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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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DOI
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2.

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
Intézményi repozitóriumban (DEA) tárolt változat
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3.

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
Internet cím:Szerző által megadott URL
DOI
Intézményi repozitóriumban (DEA) tárolt változat
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