TY - JOUR AU - Gáborová, Mária AU - Vágvölgyi, Máté AU - Tayeb, Bizhar Ahmed AU - Minorics, Renáta AU - Zupkó, István AU - Jurček, Ondřej AU - Béni, Szabolcs AU - Kubínová, Renata AU - Balogh, György Tibor AU - Hunyadi, Attila TI - Diterpenes Isolated from Three Different Plectranthus Sensu Lato Species and Their Antiproliferative Activities against Gynecological and Glioblastoma Cancer Cells JF - ACS OMEGA J2 - ACS OMEGA PY - 2024 SN - 2470-1343 DO - 10.1021/acsomega.4c00800 UR - https://m2.mtmt.hu/api/publication/34779108 ID - 34779108 LA - English DB - MTMT ER - TY - JOUR AU - Vágvölgyi, Máté AU - Laczkó, Dávid AU - Santa Maria, Anaraquel AU - Vigh, Judit Piroska AU - Walter, Fruzsina AU - Berkecz, Róbert AU - Deli, Mária Anna AU - Tóth, Gábor AU - Hunyadi, Attila TI - 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 JF - PLOS ONE J2 - PLOS ONE VL - 19 PY - 2024 IS - 2 PG - 15 SN - 1932-6203 DO - 10.1371/journal.pone.0290526 UR - https://m2.mtmt.hu/api/publication/34691003 ID - 34691003 N1 - Institute of Pharmacognosy, University of Szeged, Szeged, Hungary Institute of Biophysics, HUN-REN Biological Research Centre, Szeged, Hungary Wyss Institute for Biologically Inspired Engineering, Harvard University, Boston, MA, United States Doctoral School of Biology, University of Szeged, Szeged, Hungary Institute of Pharmaceutical Analysis, University of Szeged, Szeged, Hungary NMR Group, Department of Inorganic and Analytical Chemistry, Budapest University of Technology and Economics, Budapest, Hungary Interdisciplinary Centre of Natural Products, University of Szeged, Szeged, Hungary HUN-REN-SZTE Biologically Active Natural Products Research Group, Szeged, Hungary Export Date: 18 March 2024 CODEN: POLNC Correspondence Address: Hunyadi, A.; Institute of Pharmacognosy, Hungary; email: hunyadi.attila@szte.hu AB - 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. LA - English DB - MTMT ER - TY - CONF AU - Háznagy, Márton Benedek AU - Vágvölgyi, Máté AU - Krishnan, Sandhya R. AU - Gertsch, Jürg AU - Hunyadi, Attila ED - Hohmann, Judit TI - Antitrypanosomal activity of natural and semi-synthetic ecdysteroids T2 - 4th Symposium of Young Researchers on Pharmacognosy PB - Institute of Pharmacognosy, Faculty of Pharmacy, University of Szeged C1 - Szeged PY - 2023 SP - 16 EP - 16 PG - 1 DO - 10.14232/syrmpnpr.2023.10 UR - https://m2.mtmt.hu/api/publication/33963548 ID - 33963548 LA - English DB - MTMT ER - TY - CONF AU - Gáborová, Mária AU - Vágvölgyi, Máté AU - Hunyadi, Attila AU - Béni, Szabolcs AU - Kubínová, Renata ED - Hohmann, Judit TI - Structure elucidation of diterpenoids isolated from three Plectranthus sensu lato species T2 - 4th Symposium of Young Researchers on Pharmacognosy PB - Institute of Pharmacognosy, Faculty of Pharmacy, University of Szeged C1 - Szeged PY - 2023 SP - 8 EP - 8 PG - 1 DO - 10.14232/syrmpnpr.2023.2 UR - https://m2.mtmt.hu/api/publication/33963351 ID - 33963351 LA - English DB - MTMT ER - TY - JOUR AU - Krstić, Gordana AU - Saidu, Muhammad Bello AU - Barta, Anita AU - Vágvölgyi, Máté AU - Ali, Hazhmat AU - Zupkó, István AU - Berkecz, Róbert AU - Gallah, Umar Shehu AU - Rédei, Dóra AU - Hohmann, Judit TI - Anticancer Meroterpenoids from Centrapalus pauciflorus leaves: Chromone- and 