Artykuły naukowe (WM)

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Vitamin B12-Enriched Yarrowia lipolytica Biomass Obtained from Biofuel Waste
(Springer, 2020) Jach, Monika Elżbieta; Masłyk, Maciej; Juda, Marek; Sajnaga, Ewa; Malm, Anna
The aim of the study was to obtain vitamin B12-enriched biomass of non-conventional yeast Yarrowia lipolytica A-101. The cultivations were performed on waste from biofuel production in aerobic conditions at different temperatures (20–30 °C) and pH values (4.0–7.0) of the medium, with and without the addition of cobalt, L-methionine, molybdenum, δ-aminolevulinic acid, and niacin. A temperature of 30 °C and pH between 5 and 6 were the optimal conditions for obtaining B12-enriched yeast biomass on biofuel waste. In such conditions, Y. lipolytica A-101 contained 9 µg of vitamin B12 per 100 g of dried biomass. The addition of the ingredients mentioned above to the medium did not exert a significant effect on the B12 concentration. Y. lipolytica are able to accumulate this vitamin from the medium in a similar manner to animal cells. Additionally, it should be noted that the dried biomass of Y. lipolytica appeared to be safe for consumption. Taken together, these data showed that Y. lipolytica can be used as a nutritional supplement to increase the intake of vitamin B12, especially at risk of vitamin B12 deficiency.
Statistical evaluation of growth parameters in biofuel waste as a culture medium for improved production of single cell protein and amino acids by Yarrowia lipolytica
(Springer, 2020) Jach, Monika Elżbieta; Baj, Tomasz; Juda, Marek; Świder, Robert; Mickowska, Barbara; Malm, Anna
Yarrowia lipolytica is an oleaginous yeast species with the ability to grow on a number of substrates types, especially industrial wastes. This paper concerns the statistical optimization of fermentation parameters and media to ensure consistent and improved Y. lipolytica protein production. A strain of Y. lipolytica A-101 was observed to be proﬁcient in producing single cell protein, amino acids, and vitamin B12 while utilizing biofuel waste instead of a complete YPD medium for yeast growth. A fractional fractal design experiment was then applied, and the two fermentation param- eters of temperature and pH were recognized to have a signiﬁcant eﬀect on the protein and amino acid production. Subsequently, the response surface methodology with a three-level complete factorial design was employed to optimize these inﬂuential parameters. Therefore, ﬁve diﬀerent measuring systems were utilized to construct a quad- ratic model and a second-order polynomial equation. Optimal levels of parameters were then obtained by analysis of the model and the numerical optimization method. When the Y. lipolytica A-101 was cultivated at optimized pH (5.0) using biofuel waste as a medium, the protein concentration was increased to 8.28—a 44% enhancement as com- pared to the original (3.65). This study has thus demonstrated a beneﬁcial way to cultivate Y. lipolytica A-101 on biofuel waste for enhanced production of single cell protein and amino acids for use in human diet and in animal feed.
Bradyrhizobia associated with Laburnum anagyroides, an exotic legume grown in Poland
(Springer, 2020) Sajnaga, Ewa; Jach, Monika Elżbieta
We isolated 18 rhizobial strains from root nodules of a leguminous shrub Laburnum anagyroides (common laburnum) grown in Southeast Poland as an exotic plant. With the use of BOX-PCR fingerprinting, the isolates were clustered into 2 main groups and one separate lineage, which was congruent with the ITS-RFLP results. The phylogenetic trees constructed based on 16S rRNA and combined atpD, dnaK, glnA, and recA gene sequence data separated the representative strains into three evolutionary lineages within the Bradyrhizobium jicamae supergroup, with Bradyrhizobium algeriense and Bradyrhizobium valentinum as the closest relatives. The nodA and nifH gene phylogenies proved that the L. anagyroides symbionts carry a symbiotic gene variant known as Clade IV, representing the symbiovar retamae. Phenotypic characteristics of the isolates and reference strains are also reported. Our study of the rhizobia nodulating L. anagyroides growing in Poland complements earlier few findings on the symbiotic associations of this Genisteae species.
