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Metabolomic Profiling and Cytotoxic Tetrahydrofurofuran Lignans Investigations from Premna odorata Blanco

Metabolomic profiling of different Premna odorata Blanco (Lamiaceae) organs, bark, wood, young stems, flowers, and fruits dereplicated 20, 20, 10, 20, and 20 compounds, respectively, using LC–HRESIMS. The identified metabolites (1–34) belonged to different chemical classes, including iridoids, flavo...

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Autores principales: Elmaidomy, Abeer H., Mohammed, Rabab, M. Hassan, Hossam, I. Owis, Asmaa, E. Rateb, Mostafa, A. Khanfar, Mohammad, Krischke, Markus, J. Mueller, Martin, Ramadan Abdelmohsen, Usama
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6836009/
https://www.ncbi.nlm.nih.gov/pubmed/31614908
http://dx.doi.org/10.3390/metabo9100223
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author Elmaidomy, Abeer H.
Mohammed, Rabab
M. Hassan, Hossam
I. Owis, Asmaa
E. Rateb, Mostafa
A. Khanfar, Mohammad
Krischke, Markus
J. Mueller, Martin
Ramadan Abdelmohsen, Usama
author_facet Elmaidomy, Abeer H.
Mohammed, Rabab
M. Hassan, Hossam
I. Owis, Asmaa
E. Rateb, Mostafa
A. Khanfar, Mohammad
Krischke, Markus
J. Mueller, Martin
Ramadan Abdelmohsen, Usama
author_sort Elmaidomy, Abeer H.
collection PubMed
description Metabolomic profiling of different Premna odorata Blanco (Lamiaceae) organs, bark, wood, young stems, flowers, and fruits dereplicated 20, 20, 10, 20, and 20 compounds, respectively, using LC–HRESIMS. The identified metabolites (1–34) belonged to different chemical classes, including iridoids, flavones, phenyl ethanoids, and lignans. A phytochemical investigation of P. odorata bark afforded one new tetrahydrofurofuran lignan, 4β-hydroxyasarinin 35, along with fourteen known compounds. The structure of the new compound was confirmed using extensive 1D and 2D NMR, and HRESIMS analyses. A cytotoxic investigation of compounds 35–38 against the HL-60, HT-29, and MCF-7 cancer cell lines, using the MTT assay showed that compound 35 had cytotoxic effects against HL-60 and MCF-7 with IC(50) values of 2.7 and 4.2 µg/mL, respectively. A pharmacophore map of compounds 35 showed two hydrogen bond acceptor (HBA) aligning the phenoxy oxygen atoms of benzodioxole moieties, two aromatic ring features vectored on the two phenyl rings, one hydrogen bond donor (HBD) feature aligning the central hydroxyl group and thirteen exclusion spheres which limit the boundaries of sterically inaccessible regions of the target’s active site.
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spelling pubmed-68360092019-11-25 Metabolomic Profiling and Cytotoxic Tetrahydrofurofuran Lignans Investigations from Premna odorata Blanco Elmaidomy, Abeer H. Mohammed, Rabab M. Hassan, Hossam I. Owis, Asmaa E. Rateb, Mostafa A. Khanfar, Mohammad Krischke, Markus J. Mueller, Martin Ramadan Abdelmohsen, Usama Metabolites Article Metabolomic profiling of different Premna odorata Blanco (Lamiaceae) organs, bark, wood, young stems, flowers, and fruits dereplicated 20, 20, 10, 20, and 20 compounds, respectively, using LC–HRESIMS. The identified metabolites (1–34) belonged to different chemical classes, including iridoids, flavones, phenyl ethanoids, and lignans. A phytochemical investigation of P. odorata bark afforded one new tetrahydrofurofuran lignan, 4β-hydroxyasarinin 35, along with fourteen known compounds. The structure of the new compound was confirmed using extensive 1D and 2D NMR, and HRESIMS analyses. A cytotoxic investigation of compounds 35–38 against the HL-60, HT-29, and MCF-7 cancer cell lines, using the MTT assay showed that compound 35 had cytotoxic effects against HL-60 and MCF-7 with IC(50) values of 2.7 and 4.2 µg/mL, respectively. A pharmacophore map of compounds 35 showed two hydrogen bond acceptor (HBA) aligning the phenoxy oxygen atoms of benzodioxole moieties, two aromatic ring features vectored on the two phenyl rings, one hydrogen bond donor (HBD) feature aligning the central hydroxyl group and thirteen exclusion spheres which limit the boundaries of sterically inaccessible regions of the target’s active site. MDPI 2019-10-13 /pmc/articles/PMC6836009/ /pubmed/31614908 http://dx.doi.org/10.3390/metabo9100223 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Elmaidomy, Abeer H.
Mohammed, Rabab
M. Hassan, Hossam
I. Owis, Asmaa
E. Rateb, Mostafa
A. Khanfar, Mohammad
Krischke, Markus
J. Mueller, Martin
Ramadan Abdelmohsen, Usama
Metabolomic Profiling and Cytotoxic Tetrahydrofurofuran Lignans Investigations from Premna odorata Blanco
title Metabolomic Profiling and Cytotoxic Tetrahydrofurofuran Lignans Investigations from Premna odorata Blanco
title_full Metabolomic Profiling and Cytotoxic Tetrahydrofurofuran Lignans Investigations from Premna odorata Blanco
title_fullStr Metabolomic Profiling and Cytotoxic Tetrahydrofurofuran Lignans Investigations from Premna odorata Blanco
title_full_unstemmed Metabolomic Profiling and Cytotoxic Tetrahydrofurofuran Lignans Investigations from Premna odorata Blanco
title_short Metabolomic Profiling and Cytotoxic Tetrahydrofurofuran Lignans Investigations from Premna odorata Blanco
title_sort metabolomic profiling and cytotoxic tetrahydrofurofuran lignans investigations from premna odorata blanco
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6836009/
https://www.ncbi.nlm.nih.gov/pubmed/31614908
http://dx.doi.org/10.3390/metabo9100223
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