Synthesis and Influence of 3-Amino Benzoxaboroles Structure on Their Activity against Candida albicans
Benzoxaboroles emerged recently as molecules of high medicinal potential with Kerydin®
Prospects of in vivo 31P NMR method in glyphosate degradation studies in whole cell system
Abstract The degradation of the phosphonate herbicide glyphosate ( N -phosphonomethylglycine) by four taxonomically distinct microorganisms was studied in vivo in whole cell system using phosphorus nuclear magnetic spectroscopy ( 31 P NMR). The time-course of glyphosate metabolization in dense cell cultures was followed by means of 31 P NMR up to 21 days after the addition. The results obtained by this non-invasive way confirmed that the cells of Spirulina platensis and Streptomyces lusitanus biodegrade herbicide. Moreover, phosphorus starvation influenced the rate of glyphosate degradation by S. platensis . On the other hand, the results of similar measurements in the cultures of green alg…
The Biomass of Algae and Algal Extracts in Agricultural Production
Fertilizers and plant growth regulators (PGRs) based on seaweeds are commonly known, having been produced and utilized for dozens of years. Algae are rich in carbohydrates, proteins, minerals and chemical compounds that belong mainly to the following groups: polysaccharides, polyphenols, phlorotannins, plant pigments, unsaturated fatty acids, sterols and plant hormones.
Algae in Biotechnological Processes
As photoautotrophic organisms, algae possess all of the valuable features that determine their role as the primary producers in the biosphere. A wide range of tolerance based on their extremely efficient adaptation to biochemical processes, as well as the specific cellular structure of these organisms, when correlated with the ecological plasticity of microalgae in particular, predispose these biota to growing and developing under either laboratory or industrial conditions. Hence, the natural features of algae have opened wide the door for the multidirectional biotechnological use of these organisms, with a dynamically growing number of such applications fully supporting this thesis. Among …
Antifungal activity and tautomeric cyclization equilibria of formylphenylboronic acids
2-Formylphenylboronic acid and four isomeric fluoro-2-formylphenylboronic acids have been found active against a series of fungal strains: Aspergillus, Fusarium, Penicillium and Candida. The level of antifungal activity was evaluated by agar diffusion tests as well as the determination of minimum inhibitory concentrations (MICs) by serial dilution method. Among the tested compounds, 4-fluoro-2-formylphenylboronic acid - an analogue of the known antifungal drug Tavaborole (AN2690) - proved to be the most potent antifungal agent. The tautomeric equilibrium leading to the formation of 3-hydroxybenzoxaboroles as well as the position of the fluorine substituent were revealed to play a crucial ro…
Phosphonate degradation by Spirulina strains: cyanobacterial biofilters for the removal of anticorrosive polyphosphonates from wastewater
The ability of Spirulina spp. to metabolize the recalcitrant xenobiotic Dequest 2054(®) [hexamethylenediamine-N,N,N',N'-tetrakis(methylphosphonic acid)], a CaSO(4) inhibitor used for boiler treatment and reverse osmosis desalination, was investigated. The compound served as sole source of phosphorus, but not of nitrogen, for cyanobacterial growth. In vivo utilization was followed by (31)P NMR analysis. The disappearance of the polyphosphonate proceeded only with actively dividing cells, and no release of inorganic phosphate was evident. However, no difference was found between P-starved and P-fed cultures. Maximal utilization reached 1.0 ± 0.2 mmoll(-1), corresponding to 0.56 ± 0.11 mmol g(…
Formation of Variously Shaped Gold Nanoparticles by Anabaena laxa
