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Anti-inflammatory Activity of Natural Geranylated Flavonoids: Cyclooxygenase and Lipoxygenase Inhibitory Properties and Proteomic Analysis

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    Anti-inflammatory Activity of Natural Geranylated Flavonoids: Cyclooxygenase and Lipoxygenase Inhibitory Properties and Proteomic Analysis
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    † †Department of Natural Drugs and ‡Department of Molecular Biology and Pharmaceutical Biotechnology, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences Brno, 61242 Brno, Czech Republic
    § Laboratory of Plant Biotechnologies, Institute of Experimental Botany, The Czech Academy of Sciences, 16502 Prague, Czech Republic
    ∥ ⊥Institute of Pharmacy/Pharmacognosy and Center for Molecular Biosciences Innsbruck (CMBI) and ∥Institute of Pharmacy/Pharmaceutical Chemistry and CMBI, University of Innsbruck, 6020 Innsbruck, Austria
    □ Department of Pharmaceutical and Pharmacological Sciences, University of Padua, 35131 Padua, Italy
    ○ Mass Spectrometry Group, Institute of Organic Chemistry and Biochemistry, The Czech Academy of Sciences, CZ-16610 Prague, Czech Republic
    Veterinary Research Institute, CZ-62100 Brno, Czech Republic
    *E-mail: [email protected]. Tel: +420-541562830.
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    Journal of Natural Products

    Cite this: J. Nat. Prod. 2017, 80, 4, 999–1006
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    https://doi.org/10.1021/acs.jnatprod.6b01011
    Published March 21, 2017
    Copyright © 2017 The American Chemical Society and American Society of Pharmacognosy
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    Abstract

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    Geranyl flavones have been studied as compounds that potentially can be developed as anti-inflammatory agents. A series of natural geranylated flavanones was isolated from Paulownia tomentosa fruits, and these compounds were studied for their anti-inflammatory activity and possible mechanism of action. Two new compounds were characterized [paulownione C (17) and tomentodiplacone O (20)], and all of the isolated derivatives were assayed for their ability to inhibit cyclooxygenases (COX-1 and COX-2) and 5-lipoxygenase (5-LOX). The compounds tested showed variable degrees of activity, with several of them showing activity comparable to or greater than the standards used in COX-1, COX-2, and 5-LOX assays. However, only the compound tomentodiplacone O (20) showed more selectivity against COX-2 versus COX-1 when compared with ibuprofen. The ability of the test compounds to interact with the above-mentioned enzymes was supported by docking studies, which revealed the possible incorporation of selected test substances into the active sites of these enzymes. Furthermore, one of the COX/LOX dual inhibitors, diplacone (14) (a major geranylated flavanone of P. tomentosa), was studied in vitro to obtain a proteomic overview of its effect on inflammation in LPS-treated THP-1 macrophages, supporting its previously observed anti-inflammatory activity and revealing the mechanism of its anti-inflammatory effect.

    Copyright © 2017 The American Chemical Society and American Society of Pharmacognosy

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    Cite this: J. Nat. Prod. 2017, 80, 4, 999–1006
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    https://doi.org/10.1021/acs.jnatprod.6b01011
    Published March 21, 2017
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