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001-es BibID:BIBFORM090960
035-os BibID:(WOS)000595546200005 (Scopus)85096236870
Első szerző:Bús Csaba
Cím:Oxidized Juncuenin B Analogues with Increased Antiproliferative Activity on Human Adherent Cell Lines: Semisynthesis and Biological Evaluation / Csaba Bús, Ágnes Kulmány, Norbert Kúsz, Tímea Gonda, István Zupkó, Attila Mándi, Tibor Kurtán, Barbara Tóth, Judit Hohmann, Attila Hunyadi, Andrea Vasas
Dátum:2020
ISSN:0163-3864 1520-6025
Megjegyzések:Phenanthrenes have become the subject of intensive research during the past decades because of their structural diversity and wide range of pharmacological activities. Earlier studies demonstrated that semisynthetic derivatization of these natural compounds could result in more active agents, and oxidative transformations are particularly promising in this regard. In our work, a natural phenanthrene, juncuenin B, was transformed by hypervalent iodine(III) reagents using a diversity-oriented approach. Eleven racemic semisynthetic compounds were produced, the majority containing an alkyl substituted p-quinol ring. Purification of the compounds was carried out by chromatographic techniques, and their structures were elucidated by 1D and 2D NMR spectroscopic methods. Stereoisomers of the bioactive derivatives were separated by chiral-phase HPLC and the absolute configurations of the active compounds, 2,6-dioxo-1,8a-dimethoxy-1,7-dimethyl-8-vinyl-9,10-dihydrophenanthrenes (1a-d), and 8a-ethoxy-1,7-dimethyl-6-oxo-8-vinyl-9,10-dihydrophenanthrene-2-ols (7a,b) were determined by ECD measurements and TDDFT-ECD calculations. The antiproliferative activities of the compounds were tested on different (MCF-7, T47D, HeLa, SiHa, C33A, A2780) human gynecological cancer cell lines. Compounds 1a-d, 4a, 6a, and 7a possessed higher activity than juncuenin B on several tumor cell lines. The structure-activity relationship studies suggested that the p-quinol (2,5-cyclohexadien-4-hydroxy-1-one) moiety has a considerable effect on the antiproliferative properties, and substantial differences could be identified in the activities of the stereoisomers.
Tárgyszavak:Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban
folyóiratcikk
Megjelenés:Journal of Natural Products. - 83 : 11 (2020), p. 3250-3261. -
További szerzők:Kulmány Ágnes Kúsz Norbert Gonda Tímea Zupkó István Mándi Attila (1981-) (vegyész, német szakfordító) Kurtán Tibor (1973-) (vegyész, angol szakfordító) Tóth Barbara Hohmann Judit Hunyadi Attila Vasas Andrea
Pályázati támogatás:UNKP-18-3-SZTE-169
Egyéb
UNKP-19-3-SZTE-169
Egyéb
20391-3/2018/FEKUSTRAT
Egyéb
NKFIH K128963
Egyéb
NKFIH K119770
Egyéb
NKFIH K120181
Egyéb
GINOP-2.3.2-15-2016-00012
GINOP
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2.

001-es BibID:BIBFORM077125
Első szerző:Rédei Dóra
Cím:14-Noreudesmanes and a phenylpropane heterodimer from sea buckthorn berry inhibit Herpes simplex type 2 virus replication / Rédei Dóra, Kúsz Norbert, Rafai Tímea, Bogdanov Anita, Burián Katalin, Csorba Attila, Mándi Attila, Kurtán Tibor, Vasas Andrea, Hohmann Judit
Dátum:2019
ISSN:0040-4020
Megjegyzések:Two new 14-noreudesmane sesquiterpenes, one new phenylpropane heterodimer, caulilexin C, and uvaol were isolated from the 70% MeOH extract of the fruit peel of Elaeagnus rhamnoides. The structures of the compounds were elucidated by HRESIMS and advanced NMR methods. The absolute configuration of (R)-6,9-dihydroxy-1-oxo-14-noreudesm-5,7,9-triene was determined by the TDDFT-ECD method. The new compounds, together with structurally similar naphthalenes (musizin, musizin-8-O-glucoside, torachrysone-8-O-glucoside) and 1,4-naphthoquinone (2-methylstipandrone), isolated previously from Rumex aquaticus, were investigated for their antiviral activity against Herpes simplex virus type 2 (HSV-2) using two different methods. Applying the traditional virus yield reduction test, (R)-6,9-dihydroxy-1-oxo-14-noreudesm-5,7,9-triene, 1-[3-methoxy-4-(2-methoxy-4-(1E)-propenyl-phenoxy)-phenyl]-propane-1,2-diol, and musizin caused a 2.00 log10, 3.49 log10, and 2.33 log10 reduction of HSV-2 yield, respectively, at a concentration of 12.5 mM. 2-Hydroxy-1-methoxy-6,9-dioxo-14-noreudesm-1,3,5(10),7-tetraene exhibited an antiviral effect at concentration of 50 mM only. Similar results were obtained when the qPCR method was used to test the antiviral activity of the compounds.