Anew aspect of this study is the biocatalysis ability of Anabaena laxa—fresh-water strain—which to date has not been studied with respect to the formation of gold nanoparticles. The results of our study have shown that A. laxa is able to form gold nanoparticles (AuNPs) at good yields within 24 h of incubation at all three tested concentrations (0.1, 0.5 and 1 mM) of hydrogen tetrachloroaurate (III). After 24 h, nanoparticles were mostly localized in the growth medium, which significantly facilitates their isolation. However, the elongation of this process is accompanied by their concentration in the exopolysaccharide (EPS) layer of the cyanobacterial cells. There is a correlation between th…
The aminophosphonate glyphosine enhances phycobiliprotein yields from selected cyanobacterial cultures
Among added-value products obtained from cyanobacterial cultures are phycobiliproteins, photosynthetic pigments that have found an increasing number of applications as natural dyes for food, cosmetics, pharmaceuticals, and antioxidants. To obtain sustainable production, we aimed at maximizing phycobilin yield through the increase of either the final biomass or the specific content of these pigments by varying culture parameters, such as chemical composition and pH of the medium or quality and intensity of the light. Here, we report that the addition to the culture medium of millimolar or submillimolar concentrations of the aminophosphonate glyphosine [(N,N-bis(phosphonomethyl)glycine], form…
Synthesis, structure, properties and antimicrobial activity of para trifluoromethyl phenylboronic derivatives
The [2-formyl-4-(trifluoromethyl)phenyl]boronic acid as well as its benzoxaborole and bis(benzoxaborole) derivatives were obtained and their properties studied. The 2-formyl compound displays an unusual structure in the crystalline state, with a significant twist of the boronic group, whereas in DMSO solution it tautomerizes with formation of a cyclic isomer. All the studied compounds exhibit relatively high acidity as well as a reasonable antimicrobial activity. Docking studies showed interactions of all the investigated compounds with the binding pocket of Candida albicans LeuRS. High activity against Bacillus cereus was determined for the 2-formyl compound as well as for the novel bis(be…
The influence of fluorine position on the properties of fluorobenzoxaboroles
5-Fluoro-2,1-benzoxaborol-1(3H)-ol, a potent antifungal drug also known as Tavaborole or AN2690, has been compared with its three isomers in terms of its activity against several fungi as well as pKa and multinuclear NMR characterization. The molecular and crystal structure of 6-fluoro-2,1-benzoxaborol-1(3H)-ol was determined and compared with that of AN2690.
Mechanochemical synthesis of antifungal bis(benzoxaboroles)
Several piperazine bis(benzoxaboroles) have been obtained both in solution as well as in the solid state. The environmentally friendly mechanochemical approach – hitherto not applied for the preparation of benzoxaboroles – was particularly beneficial in the case of two products afforded in low yields in solution. The in vitro studies showed high potential of the studied bis(fluorobenzoxaboroles) as antifungal agents, highlighting also the influence of the fluorine substituent position on their microbiological activity. The highest activity against A. niger, A. terreus, P. ochrochloron, C. tenuis and C. albicans was displayed by the analogue of the known benzoxaborole antifungal drug Kerydin…
Phosphonates as Unique Components of Plant Seeds—A Promising Approach to Use Phosphorus Profiles in Plant Chemotaxonomy
Phosphorus is one of the most important elements essential for all living beings. Plants accumulate and store phosphorous in various forms that have diverse physiological and biochemical functions. In this study, we determine and then examine the phosphorus profiles of seeds of plants belonging to different taxa based on extractable inorganic phosphates and organic forms of phosphorus. We paid particular attention to the presence of natural phosphonates in the tested materials. The inorganic phosphates were determined colorimetrically, whereas phosphorus profiles were created by using 31P NMR spectroscopy. Our study on phosphorus profiles revealed that the obtainedsets of data vary signific…
Biocatalytic hydrogenation of the C=C bond in the enone unit of hydroxylated chalcones-process arising from cyanobacterial adaptations.