2,4-Chromadione-Monoterpene Derivatives JF - ACS OMEGA J2 - ACS OMEGA VL - 8 PY - 2023 IS - 34 SP - 31389 EP - 31398 PG - 10 SN - 2470-1343 DO - 10.1021/acsomega.3c03884 UR - https://m2.mtmt.hu/api/publication/34103969 ID - 34103969 N1 - Department of Pharmacognosy, University of Szeged, Eötvös u. 6, Szeged, 6720, Hungary University of Belgrade, Faculty of Chemistry, Studentski trg 12-16, Belgrade, 11158, Serbia Institute of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6, Szeged, 6720, Hungary Institute of Pharmaceutical Analysis, University of Szeged, Somogyi u. 4, Szeged, 6720, Hungary Bioresource Department, National Research Institute for Chemical Technology (NARICT), Zaria, 1052, Nigeria ELKH-USZ Biologically Active Natural Products Research Group, University of Szeged, Eötvös u. 6, Szeged, 6720, Hungary Export Date: 19 October 2023 Correspondence Address: Rédei, D.; Department of Pharmacognosy, Eötvös u. 6, Hungary; email: redei.dora@szte.hu Correspondence Address: Hohmann, J.; Department of Pharmacognosy, Eötvös u. 6, Hungary; email: hohmann.judit@szte.hu Funding details: TKP2021-EGA-32 Funding details: Nemzeti Kutatási Fejlesztési és Innovációs Hivatal, NKFIH, K 143690, ÚNKP-22-4-SZTE-169 Funding details: Nemzeti Kutatási, Fejlesztési és Innovaciós Alap, NKFIA Funding text 1: The authors thank the financial support provided by the Ministry of Innovation and Technology of Hungary from NKFIH Fund, project no. TKP2021-EGA-32. Support from Hungarian Research and Innovation Foundation (NKFI), grant number K 143690, is acknowledged. M. Vágvölgyi was supported by the ÚNKP-22-4-SZTE-169 New National Excellence Program of the Ministry for Culture and Innovation from the source of the National Research, Development and Innovation Fund. LA - English DB - MTMT ER - TY - CHAP AU - Alaa, A.M. Osman AU - Laczkó, Dávid AU - Vágvölgyi, Máté AU - Hunyadi, Attila AU - Ducza, Eszter ED - Muszynska, Bozena TI - Effects of calonysterone and 20-hydroxyecdysone in the obese rat model T2 - Natural vs. Artificial Networks: The Usefulness of the Concept in Health, Life, and Technical Sciences PB - Zakład Optymalizacji Zawodowej Ośrodek Umea Shinoda-Kuracejo CY - Martin CY - Krakow CY - Szeged SN - 9788395955457 PY - 2022 SP - 83 PG - 1 UR - https://m2.mtmt.hu/api/publication/33552107 ID - 33552107 AB - Obesity is a global pandemic and a serious health problem. Phytoecdysteroids, the polyhydroxylated steroids of the C-27 cholesterol skeleton, has a wide variety of beneficial effects including anabolic, antidiabetic, and anti-obesity. Our studies aimed to investigate the effects of two phytoecdysteroids derivatives (calonysterone and 20-hydroxyecdysone) on body weight, blood glucose, antioxidant capacity, and the level of adipokines, the expression of cytokines of lowgrade inflammation, and the epigenetic modification in the obese rat model. 