Two new prenylated flavonoids, 4',5-dihydroxy-6,7-(2,2-dimethylpyrano)-2'-methoxy-8-γ,γ-dimethylallylflavone 1 and 3'-hydroxycycloartocarpin 2 along with six known flavonoids, 5,7-dihydroxy-4'-methoxy-8-prenylflavanone 3, isobavachalcone 4, pyranocycloartobiloxanthone A 5, artocarpin 6, chaplashin 7 and cycloartocarpin 8 were isolated for the first time from the leaves and the heartwoods of Artocarpus anisophyllus Miq. The structures of isolated flavonoids were elucidated spectroscopically using 1D and 2D NMR, FTIR, MS, UV and also by comparison with literature data. These flavonoids were screened for their antioxidant and tyrosinase inhibitory activities. The dichloromethane and ethyl acetate crude extracts together with 3'-hydroxycycloartocarpin 2, pyranocycloartobiloxanthone A 5 and artocarpin 6 showed DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging activity with SC 50 values of 80.2, 40.0, 152.9, 20.2 and 140.0 µg/mL in 30 min, respectively. Pyranocycloartobiloxanthone A 5 exhibited significant tyrosinase inhibitory activity against tyrosinase from mushroom with IC 50 values of 60.5 µg/mL.
Prediction of anti-Alzheimer's activity of flavonoids targeting acetylcholinesterase in silico http://researchonline.ljmu.ac.uk/5218/ Article LJMU has developed LJMU Research Online for users to access the research output of the University more effectively. Copyright © and Moral Rights for the papers on this site are retained by the individual authors and/or other copyright owners. Users may download and/or print one copy of any article(s) in LJMU Research Online to facilitate their private study or for non-commercial research. You may not engage in further distribution of the material or use it for any profit-making activities or any commercial gain.The version presented here may differ from the published version or from the version of the record. Please see the repository URL above for details on accessing the published version and note that access may require a subscription. Objective -The aim of the in silico study was to establish protocols to predict the most effective flavonoid from prenylated and pyrano-flavonoid classes for AchE inhibition linking to the pote tial treat e t of Alzhei er's disease.Methodology -Three flavonoids isolated from Artocarpus anisophyllus Miq. were selected for the study. With these compounds, Lipinski filter, ADME/Tox screening, molecular docking and QSAR were performed in silico. In vitro activity was evaluated by bioactivity staining ased o the Ell a 's ethod.Results -In the Lipinski filter and ADME/Tox screening, all test compounds produced positive results, but in the target fishing, only one flavonoid could successfully target AchE. Molecular docking was performed on this flavonoid, and this compound gained the score as -13.5762. From the QSAR analysis the IC50 was found to be 1659.59 nM. Again, 100 derivatives were generated from the parent compound and docking was performed. The derivative number 20 was the best scorer i.e., -31.6392 and IC50 was predicted as 6.025 nM. Conclusion -Results indicated that flavonoids could be efficient inhibitors of AchE and thus, could be useful in the management of Alzhei er's disease.
A new dihydrochalcone, 2',4'-dihydroxy-3,4-(2″,2″-dimethylchromeno)-3'-prenyldihydrochalcone (1) together with 4-hydroxyonchocarpin (2), isobavachalcone (3), 4',5-dihydroxy-6,7-(2,2-dimethylpyrano)-2'-methoxy-8-γ,γ-dimethylallyflavone (4), artocarpin (5) and cycloheterophyllin (6) were successfully isolated from the leaves and heartwoods of Artocarpus lowii King (Moraceae). The structures of these compounds were fully characterised using spectroscopic methods and by direct comparison with published data. These compounds were tested for their antioxidant and tyrosinase inhibitory activities. Compound (1) displayed moderate antioxidant activity towards DPPH and tyrosinase inhibitory activities with SC value of 223.8 μM and IC value of 722.5 μM, respectively. Among the isolated compounds, cycloheterophyllin (6) showed the most potential antioxidant activity with SC value of 320.0 and 102.8 μM for ABTS and DPPH radicals scavenging activities, respectively, and also exhibited highest FRAP equivalent value of 4.7 ± 0.09 mM. Compound (6) showed tyrosinase inhibitory activity with the IC value of 104.6 μM.
Antimicrobial activities of flavonoids isolated from the leaves and heartwoods of Artocarpus anisophyllus Miq. and Artocarpus lowii King were evaluated. Gram positive bacteria (Staphylococcus aureus and Bacillus cereus), Gram negative bacteria (Escherichia coli and Pseudomonas putida) and fungi (Candida albicans and Candida glabrata) were used in this study. Disc diffusion method was used as the qualitative assay while minimum inhibitory concentration and minimum microbicidal concentration methods were used as the quantitative assays. Artocarpin (8) showed strong antimicrobial activity towards all bacteria with inhibition zone diameter more than 11 mm and minimum microbicidal concentration value of 0.45 mg/mL. Isobavachalcone (3) exhibited strong antibacterial activity towards Gram positive bacteria with minimum microbicidal concentration value of 0.45 mg/mL. The findings of this study revealed that the isolated flavonoids from A. anisophyllus and A. lowii have potential to be developed as antimicrobial agents.
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