Production of enriched in B vitamins biomass of Yarrowia lipolytica grown in biofuel waste
(Elsevier, King Saud University, 2021) Jach, Monika Elżbieta; Sajnaga, Ewa; Janeczko, Monika; Juda, Marek; Kochanowicz, Elżbieta; Baj, Tomasz; Malm, Anna
Yarrowia lipolytica as an oleaginous yeast is capable of growing in various non-conventional hydrophobic substrate types, especially industrial wastes. In this study, the content of thiamine (vitamin B1), riboflavin (vitamin B2), pyridoxine (vitamin B6), biotin (vitamin B7) and folic acid (vitamin B9) in the wet biomass of Y. lipolytica strains cultivated in biofuel waste (SK medium), compared to the standard laboratory YPD medium, was assessed. Additionally, the biomass of Y. lipolytica A-101 grown in biofuel waste (SK medium) was dried and examined for B vitamins concentration according to the recommended microbial methods by AOAC Official Methods. The mean values of these vitamins per 100 g of dry weight of Y. lipolytica grown in biofuel waste (SK medium) were as follows: thiamine 1.3 mg/100 g, riboflavin 5.3 mg/100 g, pyridoxine 4.9 mg/100 g, biotin 20.0 µg/100 g, and folic acid 249 µg/100 g. We have demonstrated that the dried biomass is a good source of B vitamins which can be used as nutraceuticals to supplement human diet, especially for people at risk of B vitamin deficiencies in developed countries. Moreover, the biodegradation of biofuel waste by Y. lipolytica is desired for environmental protection.
Role of Phytoestrogen-Rich Bioactive Substances (Linum usitatissimum L., Glycine max L., Trifolium pratense L.) in Cardiovascular Disease Prevention in Postmenopausal Women: A Systematic Review and Meta-Analysis
(MDPI, 2022) Jach, Monika Elżbieta; Błaszczuk, Agata; Baranska, Agnieszka; Kanadys, Wiesław; Malm, Maria; Religioni, Urszula; Wróbel, Rafał; Herda, Jolanta; Polz-Dacewicz, Małgorzata
The aim of this report was to determine the impact of flaxseed, soy and red clover, and their bioactive substances on the lipid profile in postmenopausal women in cardiovascular diseases prevention. We used the following databases: MEDLINE (PubMed), EMBASE and the Cochrane Library. Meta-analysis indicates that the intake of flaxseed by postmenopausal women is associated with a statistically significant reduction in total cholesterol (TC) levels (weighted-mean difference (WMD) = −0.26; 95% confidence interval (95% CI): −0.38 to −0.13; p = 0.0001), low-density lipoprotein cholesterol (LDL-C) levels (WMD = −0.19; 95% CI: −0.30 to −0.08; p = 0.0006), and high-density lipoprotein cholesterol (HDL-C) levels (WMD = −0.06; 95% CI: −0.11 to −0.01; p = 0.0150). The effect of soy protein on the lipid profile showed a significant decrease in TC levels: WMD = −0.15; 95% CI: −0.25–0.05; p = 0.0048, LDL-C levels: WMD = −0.15; 95% CI: −0.25–0.05; p = 0.0067, as well as a significant increase in HDL-C levels: WMD = 0.05; 95% CI: 0.02–0.08; p = 0.0034. Changes in the lipid profile showed a significant reduction in TC levels after the use of red clover (WMD = −0.11; 95% CI: −0.18–−0.04; p = 0.0017) and a significant increase in HDL-C levels (WMD = 0.04; 95% CI: 0.01 to 0.07; p = 0.0165). This meta-analysis provides evidence that consuming flaxseed, soy and red clover can have a beneficial effect on lipids in postmenopausal women and suggest a favorable effect in preventing cardiovascular diseases.
