TY - JOUR AU - Dibello, Estefanía AU - Oddone, Natalia AU - Franco, Jaime AU - Tóthné Illyés, Tünde Zita AU - Medeiros, Andrea AU - Kiss, Attila AU - Hőgye, Fanni AU - E Kövér, Katalin AU - Szilágyi, László AU - Comini, Marcelo A. TI - Selenosugars targeting the infective stage of Trypanosoma brucei with high selectivity JF - INTERNATIONAL JOURNAL FOR PARASITOLOGY-DRUGS AND DRUG RESISTANCE J2 - INT J PARASITOL-DRUG VL - 24 PY - 2024 PG - 6 SN - 2211-3207 DO - 10.1016/j.ijpddr.2024.100529 UR - https://m2.mtmt.hu/api/publication/34743720 ID - 34743720 AB - Earlier evidences showed that diglycosyl diselenides are active against the infective stage of African trypanosomes (top hits IC50 0.5 and 1.5 μM) but poorly selective (selectivity index <10). Here we extended the study to 33 new seleno-glycoconjugates with the aim to improve potency and selectivity. Three selenoglycosides and three glycosyl selenenylsulfides displayed IC50 against bloodstream Trypanosoma brucei in the sub-μM range (IC50 0.35–0.77 μM) and four of them showed an improved selectivity (selectivity index >38-folds vs. murine and human macrohages). For the glycosyl selenylsulfides, the anti-trypanosomal activity was not significantly influenced by the nature of the moiety attached to the sulfur atom. Except for a quinoline-, and to a minor extent a nitro-derivative, the most selective hits induced a rapid (within 60 min) and marked perturbation of the LMWTredox homeostasis. The formation of selenenylsulfide glycoconjugates with free thiols has been identified as a potential mechanism involved in this process. LA - English DB - MTMT ER - TY - JOUR AU - Szűcs, Zsolt AU - Plaszkó, Tamás AU - Bódor, Eszter AU - Csoma, Hajnalka AU - Ács-Szabó, Lajos AU - Kiss, Attila AU - Vasas, Gábor AU - Gonda, Sándor TI - Antifungal Activity of Glucosinolate-Derived Nitriles and Their Synergistic Activity with Glucosinolate-Derived Isothiocyanates Distinguishes Various Taxa of Brassicaceae Endophytes and Soil Fungi JF - PLANTS-BASEL J2 - PLANTS-BASEL VL - 12 PY - 2023 IS - 14 PG - 13 SN - 2223-7747 DO - 10.3390/plants12142741 UR - https://m2.mtmt.hu/api/publication/34081680 ID - 34081680 AB - The glucosinolates of Brassicaceae plants are converted into bioactive isothiocyanates and other volatiles during a challenge by pathogens and other biotic stressors. However, the role of alternative downstream products with weaker potency (e.g., nitriles) is far from being fully understood. This study tested the possible synergistic antifungal interaction between various glucosinolate-derived nitriles and 2-phenylethyl isothiocyanate (PEITC) on 45 fungal strains, including endophytes from horseradish roots (Brassicaceae) and soil fungi, using an airtight system enabling the accurate study of extremely volatile antifungal agents. The median minimal inhibitory concentrations (MICs) were 1.28, 6.10, 27.00 and 49.72 mM for 1H-indole-3-acetonitrile (IAN), 3-phenylpropanenitrile (PPN), 4-(methylsulfanyl)-butanenitrile (MSBN) and 3-butenenitrile (BN, = allyl cyanide), respectively. Thus, nitriles were considerably weaker antifungal agents compared to PEITC with a median MIC of 0.04 mM. For the same nitriles, the median fractional inhibitory concentration indices (FICIs) of the combinations were 0.562, 0.531, 0.562 and 0.625, respectively. Altogether, 47.7%, 56.8%, 50.0% and 27.3% of tested fungal strains showed a synergistic antifungal activity (FICI ≤ 0.5) for the nitrile–isothiocyanate combinations, respectively. Hypocreales strains showed the least sensitivity towards the GSL decomposition products and their combinations. The mean MIC values for PEITC showed 0.0679 ± 0.0358, 0.0400 ± 0.0214, 0.0319 ± 0.0087 and 0.0178 ± 0.0171 mM for Hypocreales, Eurotiales, Glomerellales and Pleosporales, respectively. In addition, nitriles, especially IAN, also showed significant differences. For the same fungi, the median FICI values fell in the ranges of 0.61–0.67, 