title: Unusual Nitrogenous Phenalenone Derivatives from the Marine-Derived Fungus Coniothyrium cereale.
abstract: The new phenalenone metabolites 1, 2, 4, and 6 were isolated from the marine-derived endophytic fungus Coniothyrium cereale, in addition to the ergostane-type sterol (3) and entatrovenetinone (5). Compounds 1 and 2 represent two unusual nitrogen-containing compounds, which are composed of a sterol portion condensed via two bonds to phenalenone derivatives. Compound 6, which contains unprecedented imine functionality between two carbonyl groups to form a oxepane -imine-dione ring, exhibited a moderate cytotoxicity against K562, U266, and SKM1 cancer cell lines. Moreover, molecular docking studies were done on estrogen receptor α-ligand binding domain (ERα-LBD) to compounds 1 and 2 to correlate with binding energies and affinities calculated from molecular docking to the anti-proliferative activity.
authors: Department of Pharmacognosy, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt. elsebai72@yahoo.com.
authors: Mahmoud Fahmi
authors: MF
authors: Elsebai
authors: Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia. ghabbourh@yahoo.com.|Department of Medicinal Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt. ghabbourh@yahoo.com.
authors: Hazem A
authors: HA
authors: Ghabbour
authors: Institut de Chimie de Nice (ICN), Faculté des Sciences, Université Nice Sophia Antipolis, UMR CNRS 7272, Parc Valrose, Nice 06108 Cedex 02, France. mehiri@unice.fr.
authors: Mohamed
authors: M
authors: Mehiri
mesh_terms: D001203:Ascomycota / Q000737:chemistry*; D045744:Cell Line, Tumor; D054697:Cytostatic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D047628:Estrogen Receptor alpha / Q000378:metabolism; D006801:Humans; D020014:K562 Cells; D008958:Models, Molecular; D062105:Molecular Docking Simulation; D009584:Nitrogen / Q000737:chemistry*; D043803:Phenalenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D054697:Cytostatic Agents; D047628:Estrogen Receptor alpha; D043803:Phenalenes; C038036:phenalen-1-one; D009584:Nitrogen
keywords: Coniothyrium cereale; S-dehydroazasirosterol; conio-azasterol; endophytic fungal phenalenones; marine natural products; molecular docking