To verify the hypothesis that cyanobacteria naturally biosynthesising polyphenolic compounds possess an active enzymatic system that enables them to transform these substances, such an ability of the biocatalytic systems of whole cells of these biota was assessed for the first time. One halophilic strain and seven freshwater strains of cyanobacteria representing four of the five taxonomic orders of Cyanophyta were examined to determine the following: (i) whether they contain polyphenols, including flavonoids; (ii) the resistance of their cultures when suppressed by the presence of exogenous hydroxychalcones—precursors of flavonoid biosynthesis and (iii) whether these photoautotrophs can tra…
Supercritical Algal Extracts: A Source of Biologically Active Compounds from Nature
The paper discusses the potential applicability of the process of supercritical fluid extraction (SFE) in the production of algal extracts with the consideration of the process conditions and yields. State of the art in the research on solvent-free isolation of biologically active compounds from the biomass of algae was presented. Various aspects related with the properties of useful compounds found in cells of microalgae and macroalgae were discussed, including their potential applications as the natural components of plant protection products (biostimulants and bioregulators), dietary feed and food supplements, and pharmaceuticals. Analytical methods of determination of the natural compou…
Possible Fungistatic Implications of Betulin Presence in Betulaceae Plants and their Hymenochaetaceae Parasitic Fungi
Betulin and its derivatives (especially betulinic acid) are known to possess very interesting prospects for their application in medicine, cosmetics and as bioactive agents in pharmaceutical industry. Usually betulin is obtained by extraction from the outer layer of a birch bark. In this work we describe a simple method of betulin isolation from bark of various species of Betulaceae trees and parasitic Hymenochaetaceae fungi associated with these trees. The composition of the extracts was studied by GC-MS, whereas the structures of the isolated compounds were confirmed by FTIR and 1H NMR. Additionally, the significant fungistatic activity of betulin towards some fi lamentous fungi was deter…
Glyphosate dose modulates the uptake of inorganic phosphate by freshwater cyanobacteria
The usefulness of glyphosate [N-(phosphonomethyl)glycine] as a source of nutritive phosphorus for species of halophilic cyanobacteria has been postulated for years. Our results indicate a stimulating effect of glyphosate on the growth of four out of five examined freshwater species, Anabaena variabilis (CCALA 007), Chroococcus minutus (CCALA 055), Fischerella cf. maior (CCALA 067) and Nostoc cf. muscorum (CCALA 129), in a manner dependent on the applied concentration. The most significant stimulation was observed at a dose of 0.1 mM glyphosate. The decrease in the amount of phosphonate, which correlated with microbial growth, demonstrated that glyphosate may play an important role in cyanob…
Phytoplankton communities of polar regions–Diversity depending on environmental conditions and chemical anthropopressure
The polar regions (Arctic and Antarctic) constitute up to 14% of the biosphere and offer some of the coldest and most arid Earth's environments. Nevertheless several oxygenic phototrophs including some higher plants, mosses, lichens, various algal groups and cyanobacteria, survive that harsh climate and create the base of the trophic relationships in fragile ecosystems of polar environments. Ecosystems in polar regions are characterized by low primary productivity and slow growth rates, therefore they are more vulnerable to disturbance, than those in temperate regions. From this reason, chemical contaminants influencing the growth of photoautotrophic producers might induce serious disorders…
Supercritical fluid extraction of algae enhances levels of biologically active compounds promoting plant growth
The aim of this research was to screen plant growth biostimulant properties of supercritical CO2 macroalgal extracts. To this end secondary metabolites were isolated from the biomass of marine macroalgae from the Baltic Sea (species of Polysiphonia, Ulva and Cladophora). Chemical characteristics of the algal extracts were determined by inductively coupled plasma atomic emission spectroscopy for inorganic constituents and high-performance liquid chromatography and spectrophotometry for organic constituents. Inorganic (macro- and microelements) and organic (plant hormones: auxins and cytokinins; polyphenols) compounds were detected in the extract. Algal extracts were tested primarily on garde…
Determination of phosphorus compounds in plant tissues: from colourimetry to advanced instrumental analytical chemistry
AbstractAlthough the spectrum of effective methods and techniques that allow determination of inorganic or total phosphorus is impressive, more precise analysis of these substances in plant tissues is not a routine or trivial task. The complexity of chemical composition of plant tissues treated as the analytical matrices is thought to be the main cause why there is no one answer, how appropriate phosphorus compounds may be determined qualitatively and quantitatively. Even if more advanced spectrophotometric measurements and classical variants of absorption (FAAS) or emission (ICP-AES/ ICP-OES) spectrometry techniques are used, it is necessary at first to isolate various forms of phosphorus …