0.52–0.61, 0.40–0.50 and 0.48–0.67, respectively, depending on the nitrile. Our results suggest that glucosinolate-derived nitriles may enhance isothiocyanate antifungal activity and that they may play an active role in shaping the plant microbiome and contribute to the filtering of microbes by plants. LA - English DB - MTMT ER - TY - JOUR AU - To Quoc, Thinh AU - Bíró, Krisztina AU - Pető, Ágota AU - Kósa, Dóra AU - Sinka, Dávid AU - Lekli, István AU - Kiss, Attila AU - Budai, István AU - Béresová, Monika AU - Vecsernyés, Miklós AU - Siposné Fehér, Pálma AU - Bácskay, Ildikó AU - Ujhelyi, Zoltán TI - Development and Evaluation of an FDM Printed Nasal Device for CPZ Solid Nanoparticles JF - MOLECULES J2 - MOLECULES VL - 28 PY - 2023 IS - 11 PG - 15 SN - 1420-3049 DO - 10.3390/molecules28114406 UR - https://m2.mtmt.hu/api/publication/33938541 ID - 33938541 AB - Nasal drug delivery has been a focus of scientific interest for decades. A number of drug delivery systems and devices are available and have been highly successful in providing better and more comfortable therapy. The benefits of nasal drug delivery are not in question. The nasal surface provides an excellent context for the targeted delivery of active substances. In addition to the large nasal surface area and intensive absorption, the active substances delivered through the nose overcome the blood–brain barrier and can be delivered directly to the central nervous system. Formulations for nasal administration are typically solutions or liquid dispersed systems such as emulsions or suspensions. Formulation techniques for nanostructures have recently undergone intensive development. Solid-phase heterogeneous dispersed systems represent a new direction in pharmaceutical formulations. The wide range of possible examples and the variety of excipients allow for the delivery of a wide range of active ingredients. The aim of our experimental work was to develop a solid drug delivery system that possesses all of the above-mentioned advantageous properties. In developing solid nanosystems, we not only exploited the advantages of size but also the adhesive and penetration-enhancing properties of excipients. During formulation, several amphiphilic compounds with adhesion properties and penetration enhancing effects were incorporated. We used chlorpromazine (CPZ), which is mainly used in the treatment of psychotic disorders such as schizophrenia and bipolar disorder. Chlorpromazine has been previously investigated by our team in other projects. With the availability of previous methods, the analytical characterization of the drug was carried out effectively. Due to the frequent and severe side effects of the drug, the need for therapeutic dose reduction is indisputable. In this series of experiments, we succeeded in constructing drug delivery systems. Finely divided Na nanoparticles were formed using a Büchi B90 nanospray dryer. An important step in the development of the drug carrier was the selection of suitable inert carrier compounds. Particle size determination and particle size distribution analysis were performed to characterize the prepared nanostructures. As safety is the most important aspect of any drug formulation, all components and systems were tested with different biocompatibility assays. The tests performed demonstrated the safe applicability of our systems. The bioavailability of chlorpromazine was studied as a function of the ratio of the active ingredient administered nasally and intravenously. As described above, most nasal formulations are liquids, but our system is solid, so there is currently no tool available to accurately target this system. As a supplement of the project, a nasal dosing device was developed, corresponding to the anatomical structure; a prototype of the device was made using 3D FDM technology. Our results lay the foundation for the design and industrial scaling of a new approach to the