@article{MTMT:34791082, title = {Stereoselective Synthesis and Catalytical Application of Perillaldehyde-Based 3-Amino-1,2-diol Regioisomers}, url = {https://m2.mtmt.hu/api/publication/34791082}, author = {Háznagy, Márton Benedek and Csámpai, Antal and Ugrai, Imre and Barnabás, Molnár and Matti, Haukka and Szakonyi, Zsolt}, doi = {10.3390/ijms25084325}, journal-iso = {INT J MOL SCI}, journal = {INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES}, volume = {25}, unique-id = {34791082}, issn = {1661-6596}, abstract = {A library of regioisomeric monoterpene-based aminodiols was synthesised and applied as chiral catalysts in the addition of diethylzinc to benzaldehyde. The synthesis of the first type of aminodiols was achieved starting from (−)-8,9-dihydroperillaldehyde via reductive amination, followed by Boc protection and dihydroxylation with the OsO4/NMO system. Separation of formed stereoisomers resulted in a library of aminodiol diastereoisomers. The library of regioisomeric analogues was obtained starting from (−)-8,9-dihydroperillic alcohol, which was transformed into a mixture of allylic trichloroacetamides via Overman rearrangement. Changing the protecting group to a Boc function, the protected enamines were subjected to dihydroxylation with the OsO4/NMO system, leading to a 71:16:13 mixture of diastereoisomers, which were separated, affording the three isomers in isolated form. The obtained primary aminodiols were transformed into secondary derivatives. The regioselectivity of the ring closure of the N-benzyl-substituted aminodiols with formaldehyde was also investigated, resulting in 1,3-oxazines in an exclusive manner. To explain the stability difference between diastereoisomeric 1,3-oxazines, a series of comparative theoretical modelling studies was carried out. The obtained potential catalysts were applied in the reaction of aromatic aldehydes and diethylzinc with moderate to good enantioselectivities (up to 94% ee), whereas the opposite chiral selectivity was observed between secondary aminodiols and their ring-closed 1,3-oxazine analogues.}, year = {2024}, eissn = {1422-0067}, orcid-numbers = {Csámpai, Antal/0000-0003-2107-7309; Matti, Haukka/0000-0002-6744-7208; Szakonyi, Zsolt/0000-0003-2432-8409} } @article{MTMT:34789041, title = {Synthesis of Estrone Heterodimers and Evaluation of Their In Vitro Antiproliferative Activity}, url = {https://m2.mtmt.hu/api/publication/34789041}, author = {Bózsity-Faragó, Noémi and Nagy, Viktória and Szabó, Johanna and Pálházi, Balázs and Kele, Zoltán and Resch, Vivien Erzsébet and Paragi, Gábor and Zupkó, István and Minorics, Renáta and Mernyák, Erzsébet}, doi = {10.3390/ijms25084274}, journal-iso = {INT J MOL SCI}, journal = {INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES}, volume = {25}, unique-id = {34789041}, issn = {1661-6596}, abstract = {Directed structural modifications of natural products offer excellent opportunities to develop selectively acting drug candidates. Natural product hybrids represent a particular compound group. The components of hybrids constructed from different molecular entities may result in synergic action with diminished side effects. Steroidal homo- or heterodimers deserve special attention owing to their potentially high anticancer effect. Inspired by our recently described antiproliferative core-modified estrone derivatives, here, we combined them into heterodimers via Cu(I)-catalyzed azide–alkyne cycloaddition reactions. The two trans-16-azido-3-(O-benzyl)-17-hydroxy-13α-estrone derivatives were reacted with 3-O-propargyl-D-secoestrone alcohol or oxime. The antiproliferative activities of the four newly synthesized dimers were evaluated against a panel of human adherent gynecological cancer cell lines (cervical: Hela, SiHa, C33A; breast: MCF-7, T47D, MDA-MB-231, MDA-MB-361; ovarian: A2780). One heterodimer (12) exerted substantial antiproliferative activity against all investigated cell lines in the submicromolar or low micromolar range. A pronounced proapoptotic effect was observed by fluorescent double staining and flow cytometry on three cervical cell lines. Additionally, cell cycle blockade in the G2/M phase was detected, which might be a consequence of the effect of the dimer on tubulin polymerization. Computational calculations on the taxoid binding site of tubulin revealed potential binding of both steroidal building blocks, mainly with hydrophobic interactions and water bridges.