Modulation of the growth and metabolic response of cyanobacteria by the multifaceted activity of naringenin
The interactions between the plant-derived bioflavonoid, naringenin, and prokaryotic microalgae representatives (cyanobacteria), were investigated with respect to its influence on the growth and metabolic response of these microorganisms. To achieve reliable results, the growth of cyanobacteria was determined based on measurements of chlorophyll content, morphological changes were assessed through microscopic observations, and the chemical response of cells was determined using liquid and gas chromatography (HPLC; GC-FID). The results show that micromolar levels of naringenin stimulated the growth of cyanobacteria. Increased growth was observed for halophilic strains at naringenin concentra…
Synthesis, Properties and Antimicrobial Activity of 5-Trifluoromethyl-2-formylphenylboronic Acid
2-Formylphenylboronic acids display many interesting features, not only from synthetic but also from an application as well as structural points of view. 5-Trifluoromethyl-2-formyl phenylboronic acid has been synthesized and characterized in terms of its structure and properties. The presence of an electron-withdrawing substituent results in a considerable rise in the acidity in comparison with its analogues. In some solutions, the title compound isomerizes with formation of the corresponding 3-hydroxybenzoxaborole. Taking into account the probable mechanism of antifungal action of benzoxaboroles, which blocks the cytoplasmic leucyl-tRNA synthetase (LeuRS) of the microorganism, docking stud…
Analytical insight into degradation processes of aminopolyphosphonates as potential factors that induce cyanobacterial blooms
Aminopolyphosphonates (AAPs) are commonly used industrial complexones of metal ions, which upon the action of biotic and abiotic factors undergo a breakdown and release their substructures. Despite the low toxicity of AAPs towards vertebrates, products of their transformations, especially those that contain phosphorus and nitrogen, can affect algal communities. To verify whether such chemical entities are present in water ecosystems, much effort has been made in developing fast, inexpensive, and reliable methods for analyzing phosphonates. However, unfortunately, the methods described thus far require time-consuming sample pretreatment and offer relatively high values of the limit of detect…
Biocatalytic transformations of chalcones by cyanobacteria – HPLC–MS study
The toxicity of Roundup® 360 SL formulation and its main constituents: Glyphosate and isopropylamine towards non-target water photoautotrophs
The toxicity of commercial formulation of Roundup® 360 SL, widely used, nonselective herbicide and its main constituents, glyphosate (PMG), equimolar (1:1) isopropylamine salt of glyphosate (GIPA) and isopropylamine (IPA) was examined towards eight aquatic microphotoautotrophs; seven cyanobacterial strains representing either saline or freshwater communities, and common eukaryotic algae Chlorella vulgaris Beijerinck. Autotrophs were cultured 21 days in their appropriate standard media supplemented with various amounts of Roundup®, glyphosate, GIPA and IPA. The determination of the growth of examined photoautotrophs was performed by time-course measurements of total chlorophyll content in ex…
Investigation of fungicidal activity of 3-piperazine-bis(benzoxaborole) and its boronic acid analogue
3-Piperazine-bis(benzoxaborole) and its bis(phenylboronic acid) analogue were investigated in terms of their fungicidal activity. The study was carried out against five filamentous fungi: Aspergillus terreus, Fusarium dimerum, Fusarium solani, Penicillium ochrochloron and Aspergillus niger. 3-Piperazine-bis(benzoxaborole) revealed higher inhibitory activity towards the examined strains than standard antibiotic (amphotericin B), whereas bis(phenylboronic acid) proved to be inactive. The study unequivocally showed that the presence of the heterocyclic benzoxaborole system is essential for antifungal action of the examined compounds. Copyright © 2014 John Wiley & Sons, Ltd.
Novel, automated, semi-industrial modular photobioreactor system for cultivation of demanding microalgae that produce fine chemicals - The next story of H. pluvialis and astaxanthin
Abstract Recently, there has been increased interest in the use of microorganisms in the production of pharmaceuticals, nutraceuticals and energy supply products, which is due to their rapid growth rate and ability to biosynthesize fine chemicals or biotransform specific xenobiotics. To achieve the desired scale of production and optimization of microbial cultures, it is necessary to design bioreactors that enable process automation, control of working parameters, reduction of microbial and chemical contaminations, and culture independence of climate conditions. In response to this need, an original, modular airlift-type photobioreactor system was designed and manufactured. This novel semit…
Phosphorus NMR as a tool to study mineralization of organophosphonates—The ability of Spirulina spp. to degrade glyphosate
Abstract A commercially available mixed culture of Spirulina spp. exhibited a remarkable ability to degrade the widely used organophosphorus herbicide glyphosate, that served as sole source of either phosphorus or nitrogen for cyanobacterial growth. 31P NMR analysis of spent media appeared to be an effective and simple technique to follow disappearance of the phosphonate and release of inorganic phosphate in biodegradation process(es).
