1,6-diphenylquinolin-2-oneas derivatives as fluorescent molecular sensors for monitoring the progress of photopolymerisation processes by Fluorescence Probe Technique (FPT) has been tested. The progress of cationic, free-radical and thiol-ene photopolymerisation for commercially available monomers: triethylene glycol divinyl ether (TEGDVE), trimethylolpropane triacrylate (TMPTA) and trimethylpropane tris(3-mercaptopropropionate) (MERCAPTO) was monitored. It was found that new derivatives of 1,6-diphenylquinolin-2-one shifted their fluorescence spectra towards shorter wavelengths with the progress of polymerisation, which enabled monitoring the progress in terms of fluorescence intensity ratios as the progress indicator. Derivatives of 1,6-diphenylquinolin-2-one show sensitivity to changes in both polarity and viscosity in the surrounding microenvironment during photopolymerisation processes. Therefore, it was shown that they are good candidates to act as fluorescent sensors for monitoring the kinetics of very quick processes, such as photopolymerisation processes. Furthermore, the effect of the nature of substituents attached to the 1,6-diphenylquinolin-2-one ring on the characteristics of emission spectra was identified. Moreover, the sensitivity of fluorescent sensors was compared with commercially available model sensors, such as 7-diethylamino-4-methylcoumarin (Coumarin 1) and trans-2-(2′,5′-dimethoxyphenyl)ethenyl-2,3,4,5,6-pentafluorobenzene (25ST). Moreover, it was also proven that selected derivatives of 1,6-diphenylquinolin-2-one exhibit an accelerating effect on the progress of cationic photopolymerisation of vinyl monomers (TEGDVE). Thus, the new 1,6-diphenylquinolin-2-one derivatives can be successfully used both as molecular fluorescence sensors to monitor the progress of photopolymerisation processes and as diaryliodonium salt photosensitisers to initiate cationic photopolymerisation processes in a UV-A range of 365 nm.