C-geranylated flavonoids from Paulownia tomentosa Steud. fruit
as potential anti-inflammatory agents

J 2022

C-geranylated flavonoids from Paulownia tomentosa Steud. fruit as potential anti-inflammatory agents

MOLČANOVÁ, Lenka, Jakub TREML, Veronika BREZANI, Petr MARSIK, Sebnem KURHAN et. al.

Basic information

Original name

C-geranylated flavonoids from Paulownia tomentosa Steud. fruit as potential anti-inflammatory agents

Authors

MOLČANOVÁ, Lenka (703 Slovakia, belonging to the institution), Jakub TREML (203 Czech Republic, belonging to the institution), Veronika BREZANI, Petr MARSIK, Sebnem KURHAN, Zdenek TRAVNICEK, Pavel UHRIN and Karel ŠMEJKAL (203 Czech Republic, guarantor, belonging to the institution)

Edition

JOURNAL OF ETHNOPHARMACOLOGY, CLARE, ELSEVIER IRELAND LTD, 2022, 0378-8741

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

30104 Pharmacology and pharmacy

Country of publisher

Ireland

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 5.400

RIV identification code

RIV/00216224:14160/22:00129753

Organization unit

Faculty of Pharmacy

DOI

http://dx.doi.org/10.1016/j.jep.2022.115509

UT WoS

000830216700002

Keywords in English

Anti-inflammatory; Geranylated flavonoids; NF -KB; Paulownia tomentosa; THP-1-XBlue TM-MD2-CD14

Abstract

V originále

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.

Links

MUNI/A/1654/2020, interní kód MU

Name: Testování biologické aktivity vybraných přírodních látek in vitro

Investor: Masaryk University

MUNI/A/1688/2020, interní kód MU

Name: Izolace sekundárních metabolitů s potenciální biologickou aktivitou z rostlinných zdrojů (Acronym: Izolace sekundárních metabolitů)

Investor: Masaryk University

Citovat

MOLČANOVÁ, Lenka, Jakub TREML, Veronika BREZANI, Petr MARSIK, Sebnem KURHAN, Zdenek TRAVNICEK, Pavel UHRIN and Karel ŠMEJKAL. C-geranylated flavonoids from Paulownia tomentosa Steud. fruit as potential anti-inflammatory agents. JOURNAL OF ETHNOPHARMACOLOGY. CLARE: ELSEVIER IRELAND LTD, 2022, vol. 296, October, p. 1-14. ISSN 0378-8741. Available from: https://dx.doi.org/10.1016/j.jep.2022.115509.

@article{1875169,
   author = {Molčanová, Lenka and Treml, Jakub and Brezani, Veronika and Marsik, Petr and Kurhan, Sebnem and Travnicek, Zdenek and Uhrin, Pavel and Šmejkal, Karel},
   article_location = {CLARE},
   article_number = {October},
   doi = {http://dx.doi.org/10.1016/j.jep.2022.115509},
   keywords = {Anti-inflammatory; Geranylated flavonoids; NF -KB; Paulownia tomentosa; THP-1-XBlue TM-MD2-CD14},
   language = {eng},
   issn = {0378-8741},
   journal = {JOURNAL OF ETHNOPHARMACOLOGY},
   title = {C-geranylated flavonoids from Paulownia tomentosa Steud. fruit as potential anti-inflammatory agents},
   url = {https://www.sciencedirect.com/science/article/pii/S0378874122005487?via%3Dihub},
   volume = {296},
   year = {2022}
}

TY  - JOUR
ID  - 1875169
AU  - Molčanová, Lenka - Treml, Jakub - Brezani, Veronika - Marsik, Petr - Kurhan, Sebnem - Travnicek, Zdenek - Uhrin, Pavel - Šmejkal, Karel
PY  - 2022
TI  - C-geranylated flavonoids from Paulownia tomentosa Steud. fruit as potential anti-inflammatory agents
JF  - JOURNAL OF ETHNOPHARMACOLOGY
VL  - 296
IS  - October
SP  - 1-14
EP  - 1-14
PB  - ELSEVIER IRELAND LTD
SN  - 03788741
KW  - Anti-inflammatory
KW  - Geranylated flavonoids
KW  - NF -KB
KW  - Paulownia tomentosa
KW  - THP-1-XBlue TM-MD2-CD14
UR  - https://www.sciencedirect.com/science/article/pii/S0378874122005487?via%3Dihub
N2  - 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.
ER  -

MOLČANOVÁ, Lenka, Jakub TREML, Veronika BREZANI, Petr MARSIK, Sebnem KURHAN, Zdenek TRAVNICEK, Pavel UHRIN and Karel ŠMEJKAL. C-geranylated flavonoids from Paulownia tomentosa Steud. fruit as potential anti-inflammatory agents. \textit{JOURNAL OF ETHNOPHARMACOLOGY}. CLARE: ELSEVIER IRELAND LTD, 2022, vol.~296, October, p.~1-14. ISSN~0378-8741. Available from: https://dx.doi.org/10.1016/j.jep.2022.115509.

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