Biodegradation of the aminopolyphosphonate DTPMP by the cyanobacteriumAnabaena variabilisproceeds via a C-P lyase-independent pathway
Cyanobacteria, the only prokaryotes capable of oxygenic photosynthesis, play a major role in carbon, nitrogen and phosphorus global cycling. Under conditions of increased P availability and nutrient loading, some cyanobacteria are capable of blooming, rapidly multiplying and possibly altering the ecological structure of the ecosystem. Because of their ability of using non-conventional P sources, these microalgae can be used for bioremediation purposes. Under this perspective, the metabolization of the polyphosphonate diethylenetriaminepenta(methylenephosphonic) acid (DTPMP) by the strain CCALA 007 of Anabaena variabilis was investigated using 31 P NMR analysis. Results showed a quantitative…
’Structural constraints in cyanobacteria-mediated whole-cell biotransformation of methoxylated and methylated derivatives of 2′-hydroxychalcone
Halophilic and freshwater strains of cyanobacteria representing the Oscillatoriales, Nostocales, Chroococcales, and Synechococcales orders of Cyanophyta were examined to determine (i) the resistance of their cultures when suppressed by the presence of exogenous methoxylated and methylated derivatives of 2'-hydroxychalcone, (ii) morphological changes in cells treated with the tested chalcones and, most importantly, (iii) whether these photoautotrophic microorganisms transform chalcone derivatives in a structure- or strain-dependent manner. The growth of cyanobacterial cultures depended on chalcone derivatives and the strain; nevertheless, trends for correlations between these parameters are …
Amino polyphosphonates - chemical features and practical uses, environmental durability and biodegradation
Growing concerns about the quality of the environment led to the introduction of complex system of safety assessment of synthetically manufactured and commonly applied chemicals. Sometimes, however, our knowledge of consequences that result from the usage of these substances, appears far later, than at the beginning of their application. Such situation is observed in the case of aminopolyphosphonates being an important subgroup of organophosphorus compounds. The increasing industrial and household applications, led to introduce thousand tons of polyphosphonates every year into the environment. These substances are difficult to determine in environmental samples because of lack of appropriat…
Boronic Acids of Pharmaceutical Importance Affect the Growth and Photosynthetic Apparatus of Cyanobacteria in a Dose-Dependent Manner
The dynamic increase in the commercial application of antimicrobial derivatives of boronic acids, and potential impact of their presence in aquatic systems, supports the necessity to study the toxicity of these substances towards microorganisms of crucial meaning in the environment. One example of the mentioned derivatives is tavaborole (5-fluoro-substituted benzoxaborole), a pharmaceutical agent with antifungal activity. Cyanobacteria were used as model organisms, which are photoautotrophic prokaryotes, as representative aquatic bacteria and photoautotrophs associated with the plant kingdom. To the best of our knowledge, we investigated this issue for the first time. In order to recognize …
Dual action of phosphonate herbicides in plants affected by herbivore—Model study on black bean aphid Aphis fabae rearing on broad bean Vicia faba plants
Abstract The interactions between plants, herbicides and herbivore insects were studied as an aspect of possible side effect of the using of phosphonate herbicides. The experimental system was composed of phosphonate herbicides, broad bean Vicia faba (L.) plants and black bean aphid Aphis fabae (Scopoli). Two means of herbicide application, namely standard spraying and direct introduction of the herbicide into stem via glass capillary, were examined. The results obtained for N-2-piridylaminomethylene bisphosphonic acid and its derivatives show 10 times higher inhibition of the plant growth if glass capillary mode was used. When plants were infested by aphids 24 h after the use of herbicide,…
The overproduction of 2,4-DTBP accompanying to the lack of available form of phosphorus during the biodegradative utilization of aminophosphonates by Aspergillus terreus
Although information about the ability of some filamentous fungi to biodegrade organophosphonates is available, the knowledge about accompanying changes in fungal metabolism is very limited. The aim of our study was to determine the utilization of the chosen, structurally diverse aminophosphonates by Aspergillus terreus (Thom), in the context of the behaviour of this fungus while growing in unfavourable conditions, namely the lack of easily available phosphates. We found that all the studied compounds were utilized by fungus as nutritive sources of phosphorus, however, their effect on the production of fungal biomass depended on their structure. We also observed an interesting change in the…
Antifungal activity of the carrot seed oil and its major sesquiterpene compounds.