design and production of a high-bioavailability nasal medicinal product. LA - English DB - MTMT ER - TY - JOUR AU - Király, Sándor Balázs AU - Tóth, László AU - Kovács, Tibor AU - Bényei, Attila Csaba AU - Lisztes, Erika AU - Tóth, Balázs István AU - Bíró, Tamás AU - Kiss, Attila AU - E Kövér, Katalin AU - Mándi, Attila AU - Kurtán, Tibor TI - Multifaceted Domino Knoevenagel‐Cyclization Reactions; Four Movements for 2H‐Chromenes and Chromans JF - ADVANCED SYNTHESIS & CATALYSIS J2 - ADV SYNTH CATAL VL - 365 PY - 2023 IS - 19 SP - 3301 EP - 3319 PG - 19 SN - 1615-4150 DO - 10.1002/adsc.202300083 UR - https://m2.mtmt.hu/api/publication/33683947 ID - 33683947 AB - Domino Knoevenagel-cyclization reactions of 2H-chromene and chroman derivatives containing o-formylaryl amine or ether side-chain was carried out to produce four series of chiral condensed heterocycles representing four novel skeletons and exhibiting antiproliferative activity. The cyclization step occurred with four different mechanisms: a concerted intramolecular hetero Diels-Alder reaction (IMHDA), a stepwise polar [2+2] cycloaddition, a [1,5]-hydride shift-6-endo cyclization or a multi-step nitro hetero Diels-Alder-ring-opening-Cadogan-type cyclization sequence. The latter reaction provided a new route to hydroxyindoles by an inverse Cadogan-type cyclization, in which the nitro group is deoxygenated by a nitro IMHDA-ring-opening sequence. The cyclization mechanisms and their stereoselectivity were studied by DFT calculations, based on which we proposed a mechanism for the multi-step cyclization to hydroxyindoles and explained the observed diastereoselectivity. LA - English DB - MTMT ER - TY - JOUR AU - Gonda, Sándor AU - Szűcs, Zsolt AU - Plaszkó, Tamás AU - Cziáky, Zoltán AU - Kiss, Attila AU - Sinka, Dávid AU - Bácskay, Ildikó AU - Vasas, Gábor TI - Quality-controlled LC-ESI-MS food metabolomics of fenugreek (Trigonella foenum-graecum) sprouts: insights into changes in primary and specialized metabolites JF - FOOD RESEARCH INTERNATIONAL J2 - FOOD RES INT VL - 164 PY - 2023 PG - 13 SN - 0963-9969 DO - 10.1016/j.foodres.2022.112347 UR - https://m2.mtmt.hu/api/publication/33526936 ID - 33526936 N1 - Department of Botany, Division of Pharmacognosy, University of Debrecen, Egyetem tér 1, Debrecen, 4032, Hungary Healthcare Industry Institute, University of Debrecen, Debrecen, 4032, Hungary University of Nyíregyháza, Agricultural and Molecular Research and Service Institute, 4400 Nyíregyháza, Sóstói út 31/b, Hungary University of Debrecen, Department of Organic Chemistry, H-4010 Debrecen, Egyetem tér 1, Hungary University of Debrecen, Department of Pharmaceutical Technology, H-4032, Nagyerdei körút 98, Hungary Export Date: 8 September 2023 CODEN: FORIE Correspondence Address: Gonda, S.; Department of Botany, Egyetem tér 1, Hungary; email: gondasandor@gmail.com AB - Fenugreek (Trigonella foenum-graecum L.) is an important food and spice with bioactive compounds against diabetes. In this study, fenugreek seeds germinating in darkness for 72 h were studied using quantification of trigonelline and 4-hydroxyisoleucine and an LC-ESI-MS/MS-based metabolomic approach capable of accurately estimating 237 features from various primary and specialized compound classes. During germination, the concentrations of trigonelline and 4-hydroxyisoleucine rose by 33.5% and 33.3%, respectively. At the same time, untargeted metabolomics revealed 9 putative flavonoids increasing 1.19- to 2.77- fold compared to the dormant seeds. A set of 19 steroid saponins rose by 1.08- to 31.86-fold. Primary metabolites however showed much more variability: abundance changes in amino acid derivatives, peptides and saccharides fell in the 0.09- to 22.25-fold, 0.93- to 478.79-fold and 0.36- to 941.58-fold ranges, respectively. To increase biosynthesis of specialized metabolites during germination, sprouts were exposed to 1–100 mM methyl jasmonate (MeJA) and methyl