Utilization of Legume-Nodule Bacterial Symbiosis in Phytoremediation of Heavy Metal-Contaminated Soils
(MDPI, 2022) Jach, Monika Elżbieta; Sajnaga, Ewa; Ziaja, Maria
With the increasing industrial activity of the growing human population, the accumulation of various contaminants in soil, including heavy metals, has increased rapidly. Heavy metals as non-biodegradable elements persist in the soil environment and may pollute crop plants, further accumulating in the human body causing serious conditions. Hence, phytoremediation of land contamination as an environmental restoration technology is desirable for both human health and broad-sense ecology. Legumes (Fabaceae), which play a special role in nitrogen cycling, are dominant plants in contaminated areas. Therefore, the use of legumes and associated nitrogen-fixing rhizobia to reduce the concentrations or toxic effects of contaminants in the soil is environmentally friendly and becomes a promising strategy for phytoremediation and phytostabilization. Rhizobia, which have such plant growth-promoting (PGP) features as phosphorus solubilization, phytohormone synthesis, siderophore release, production of beneficial compounds for plants, and most of all nitrogen fixation, may promote legume growth while diminishing metal toxicity. The aim of the present review is to provide a comprehensive description of the main effects of metal contaminants in nitrogen-fixing leguminous plants and the benefits of using the legume–rhizobium symbiosis with both wild-type and genetically modified plants and bacteria to enhance an efficient recovery of contaminated lands.
Yeast Protein as an Easily Accessible Food Source
(MDPI, 2022) Jach, Monika Elżbieta; Serefko, Anna; Ziaja, Maria; Kieliszek, Marek
In recent years, the awareness and willingness of consumers to consume healthy food has grown significantly. In order to meet these needs, scientists are looking for innovative methods of food production, which is a source of easily digestible protein with a balanced amino acid composition. Yeast protein biomass (single cell protein, SCP) is a bioavailable product which is obtained when primarily using as a culture medium inexpensive various waste substrates including agricultural and industrial wastes. With the growing population, yeast protein seems to be an attractive alternative to traditional protein sources such as plants and meat. Moreover, yeast protein biomass also contains trace minerals and vitamins, including B-group. Thus, using yeast in the production of protein provides both valuable nutrients and enhances purification of wastes. In conclusion, nutritional yeast protein biomass may be the best option for human and animal nutrition with a low environmental footprint. The rapidly evolving SCP production technology and discoveries from the world of biotechnology can make a huge difference in the future for the key improvement of hunger problems and the possibility of improving world food security. On the market of growing demand for cheap and environmentally clean SCP protein with practically unlimited scale of production, it may soon become one of the ingredients of our food. The review article presents the possibilities of protein production by yeast groups with the use of various substrates, as well as the safety of yeast protein used as food.
Yarrowia lipolytica as an Alternative and Valuable Source of Nutritional and Bioactive Compounds for Humans
(MDPI, 2022) Jach, Monika Elżbieta; Malm, Anna
Yarrowia lipolytica, an oleagineous species of yeast, is a carrier of various important nutrients. The biomass of this yeast is an extensive source of protein, exogenous amino acids, bioavailable essential trace minerals, and lipid compounds as mainly unsaturated fatty acids. The biomass also contains B vitamins, including vitamin B12, and many other bioactive components. Therefore, Y. lipolytica biomass can be used in food supplements for humans as safe and nutritional additives for maintaining the homeostasis of the organism, including for vegans and vegetarians, athletes, people after recovery, and people at risk of B vitamin deficiencies.
Green in water sonochemical synthesis of tetrazolopyrimidine derivatives by a novel core-shell magnetic nanostructure catalyst
(Elsevier, 2018) Demchuk, Oleg M.; Maleki, Ali; Rahimi, Jamal; Wilczewska, Agnieszka Z.; Jasiński, Radomir
A green approach for the one-pot four-component sonochemical synthesis of 5-methyl-7-aryl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylic esters from the reaction of 2-cyano-guanidine, sodium azide, various aromatic aldehydes and methyl or ethyl acetoacetate in the presence of a catalytic amount of Fe2O3@SiO2-(CH2)3NHC(O)(CH2)2PPh2 as a new hybrid organic–inorganic core–shell nanomagnetic catalyst is described. This is the first design, preparation, characterization and application of the present nanomaterial and also the first ultrasound irradiated synthesis of the biologically and pharmaceutically important heterocyclic compounds in water as a green solvent. This novel sonocatalysis/nanocatalysis protocol offers several advantages such as high yields, short reaction times, environmentally-friendly reaction media, easily isolation of the products, simple preparation, full characterization and recoverability of the nanocatalyst by an external magnet and reusing several times without significant loss of activity.
