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Unusual Nitrogenous Phenalenone Derivatives from the Marine-Derived Fungus Coniothyrium cereale

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 p...

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Autores principales: Elsebai, Mahmoud Fahmi, Ghabbour, Hazem A., Mehiri, Mohamed
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273853/
https://www.ncbi.nlm.nih.gov/pubmed/26840293
http://dx.doi.org/10.3390/molecules21020178
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author Elsebai, Mahmoud Fahmi
Ghabbour, Hazem A.
Mehiri, Mohamed
author_facet Elsebai, Mahmoud Fahmi
Ghabbour, Hazem A.
Mehiri, Mohamed
author_sort Elsebai, Mahmoud Fahmi
collection PubMed
description 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.
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spelling pubmed-62738532018-12-28 Unusual Nitrogenous Phenalenone Derivatives from the Marine-Derived Fungus Coniothyrium cereale Elsebai, Mahmoud Fahmi Ghabbour, Hazem A. Mehiri, Mohamed Molecules Article 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. MDPI 2016-02-01 /pmc/articles/PMC6273853/ /pubmed/26840293 http://dx.doi.org/10.3390/molecules21020178 Text en © 2016 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons by Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Elsebai, Mahmoud Fahmi
Ghabbour, Hazem A.
Mehiri, Mohamed
Unusual Nitrogenous Phenalenone Derivatives from the Marine-Derived Fungus Coniothyrium cereale
title Unusual Nitrogenous Phenalenone Derivatives from the Marine-Derived Fungus Coniothyrium cereale
title_full Unusual Nitrogenous Phenalenone Derivatives from the Marine-Derived Fungus Coniothyrium cereale
title_fullStr Unusual Nitrogenous Phenalenone Derivatives from the Marine-Derived Fungus Coniothyrium cereale
title_full_unstemmed Unusual Nitrogenous Phenalenone Derivatives from the Marine-Derived Fungus Coniothyrium cereale
title_short Unusual Nitrogenous Phenalenone Derivatives from the Marine-Derived Fungus Coniothyrium cereale
title_sort unusual nitrogenous phenalenone derivatives from the marine-derived fungus coniothyrium cereale
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273853/
https://www.ncbi.nlm.nih.gov/pubmed/26840293
http://dx.doi.org/10.3390/molecules21020178
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