salicylate (MeSA). The hormone treatments affected normal metabolism: 67.1–83.1 % and 64.1–83.5 % of compounds showed a reduction compared to the controls in 100 mM MeJA and MeSA treatments at different sampling time points. Contrary to expectations, the abundance of flavonoids decreased, compared to the control sprouts (0.75- and 0.68-fold change medians, respectively). The same was observed for most, but not all steroid saponins. The quality-controlled untargeted metabolomics approach proved to yield excellent insight into the metabolic changes during germination of fenugreek. The results suggest that although fenugreek germination causes major shifts in plant metabolism, there are no major qualitative changes in bioactive specialized metabolites during the first three days. This stability likely translates into good bioactivity that is similar to that of the seeds. Because the large changes in the primary metabolites likely alter the nutritive value of the seed, further studies are warranted. LA - English DB - MTMT ER - TY - JOUR AU - Sinka, Dávid AU - Doma, Enikő AU - Szendi, Nóra AU - Páll, Jázmin AU - Kósa, Dóra AU - Pető, Ágota AU - Siposné Fehér, Pálma AU - Ujhelyi, Zoltán AU - Fenyvesi, Ferenc AU - Váradi, Judit AU - Vecsernyés, Miklós AU - Szűcs, Zsolt AU - Gonda, Sándor AU - Cziáky, Zoltán AU - Kiss, Attila AU - Vasas, Gábor AU - Bácskay, Ildikó TI - Formulation, Characterization and Permeability Studies of Fenugreek (Trigonella foenum-graecum) Containing Self-Emulsifying Drug Delivery System (SEDDS) JF - MOLECULES J2 - MOLECULES VL - 27 PY - 2022 IS - 9 PG - 18 SN - 1420-3049 DO - 10.3390/molecules27092846 UR - https://m2.mtmt.hu/api/publication/32801731 ID - 32801731 AB - Fenugreek is used as a spice and a traditional herbal medicine for a variety of purposes, given its antidiabetic and antioxidant effects. Self-emulsifying drug delivery systems (SEDDS) of herbal drugs are targets of extensive research aiming to increase bioavailability and stability. The study's objective was to formulate SEDDS containing Trigonella foenum-graecum extract to improve the stability of herbal extract and to increase their permeability through a Caco-2 monolayer. A characterized fenugreek dry extract was used for the formulations, while the SEDDS properties were examined by particle size analysis and zeta potential measurements. Permeability assays were carried out on Caco-2 cell monolayers, the integrity of which was monitored by follow-up trans-epithelial electric resistance measurements (TEER). Cytocompatibility was tested by the MTT method, and an indirect dissolution test was performed, using DPPH antioxidant reagent. Two different SEDDS compositions were formulated from a standardized fenugreek dry extract at either the micro- or the nanoemulsion scale with sufficient stability, enhanced bioavailability of the compounds, and sustained release from HPMC capsules. Based on our results, a modern, non-toxic, cytocompatible fenugreek SEDDS formulation with high antioxidant capacity was developed in order to improve the permeability and bioavailability of all components. LA - English DB - MTMT ER - TY - JOUR AU - Gyöngyösi, Alexandra AU - Vivien, Verner AU - Bakai-Bereczki, Ilona AU - Kiss, Attila AU - Rita, Zilinyi AU - Tósaki, Árpád AU - Bak, István AU - Borbás, Anikó AU - Herczegh, Pál AU - Lekli, István TI - Basic Pharmacological Characterization of EV-34, a New H2S-Releasing Ibuprofen Derivative. JF - MOLECULES J2 - MOLECULES VL - 26 PY - 2021 IS - 3 PG - 12 SN - 1420-3049 DO - 10.3390/molecules26030599 UR - https://m2.mtmt.hu/api/publication/31841366 ID - 31841366 N1 - Export Date: 13 September 2021 AB - Cardioprotective effects of H2S are being suggested by numerous studies. Furthermore, H2S plays a role in relaxation of vascular smooth muscle, protects against oxidative stress, and modulates inflammation. Long-term high-dose use of NSAIDs, such as ibuprofen, have been associated