Glucopyranosylbianthrones from the Algerian Asphodelus tenuifolius : Structural Insights and Biological Evaluation on Melanoma Cancer Cells
Two new glucopyranosylbianthrones (1 and 2) were isolated from the aerial part of the plant Asphodelus tenuifolius, collected in Southwest Algeria. The 2D structures of 1 and 2 were defined by NMR analysis, HRESIMS data, and comparison with literature data. The comparison of experimental and calculated electronic circular dichroism and NMR data led to characterization of the ( M) and ( P) atropisomeric forms of the glucopyranosylbianthrones, asphodelins (1) and (2), respectively. The in vitro activities of these two metabolites were evaluated in human melanoma A375 cells, and both the compounds inhibited cell proliferation in a concentration-dependent manner, with IC50 values of 20.6 ± 0.8 and 23.2 ± 1.1 μM, respectively. Considering their biological profile, an inverse virtual screening approach was employed to identify and suggest putative anticancer interacting targets.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2018 |
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| Erschienen: |
2018 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:81 |
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| Enthalten in: |
Journal of natural products - 81(2018), 8 vom: 24. Aug., Seite 1786-1794 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Khalfaoui, Ayoub [VerfasserIn] |
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| Links: |
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| Themen: |
Anthracenes |
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| Anmerkungen: |
Date Completed 14.11.2019 Date Revised 14.11.2019 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1021/acs.jnatprod.8b00234 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM287031586 |
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| 245 | 1 | 0 | |a Glucopyranosylbianthrones from the Algerian Asphodelus tenuifolius |b Structural Insights and Biological Evaluation on Melanoma Cancer Cells |
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| 500 | |a Date Completed 14.11.2019 | ||
| 500 | |a Date Revised 14.11.2019 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a Two new glucopyranosylbianthrones (1 and 2) were isolated from the aerial part of the plant Asphodelus tenuifolius, collected in Southwest Algeria. The 2D structures of 1 and 2 were defined by NMR analysis, HRESIMS data, and comparison with literature data. The comparison of experimental and calculated electronic circular dichroism and NMR data led to characterization of the ( M) and ( P) atropisomeric forms of the glucopyranosylbianthrones, asphodelins (1) and (2), respectively. The in vitro activities of these two metabolites were evaluated in human melanoma A375 cells, and both the compounds inhibited cell proliferation in a concentration-dependent manner, with IC50 values of 20.6 ± 0.8 and 23.2 ± 1.1 μM, respectively. Considering their biological profile, an inverse virtual screening approach was employed to identify and suggest putative anticancer interacting targets | ||
| 650 | 4 | |a Journal Article | |
| 650 | 7 | |a Anthracenes |2 NLM | |
| 650 | 7 | |a Antineoplastic Agents, Phytogenic |2 NLM | |
| 650 | 7 | |a Plant Extracts |2 NLM | |
| 700 | 1 | |a Chini, Maria G |e verfasserin |4 aut | |
| 700 | 1 | |a Bouheroum, Mohamed |e verfasserin |4 aut | |
| 700 | 1 | |a Belaabed, Soumia |e verfasserin |4 aut | |
| 700 | 1 | |a Lauro, Gianluigi |e verfasserin |4 aut | |
| 700 | 1 | |a Terracciano, Stefania |e verfasserin |4 aut | |
| 700 | 1 | |a Vaccaro, Maria C |e verfasserin |4 aut | |
| 700 | 1 | |a Bruno, Ines |e verfasserin |4 aut | |
| 700 | 1 | |a Benayache, Samir |e verfasserin |4 aut | |
| 700 | 1 | |a Mancini, Ines |e verfasserin |4 aut | |
| 700 | 1 | |a Bifulco, Giuseppe |e verfasserin |4 aut | |
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