Tárgyszavak:Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban
Elaeagnus rhamnoides
Hippophae rhamnoides
Sea buckthorn
Noreudesmane
Phenylpropane dimer
Anti-HSV2-activity
Megjelenés:Tetrahedron. - 75 : 10 (2019), p. 1364-1370. -
További szerzők:Kúsz Norbert Rafai Tímea Bogdanov Anita Burián Katalin Csorba Attila Mándi Attila (1981-) (vegyész, német szakfordító) Kurtán Tibor (1973-) (vegyész, angol szakfordító) Vasas Andrea Hohmann Judit
Pályázati támogatás:GINOP-2.3.2-15-2016-00012
GINOP
K120181
OTKA
PD121020
OTKA
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3.

001-es BibID:BIBFORM066440
Első szerző:Tóth Barbara
Cím:Screening of Luzula species native to the Carpathian Basin for anti-inflammatory activity and bioactivity-guided isolation of compounds from Luzula luzuloides (Lam.) Dandy & Wilmott / Barbara Tóth, Fang-Rong Chang, Tsong-Long Hwang, Ádám Szappanos, Attila Mándi, Attila Hunyadi, Tibor Kurtán, Gusztáv Jakab, Judit Hohmann, Andrea Vasas
Dátum:2017
ISSN:0367-326X
Megjegyzések:The present study focused on the anti-in flammatory screening of Luzula species native to the Carpathian Basin and bioactivity-guided isolation of compounds ofLuzula luzuloides (Lam.) Dandy & Wilmott. The anti-in flammatory properties of extracts with different polarity prepared from Luzula species were determined. Among them, the CH2Cl2-soluble fraction of L. luzuloides possessed strong inhibitory effects on superoxide anion generation (99.39 ? 0.37%) and elastase release (114.22 ? 3.13%) in fMLP/CB-induced human neutrophils at concentration of 10 ?g/mL. From this fraction, six compounds (1-6) were isolated by the combination of different chromatographic methods. The structures of the compounds were determined by means of MS, 1D and 2D NMR spectroscopy. The results allowed the identi fication of the new 1,6-dihydroxy-2-keto-1,7-dimethyl-8-vinyl-1,2-dihydrophenanthrene (1) from the plant, named luzulin A. Chiral HPLC and HPLC-ECD analysis revealed that 1 possesses low enantiomeric excess and TDDFT-ECD calculations afforded the con figurational assignment of the separated enantiomers. Three known phenanthrenes [juncuenin B (2), dehydrojuncuenin B (3) and juncusol (4)] and two flavonoids [apigenin (5) and luteolin (6)] were also isolated. The anti-in flammatory activity of the isolated compounds was tested and IC50 values were determined. This was the first time that phenanthrenes were detected in a Luzula species. The oxidative transformation of juncuenin B (3) led to the isolation of its possible biometabolites, namely luzulin A (1), dehydrojuncuenin B (4), and juncuenin D (7). The isolated compounds (1-4) con firm that besides flavonoids, phenanthrenes could also serve as chemotaxonomic markers for Luzula species and prove the close relationship of Juncus and Luzula genus.
Tárgyszavak:Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban
Juncaceae
Luzula luzuloides
Phenanthrenes
Flavonoids
Anti-in flammatory activity
Electronic circular dichroism
Megjelenés:Fitoterapia 116 (2017), p. 131-138. -
További szerzők:Chang, Fang-Rong Hwang, Tsong-Long Szappanos Ádám (1989-) (vegyész) Mándi Attila (1981-) (vegyész, német szakfordító) Hunyadi Attila Kurtán Tibor (1973-) (vegyész, angol szakfordító) Jakab Gusztáv Hohmann Judit Vasas Andrea
Pályázati támogatás:K109846
OTKA
NKFI K 120181, PD 121020
Egyéb
NIIFI 10038
Egyéb
Internet cím:DOI
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4.