with enhanced cardiovascular risk. The goal of the present work is the synthesis and basic pharmacological characterization of a newly designed H2S-releasing ibuprofen derivative.Following the synthesis of EV-34, a new H2S-releasing derivative of ibuprofen, oxidative stability assays were performed (Fenton and porphyrin assays). Furthermore, stability of the molecule was studied in rat serum and liver lysates. H2S-releasing ability of the EC-34 was studied with a hydrogen sulfide sensor. MTT (3-(4,5-dimethylthiazol 2-yl)-2,5-(diphenyltetrazolium bromide)) assay was carried out to monitor the possible cytotoxic effect of the compound. Cyclooxygenase (COX) inhibitory property of EV-34 was also evaluated. Carrageenan assay was carried out to compare the anti-inflammatory effect of EV-34 to ibuprofen in rat paws.The results revealed that the molecule is stable under oxidative condition of Fenton reaction. However, EV-34 undergoes biodegradation in rat serum and liver lysates. In cell culture medium H2S is being released from EV-34. No cytotoxic effect was observed at concentrations of 10, 100, 500 µM. The COX-1 and COX-2 inhibitory effects of the molecule are comparable to those of ibuprofen. Furthermore, based on the carrageenan assay, EV-34 exhibits the same anti-inflammatory effect to that of equimolar amount of ibuprofen (100 mg/bwkg).The results indicate that EV-34 is a safe H2S releasing ibuprofen derivative bearing anti-inflammatory properties. LA - English DB - MTMT ER - TY - JOUR AU - Szappanos, Ádám AU - Mándi, Attila AU - Gulácsi, Katalin AU - Lisztes, Erika AU - Tóth, Balázs István AU - Bíró, Tamás AU - Kónya-Ábrahám, Anita AU - Kiss, Attila AU - Bényei, Attila Csaba AU - Antus, Sándor AU - Kurtán, Tibor TI - Synthesis and HPLC-ECD Study of Cytostatic Condensed O,N-Heterocycles Obtained from 3-Aminoflavanones JF - BIOMOLECULES J2 - BIOMOLECULES VL - 10 PY - 2020 IS - 10 PG - 42 SN - 2218-273X DO - 10.3390/biom10101462 UR - https://m2.mtmt.hu/api/publication/31636673 ID - 31636673 N1 - Funding Agency and Grant Number: Janos Bolyai Research Scholarship of the Hungarian Academy of SciencesHungarian Academy of Sciences; New National Excellence Program of the Ministry for Innovation and Technology [uNKP-19-4-DE-285, uNKP-20-5-DE-422]; National Research Development and Innovation Office [PD-134791] Funding text: The CPU time from the Governmental Information Technology Development Agency (KIFu) is gratefully acknowledged. A.M. and B.I.T: thank the Janos Bolyai Research Scholarship of the Hungarian Academy of Sciences for financial support. B.I.T. was also supported by the New National Excellence Program of the Ministry for Innovation and Technology (uNKP-19-4-DE-285 and uNKP-20-5-DE-422). E.L. was supported by the National Research Development and Innovation Office (PD-134791). Department of Organic Chemistry, University of Debrecen, P. O. Box 400, Debrecen, 4002, Hungary Doctoral School of Chemistry, University of Debrecen, Egyetem tér 1, Debrecen, 4032, Hungary Department of Physiology, University of Debrecen, Debrecen, 4012, Hungary Department of Immunology, University of Debrecen, Debrecen, 4032, Hungary Department of Physical Chemistry, University of Debrecen, Debrecen, 4032, Hungary Export Date: 6 February 2021 Correspondence Address: Kurtán, T.; Department of Organic Chemistry, P. O. Box 400, Hungary; email: kurtan.tibor@science.unideb.hu Funding details: European Commission, EC Funding details: Nemzeti Kutatási Fejlesztési és Innovációs Hivatal, NKFIH, K‐112951, K‐120181, FK‐134725, NN128368 Funding details: European Regional Development Fund, FEDER, GINOP‐2.3.2‐15‐2016‐00008 Funding details: Magyar Tudományos Akadémia, MTA Funding details: Nemzeti Kutatási Fejlesztési és Innovációs Hivatal, NKFIH, PD‐134791 Funding details: Ministry for Innovation and Technology, ÚNKP‐20‐5‐DE‐422, ÚNKP‐19‐4‐DE‐285 Funding text 1: Funding: This research was funded by the National