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Embellicines C-E: Macrocyclic Alkaloids with a Cyclopenta[b]fluorene Ring System from the Fungus Sarocladium sp.

[Image: see text] Macrocyclic alkaloids with a cyclopenta[b]fluorene ring system are a relatively young structural class of fungal metabolites, with the first members reported in 2013. Bioassay-guided fractionation of a Sarocladium sp. (fungal strain MSX6737) led to a series of both known and new me...

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Autores principales: Al Subeh, Zeinab Y., Flores-Bocanegra, Laura, Raja, Huzefa A., Burdette, Joanna E., Pearce, Cedric J., Oberlies, Nicholas H.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society and American Society of Pharmacognosy 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10043936/
https://www.ncbi.nlm.nih.gov/pubmed/36884371
http://dx.doi.org/10.1021/acs.jnatprod.2c01048
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author Al Subeh, Zeinab Y.
Flores-Bocanegra, Laura
Raja, Huzefa A.
Burdette, Joanna E.
Pearce, Cedric J.
Oberlies, Nicholas H.
author_facet Al Subeh, Zeinab Y.
Flores-Bocanegra, Laura
Raja, Huzefa A.
Burdette, Joanna E.
Pearce, Cedric J.
Oberlies, Nicholas H.
author_sort Al Subeh, Zeinab Y.
collection PubMed
description [Image: see text] Macrocyclic alkaloids with a cyclopenta[b]fluorene ring system are a relatively young structural class of fungal metabolites, with the first members reported in 2013. Bioassay-guided fractionation of a Sarocladium sp. (fungal strain MSX6737) led to a series of both known and new members of this structural class (1–5), including the known embellicine A (1), three new embellicine analogues (2, 4, and 5), and a semisynthetic acetylated analogue (3). The structures were identified by examining both high-resolution electrospray ionization mass spectrometry data and one-dimensional and two-dimensional NMR spectra. The relative configurations of these molecules were established via (1)H–(1)H coupling constants and nuclear Overhauser effect spectroscopy, while comparisons of the experimental electronic circular dichroism (ECD) spectra with the time-dependent density functional theory ECD calculations were utilized to assign their absolute configurations, which were in good agreement with the literature. These alkaloids (1–5) showed cytotoxic activity against a human breast cancer cell line (MDA-MB-231) that ranged from 0.4 to 4.8 μM. Compounds 1 and 5 were also cytotoxic against human ovarian (OVCAR3) and melanoma (MDA-MB-435) cancer cell lines.
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spelling pubmed-100439362023-03-29 Embellicines C-E: Macrocyclic Alkaloids with a Cyclopenta[b]fluorene Ring System from the Fungus Sarocladium sp. Al Subeh, Zeinab Y. Flores-Bocanegra, Laura Raja, Huzefa A. Burdette, Joanna E. Pearce, Cedric J. Oberlies, Nicholas H. J Nat Prod [Image: see text] Macrocyclic alkaloids with a cyclopenta[b]fluorene ring system are a relatively young structural class of fungal metabolites, with the first members reported in 2013. Bioassay-guided fractionation of a Sarocladium sp. (fungal strain MSX6737) led to a series of both known and new members of this structural class (1–5), including the known embellicine A (1), three new embellicine analogues (2, 4, and 5), and a semisynthetic acetylated analogue (3). The structures were identified by examining both high-resolution electrospray ionization mass spectrometry data and one-dimensional and two-dimensional NMR spectra. The relative configurations of these molecules were established via (1)H–(1)H coupling constants and nuclear Overhauser effect spectroscopy, while comparisons of the experimental electronic circular dichroism (ECD) spectra with the time-dependent density functional theory ECD calculations were utilized to assign their absolute configurations, which were in good agreement with the literature. These alkaloids (1–5) showed cytotoxic activity against a human breast cancer cell line (MDA-MB-231) that ranged from 0.4 to 4.8 μM. Compounds 1 and 5 were also cytotoxic against human ovarian (OVCAR3) and melanoma (MDA-MB-435) cancer cell lines. American Chemical Society and American Society of Pharmacognosy 2023-03-08 /pmc/articles/PMC10043936/ /pubmed/36884371 http://dx.doi.org/10.1021/acs.jnatprod.2c01048 Text en © 2023 The Authors. Published by American Chemical Society and American Society of Pharmacognosy https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Al Subeh, Zeinab Y.
Flores-Bocanegra, Laura
Raja, Huzefa A.
Burdette, Joanna E.
Pearce, Cedric J.
Oberlies, Nicholas H.
Embellicines C-E: Macrocyclic Alkaloids with a Cyclopenta[b]fluorene Ring System from the Fungus Sarocladium sp.
title Embellicines C-E: Macrocyclic Alkaloids with a Cyclopenta[b]fluorene Ring System from the Fungus Sarocladium sp.
title_full Embellicines C-E: Macrocyclic Alkaloids with a Cyclopenta[b]fluorene Ring System from the Fungus Sarocladium sp.
title_fullStr Embellicines C-E: Macrocyclic Alkaloids with a Cyclopenta[b]fluorene Ring System from the Fungus Sarocladium sp.
title_full_unstemmed Embellicines C-E: Macrocyclic Alkaloids with a Cyclopenta[b]fluorene Ring System from the Fungus Sarocladium sp.
title_short Embellicines C-E: Macrocyclic Alkaloids with a Cyclopenta[b]fluorene Ring System from the Fungus Sarocladium sp.
title_sort embellicines c-e: macrocyclic alkaloids with a cyclopenta[b]fluorene ring system from the fungus sarocladium sp.
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10043936/
https://www.ncbi.nlm.nih.gov/pubmed/36884371
http://dx.doi.org/10.1021/acs.jnatprod.2c01048
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