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Article

Lipoxygenase Inhibition Activity of Coumarin Derivatives—QSAR and Molecular Docking Study

1
Faculty of Food Faculty Osijek, Josip Juraj Strossmayer University, 31000 Osijek, Croatia
2
Department of Biology, Josip Juraj Strossmayer University of Osijek, 31000 Osijek, Croatia
3
Department of Agroecology and Environmental Protection, Faculty of Agrobiotechnical Sciences Osijek, Josip Juraj Strossmayer University of Osijek, 31000 Osijek, Croatia
*
Author to whom correspondence should be addressed.
Pharmaceuticals 2020, 13(7), 154; https://doi.org/10.3390/ph13070154
Received: 2 July 2020 / Revised: 13 July 2020 / Accepted: 15 July 2020 / Published: 17 July 2020
Lipoxygenases (LOXs) are a family of enzymes found in plants, mammals, and microorganisms. In animals and plants, the enzyme has the capability for the peroxidation of unsaturated fatty acids. Although LOXs participate in the plant defense system, the enzyme’s metabolites can have numerous negative effects on human health. Therefore, many types of research are searching for compounds that can inhibit LOXs. The best quantitative structure–activity relationship (QSAR) model was obtained using a Genetic Algorithm (GA). Molecular docking was performed with iGEMDOCK. The inhibition of lipoxygenase was in the range of 7.1 to 96.6%, and the inhibition of lipid peroxidation was 7.0–91.0%. Among the synthesized compounds, the strongest inhibitor of soybean LOX-3 (96.6%) was found to be 3-benzoyl-7-(benzyloxy)-2H-chromen-2-one. A lipid peroxidation inhibition of 91.0% was achieved with ethyl 7-methoxy-2-oxo-2H-chromene-3-carboxylate. The docking scores for the soybean LOX-3 and human 5-LOX also indicated that this compound has the best affinity for these LOX enzymes. The best multiple linear QSAR model contains the atom-centered fragment descriptors C-06, RDF035p, and HATS8p. QSAR and molecular docking studies elucidated the structural features important for the enhanced inhibitory activity of the most active compounds, such as the presence of the benzoyl ring at the 3-position of coumarin’s core. Compounds with benzoyl substituents are promising candidates as potent lipoxygenase inhibitors. View Full-Text
Keywords: lipoxygenase; coumarins; lipid peroxidation; antioxidant activity; QSAR; molecular docking lipoxygenase; coumarins; lipid peroxidation; antioxidant activity; QSAR; molecular docking
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MDPI and ACS Style

Lončarić, M.; Strelec, I.; Pavić, V.; Šubarić, D.; Rastija, V.; Molnar, M. Lipoxygenase Inhibition Activity of Coumarin Derivatives—QSAR and Molecular Docking Study. Pharmaceuticals 2020, 13, 154. https://doi.org/10.3390/ph13070154

AMA Style

Lončarić M, Strelec I, Pavić V, Šubarić D, Rastija V, Molnar M. Lipoxygenase Inhibition Activity of Coumarin Derivatives—QSAR and Molecular Docking Study. Pharmaceuticals. 2020; 13(7):154. https://doi.org/10.3390/ph13070154

Chicago/Turabian Style

Lončarić, Melita; Strelec, Ivica; Pavić, Valentina; Šubarić, Domagoj; Rastija, Vesna; Molnar, Maja. 2020. "Lipoxygenase Inhibition Activity of Coumarin Derivatives—QSAR and Molecular Docking Study" Pharmaceuticals 13, no. 7: 154. https://doi.org/10.3390/ph13070154

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