TY - JOUR AU - Linzembold, I. AU - Gulyás, Gergely AU - Deli, József AU - Agócs, Attila AU - Nagy, Veronika TI - Synthesis of phenolic acids esters of carotenoids JF - CAROTENOID SCIENCE J2 - CAROTENOID SCI VL - 25 PY - 2023 SP - 156 EP - 156 PG - 1 SN - 1880-5671 UR - https://m2.mtmt.hu/api/publication/34833060 ID - 34833060 LA - English DB - MTMT ER - TY - JOUR AU - Balázs, Viktória Lilla AU - Gulyás, Gergely AU - Nagy, Veronika AU - Zubay, Péter AU - Szabó, Krisztina AU - Sándor, Viktor AU - Agócs, Attila AU - Deli, József TI - Carotenoid Composition of Calendula officinalis Flowers with Identification of the Configuration of 5,8-Epoxy-carotenoids JF - ACS AGRICULTURAL SCIENCE & TECHNOLOGY J2 - ACS AGRIC SCI TECHNOL VL - 3 PY - 2023 IS - 11 SP - 1092 EP - 1102 PG - 11 SN - 2692-1952 DO - 10.1021/acsagscitech.3c00367 UR - https://m2.mtmt.hu/api/publication/34274821 ID - 34274821 N1 - Department of Pharmacognosy, Faculty of Pharmacy, University of Pécs, Rókus u. 2., Pécs, H-7624, Hungary Department of Biochemistry and Medical Chemistry, Medical School, University of Pécs, Szigeti út 12, Pécs, 7624, Hungary Institute of Bioanalytics, Medical School, University of Pécs, Szigeti út 12., Pécs, H-7624, Hungary Department of Medicinal and Aromatic Plants, Institute of Sustainable Horticulture, Hungarian University of Agriculture and Life Sciences, Villányi str. 29-43., Budapest, H-1118, Hungary Export Date: 11 December 2023 Correspondence Address: Deli, J.; Department of Pharmacognosy, Rókus u. 2., Hungary; email: jozsef.deli@aok.pte.hu LA - English DB - MTMT ER - TY - JOUR AU - Nagy, Veronika AU - Agócs, Attila AU - Balázs, Viktória Lilla AU - Purger, Dragica AU - Filep, Rita AU - Sándor, Viktor AU - Turcsi, Erika Margit AU - Gulyás, Gergely AU - Deli, József TI - Lutein Isomers: Preparation, Separation, Structure Elucidation, and Occurrence in 20 Medicinal Plants JF - MOLECULES J2 - MOLECULES VL - 28 PY - 2023 IS - 3 PG - 18 SN - 1420-3049 DO - 10.3390/molecules28031187 UR - https://m2.mtmt.hu/api/publication/33597596 ID - 33597596 N1 - Department of Biochemistry and Medical Chemistry, Medical School, University of Pécs, Szigeti út 12, Pécs, H-7624, Hungary Department of Pharmacognosy, Faculty of Pharmacy, University of Pécs, Rókus u. 2, Pécs, H-7624, Hungary Institute of Bioanalysis, Medical School, University of Pécs, Szigeti út 12, Pécs, H-7624, Hungary Cited By :2 Export Date: 3 May 2024 CODEN: MOLEF Correspondence Address: Deli, J.; Department of Biochemistry and Medical Chemistry, Szigeti út 12, Hungary; email: jozsef.deli@aok.pte.hu AB - Lutein and its cis-isomers occur in a lot of plants, including a variety of flowers. In this study, lutein isomers were produced via iodine-catalyzed isomerization, and four cis-isomers (9Z-, 9′Z-, 13Z-, and 13Z′) were isolated by means of column chromatography and semipreparative HPLC. The structures of the 9′Z- and 13′Z-isomers were elucidated via NMR measurements. These compounds were used as standards for the HPLC-DAD-MS determination of the carotenoid composition of the flowers of 20 plant species, in which lutein and its geometrical isomers are the main components. The flowers showed great variation in their cis- and trans-lutein content, and also in the presence or absence of other carotenoids, such as violaxanthin, neoxanthin, β-cryptoxanthin, and β-carotene. Some of the investigated flowers were found to be rich sources of lutein without zeaxanthin. LA - English DB - MTMT ER - TY - JOUR AU - Garai, János AU - Radnai, Balázs AU - Vámos, Eszter AU - Kovács, Dominika AU - Bagóné Vántus, Viola AU - Rumbus, Zoltán AU - Pákai, Eszter AU - Garami, András AU - Gulyás, Gergely AU - Agócs, Attila AU - Krekó, Marcell AU - Zaman, K. AU - Prókai, L. AU - Őrfi, László AU - Jakus, Péter AU - Lóránd, Tamás TI - Synthesis and evaluation of a new class of MIF-inhibitors in activated macrophage cells and in experimental septic shock in mice JF - EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY J2 - EUR J MED CHEM VL - 247 PY - 2023 PG - 11 SN - 0223-5234 DO - 10.1016/j.ejmech.2022.115050 UR - https://m2.mtmt.hu/api/publication/33546311 ID - 33546311 LA - English DB - MTMT ER - TY - JOUR AU - Huber, Imre AU - Pandur, Edina AU - Sipos, Katalin AU - Barna, Lilla AU - Harazin, András AU - Deli, Mária Anna AU - Tyukodi, Levente AU - Gulyás, Gergely AU - Kulcsár, Győző AU - Rozmer, Zsuzsanna TI - Novel cyclic C5-curcuminoids penetrating the blood-brain barrier: design, synthesis and antiproliferative activity against astrocytoma and neuroblastoma cells JF - EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES J2 - EUR J PHARM SCI VL - 173 PY - 2022 PG - 29 SN - 0928-0987 DO - 10.1016/j.ejps.2022.106184 UR - https://m2.mtmt.hu/api/publication/32779076 ID - 32779076 AB - Novel series of cyclic C5-curcuminoids 17a-j and 19-22 were prepared as cytotoxic agents and evaluated against human neuroblastoma (SH-SY5Y) or human grade IV astrocytoma (CCF-STTG1) cell lines in low (∼0.1 nM - 10 nM) concentrations. Among the tested 21 derivatives, 16 displayed potent antiproliferative activity with IC50 values in the low nanomolar to picomolar range (IC50 = 7.483-0.139 nM). Highly active compounds like N-monocarboxylic derivative 19b with IC50 = 0.139 nM value against neuroblastoma and N-alkyl substituted 11 with IC50 = 0.257 nM against astrocytoma proved some degree of selectivity toward non-cancerous astrocytes and kidney cells. This potent anticancer activity did not show a strong correlation with experimental logPTLC values, but the most potent antiproliferative molecules 11-13 and 19-22 are belonging to discrete subgroups of the cyclic C5-curcuminoids. Compounds 12, 17c and 19b were subjected to blood-brain barrier (BBB) penetration studies, too. The BBB was revealed to be permeable for all of them but, as the apparent permeability coefficient (Papp) values mirrored, in different ratios. Lower toxicity of 12, 17c and 19b was observed toward primary rat brain endothelial cells of the BBB model, which means they remained undamaged under 10 µM concentrations. Penetration depends, at least in part, on albumin binding of 12, 17c and 19b and the presence of monocarboxylic acid transporters in the case of 19b. Permeation through the BBB and albumin binding, we described here, is the first example of cyclic C5-curcuminoids as to our knowledge. LA - English DB - MTMT ER - TY - JOUR AU - Horváth, Györgyi AU - Csikós, Eszter AU - Andres, Eichertné Violetta AU - Bencsik, Tímea AU - Takátsy, Anikó AU - Gulyás, Gergely AU - Turcsi, Erika Margit AU - Deli, József AU - Szőke, Éva AU - Kemény, Ágnes AU - Payrits, Maja AU - Szente, Lajos AU - Kocsis, Marianna AU - Molnár, Péter AU - Helyes, Zsuzsanna TI - Analyzing the Carotenoid Composition of Melilot (Melilotus officinalis (L.) Pall.) Extracts and the Effects of Isolated (All-E)-lutein-5,6-epoxide on Primary Sensory Neurons and Macrophages JF - MOLECULES J2 - MOLECULES VL - 26 PY - 2021 IS - 2 PG - 13 SN - 1420-3049 DO - 10.3390/molecules26020503 UR - https://m2.mtmt.hu/api/publication/31823277 ID - 31823277 N1 - Funding Agency and Grant Number: NKFI [K 128253]; National Brain Research Program-2 [20017-1.2.1-NKP -2017-00002, GINOP-2.3.2-15-2016-00048, EFOP-362-16-2017-00006]; Janos Bolyai fellowship of the Hungarian Academy of Sciences; New National Excellence Program of the Ministry for Innovation and Technology [UNKP-18-4, UNKP-19-4]; University of Pecs [17886-4/23018] Funding text: J. Deli was supported by NKFI K 128253 grants. This work was sponsored by National Brain Research Program-2 20017-1.2.1-NKP -2017-00002. (NAP-2; Chronic Pain Research Group), GINOP-2.3.2-15-2016-00048, and EFOP-362-16-2017-00006. E. Sz oke and A. Kemeny were supported by Janos Bolyai fellowship of the Hungarian Academy of Sciences and the New National Excellence Program of the Ministry for Innovation and Technology UNKP-18-4 an UNKP-19-4. The University of Pecs is acknowledged for a support by the 17886-4/23018/FEKUTSTRAT excellence grant. LA - English DB - MTMT ER - TY - JOUR AU - Linzembold, Ildikó Erzsébet AU - Czett, Dalma AU - Böddi, Katalin AU - Kurtán, Tibor AU - Király, Sándor Balázs AU - Gulyás, Gergely AU - Takátsy, Anikó AU - Lóránd, Tamás AU - Deli, József AU - Agócs, Attila AU - Nagy, Veronika TI - Study on the Synthesis, Antioxidant Properties, and Self-Assembly of Carotenoid–Flavonoid Conjugates JF - MOLECULES J2 - MOLECULES VL - 25 PY - 2020 IS - 3 PG - 21 SN - 1420-3049 DO - 10.3390/molecules25030636 UR - https://m2.mtmt.hu/api/publication/31155279 ID - 31155279 AB - Flavonoids and carotenoids possess beneficial physiological effects, such as high antioxidant capacity, anticarcinogenic, immunomodulatory, and anti-inflammatory properties, as well as protective effects against UV light. The covalent coupling of hydrophobic carotenoids with hydrophilic flavonoids, such as daidzein and chrysin, was achieved, resulting in new amphipathic structures. 