48 male Sprague Dawley rats, aged 5-6 weeks were divided into 8 groups (6 rats/group) and fed high fat and high sugar diet (HFHSD) or a normal diet. Rats received daily oral treatments for 12 weeks of calonysterone, 20-hydroxyecdysone, vehicle, or no treatment. Body weight, caloric intake, and plasma glucose during the glucose tolerance test were measured at baseline and during the experiment. We measured the liver levels of catalase (CAT) and superoxide dismutase (SOD), total antioxidant capacity (T-AOC), and global DNA methylation using colorimetric assay kits. The hepatic expression of leptin, adiponectin, TNF α, IL-6, IL2, and IL10 mRNA and protein were measured using RT-PCR and western blot, respectively. CAT levels were increased by both treatments, while T-AOC increased by 20-hydroxyecdysone. Obese rats showed increased expression of leptin mRNA and protein levels that were reduced by calonysterone. 20-hydroxyecdysone further increased leptin mRNA but reduced protein levels. The levels of global DNA methylation were increased by both treatments. Calonysterone may have anti-obesity effects and both treatments may have antidiabetic and antioxidant effects. Our preliminary screening of the effects of treatments on markers of inflammation showed significant differences in the levels of IL-6 and IL10 between normal and obese rats. We suppose these phytoecdysteroids may affect epigenetic modification at specific gene levels too. LA - English DB - MTMT ER - TY - JOUR AU - Háznagy, Márton Benedek AU - Vágvölgyi, Máté AU - Krishnan, S R AU - Gertsch, J AU - Hunyadi, Attila TI - Antitrypanosomal activity of semisyntetic enone-type derivatives JF - PLANTA MEDICA: NATURAL PRODUCTS AND MEDICINAL PLANT RESEARCH J2 - PLANTA MED VL - 88 PY - 2022 IS - 15 SP - 1534 SN - 0032-0943 DO - 10.1055/s-0042-1759246 UR - https://m2.mtmt.hu/api/publication/33686924 ID - 33686924 LA - English DB - MTMT ER - TY - JOUR AU - Ntungwe, Epole N. AU - Stojanov, Sofija Jovanović AU - Duarte, Noélia M. AU - Candeias, Nuno R. AU - Díaz-Lanza, Ana M. AU - Vágvölgyi, Máté AU - Hunyadi, Attila AU - Pešić, Milica AU - Rijo, Patrícia TI - C20-nor-Abietane and Three Abietane Diterpenoids from Plectranthus mutabilis Leaves as P-Glycoprotein Modulators JF - ACS MEDICINAL CHEMISTRY LETTERS J2 - ACS MED CHEM LETT VL - 13 PY - 2022 IS - 4 SP - 674 EP - 680 PG - 7 SN - 1948-5875 DO - 10.1021/acsmedchemlett.1c00711 UR - https://m2.mtmt.hu/api/publication/33041582 ID - 33041582 LA - English DB - MTMT ER - TY - JOUR AU - Saidu, Muhammad Bello AU - Kúsz, Norbert AU - Tsai, Yu-Chi AU - Vágvölgyi, Máté AU - Berkecz, Róbert AU - Kókai, Dávid AU - Burián, Katalin AU - Hohmann, Judit AU - Rédei, Dóra TI - Triterpenes and Phenolic Compounds from Euphorbia deightonii with Antiviral Activity against Herpes Simplex Virus Type-2 JF - PLANTS-BASEL J2 - PLANTS-BASEL VL - 11 PY - 2022 IS - 6 PG - 10 SN - 2223-7747 DO - 10.3390/plants11060764 UR - https://m2.mtmt.hu/api/publication/32765771 ID - 32765771 N1 - This research was funded by the Economic Development and Innovation Operative Programme (GINOP-2.3.2-15-2016-00012) and the National Research, Development and Innovation Fund (NKFI) under grant number K135845. M.B.S. was supported by the Stipendium Hungaricum scholarship program. AB - Two undescribed compounds, 3 beta,7 beta-dihydroxy-24-methylenelanosta-8-ene-11-one (1) and neolignane deightonin (4) were isolated from the aerial parts of Euphorbia deightonii Croizat together with six known compounds, namely, kansenone (2), euphorbol-7-one (3), dehydrodiconiferyl diacetate (5), marylaurencinol D (6), scoparon (7), and 3,4,3'-tri-O-methylellagic