Research Development and Innovation Office (Grant numbers: K‐112951, K‐120181, FK‐134725, and NN128368). The research was supported by the EU and co‐ financed by the European Regional Development Fund under the project GINOP‐2.3.2‐15‐2016‐00008. Funding text 2: Acknowledgments: The CPU time from the Governmental Information Technology Development Agency (KIFÜ) is gratefully acknowledged. A.M. and B.I.T: thank the János Bolyai Research Scholarship of the Hungarian Academy of Sciences for financial support. B.I.T. was also supported by the New National Excellence Program of the Ministry for Innovation and Technology (ÚNKP‐19‐4‐DE‐285 and ÚNKP‐20‐5‐DE‐422). E.L. was supported by the National Research Development and Innovation Office (PD‐134791). AB - Racemic chiral O,N-heterocycles containing 2-arylchroman or 2-aryl-2H-chromene subunit condensed with morpholine, thiazole or pyrrole moieties at the C-3-C-4 bond were synthesized with various substitution patterns of the aryl group by the cyclization of cis- or trans-3-aminoflavanone analogues. The 3-aminoflavanone precursors were obtained in a Neber rearrangement of oxime tosylates of flavanones, which provided the trans diastereomer as the major product and enabled the isolation of both the cis- and trans-diastereomers. The cis- and trans-aminoflavanones were utilized to prepare three diastereomers of 5-aryl-chromeno[4,3-b][1,4]oxazines. Antiproliferative activity of the condensed heterocycles and precursors was evaluated against A2780 and WM35 cancer cell lines. For a 3-(N-chloroacetylamino)-flavan-4-ol derivative, showing structural analogy with acyclic acid ceramidase inhibitors, 0.15 M, 3.50 and 6.06 M IC50 values were measured against A2780, WM35 and HaCat cell lines, and apoptopic mechanism was confirmed. Low micromolar IC50 values down to 2.14 M were identified for the thiazole- and pyrrole-condensed 2H-chromene derivatives. Enantiomers of the condensed heterocycles were separated by HPLC using chiral stationary phase, HPLC-ECD spectra were recorded and TDDFT-ECD calculations were performed to determine the absolute configuration and solution conformation. Characteristic ECD transitions of the separated enantiomers were correlated with the absolute configuration and effect of substitution pattern on the HPLC elution order was determined. LA - English DB - MTMT ER - TY - JOUR AU - Vargáné Szalóki, Dóra AU - Tóth, László AU - Buglyó, Balázs AU - Kiss, Attila AU - Mándi, Attila AU - Mátyus, Péter AU - Antus, Sándor AU - Chen, Yinghan AU - Li, Dehai AU - Tao, Lingxue AU - Zhang, Haiyan AU - Kurtán, Tibor TI - [1,5]-Hydride Shift-Cyclization versus C(sp2)-H Functionalization in the Knoevenagel-Cyclization Domino Reactions of 1,4- and 1,5-Benzoxazepines JF - MOLECULES J2 - MOLECULES VL - 25 PY - 2020 IS - 6 PG - 19 SN - 1420-3049 DO - 10.3390/molecules25061265 UR - https://m2.mtmt.hu/api/publication/31259883 ID - 31259883 N1 - Funding Agency and Grant Number: National Research Development and Innovation Office [K-112951, K-120181]; EU - European Regional Development FundEuropean Union (EU) [GINOP-2.3.2-15-2016-00008]; Janos Bolyai Research Scholarship of the Hungarian Academy of SciencesHungarian Academy of Sciences [UNKP-19-4]; New National Excellence Program of the Ministry for Innovation and Technology Funding text: Financial support from the National Research Development and Innovation Office (Grant numbers: K-112951, K-120181) is gratefully acknowledged. This research was supported by the EU and co-financed by the European Regional Development Fund under the project GINOP-2.3.2-15-2016-00008. A.M. was supported by the Janos Bolyai Research Scholarship of the Hungarian Academy of Sciences and the UNKP-19-4 New National Excellence Program of the Ministry for Innovation and Technology. AB - Domino cyclization reactions of N-aryl-1,4- and 1,5-benzoxazepine derivatives involving [1,5]-hydride shift or C(sp2)-H functionalization