Carrot seed oil is the source of the carotane sesquiterpenes carotol, daucol and β-caryophyllene. These sesquiterpenic allelochemicals were evaluated against Alternaria alternata isolated from the surface of carrot seeds cultivar Perfekcja, a variety widely distributed in horticultural practise in Poland. Alternaria alternata is one of the most popular phytotoxic fungi infesting the carrot plant. The strongest antifungal activity was observed for the main constituent of carrot seed oil, carotol, which inhibited the radial growth of fungi by 65% at the following concentration.
Algae and Their Extracts in Medical Treatment
Scientific efforts undertaken in recent decades have undoubtedly proven that algae are an inestimable and, what is more, important renewable source of hundreds of chemical compounds characterized by a wide spectrum of biological activity. Polysaccharides, phenolic compounds and their derivatives, pigments, proteins, lipids, and fatty acids are the substances that can be isolated from seaweeds, possessing antimicrobial, antiviral, antifungal, antilipidemic, antitumor, antidiabetic, anticoagulant, antioxidant, and antiallergic properties, which can be successfully utilized for human needs. The majority of attention has been focused on marine polysaccharides and their application in medicine a…
Iron ions as the modulators of biosynthesis of cyanobacterial dyes
Biotransformations of monoterpenes by photoautotrophic micro-organisms.
Summary Monoterpenes are widely used in food technology, cosmetic and pharmaceutical industries and as compounds of agricultural importance. It is known that compounds comprising this class can be transformed by a variety of organisms, namely by: bacteria, fungi, yeasts, plants or isolated enzymes. Biotransformations, as one of the most important tools of green chemistry, allow obtaining new products using whole cells of micro-organisms or isolated enzymes in mild reaction conditions. Therefore, biotransformations of monoterpenes, by different type of reaction such as: epoxidation, oxidation and stereoselective hydroxylation, resulted in the production of so desired, enantiomerically define…
Highly effective, regiospecific reduction of chalcone by cyanobacteria leads to the formation of dihydrochalcone: two steps towards natural sweetness
Abstract Background Chalcones are the biogenetic precursors of all known flavonoids, which play an essential role in various metabolic processes in photosynthesizing organisms. The use of whole cyanobacteria cells in a two-step, light-catalysed regioselective bio-reduction of chalcone, leading to the formation of the corresponding dihydrochalcone, is reported. The prokaryotic microalgae cyanobacteria are known to produce phenolic compounds, including flavonoids, as natural components of cells. It seems logical that organisms producing such compounds possess a suitable “enzymatic apparatus” to carry out their biotransformation. Therefore, determination of the ability of whole cells of select…
Metabolic relation of cyanobacteria to aromatic compounds
Cyanobacteria, also known as blue-green (micro)algae, are able to sustain many types of chemical stress because of metabolic adaptations that allow them to survive and successfully compete in a variety of ecosystems, including polluted ones. As photoautotrophic bacteria, these microorganisms synthesize aromatic amino acids, which are precursors for a large variety of substances that contain aromatic ring(s) and that are naturally formed in the cells of these organisms. Hence, the transformation of aromatic secondary metabolites by cyanobacteria is the result of the possession of a suitable “enzymatic apparatus” to carry out the biosynthesis of these compounds according to cellular requireme…
Biochemical bases for a widespread tolerance of cyanobacteria to the phosphonate herbicide glyphosate
Possible non-target effects of the widely used, non-selective herbicide glyphosate were examined in six cyanobacterial strains, and the basis of their resistance was investigated. All cyanobacteria showed a remarkable tolerance to the herbicide up to millimolar levels. Two of them were found to possess an insensitive form of glyphosate target, the shikimate pathway enzyme 5-enol-pyruvyl-shikimate-3-phosphate synthase. Four strains were able to use the phosphonate as the only phosphorus source. Low uptake rates were measured only under phosphorus deprivation. Experimental evidence for glyphosate metabolism was also obtained in strains apparently unable to use the phosphonate. Results suggest…
Synthesis and structural elucidation of novel antifungal N-(fluorophenyl)piperazinyl benzoxaboroles and their analogues
