Isolation, characterization, antimicrobial properties, and theoretical investigations of a new isoflavanol from nigerian red propolis for therapeutic applicationsIyen, IS (Iyen, Ifeoma S.); Anyam, J (Anyam, John, V); Malu, DG (Malu, Daniel G.); Santali, E (Santali, Eman); Igoli, JO (Igoli, John O.); Ekpong, BO (Ekpong, Bassey O.); Benjamin, I (Benjamin, Innocent); Tor-Anyiin, TA (Tor-Anyiin, Terrumun A.)
Journal of Molecular Structure, 2024, Volume 1318, 139203
The chemical components of Nigerian red propolis were thoroughly examined to identify its phytochemical constituents. The investigation yielded a new isoflavanol, identified as 2 ',7-dihydroxy-3 ',4-dimethoxyisoflavan-4ol (DDI), which was isolated from the ethyl acetate extract. Using advanced spectroscopic techniques, such as 1D, 2D NMR as well as HR-LC-MS, the structure and molecular composition of the new compound was determined with extreme precision. The present study offers important information regarding the chemical structure of reddish propolis sourced from the southeast region of Nigeria. The isolated compound suggests that the botanical source of the propolis could be Dalbergia spp. antimicrobial assay of the compound isolated revealed potent antibacterial and antifungal properties with diameter zones of inhibition measuring between 27 and 32 mm. The MIC, MBC, and MFC values were between 6.25 and 25 mu g/mL. Further theoretical investigations of DDI were also carried out using DFT/D3(BJ)-B3LYP/6-311 ++ G (d, p) level of theory, of DDI in different environments (DMSO, Ethanol, Gas, and Water), that demonstrated structural stability of DDI in the different solvents with an energy gap of 7.0878 eV, 7.0831 eV, 6.9335 eV, and 7.0899 eV respectively. Molecular docking was employed substantiating the antimicrobial analysis, resulting in a score for receptors Candida tropicalis (1N9G), Escherichia coli (4LFU), Candida albicans (5K04), and Helicobacter pylori (4HI0) with binding affinity of -6.9 Kcal/mol, -8.5 Kcal/mol, -7.9 Kcal/mol, and -7.7 Kcal/mol respectively, compared with a conventional drug (fluconazole and amoxicillin) the docking proteins receptors. The docking for the DDI ligand against the receptor proteins of the studied organisms showed better inhibitory activity than the conventional drug (fluconazole), however, less activity with amoxicillin suggesting a more antifungal activity than antibacterial activity, presenting DDI ligand as a potential drug molecule against candidiasis. |
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