Cholinesterase inhibitors isolated from bilberry fruit
(Elsevier, 2014) Demchuk, Oleg M.; Borowiec, Kamila; Szwajgier, Dominik; Targoński, Zdzisław; Cybulska, Justyna; Czernecki, Tomasz; Malik, Agnieszka
Cholinesterases (ChEs) are key enzymes in the pathogenesis of Alzheimer's disease (AD). A growing body of evidence suggests that plants deliver compounds able to inhibit ChEs (e.g., huperzine A, galanthamine, and physostigmine), thus playing a beneficial therapeutic role in the treatment of AD. Screening for cholinesterase inhibitors (ChEIs) in selected fruits and vegetables showed that extract prepared from bilberry fruit effectively inhibited the activity of acetyl- and butyrylcholinesterase. The purification of ChEIs from bilberry fruit followed by HPLC-UV, FT-IR, NMR, and LC–MS demonstrated that the studied compounds were derivatives of chlorogenic and benzoic acids. These results confirm that bilberry fruit may serve as a useful source of ChEIs, leading to the attenuation of memory deficit caused by AD.
Regio- and stereoselectivity of polar [2+3] cycloaddition reactions between (Z)-C-(3,4,5-trimethoxyphenyl)-N-methylnitrone and selected (E)-2-substituted nitroethenes
(Versita, 2014) Demchuk, Oleg M.; Jasiński, Radomir; Ziółkowska, Magda; Maziarka, Agata
[2+3] Cycloaddition reactions of the highly reactive (Z)-C-(3,4,5-trimethoxyphenyl)-N-methylnitrone with (E)-2-R-nitroethenes proceed under mild conditions and yield mixtures of stereoisomeric 2-methyl-3-(3,4,5-trimethoxyphenyl)-4-nitro-5-R-isoxazolidines. The effect of regiospecificity of the cycloadditions may be accounted for by the theory of electrophilicity indexes. Stereoselectivity, however, is determined by a compilation of steric and secondary orbital effects.
Rational design of novel ligands for environmentally benign cross-coupling reactions
(Walter de Gruyter, 2011) Demchuk, Oleg M.; Kielar, Katarzyna; Pietrusiewicz, Kazimierz Michał
Transition-metal (TM) complexes of new phosphines, readily prepared by a straight forward three-step modular synthesis, were successfully employed in difficult crosscoupling reactions conducted under mild conditions (water, “open-flask”, low temperature) that aspire to meet green chemistry criteria. High yielding catalyzed by bismuth or rhodium complexes oxidative arylation of naphthoquinone gave the key 2-arylnaphthoquinone intermediates for facile bismuth triflate-catalyzed Michael addition of secondary phosphine oxides. Subsequent O-methylation and reductions of the resulting products gave access to the target air-stable phosphine ligands in good overall yields (up to 60 %).
A Quantum-Chemical DFT Approach to Elucidation of the Chirality Transfer Mechanism of the Enantioselective Suzuki–Miyaura Cross-Coupling Reaction
(Hindawi, 2017) Demchuk, Oleg M.; Jasiński, Radomir; Babyuk, Dmytro
The DFT calculations of the simplified model of the asymmetric Suzuki–Miyaura coupling reaction were performed at the M062x/LANL2DZ theory level at first. It was found that enantioselective reactions mediated by the palladium complexes of chiral C,P-ligands follow a four-stage mechanism similar to that proposed previously as one of the most credible mechanisms. It should be underlined that the presence of substituents in the substrates and the chiral ligand at ortho positions determines the energies of possible diastereoisomeric transition states and intermediates in initial reaction steps. This suggests that, in practice, a sharp selection of theoretically possible paths of chirality transfer from the catalyst to the product should have a place and, therefore, the absolute configuration of the formed atropisomeric product is defined and can be predicted.