}, year = {2024}, eissn = {1422-0067}, orcid-numbers = {Resch, Vivien Erzsébet/0000-0003-0044-5731; Paragi, Gábor/0000-0001-5408-1748; Zupkó, István/0000-0003-3243-5300; Minorics, Renáta/0000-0001-9685-813X; Mernyák, Erzsébet/0000-0003-4494-1817} } @article{MTMT:34779108, title = {Diterpenes Isolated from Three Different Plectranthus Sensu Lato Species and Their Antiproliferative Activities against Gynecological and Glioblastoma Cancer Cells}, url = {https://m2.mtmt.hu/api/publication/34779108}, author = {Gáborová, Mária and Vágvölgyi, Máté and Tayeb, Bizhar Ahmed and Minorics, Renáta and Zupkó, István and Jurček, Ondřej and Béni, Szabolcs and Kubínová, Renata and Balogh, György Tibor and Hunyadi, Attila}, doi = {10.1021/acsomega.4c00800}, journal-iso = {ACS OMEGA}, journal = {ACS OMEGA}, volume = {9}, unique-id = {34779108}, issn = {2470-1343}, year = {2024}, eissn = {2470-1343}, pages = {18495-18504}, orcid-numbers = {Vágvölgyi, Máté/0000-0002-2233-9422; Tayeb, Bizhar Ahmed/0000-0001-5197-564X; Minorics, Renáta/0000-0001-9685-813X; Zupkó, István/0000-0003-3243-5300; Béni, Szabolcs/0000-0001-7056-6825; Balogh, György Tibor/0000-0003-3347-1880; Hunyadi, Attila/0000-0003-0074-3472} } @article{MTMT:34777586, title = {C19 -diterpene alkaloids from delphinium turkmenum lipsky}, url = {https://m2.mtmt.hu/api/publication/34777586}, author = {Shakeri, Abolfazl and Samaei, Maryam and Hohmann, Judit and Iranshahy, Milad and Asili, Javad}, doi = {10.1080/14786419.2024.2327618}, journal-iso = {NAT PROD RES}, journal = {NATURAL PRODUCT RESEARCH}, unique-id = {34777586}, issn = {1478-6419}, year = {2024}, eissn = {1478-6427}, pages = {1-5}, orcid-numbers = {Hohmann, Judit/0000-0002-2887-6392} } @article{MTMT:34771221, title = {Investigation of the Allelopathic Effect of Two Invasive Plant Species in Rhizotron System}, url = {https://m2.mtmt.hu/api/publication/34771221}, author = {Bakacsy, László and Kardos, Luca Viktória and Szepesi, Ágnes and Nagy, Krisztina Napsugár and Vasas, Andrea and Feigl, Gábor}, doi = {10.3390/life14040475}, journal-iso = {LIFE-BASEL}, journal = {LIFE-BASEL}, volume = {14}, unique-id = {34771221}, abstract = {A key question in plant invasion biology is why invasive plants are more competitive in their introduced habitat than in their native habitat. Studies show that invasive species exhibit allelopathy, influencing other plants by releasing chemicals. Research on allelopathy uses in vitro tests, investigating effects on seed germination and seedling development. Although soil plays a role in modifying allelopathic effects, observations with soil are rare and almost nothing is known about the root development of test plants developing in soil and the effects of allelopathic compounds on root architecture. Our study evaluates the allelopathic effects of false indigo-bush (Amorpha fruticosa L.) and common milkweed (Asclepias syriaca L.) on oilseed rape growth as a model plant. The rhizotron system was used to study the effect of morphology and root architecture. Leaf–soil mixtures at 0.5%, 1%, and 5% concentrations were used. Shoot and root development was strongly inhibited at 5%. But there was no difference between the allelopathy of the two species, and the application of lower concentrations did not show any effect, demonstrating that soil has a significant modifying effect on their allelopathy. Our results highlight that the development of roots growing in the soil is also worth investigating in connection with allelopathy, which can strengthen the ecological importance of allelochemicals during successful invasions.}, year = {2024}, eissn = {2075-1729}, orcid-numbers = {Bakacsy, László/0000-0003-2593-1795; Vasas, Andrea/0000-0002-1818-7702; Feigl, Gábor/0000-0001-6524-9147} } @article{MTMT:34760472, title = {Aromatase Inhibitors and Plasma Lipid Changes in Postmenopausal Women with Breast Cancer: A Systematic Review and Meta-Analysis}, url = {https://m2.mtmt.hu/api/publication/34760472}, author = {Bérczi, Bálint and Borbásné Farkas, Kornélia and Hegyi, Péter and Tóth, Barbara and Csupor, Dezső and Németh, Balázs and Lukács, Anita and Czumbel, László Márk and Kerémi, Beáta and Kiss, István and Szabó, Andrea and Varga, Gábor and Gerber, Gábor and Gyöngyi, Zoltán}, doi = {10.3390/jcm13061818}, journal-iso = {J CLIN MED}, journal = {JOURNAL OF CLINICAL MEDICINE}, volume = {13}, unique-id = {34760472}, abstract = {Background: Women are typically diagnosed with estrogen receptor-positive breast cancer around the postmenopausal period when declining estrogen levels initiate changes in lipid profiles. Aromatase inhibitors (AI) are used to prevent the progression of cancer; however, a further reduction in estrogen levels may have detrimental effects on lipid levels, which was our working hypothesis. Methods: Our meta-analysis was conducted on the lipid profiles of postmenopausal breast cancer patients at baseline and at different treatment time points. Results: We identified 15 studies, including 1708 patients. Studies using anastrozole (ANA), exemestane (EXE), letrozole (LET), and tamoxifen (TMX) were involved. Subgroup analyses revealed that 3- and 12-month administrations of LET and EXE lead to negative changes in lipid profiles that tend to alter the lipid profile undesirably, unlike ANA and TMX. Conclusions: Our results suggest that, despite statistically significant results, EXE and LET may not be sufficient to cause severe dyslipidemia in patients without cardiovascular comorbidities according to the AHA/ACC Guideline on the Management of Blood Cholesterol. However, the results may raise the question of monitoring the effects of AIs in patients, especially those with pre-existing cardiovascular risk factors such as dyslipidemia.}, keywords = {[Meta-analysis]}, year = {2024}, eissn = {2077-0383}, orcid-numbers = {Borbásné Farkas, Kornélia/0000-0002-5349-6527; Hegyi, Péter/0000-0003-0399-7259; Tóth, Barbara/0000-0002-6086-8819; Csupor, Dezső/0000-0002-4088-3333; Németh, Balázs/0000-0002-4914-9872; Lukács, Anita/0000-0002-0746-8920; Czumbel, László Márk/0000-0002-5915-0383; Kerémi, Beáta/0000-0003-4000-9440; Szabó, Andrea/0000-0003-4949-9431; Varga, Gábor/0000-0002-5506-8198; Gerber, Gábor/0000-0003-0256-2608; Gyöngyi, Zoltán/0000-0001-9330-9119} } @article{MTMT:34728728, title = {Storage Conditions Influence the Quality of Ginger – A Stability Study Inspired by Clinical Trials}, url = {https://m2.mtmt.hu/api/publication/34728728}, author = {Tóth, Barbara and Horváth, Attila and Jójártné Laczkovich, Orsolya and Biró, Dalma and Matuz, Mária and Csupor, Dezső}, doi = {10.1055/a-2283-8147}, journal-iso = {PLANTA MED}, journal = {PLANTA MEDICA: NATURAL PRODUCTS AND MEDICINAL PLANT RESEARCH}, unique-id = {34728728}, issn = {0032-0943}, abstract = {Ginger has traditionally been used to treat and prevent nausea and vomiting; however, the results of clinical trials are ambiguous. The efficacy of ginger is attributed to gingerols and their metabolites, shogaols. Since these compounds have different pharmacological profiles, the clinical efficacy of ginger products is largely dependent on their chemical composition. The goal of our study was to examine the stability of ginger determining the 6-gingerol contents in order to assess the effects of different storage conditions. We have performed a 6-month stability test with dry ginger rhizome samples stored in a constant climate chamber in three different storage containers (uncovered glass container, glass container sealed with rubber stopper, plastic container). 6-gingerol contents were measured by HPLC method. The concentration of 6-gingerol decreased in all samples. In the sealed glass container, the decrease of 6-gingerol content was significantly lower than in the unsealed glass container and in the plastic container. These results demonstrate that storage conditions have a significant impact on the quality of ginger, which may also affect efficacy.}, year = {2024}, eissn = {1439-0221}, orcid-numbers = {Tóth, Barbara/0000-0002-6086-8819; Matuz, Mária/0000-0002-7877-2399; Csupor, Dezső/0000-0002-4088-3333} } @article{MTMT:34691003, title = {17-Oxime ethers of oxidized ecdysteroid derivatives modulate oxidative stress in human brain endothelial cells and dose-dependently might protect or damage the blood-brain barrier}, url = {https://m2.mtmt.hu/api/publication/34691003}, author = {Vágvölgyi, Máté and Laczkó, Dávid and Santa Maria, Anaraquel and Vigh, Judit Piroska and Walter, Fruzsina and Berkecz, Róbert and Deli, Mária Anna and Tóth, Gábor and Hunyadi, Attila}, doi = {10.1371/journal.pone.0290526}, journal-iso = {PLOS ONE}, journal = {PLOS ONE}, volume = {19}, unique-id = {34691003}, issn = {1932-6203}, abstract = {20-Hydroxyecdysone and several of its oxidized derivatives exert cytoprotective effect in mammals including humans. Inspired by this bioactivity of ecdysteroids, in the current study it was our aim to prepare a set of sidechain-modified derivatives and to evaluate their potential to protect the blood-brain barrier (BBB) from oxidative stress. Six novel ecdysteroids, including an oxime and five oxime ethers, were obtained through regioselective synthesis from a sidechain-cleaved calonysterone derivative 2 and fully characterized by comprehensive NMR techniques revealing their complete 1 H and 13 C signal assignments. Surprisingly, several compounds sensitized hCMEC/D3 brain microvascular endothelial cells to tert -butyl hydroperoxide (tBHP)-induced oxidative damage as recorded by impedance measurements. Compound 8 , containing a benzyloxime ether moiety in its sidechain, was the only one that exerted a protective effect at a higher, 10 μM concentration, while at lower (10 nM– 1 μM) concentrations it promoted tBHP-induced cellular damage. Brain endothelial cells were protected from tBHP-induced barrier integrity decrease by treatment with 10 μM of compound 8 , which also mitigated the intracellular reactive oxygen species production elevated by tBHP. Based on our results, 17-oxime ethers of oxidized ecdysteroids modulate oxidative stress of the BBB in a way that may point towards unexpected toxicity. Further studies are needed to evaluate any possible risk connected to dietary ecdysteroid consumption and CNS pathologies in which BBB damage plays an important role.}, year = {2024}, eissn = {1932-6203}, orcid-numbers = {Vágvölgyi, Máté/0000-0002-2233-9422; Santa Maria, Anaraquel/0000-0003-3505-5477; Walter, Fruzsina/0000-0001-8145-2823; Berkecz, Róbert/0000-0002-9076-2177; Deli, Mária Anna/0000-0001-6084-6524; Hunyadi, Attila/0000-0003-0074-3472} } @article{MTMT:34556248, title = {Diverse diterpenoids and a triterpenoid from Euphorbia spinidens Bornm. ex Prokh}, url = {https://m2.mtmt.hu/api/publication/34556248}, author = {Shakeri, Abolfazl and Mirahmadi, Mohammad Reza and Kunert, Olaf and Tsai, Yu-Chi and Barta, Anita and Hohmann, Judit and Asili, Javad}, doi = {10.1016/j.fitote.2024.105838}, journal-iso = {FITOTERAPIA}, journal = {FITOTERAPIA}, volume = {173}, unique-id = {34556248}, issn = {0367-326X}, year = {2024}, eissn = {1873-6971}, orcid-numbers = {Hohmann, Judit/0000-0002-2887-6392} } @article{MTMT:34541373, title = {Thymoquinone-protoflavone hybrid molecules as potential antitumor agents}, url = {https://m2.mtmt.hu/api/publication/34541373}, author = {AHMED, Sara Hassan Hassan and Tayeb, Bizhar Ahmed and Gonda, Tímea and Girst, Gábor and Szőri, Kornél and Berkecz, Róbert and Zupkó, István and Minorics, Renáta and Hunyadi, Attila}, doi = {10.1371/journal.pone.0291567}, journal-iso = {PLOS ONE}, journal = {PLOS ONE}, volume = {19}, unique-id = {34541373}, issn = {1932-6203}, abstract = {We describe herein the synthesis of eight new ester-coupled hybrid compounds from thymoquinone and protoflavone building blocks, and their bioactivity testing against multiple cancer cell lines. Among the hybrids, compound 14 showed promising activities in all cell lines studied. The highest activities were recorded against breast cancer cell lines with higher selectivity to MDA-MB-231 as compared to MCF-7. Even though the hybrids were found to be completely hydrolysed in 24 h under cell culture conditions, compound 14 demonstrated a ca. three times stronger activity against U-87 glioblastoma cells than a 1:1 mixture of its fragments. Further, compound 14 showed good tumour selectivity: it acted 4.4-times stronger on U-87 cells than on MRC-5 fibroblasts. This selectivity was much lower, only ca. 1.3-times, when the cells were co-treated with a 1:1 mixture of its non-coupled fragments. Protoflavone-thymoquinone hybrids may therefore serve as potential new antitumor leads particularly against glioblastoma.}, year = {2024}, eissn = {1932-6203}, orcid-numbers = {Tayeb, Bizhar Ahmed/0000-0001-5197-564X; Szőri, Kornél/0000-0003-3337-8635; Berkecz, Róbert/0000-0002-9076-2177; Zupkó, István/0000-0003-3243-5300; Minorics, Renáta/0000-0001-9685-813X; Hunyadi, Attila/0000-0003-0074-3472} }