ETHNOPHARMACOLOGICAL RELEVANCE: Paulownia tomentosa Steud., a traditional Chinese medicinal plant, was used for many centuries in Chinese herbal medicine as a component of remedies for many illnesses, including inflammatory diseases. It is a rich source of phenolic compounds, mainly geranylated flavonoids, which are currently studied for their promising biological activities. AIM OF THE STUDY: The study aimed to isolate minor geranylated flavanones and flavones from P. tomentosa fruit and evaluate their cytotoxicity and possible anti-inflammatory effects in a cell-based model of inflammation. MATERIALS AND METHODS: Chromatographic separation of chloroform portion of the ethanolic extract of P. tomentosa fruit led to the isolation of twenty-seven flavonoids (1-27), twenty-six of them geranylated with different modifications and one non-geranylated flavanone, and two phenolic compounds. Compounds were identified using UV, IR, HRMS, NMR, and CD spectroscopy. Ten of these compounds (7-10, 12, 21, 22, 24, 25, and 27) were determined to be new flavonoid derivatives obtained from a natural source for the first time. Selected compounds were analyzed for cytotoxicity and anti-inflammatory potential to affect the activation of nuclear factor κB/activator protein 1 (NF-κB/AP-1) after lipopolysaccharide (LPS) stimulation. RESULTS: All the test compounds (1-21 and 23-26) reduced the activation of NF-κB/AP-1 24 h after the addition of LPS. Eight compounds (5, 14-18, 21, and 26) were more active than prednisone, a widely used anti-inflammatory drug. However, this effect was not seen significantly on the level of TNF-α and IL-1β, which can be explained by the plurality of possible outcomes of activation of the NF-κB pathway in cells. CONCLUSIONS: Results of the presented study confirmed that constituents from traditional Chinese medicinal plant P. tomentosa Steud. have promising anti-inflammatory activities and can serve as a potential source of inspiration for new anti-inflammatory medications.

Department of Food Quality and Safety Czech University of Life Sciences Prague Kamýcká 129 CZ 16500 Prague 6 Suchdol Czech Republic

Department of Molecular Pharmacy Faculty of Pharmacy Masaryk University Palackého tř 1946 1 CZ 61200 Brno Czech Republic

Department of Natural Drugs Faculty of Pharmacy Masaryk University Palackého tř 1946 1 CZ 61200 Brno Czech Republic

Institute of Vascular Biology and Thrombosis Research Center for Physiology and Pharmacology Medical University of Vienna Vienna Austria

Regional Centre of Advanced Technologies and Materials Czech Advanced Technology and Research Institute Palacký University Šlechtitelů 27 CZ 77900 Olomouc Czech Republic

Veterinary Research Institute Hudcova 296 70 CZ 62100 Brno Czech Republic

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$a Molčanová, Lenka $u Department of Natural Drugs, Faculty of Pharmacy, Masaryk University, Palackého tř. 1946/1, CZ-61200, Brno, Czech Republic. Electronic address: lenka.molcanova1993@gmail.com

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$a C-geranylated flavonoids from Paulownia tomentosa Steud. fruit as potential anti-inflammatory agents / $c L. Molčanová, J. Treml, V. Brezáni, P. Maršík, S. Kurhan, Z. Trávníček, P. Uhrin, K. Šmejkal

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$a ETHNOPHARMACOLOGICAL RELEVANCE: Paulownia tomentosa Steud., a traditional Chinese medicinal plant, was used for many centuries in Chinese herbal medicine as a component of remedies for many illnesses, including inflammatory diseases. It is a rich source of phenolic compounds, mainly geranylated flavonoids, which are currently studied for their promising biological activities. AIM OF THE STUDY: The study aimed to isolate minor geranylated flavanones and flavones from P. tomentosa fruit and evaluate their cytotoxicity and possible anti-inflammatory effects in a cell-based model of inflammation. MATERIALS AND METHODS: Chromatographic separation of chloroform portion of the ethanolic extract of P. tomentosa fruit led to the isolation of twenty-seven flavonoids (1-27), twenty-six of them geranylated with different modifications and one non-geranylated flavanone, and two phenolic compounds. Compounds were identified using UV, IR, HRMS, NMR, and CD spectroscopy. Ten of these compounds (7-10, 12, 21, 22, 24, 25, and 27) were determined to be new flavonoid derivatives obtained from a natural source for the first time. Selected compounds were analyzed for cytotoxicity and anti-inflammatory potential to affect the activation of nuclear factor κB/activator protein 1 (NF-κB/AP-1) after lipopolysaccharide (LPS) stimulation. RESULTS: All the test compounds (1-21 and 23-26) reduced the activation of NF-κB/AP-1 24 h after the addition of LPS. Eight compounds (5, 14-18, 21, and 26) were more active than prednisone, a widely used anti-inflammatory drug. However, this effect was not seen significantly on the level of TNF-α and IL-1β, which can be explained by the plurality of possible outcomes of activation of the NF-κB pathway in cells. CONCLUSIONS: Results of the presented study confirmed that constituents from traditional Chinese medicinal plant P. tomentosa Steud. have promising anti-inflammatory activities and can serve as a potential source of inspiration for new anti-inflammatory medications.

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$a Treml, Jakub $u Department of Molecular Pharmacy, Faculty of Pharmacy, Masaryk University, Palackého tř. 1946/1, CZ-61200, Brno, Czech Republic. Electronic address: tremlj@pharm.muni.cz

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$a Brezáni, Veronika $u Department of Molecular Pharmacy, Faculty of Pharmacy, Masaryk University, Palackého tř. 1946/1, CZ-61200, Brno, Czech Republic; Veterinary Research Institute, Hudcova 296/70, CZ-62100, Brno, Czech Republic. Electronic address: veronika.lelakova@gmail.com

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$a Maršík, Petr $u Department of Food Quality and Safety, Czech University of Life Sciences Prague, Kamýcká 129, CZ-16500, Prague 6-Suchdol, Czech Republic. Electronic address: marsik@af.czu.cz

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$a Kurhan, Sebnem $u Department of Food Quality and Safety, Czech University of Life Sciences Prague, Kamýcká 129, CZ-16500, Prague 6-Suchdol, Czech Republic. Electronic address: kurhan@af.czu.cz

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$a Trávníček, Zdeněk $u Regional Centre of Advanced Technologies and Materials, Czech Advanced Technology and Research Institute, Palacký University, Šlechtitelů 27, CZ-77900, Olomouc, Czech Republic. Electronic address: zdenek.travnicek@upol.cz

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$a Uhrin, Pavel $u Institute of Vascular Biology and Thrombosis Research, Center for Physiology and Pharmacology, Medical University of Vienna, Vienna, Austria. Electronic address: Pavel.Uhrin@meduniwien.ac.at

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$a Šmejkal, Karel $u Department of Natural Drugs, Faculty of Pharmacy, Masaryk University, Palackého tř. 1946/1, CZ-61200, Brno, Czech Republic. Electronic address: smejkalk@pharm.muni.cz

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