A clean and simple method for deprotection of phosphines from borane complexes
(Walter de Gruyter, 2017) Demchuk, Oleg M.; Jasiński, Radomir; Strzelecka, Dorota; Dziuba, Kamil; Kula, Karolina; Chrzanowski, Jacek; Krasowska, Dorota
Simple, efficient, clean, and stereospecific protocols of protection of phosphorus atom with borane and deprotection from the borane complexes of the tertiary phosphines in mild conditions are reported. The proposed protection/deprotection reactions tolerate a range of functional groups and lead to pure products with excellent yield with no need for application of chromatographic or crystallisation purification procedures. For the first time mechanisms of the reactions of phosphine protection and deprotection have been studied based on experimental kinetic data as well as quantumchemical calculations, which allows designing reaction conditions suitable for a given substrate.
New Insights into the Mechanism of Reduction of Tertiary Phosphine Oxides by Means of Phenylsilane
(Wiley-Blackwell, 2015) Demchuk, Oleg M.; Jasiński, Radomir; Pietrusiewicz, Kazimierz Michał
The mechanism of the reduction of phosphine oxides by PhSiH3 was established on the basis of kinetic measurements and Density Functional Theory (DFT) calculations. In particular, it has been proved that the model reaction between tri-n-butylphosphine oxide and phenylsilane occurs via a nonpolar mechanism. The data presented herein allow prediction and verification of the applicability of the new reduction reagents and conditions for industrially attractive processes.
Metathetic approach to new NORPHOS-related bisphosphanes: facile synthesis and application in asymmetric hydrogenation
(Walter de Gruyter, 2021) Demchuk, Oleg M.; Szwaczko, Katarzyna; Mirosław, Barbara; Wójciuk, Grzegorz; Mazur, Liliana; Pietrusiewicz, Kazimierz Michał
A highly efficient synthesis of new chiral bisphosphanes derived from the renowned NORPHOS ligand is presented. The synthesis involves ring-opening metathesis of NORPHOS dioxide with an external olefin, followed by saturation of the new double bonds and adjustment of the oxidation level of phosphorus centers oxidation level. The synthesized bisphosphanes retain the configuration and enantiomeric purity of the starting NORPHOS. Their utility as ligands in asymmetric catalysis is exemplified using an open-NORPHOS ligand in some benchmark Rh-catalyzed hydrogenations of enamides where excellent chemical yields and enantiomeric purities of the products have been secured. The proposed protocol demonstrated the possibility of a straightforward synthesis of new chiral catalysts to be utilized in the asymmetric synthesis of pharmaceutically important compounds, such as amino acid derivatives.
A straightforward, environmentally benefcial synthesis of spiro[diindeno[1,2‑b:2′,1′‑e]py ridine‑11,3′‑indoline]‑2′,10,12‑tri ones mediated by a nano‑ordered reusable catalyst
(Nature Research, 2021) Demchuk, Oleg M.; Fathi, Mahsa; Naimi-Jamal, M. Reza; Dekamin, Mohammad G.; Panahi, Leila
A library of new spiro[diindeno[1,2-b:2′,1′-e]pyridine-11,3′-indoline]-2′,10,12-trione derivatives has been prepared in an efficient, one-pot pseudo four-component method mediated by a reusable heterogeneous nano-ordered mesoporous SO3H functionalized-silica (MCM-41-SO3H) catalyst. Excellent yields, short reaction times, as well as convenient non-chromatographic purification of the products and environmental benefits such as green and metal-free conditions constitute the main advantages of the developed synthetic methodology. The obtained fused indole-indenone dyes would be of interest to pharmaceutical and medicinal chemistry. Furthermore, due to their sensitivity to pH changes, they could be used as novel pH indicators.