001-es BibID:BIBFORM066257
035-os BibID:(WOS)000394410600007 (Scopus)84999089908
Első szerző:Tóth Barbara
Cím:Phenanthrenes from Juncus inflexus with Antimicrobial Activity against Methicillin-Resistant Staphylococcus aureus / Barbara Tóth, Erika Liktor-Busa, Norbert Kúsz, Ádám Szappanos, Attila Mándi, Tibor Kurtán, Edit Urbán, Judit Hohmann, Fang-Rong Chang, Andrea Vasas
Dátum:2016
ISSN:0163-3864
Megjegyzések:The present study has focused on an investigation of the antibacterial effects of Juncus inflexus and the isolation and identification of its active compounds. Eleven phenanthrenes were isolated from a methanolic extract of the roots. Four compounds (jinflexins AD, 14) are new natural products, while seven phenanthrenes [juncuenins A (5), B (6), and D (8), juncusol (7), dehydrojuncuenins A (9) and B (11), and dehydrojuncusol (10)] were isolated for the first time from the plant. Jinflexin D (4) is a dimer with an unprecedented heptacyclic ring system. The absolute configurations of the new compounds were determined by TDDFT-ECD calculations, and their enantiomeric purity was checked by chiral HPLC analysis. Extracts of different polarity (n-hexane, dichloromethane, and ethyl acetate) were evaluated for their antimicrobial effects against methicillin-resistant Staphylococcus aureus, extended-spectrum beta-lactamase (ESBL)-producing Citrobacter freundii, Escherichia coli, Enterobacter cloacae, Klebsiella pneumoniae, multiresistant Acinetobacter baumannii, and Pseudomonas aeruginosa. The MIC values of the isolated compounds were determined by a microdilution method. Jinflexin B (2), juncusol (7), juncuenin D (8), and dehydrojuncuenin B (11) showed significant activity (MIC value range 12.5100 mu g/mL) against MRSA strains.
Tárgyszavak:Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban
folyóiratcikk
Megjelenés:Journal of Natural Products. - 79 : 11 (2016), p. 2814-2823. -
További szerzők:Liktor-Busa Erika Kúsz Norbert Szappanos Ádám (1989-) (vegyész) Mándi Attila (1981-) (vegyész, német szakfordító) Kurtán Tibor (1973-) (vegyész, angol szakfordító) Urbán Edit Hohmann Judit Chang, Fang-Rong Vasas Andrea
Pályázati támogatás:K109846
OTKA
K105871
OTKA
NIIFI 10038
Egyéb
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5.

001-es BibID:BIBFORM099049
035-os BibID:(cikkazonosító)2088 (scopus)85121422508 (wos)000736882800001
Első szerző:Vasas Andrea
Cím:Isolation, Structure Determination of Sesquiterpenes from Neurolaena lobata and Their Antiproliferative, Cell Cycle Arrest-Inducing and Anti-Invasive Properties against Human Cervical Tumor Cells / Vasas Andrea, Lajter Ildikó, Kúsz Norbert, Király Sándor Balázs, Kovács Tibor, Kurtán Tibor, Bózsity Noémi, Nagy Nikolett, Schelz Zsuzsanna, Zupkó István, Krupitza Georg, Frisch Richard, Mándi Attila, Hohmann Judit
Dátum:2021
ISSN:1999-4923
Megjegyzések:Seven new germacranolides (1-3, 5-8), among them a heterodimer (7), and known germacranolide (4), eudesmane (9) and isodaucane (10) sesquiterpenes were isolated from the aerial parts of Neurolaena lobata. Their structures were determined by using a combination of different spectroscopic methods, including HR-ESIMS and 1D and 2D NMR techniques supported by DFT-NMR calculations. The enantiomeric purity of the new compounds was investigated by chiral HPLC analysis, while their absolute configurations were determined by TDDFT-ECD and OR calculations. Due to the conformationally flexible macrocycles and difficulties in assigning the relative configuration, 13C and 1H NMR chemical shift and ECD and OR calculations were performed on several stereoisomers of two derivatives. The isolated compounds (1?10) were shown to have noteworthy antiproliferative activities against three human cervical tumor cell line with different HPV status (HeLa, SiHa and C33A). Additionally, lobatolide C (6) exhibited substantial antiproliferative properties, antimigratory effect, and it induced cell cycle disturbance in SiHa cells.
Tárgyszavak:Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban
folyóiratcikk
Neurolaena lobata
Asteraceae
germacranolides
eudesmanes
isodaucane
sesquiterpenes
antiproliferative
antimigratory effect
SiHa cells
Megjelenés:Pharmaceutics. - 13 : 12 (2021), p. 1-25. -
További szerzők:Lajter Ildikó Kúsz Norbert Király Sándor Balázs (1991-) (vegyész) Kovács Tibor (1990-) (vegyész) Kurtán Tibor (1973-) (vegyész, angol szakfordító) Bózsity Noémi Nagy Nikoletta Schelz Zsuzsanna Zupkó István Krupitza, Georg Frisch, Richard Mándi Attila (1981-) (vegyész, német szakfordító) Hohmann Judit
Pályázati támogatás:GINOP-2.3.2-15-2016-00012
GINOP
20391-3/2018/FEKUSTRAT
Egyéb
NKFI FK 134653
Egyéb
NKFI K 138672
Egyéb
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DOI
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