were investigated. Neuroprotective and acetylcholinesterase activities of the products were studied. Domino Knoevenagel-[1,5]-hydride shift-cyclization reaction of N-aryl-1,4-benzoxazepine derivatives with 1,3-dicarbonyl reagents having active methylene group afforded the 1,2,8,9-tetrahydro-7bH-quinolino [1,2-d][1,4]benzoxazepine scaffold with different substitution pattern. The C(sp3)-H activation step of the tertiary amine moiety occurred with complete regioselectivity and the 6-endo cyclization took place in a complete diastereoselective manner. In two cases, the enantiomers of the chiral condensed new 1,4-benzoxazepine systems were separated by chiral HPLC, HPLC-ECD spectra were recorded, and absolute configurations were determined by time-dependent density functional theory- electronic circular dichroism (TDDFT-ECD) calculations. In contrast, the analogue reaction of the regioisomeric N-aryl-1,5-benzoxazepine derivative did not follow the above mechanism but instead the Knoevenagel intermediate reacted in an SEAr reaction [C(sp2)-H functionalization] resulting in a condensed acridane derivative. The AChE inhibitory assays of the new derivatives revealed that the acridane derivative had a 6.98 μM IC50 value. LA - English DB - MTMT ER - TY - JOUR AU - Riba, Milán AU - Kiss, Attila AU - Gonda, Sándor AU - Parizsa, Péter AU - Deák, Balázs AU - Török, Péter AU - Valkó, Orsolya AU - Felföldi, Tamás AU - Vasas, Gábor TI - Chemotyping of terrestrial Nostoc-like isolates from alkali grassland areas by non-targeted peptide analysis JF - ALGAL RESEARCH-BIOMASS BIOFUELS AND BIOPRODUCTS J2 - ALGAL RES VL - 46 PY - 2020 PG - 18 SN - 2211-9264 DO - 10.1016/j.algal.2020.101798 UR - https://m2.mtmt.hu/api/publication/31142376 ID - 31142376 N1 - Department of Botany, Institute of Biology and Ecology, Faculty of Science and Technology, University of Debrecen, Debrecen, H-4032, Hungary Department of Organic Chemistry, Institute of Chemistry, Faculty of Science and Technology, University of Debrecen, Debrecen, H-4032, Hungary MTA-DE Biodiversity and Ecosystem Services Research Group, Debrecen, H-4032, Hungary MTA-DE Lendület Functional and Restoration Ecology Research Group, Debrecen, H-4032, Hungary MTA-DE Lendület Seed Ecology Research Group, Debrecen, H-4032, Hungary Department of Microbiology, ELTE Eötvös Loránd University, Budapest, H-1117, Hungary Cited By :8 Export Date: 20 November 2023 Correspondence Address: Vasas, G.; Department of Botany, Hungary; email: vasas.gabor@science.unideb.hu AB - The Nostoc genus is a well-known heterocytous, filamentous cyanobacterium which can be found all over the world. The size of terrestrial and/or freshwater colonies can be microscopic and macroscopic as well. In addition, Nostoc species are one of the most common photosynthetic cyanobacterial partners in symbiotic interactions. Terrestrial cyanobacterial colonies were collected and isolated in this study from various alkali grassland habitats (Great Hungarian Plain). Altogether 133 colonies were isolated from the 65 collected samples. The peptide patterns of the Nostoc-like strains were examined using HPLC-ESI-MS/MS and 41 peptides were identified from 45 isolated Nostoc-like strains; these compounds belonged to 4 different peptide classes. Twelve nostoginin/microginin, 16 anabaenopeptin, 12 banyaside/suomilide variants were identified. 37% of our isolated Nostoc-like strains produced some of the peptide metabolites we tested. These strains showed distinct chemotypes according to their peptide patterns, and can be divided into 4 groups based on their metabolisms. Strains either contained: (1) nostoginins/microginins, (2) anabaenopeptins, (3) anabaenopeptins and banyasides or (4) banyasides as major compounds. Banyasides were present in many of our strains and showed very high intensity in some cases. A number of previously unknown banyaside variants have been identified. LA - English DB - MTMT ER -