C-geranylated flavonoids from Paulownia tomentosa Steud. fruit as potential anti-inflammatory agents. (5th October 2022)

• Record Type: Journal Article
• Authors: Molčanová, Lenka; Treml, Jakub; Brezáni, Veronika; Maršík, Petr; Kurhan, Sebnem; Trávníček, Zdeněk; Uhrin, Pavel; Šmejkal, Karel
• Is Part Of: Journal of ethnopharmacology. Volume 296(2022)
• Publication Date: 2022-10-05
• Subjects: Anti-inflammatory -- Geranylated flavonoids -- NF-κB -- Paulownia tomentosa -- THP-1-XBlue™-MD2-CD14; Ethnopharmacology -- Periodicals; Pharmacognosy -- Periodicals; Herbs -- Periodicals; Herbs -- Periodicals; Pharmacognosy -- Periodicals; Pharmacognosie -- Périodiques; Herbes -- Périodiques; 615.1
• DOI: 10.1016/j.jep.2022.115509
• Languages: English
• ISSNs: 0378-8741

Abstract

Abstract: 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 κ B/activator protein 1 (NF- κ B/AP-1) after lipopolysaccharide (LPS) stimulation. Results: All the test compounds (1 –21 and 23 –26 ) reduced the activation of NF- κ B/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-1 β, which can be explained by the plurality of possible outcomes of activation of the NF- κ B 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. Graphical abstract: Image 1 Highlights: Geranylated flavonoids were isolated from the fruit of Paulownia tomentosa Steud. Ten compounds were obtained from a natural source for the first time. Anti-inflammatory potential to affect the activation of NF- κ B/AP-1 was evaluated. Eight compounds were more active than anti-inflammatory drug prednisone.