Abstract Series of novel N-(fluorophenyl)piperazine derivatives of phenylboronic compounds including benzoxaboroles, phenylboronic acids and phenylboronic methyl monoester have been obtained by facile synthetic methods starting from 2-formylphenylboronic acid. Molecular and crystal structures of those novel derivatives have been investigated by single crystal X-ray diffraction method. The Bond Valence Vector Model was used to describe strains in the boron coordination sphere. Microbiological activity of novel benzoxaboroles as well as their corresponding acid analogues against: A. niger, A. terreus, P. ochrochloron, C. tenuis and F. dimerum has been evaluated. The presence of heterocyclic b…
Evaluation of wood-polyethylene composites biodegradability caused by filamentous fungi
Abstract This study describes the impact of filamentous fungi on wood-polymer composites (WPCs) containing various types of fillers (coniferous, deciduous, cellulose) in the amount of 30 wt.% to 50 wt.%. The selection of fungal strain of filamentous fungi was performed prior to the study on the impact of the wood type on the progress of WPCs biodegradability. The changes associated with various water absorption of the examined WPCs, were observed using scanning electron microscopy (SEM). The impact of fungal mycelium, which had affected the changes in WPCs material, was examined using thermogravimetric analysis (TG). The results showed, that the growth of mycelium on WPCs, influenced mainly…
Valuable natural products from marine and freshwater macroalgae obtained from supercritical fluid extracts
The biologically active compounds (fatty acids, pigments, phenolics, and flavonoid content) were studied in supercritical fluid extracts from the biomass of marine (Ulva clathrata, Cladophora glomerata, Polysiphonia fucoides, and their multi-species mixture) and freshwater (C. glomerata) macroalgae. Different extraction techniques were used in order to compare differences in the biologically active compound composition of the macroalgal extracts. The results indicated that the saturated and unsaturated fatty acids ranged from C9:0 to C22:0. The analysis of differences in the composition of unsaturated to saturated fatty acids in extracts showed that palmitic acid (C16:0) and oleic acid (C18…
Recent advances in the research on herbicidally active aminomethylelebisphosphonic acids.
Influence of the mode of application of herbicidally active N-pyridylaminomethylenebi-sphosphonic acids on their uptake by plants was studied in some detail. The experimental evidence is given that accounts for a multiple mode of action of these herbicides.
Resistance of Conifer Needle Polyolefin Composites (CNPCs) Against Biodecomposition Caused by Fungi
This study describes the resistance of composites filled with conifer needles to biodecomposition processes caused by a single strain of Aspergillus niger as well as by a consortium of microorganisms present in the compost substrates (forest or spent mushroom composts). The impact of various types of conifer needles on the growth of A. niger was studied to determine whether the filler can show the fungistatic effect. The changes in chemical composition of the composites surfaces were examined using attenuated total reflectance Fourier transform infrared spectroscopy (FTIR/ATR). The results showed that the fungistatic effects of conifer needles polyolefin composites (CNPCs) were associated w…
Influence of monoterpenoids on the growth of freshwater cyanobacteria
Abstract Cyanobacteria are characterized by a very high tolerance to environmental factors. They are found in salt water, fresh water, thermal springs, and Antarctic waters. The wide spectrum of habitats suitable for those microorganisms is related to their particularly effective metabolism; resistance to extreme environmental conditions; and the need for only limited environmental resources such as water, carbon dioxide, simple inorganic salts, and light. These metabolic characteristics have led to cyanobacterial blooms and the production of cyanotoxins, justifying research into effective ways to counteract the excessive proliferation of these microorganisms. A new and interesting idea fo…
Biologically Active Organic Compounds, Especially Plant Promoters, in Algae Extracts and Their Potential Application in Plant Cultivation
Degradation of Amino-(3-methoxyphenyl)methanephosphonic Acid by Alternaria sp
Alternaria sp. isolated from the surface of carrot ( Daucus carota ) seeds appeared to be able to degrade amino-(4-methoxyphenyl)-methanephosphonic acid using it as a sole source of carbon, nitrogen, and phosphorus for growth.