acid (8). The structures of the isolated compounds were determined by HRESIMS, 1D (H-1, C-13 JMOD) and 2D NMR (HSQC, HMBC, H-1-H-1 COSY, NOESY) spectroscopic analysis, and by comparison of the assignments with literature data. The anti-herpes simplex virus type-2 activity of the isolated compounds were investigated by qRT-PCR assay on Vero cells after determining cytotoxic concentration 50% (CC50). Compounds 1, 3, 4, and 7 exhibited inhibitory effects with respective IC50 values of 7.05, 2.42, 11.73, and 0.032 mu M. Scoparon (7) showed the strongest anti-HSV activity with a selectivity index of 10.93. LA - English DB - MTMT ER - TY - JOUR AU - Szerencsés, Bettina AU - Vörös, Mónika AU - Bagi, Kristóf AU - Háznagy, Márton Benedek AU - Hunyadi, Attila AU - Vágvölgyi, Csaba AU - Pfeiffer, Ilona AU - Vágvölgyi, Máté TI - Semi-Synthetic Ecdysteroid 6-Oxime Derivatives of 20-Hydroxyecdysone Possess Anti-Cryptococcal Activity JF - MICROBIOLOGY RESEARCH J2 - MICROBIOL RES-ITALY VL - 13 PY - 2022 IS - 4 SP - 985 EP - 994 PG - 10 SN - 2036-7473 DO - 10.3390/microbiolres13040071 UR - https://m2.mtmt.hu/api/publication/33538161 ID - 33538161 N1 - Department of Microbiology, Faculty of Science and Informatics, University of Szeged, Szeged, 6726, Hungary Institute of Pharmacognosy, Faculty of Pharmacy, University of Szeged, Szeged, 6720, Hungary Export Date: 28 March 2023 Correspondence Address: Vágvölgyi, C.; Department of Microbiology, Hungary; email: csaba@bio.u-szeged.hu Correspondence Address: Pfeiffer, I.; Department of Microbiology, Hungary; email: pfeiffer@bio.u-szeged.hu Chemicals/CAS: ecdysterone, 5289-74-7; indometacin, 53-86-1, 74252-25-8, 7681-54-1; quinidine, 56-54-2; verapamil, 152-11-4, 52-53-9 AB - Cryptococcosis, a life-threatening fungal infection, frequently occurs in patients suffering from AIDS. The treatment of the disease is hampered by the limited number of the effective drugs and the increasing resistance; therefore, to find new active substances is needed. As meningitis is the most serious infection affecting the AIDS patients, effective drugs have to be capable of entering to the central nervous system. Ecdysteroids are natural bioactive molecules with considerable anabolic activity and without toxic side effects on humans. The aim of this work was to study the anti-cryptococcal activity of a natural ecdysteroid, 20E, and its three semi-synthetic derivatives obtained by structural modification of the original molecule. We established the minimum inhibitory concentration of the compounds with microdilution method and demonstrated their fungicidal activity by flow cytometry and cultivation of the drug-treated cells. The interaction of the compounds with each other and efflux transporter inhibitors was assessed by checkerboard titration method. Two derivatives, 20E-EOx and 20E-ZOx, inhibited the growth of Cryptococcus neoformans with minimum inhibitory concentration 2 mg/mL and 1 mg/mL, respectively; both compounds possess fungicidal effect. A combination of the ecdysteroids with each other and verapamil resulted in additive interaction. This study confirmed that structural modification of an originally non-antimicrobial molecule can enhance its effectiveness. LA - English DB - MTMT ER -