A representative of arylcyanomethylenequinone oximes effectively inhibits growth and formation of hyphae in Candida albicans and influences the activity of protein kinases in vitro
(Elsevier, 2018) Masłyk, Maciej; Janeczko, Monika; Demchuk, Oleg M.; Boguszewska-Czubara, Anna; Golczyk, Hieronim; Sierosławska, Anna; Rymuszka, Anna; Martyna, Aleksandra; Kubiński, Konrad
In this study, we applied various assays to reveal new activities of phenylcyanomethylenequinone oxime-4-(hydroxyimino) cyclohexa-2,5-dien-1-ylidene](phenyl)ethanenitrile (4-AN) for potential anti-microbial applications. These assays demonstrated (a) the antimicrobial effect on bacterial and fungal cultures, (b) the effect on the in vitro activity of the kinase CK2, (c) toxicity towards human erythrocytes, the Caco-2 cancer cell line, and embryonic development of Zebrafish. We demonstrated the activity of 4-AN against selected bacteria and Candida spp. The MIC ranging from 4 µg/ml to 125 µg/ml proved effective in inhibition of formation of hyphae and cell aggregation in Candida, which was demonstrated at the cytological level. Noteworthy, 4-AN was found to inhibit the CK2 kinase with moderate potency. Moreover, at low concentrations, it did not exert any evident toxic effects on human erythrocytes, Caco-2 cells, or Zebrafish embryos. 4-AN can be a potential candidate as a novel drug against Candida infections.
New Supramolecular Drug Carriers: The Study of Organogel Conjugated Gold Nanoparticles
(MDPI, 2021) Demchuk, Oleg M.; Kowalczuk, Joanna; Łapiński, Andrzej; Stolarczyk, Elżbieta; Kubiński, Konrad; Janeczko, Monika; Martyna, Aleksandra; Masłyk, Maciej; Turczyniak-Surdacka, Sylwia
An aqueous solution of sodium citrate stabilized gold nanoparticles (AuNP) in the presence of N-lauroyl-L-alanine (C12ALA) forms a stable gel. The structure of the gel and the distribution profile of AuNP in it were analyzed. Will nanoparticles separated from each other with sodium citrate behave in the same way in solution and trapped in the gel matrix? Will the spatial limitation of solvent molecules aggregate nanoparticles and destroy their homogeneity? These questions are very important from the point of view of the use of gold nanoparticles, trapped in the gel structure, as carriers of drugs in the slow-release process. The lack of homogeneity of this distribution will have a major impact on the rate of release of the appropriate amount of therapeutic drug from the matrix. In this work, we attempt to answer these questions. The performed biological assays revealed that both C12ALA and C12ALA-AuNP show an excellent level of biological neutrality. They might be used as a transporting medium for a drug delivery without affecting the drug’s activity.
Antifungal Agent 4-AN Changes the Genome-Wide Expression Profile, Downregulates Virulence-Associated Genes and Induces Necrosis in Candida albicans Cells
(MDPI, 2020) Martyna, Aleksandra; Masłyk, Maciej; Janeczko, Monika; Kochanowicz, Elżbieta; Gielniewski, Bartłomiej; Świercz, Aleksandra; Demchuk, Oleg M.; Kubiński, Konrad
In the light of the increasing occurrence of antifungal resistance, there is an urgent need to search for new therapeutic strategies to overcome this phenomenon. One of the applied approaches is the synthesis of small-molecule compounds showing antifungal properties. Here we present a continuation of the research on the recently discovered anti-Candida albicans agent 4-AN. Using next generation sequencing and transcriptional analysis, we revealed that the treatment of C. albicans with 4-AN can change the expression profile of a large number of genes. The highest upregulation was observed in the case of genes involved in cell stress, while the highest downregulation was shown for genes coding sugar transporters. Real-time PCR analysis revealed 4-AN mediated reduction of the relative expression of genes engaged in fungal virulence (ALS1, ALS3, BCR1, CPH1, ECE1, EFG1, HWP1, HYR1 and SAP1). The determination of the fractional inhibitory concentration index (FICI) showed that the combination of 4-AN with amphotericin B is synergistic. Finally, flow cytometry analysis revealed that the compound induces mainly necrosis in C. albicans cells.

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