CCDC 1998837: Experimental Crystal Structure Determination
Related Article: Dorota Wieczorek, Ewa Kaczorowska, Marta Wiśniewska, Izabela D. Madura, Magdalena Leśniak, Jacek Lipok, Agnieszka Adamczyk-Woźniak|2020|Molecules|25|5999|doi:10.3390/molecules25245999
CCDC 2082738: Experimental Crystal Structure Determination
Related Article: Agnieszka Adamczyk-Wo��niak, Magdalena Tarkowska, Zofia Lazar, Ewa Kaczorowska, Izabela D. Madura, Anna Maria D��browska, Jacek Lipok, Dorota Wieczorek|2021|Bioorg.Chem.|119|105560|doi:10.1016/j.bioorg.2021.105560
CCDC 1822975: Experimental Crystal Structure Determination
Related Article: Krzysztof M. Borys, Alicja Matuszewska, Dorota Wieczorek, Karolina Kopczyńska, Jacek Lipok, Izabela D. Madura, Agnieszka Adamczyk-Woźniak|2019|J.Mol.Struct.|1181|587|doi:10.1016/j.molstruc.2019.01.018
CCDC 1959978: Experimental Crystal Structure Determination
Related Article: Agnieszka Adamczyk-Woźniak, Jan T. Gozdalik, Dorota Wieczorek, Izabela D. Madura, Ewa Kaczorowska, Ewa Brzezińska, Andrzej Sporzyński, Jacek Lipok|2020|Molecules|25|799|doi:10.3390/molecules25040799
CCDC 1822973: Experimental Crystal Structure Determination
Related Article: Krzysztof M. Borys, Alicja Matuszewska, Dorota Wieczorek, Karolina Kopczyńska, Jacek Lipok, Izabela D. Madura, Agnieszka Adamczyk-Woźniak|2019|J.Mol.Struct.|1181|587|doi:10.1016/j.molstruc.2019.01.018
CCDC 1822974: Experimental Crystal Structure Determination
Related Article: Krzysztof M. Borys, Alicja Matuszewska, Dorota Wieczorek, Karolina Kopczyńska, Jacek Lipok, Izabela D. Madura, Agnieszka Adamczyk-Woźniak|2019|J.Mol.Struct.|1181|587|doi:10.1016/j.molstruc.2019.01.018
CCDC 1822972: Experimental Crystal Structure Determination
Related Article: Krzysztof M. Borys, Alicja Matuszewska, Dorota Wieczorek, Karolina Kopczyńska, Jacek Lipok, Izabela D. Madura, Agnieszka Adamczyk-Woźniak|2019|J.Mol.Struct.|1181|587|doi:10.1016/j.molstruc.2019.01.018
CCDC 1027467: Experimental Crystal Structure Determination
Related Article: Agnieszka Adamczyk-Woźniak, Małgorzata K. Cabaj, Paulina M. Dominiak, Patrycja Gajowiec, Błażej Gierczyk, Jacek Lipok, Łukasz Popenda, Grzegorz Schroeder, Ewelina Tomecka, Piotr Urbański, Dorota Wieczorek, Andrzej Sporzyński|2015|Bioorg.Chem.|60|130|doi:10.1016/j.bioorg.2015.05.004
CCDC 1998838: Experimental Crystal Structure Determination
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CCDC 1822976: Experimental Crystal Structure Determination
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