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001-es BibID:BIBFORM074136
Első szerző:Abdelwahab, Miada F.
Cím:Induced secondary metabolites from the endophytic fungus Aspergillus versicolor through bacterial co-culture and OSMAC approaches / Miada F. Abdelwahab, Tibor Kurtán, Attila Mándi, Werner E.G. Müller, Mostafa A. Fouad, Mohamed S. Kamel, Zhen Liu, Weaam Ebrahim, Georgios Daletos, Peter Proksch
Dátum:2018
ISSN:0040-4039
Megjegyzések:Two new cryptic 3,4-dihydronaphthalen-(2H)-1-one (1-tetralone) derivatives, aspvanicin A (1) and its epimer aspvanicin B (2), as well as several known cryptic metabolites (3-8), were obtained from the ethyl acetate extract of the co-culture of the endophytic fungus Aspergillus versicolor KU258497 with the bacterium Bacillus subtilis 168 trpC2 on solid rice medium. When A. versicolor was cultured axenically in liquid Wickerham medium supplemented with 3.5% DMSO, an additional three known secondary metabolites (9?11) were isolated that were lacking when the fungus was fermented on rice medium. The structures of the new compounds were elucidated using one- and two-dimensional NMR spectroscopy as well as HRESIMS. The relative and absolute configurations of 1 and 2 were determined by the combination of NMR and electronic circular dichroism (ECD) analysis aided by DFT conformational analysis and TDDFT-ECD calculations. The ECD calculations revealed that although the sign of the blue-shifted overlapping n-?* ECD transition follows the helicity rule of cyclic aryl ketones, the calculation of low-energy conformers and ECD spectra was necessary to determine the stereochemistry. All metabolites were assessed for their antibacterial and cytotoxic activities; one of the new diastereomers, compound 2, showed moderate cytotoxic activity against the mouse lymphoma cell line L5178Y.
Tárgyszavak:Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban
Aspergillus versicolor
Tetralone derivatives
Absolute configuration
ECD calculations
Megjelenés:Tetrahedron Letters 59 : 27 (2018), p. 2647-2652. -
További szerzők:Kurtán Tibor (1973-) (vegyész, angol szakfordító) Mándi Attila (1981-) (vegyész, német szakfordító) Müller, Werner E. G. Fouad, Mostafa A. Kamel, Mohamed S. Liu, Zhen Ebrahim, Weaam Daletos, Georgios Proksch, Peter
Pályázati támogatás:NKFI K120181, PD121020
OTKA
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DOI
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2.

001-es BibID:BIBFORM078385
Első szerző:Abdel-Wahab, Nada
Cím:Induction of Secondary Metabolites from the Marine-Derived Fungus Aspergillus versicolor through Co-cultivation with Bacillus subtilis / Nada M. Abdel-Wahab, Sebastian Scharf, Ferhat C. Özkaya, Tibor Kurtán, Attila Mándi, Mostafa A. Fouad, Mohamed S. Kamel, Werner E. G. Müller, Rainer Kalscheuer, Wenhan Lin, Georgios Daletos, Weaam Ebrahim, Zhen Liu, Peter Proksch
Dátum:2019
ISSN:0032-0943
Megjegyzések:A new cyclic pentapeptide, cotteslosin C (1), a new aflaquinolone, 22-epi-aflaquinolone B (3), and two new anthraquinones (9 and 10), along with thirty known compounds (2, 4???8, 11???34) were isolated from a co-culture of the sponge-associated fungus Aspergillus versicolor with Bacillus subtilis. The new metabolites were only detected in the co-culture extract, but not when the fungus was grown under axenic conditions. Furthermore, the co-culture extract exhibited an enhanced accumulation of the known constituents versicolorin B (14), averufin (16), and sterigmatocyctin (19) by factors of 1.5, 2.0, and 4.7, respectively, compared to the axenic fungal culture. The structures of the isolated compounds were elucidated on the basis of 1D and 2D NMR spectra and mass spectrometry as well as by comparison with literature data. The absolute configuration of compounds 3, 9, and 10 was determined by ECD (electronic circular dichroism) analysis aided by TDDFT-ECD (time-dependent density functional theory electronic circular dichroism) calculations. Compounds 15, 18???21, and 26 exhibited strong to moderate cytotoxic activity against the mouse lymphoma cell line L5178Y, with IC50 values ranging from 2.0 to 21.2??M, while compounds 14, 16, 31, 32, and 33 displayed moderate inhibitory activities against several gram-positive bacteria, with MIC values ranging from 12.5 to 50??M.
Tárgyszavak:Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban
sponge-derived fungus
Aspergillus versicolor
cyclic pentapeptide
co-culture
ECD calculations
cytotoxicity
antibacterial activity
Megjelenés:Planta Medica. - 85 : 06 (2019), p. 503-512. -
További szerzők:Scharf, Sebastian Özkaya, Ferhat Kurtán Tibor (1973-) (vegyész, angol szakfordító) Mándi Attila (1981-) (vegyész, német szakfordító) Fouad, Mostafa A. Kamel, Mohamed S. Müller, Werner E. G. Kalscheuer, Rainer Lin, Wen Han Daletos, Georgios Ebrahim, Weaam Liu, Zhen Proksch, Peter
Pályázati támogatás:K120181
OTKA
PD121020
OTKA
Internet cím:Szerző által megadott URL
DOI
Intézményi repozitóriumban (DEA) tárolt változat
Borító:
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