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Exploring the 2′-Hydroxy-Chalcone Framework for the Development of Dual Antioxidant and Soybean Lipoxygenase Inhibitory Agents
| Content Provider | MDPI |
|---|---|
| Author | Kostopoulou, Ioanna Tzani, Andromachi Polyzos, Nestor-Ioannis Karadendrou, Maria-Anna Kritsi, Eftichia Pontiki, Eleni Liargkova, Thalia Hadjipavlou-Litina, Dimitra Zoumpoulakis, Panagiotis Detsi, Anastasia |
| Copyright Year | 2021 |
| Description | 2′-hydroxy-chalcones are naturally occurring compounds with a wide array of bioactivity. In an effort to delineate the structural features that favor antioxidant and lipoxygenase (LOX) inhibitory activity, the design, synthesis, and bioactivity profile of a series of 2′-hydroxy-chalcones bearing diverse substituents on rings A and B, are presented. Among all the synthesized derivatives, chalcone 4b, bearing two hydroxyl substituents on ring B, was found to possess the best combined activity (82.4% DPPH radical scavenging ability, 82.3% inhibition of lipid peroxidation, and satisfactory LOX inhibition value (IC50 = 70 μM). Chalcone 3c, possessing a methoxymethylene substituent on ring A, and three methoxy groups on ring B, exhibited the most promising LOX inhibitory activity (IC50 = 45 μM). A combination of in silico techniques were utilized in an effort to explore the crucial binding characteristics of the most active compound 3c and its analogue 3b, to LOX. A common H-bond interaction pattern, orienting the hydroxyl and carbonyl groups of the aromatic ring A towards Asp768 and Asn128, respectively, was observed. Regarding the analogue 3c, the bulky (-OMOM) group does not seem to participate in a direct binding, but it induces an orientation capable to form H-bonds between the methoxy groups of the aromatic ring B with Trp130 and Gly247. |
| Starting Page | 2777 |
| e-ISSN | 14203049 |
| DOI | 10.3390/molecules26092777 |
| Journal | Molecules |
| Issue Number | 9 |
| Volume Number | 26 |
| Language | English |
| Publisher | MDPI |
| Publisher Date | 2021-05-08 |
| Access Restriction | Open |
| Subject Keyword | Molecules Medicinal Chemistry Chalcones Aurones Butein Sulfuretin Antioxidant Activity Lipoxygenase Inhibition Molecular Docking |
| Content Type | Text |
| Resource Type | Article |