7-Azidohexyl ethers of daidzein and chrysin were prepared in five steps, and their azide-alkyne [4 + 2] cycloaddition with pentynoates of 80-apo-β-carotenol, zeaxanthin, and capsanthin afforded carotenoid–flavonoid conjugates. The trolox-equivalent antioxidant capacity against ABTS•+ radical cation and self-assembly of the final products were examined. The 1:1 flavonoid–carotenoid hybrids generally showed higher antioxidant activity than their parent flavonoids but lower than that of the corresponding carotenoids. The diflavonoid hybrids of zeaxanthin and capsanthin, however, were found to exhibit a synergistic enhancement in antioxidant capacities. ECD (electronic circular dichroism) and UV-vis analysis of zeaxanthin–flavonoid conjugates revealed that they form different optically active J-aggregates in acetone/water and tetrahydrofuran/water mixtures depending on the solvent ratio and type of the applied aprotic polar solvent, while the capsanthin derivatives showed no self-assembly. The zeaxanthin bis-triazole conjugates with daidzein and with chrysin, differing only in the position of a phenolic hydroxyl group, showed significantly different aggregation profile upon the addition of water. LA - English DB - MTMT ER - TY - JOUR AU - Isbera, Mostafa AU - Bognár, Balázs AU - Gulyás, Gergely AU - Kish, K. AU - Kálai, Tamás TI - Syntheses of Pyrazine-, Quinoxaline-, and Imidazole-Fused Pyrroline Nitroxides JF - SYNTHESIS-STUTTGART J2 - SYNTHESIS-STUTTGART VL - 51 PY - 2019 IS - 23 SP - 4463 EP - 4472 PG - 10 SN - 0039-7881 DO - 10.1055/s-0039-1690678 UR - https://m2.mtmt.hu/api/publication/30931345 ID - 30931345 LA - English DB - MTMT ER - TY - JOUR AU - Berzaghi, R. AU - Agócs, Attila AU - Gulyás, Gergely AU - Kocsis, Béla AU - Ribas, J.C. AU - Lóránd, Tamás TI - Novel cell wall antifungals reveal a special synergistic activity in pbr1 mutants resistant to the glucan synthesis antifungals papulacandins and echinocandins JF - FRONTIERS IN MICROBIOLOGY J2 - FRONT MICROBIOL VL - 10 PY - 2019 PG - 12 SN - 1664-302X DO - 10.3389/fmicb.2019.01692 UR - https://m2.mtmt.hu/api/publication/30758489 ID - 30758489 LA - English DB - MTMT ER - TY - JOUR AU - Huber, Imre AU - Zupkó, István AU - Gyovai, András AU - Horváth, Péter AU - Kiss, Eszter AU - Gulyás, Gergely AU - Schmidt, János AU - Perjési, Pál TI - A novel cluster of C5-curcuminoids: design, synthesis, in vitro antiproliferative activity and DNA binding of bis(arylidene)-4-cyclanone derivatives based on 4-hydroxycyclohexanone scaffold JF - RESEARCH ON CHEMICAL INTERMEDIATES J2 - RES CHEM INTERMEDIAT VL - 45 PY - 2019 IS - 9 SP - 4711 EP - 4735 PG - 25 SN - 0922-6168 DO - 10.1007/s11164-019-03859-4 UR - https://m2.mtmt.hu/api/publication/30705043 ID - 30705043 N1 - Department of Pharmaceutical Chemistry, University of Pécs, Pecs, 7624, Hungary Department of Pharmacodynamics and Biopharmacy, University of Szeged, Szeged, 6720, Hungary Department of Pharmaceutical Chemistry, Semmelweis University, Budapest, 1092, Hungary Department of Biochemistry and Medical Chemistry, University of Pécs, Pecs, 7624, Hungary Cited By :7 Export Date: 19 October 2023 CODEN: RCINE Correspondence Address: Huber, I.; Department of Pharmaceutical Chemistry, Hungary; email: imre.huber@aok.pte.hu Funding details: Pécsi Tudományegyetem, PTE, PTE ÁOK-KA-34039-12/10-11 Funding text 1: Open access funding provided by University of Pécs (PTE). This work was supported by the University of Pécs, Faculty of Medicine Research Fund PTE ÁOK-KA-34039-12/10-11. LA - English DB - MTMT ER -