Bioassay-guided fractionations of Cannabis sativa extract and HPLC-assisted purifications of anti-proliferative active fractions lead to the isolation of 16 known and one new phytomolecule and their in-silico analysis
Abstract The comprehensive anti-cancer activities of cannabinoid acids and non-cannabinoids are not fully explored. Herein we report simple extraction, faster bioassay-guided fractionation, and HPLC-assisted purification of bioactive secondary metabolite and their identification. Anti-proliferative activity of six cannabinoid acids and eleven non-cannabinoids from the leaves of Cannabis sativa was evaluated. HPLC- assisted purification from the bioactive fractions leads to isolate one new compound Methoxy Canniprene (methoxy isoprenyl bibenzyl), including all six CBDA’s eleven non-cannabinoids in a single step, and NMR, HR-ESI-MS studies, and comparison with the literature data authenticated their structures. The crude extract ($ IC_{50} $ range: 18.0–37.2 μg/mL), Fraction A to D (11.9–222 μg/mL), and purified different cannabinoid and non cannabinoids ($ IC_{50} $ range: 0.5–100 μM) displayed potent anti-proliferative activities against almost all the tested five human cancer cell lines. Computational analysis based on molecular docking studies and absolute binding free energy calculation have identified targets for various cancer-associated proteins, including Aldehyde dehydrogenase 1 A1, Topoisomerase I, GSK-3 Beta, Protein Kinase C beta II, and Neurotrophic Tyrosine Kinase receptor type 1..
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2024 |
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| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:33 |
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| Enthalten in: |
Medicinal chemistry research - 33(2024), 4 vom: 05. März, Seite 635-650 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Nalli, Yedukondalu [VerfasserIn] |
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| Links: |
Volltext [lizenzpflichtig] |
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| Themen: |
Anti-proliferative activity |
| Anmerkungen: |
© The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2024. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.. corrected publication 2024 |
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| doi: |
10.1007/s00044-024-03199-y |
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| 520 | |a Abstract The comprehensive anti-cancer activities of cannabinoid acids and non-cannabinoids are not fully explored. Herein we report simple extraction, faster bioassay-guided fractionation, and HPLC-assisted purification of bioactive secondary metabolite and their identification. Anti-proliferative activity of six cannabinoid acids and eleven non-cannabinoids from the leaves of Cannabis sativa was evaluated. HPLC- assisted purification from the bioactive fractions leads to isolate one new compound Methoxy Canniprene (methoxy isoprenyl bibenzyl), including all six CBDA’s eleven non-cannabinoids in a single step, and NMR, HR-ESI-MS studies, and comparison with the literature data authenticated their structures. The crude extract ($ IC_{50} $ range: 18.0–37.2 μg/mL), Fraction A to D (11.9–222 μg/mL), and purified different cannabinoid and non cannabinoids ($ IC_{50} $ range: 0.5–100 μM) displayed potent anti-proliferative activities against almost all the tested five human cancer cell lines. Computational analysis based on molecular docking studies and absolute binding free energy calculation have identified targets for various cancer-associated proteins, including Aldehyde dehydrogenase 1 A1, Topoisomerase I, GSK-3 Beta, Protein Kinase C beta II, and Neurotrophic Tyrosine Kinase receptor type 1. | ||
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