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001-es BibID:	BIBFORM074136
035-os BibID:	(Scopus)85047605232 (WoS)000436204800008
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
Internet cím:	Szerző által megadott URL DOI Intézményi repozitóriumban (DEA) tárolt változat
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