Phytochemical and antiviral investigation of Cynanchum acutum L. extract and derived semi-synthetic analogs targeting SARS-CoV-2 main protease
Reda F A Abdelhameed, Ahmed K Ibrahim, Khaled M Darwish, Asmaa M Atta, Sarah Shabayek, Mona Timan Idriss, Amany K Ibrahim, Safwat A Ahmed, Jihan M Badr, Asma Ahmad Nashawi, Samar S A Murshid, Manar O Lashkar, Sameh S Elhady, Eman S Habib
Future Journal of Pharmaceutical Sciences, doi:10.1186/s43094-025-00907-2
Background The genus Cynanchum, family Apocynaceae is a group of climbing vines that have long been in folk medicine used as antitussives, analgesics, anticonvulsants, expectorants, diuretics, antifebriles, and tonics.
Results Cynanchum acutum crude extract was investigated to determine its chemical composition through LC-ESI-TOF-MS/MS technique, where 46 hits were observed. Among these compounds, quercetin-3-O-β-galactoside was previously reported within the plant as a major component. This compound was isolated and purified using different chromatographic techniques, and its concentration was estimated using high-performance thin-layer chromatography (HPTLC). Two semi-synthetic derivatives were synthesized from this compound, namely 7-benzyl-and 7-bromoethyl quercetin-3-O-β-galactosides. Both analogs, which are more hydrophobic, were developed as an attempt to improve the physiochemical properties and, in turn, the pharmacokinetics of the parent compound. Our study also includes the determination of antiviral activity against COVID-19 of Cynanchum acutum crude extract along with quercetin-3-O-β-galactoside in addition to the two semi-synthesized derivatives. The antiviral assay revealed that the synthetic benzyl derivative of quercetin-3-O-β-galactoside demonstrated promising activity against severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2). The potential molecular aspects of the parent and semi-synthetic analogs were highlighted through molecular modeling simulation of docking the compounds at the viral main protease (Mpro) binding pocket. In silico findings demonstrated significant affinity and residue-wise binding interactions in relation to the co-crystallized small molecule Mpro inhibitor.
Conclusion Collectively, our study adds to the current knowledge of SARS-CoV-2 pharmacotherapy by introducing drug-like small molecules with potential activity profiles.
Supplementary Information The online version contains supplementary material available at https:// doi. org/ 10. 1186/ s43094-025-00907-2 .
Additional file1 Author contributions R.
Declarations Ethics approval and consent to participate The study protocol was approved by the ethical committee of the Faculty of Pharmacy at Suez Canal University (approval number: 202010M2).
Competing interests The authors declare that they have no competing interests.
Publisher's Note Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
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"abstract": "<jats:title>Abstract</jats:title>\n <jats:sec>\n <jats:title>Background</jats:title>\n <jats:p>\n The genus\n <jats:italic>Cynanchum</jats:italic>\n , family Apocynaceae is a group of climbing vines that have long been in folk medicine used as antitussives, analgesics, anticonvulsants, expectorants, diuretics, antifebriles, and tonics.\n </jats:p>\n </jats:sec>\n <jats:sec>\n <jats:title>Results</jats:title>\n <jats:p>\n <jats:italic>Cynanchum acutum</jats:italic>\n crude extract was investigated to determine its chemical composition through LC-ESI-TOF-MS/MS technique, where 46 hits were observed. Among these compounds, quercetin-3-\n <jats:italic>O</jats:italic>\n -\n <jats:italic>β</jats:italic>\n -galactoside was previously reported within the plant as a major component. This compound was isolated and purified using different chromatographic techniques, and its concentration was estimated using high-performance thin-layer chromatography (HPTLC). Two semi-synthetic derivatives were synthesized from this compound, namely 7-benzyl- and 7-bromoethyl quercetin-3-\n <jats:italic>O</jats:italic>\n -\n <jats:italic>β</jats:italic>\n -galactosides. Both analogs, which are more hydrophobic, were developed as an attempt to improve the physiochemical properties and, in turn, the pharmacokinetics of the parent compound. Our study also includes the determination of antiviral activity against COVID-19 of\n <jats:italic>Cynanchum acutum</jats:italic>\n crude extract along with quercetin-3-\n <jats:italic>O</jats:italic>\n -\n <jats:italic>β</jats:italic>\n -galactoside in addition to the two semi-synthesized derivatives. The antiviral assay revealed that the synthetic benzyl derivative of quercetin-3-\n <jats:italic>O</jats:italic>\n -\n <jats:italic>β</jats:italic>\n -galactoside demonstrated promising activity against severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2). The potential molecular aspects of the parent and semi-synthetic analogs were highlighted through molecular modeling simulation of docking the compounds at the viral main protease (Mpro) binding pocket. In silico findings demonstrated significant affinity and residue-wise binding interactions in relation to the co-crystallized small molecule Mpro inhibitor.\n </jats:p>\n </jats:sec>\n <jats:sec>\n <jats:title>Conclusion</jats:title>\n <jats:p>Collectively, our study adds to the current knowledge of SARS-CoV-2 pharmacotherapy by introducing drug-like small molecules with potential activity profiles.</jats:p>\n </jats:sec>\n <jats:sec>\n <jats:title>Graphical abstract</jats:title>\n </jats:sec>",
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