Antiproliferative and cytotoxic activities of C-Geranylated
flavonoids from Paulownia tomentosa Steud. Fruit

J 2021

Antiproliferative and cytotoxic activities of C-Geranylated flavonoids from Paulownia tomentosa Steud. Fruit

MOLČANOVÁ, Lenka, Tereza KAUEROVÁ, S. DALL'ACQUA, P. MARSIK, Peter KOLLÁR et. al.

Základní údaje

Originální název

Antiproliferative and cytotoxic activities of C-Geranylated flavonoids from Paulownia tomentosa Steud. Fruit

Autoři

MOLČANOVÁ, Lenka (703 Slovensko, garant, domácí), Tereza KAUEROVÁ (203 Česká republika, domácí), S. DALL'ACQUA, P. MARSIK, Peter KOLLÁR (203 Česká republika, domácí) a Karel ŠMEJKAL (203 Česká republika, domácí)

Vydání

Bioorganic Chemistry, SAN DIEGO, ACADEMIC PRESS INC ELSEVIER SCIENCE, 2021, 0045-2068

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

30104 Pharmacology and pharmacy

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 5.307

Kód RIV

RIV/00216224:14160/21:00121331

Organizační jednotka

Farmaceutická fakulta

DOI

http://dx.doi.org/10.1016/j.bioorg.2021.104797

UT WoS

000656969400005

Klíčová slova anglicky

Antiproliferative activity; Cytotoxic activity; Flavonoid; Geranyl; Paulownia tomentosa; Prenyl; THP-1 cell line

Štítky

rivok, ÚFTo, ÚPL

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 20. 4. 2022 10:34, JUDr. Sabina Krejčiříková

Anotace

V originále

Prenylated or geranylated flavonoids have been studied for their promising antiproliferative and cytotoxic activities. Twelve natural geranylated flavonoids (1-12) were isolated from the fruit of Paulownia tomentosa Steud. Their structures were elucidated using UV and IR spectroscopy, mass spectrometry, and 1D and 2D NMR spectroscopy. The absolute configurations were determined using NMR and circular dichroism. Seven of the compounds were characterized as new geranylated derivatives isolated from a natural source for the first time, namely 3 '-O-methyl-5 '-hydroxyisodiplacone (3), paulodiplacone A (5), tomentone II (6), tomentone B (7), tomentodiplacone P (8), paulodiplacone B (9), and tomentoflavone A (12). After 24 h of incubation at concentrations in the range 1-30 mu M, the isolated compounds were tested for their antiproliferative and cytotoxic potentials against the human monocytic leukaemia cell line THP-1, using WST-1 and LDH assays, respectively. Almost all of the test compounds induced a concentration-dependent reduction in the metabolic activity of THP-1 cells and a concentration-dependent reduction in the cell viability. Diplacone (1) was the most potent antiproliferative and cytotoxic agent (IC50 9.31 +/- 0.72 mu M, LC50 18.01 +/- 1.19 mu M). 3 '-O-Methyl-5 '-hydroxydiplacone (2) showed relatively strong antiproliferative effect (IC50 12.61 +/- 0.90 mu M) and weaker cytotoxic activity (LC50 > 30 mu M), indicating that it may serve as a potential lead compound for further testing. The structure-activity relationship for the 12 isolated compounds is discussed.

Citovat

MOLČANOVÁ, Lenka, Tereza KAUEROVÁ, S. DALL'ACQUA, P. MARSIK, Peter KOLLÁR a Karel ŠMEJKAL. Antiproliferative and cytotoxic activities of C-Geranylated flavonoids from Paulownia tomentosa Steud. Fruit. Bioorganic Chemistry. SAN DIEGO: ACADEMIC PRESS INC ELSEVIER SCIENCE, 2021, roč. 111, č. 104797, s. 1-12. ISSN 0045-2068. Dostupné z: https://dx.doi.org/10.1016/j.bioorg.2021.104797.

@article{1757217,
   author = {Molčanová, Lenka and Kauerová, Tereza and Dall'Acqua, S. and Marsik, P. and Kollár, Peter and Šmejkal, Karel},
   article_location = {SAN DIEGO},
   article_number = {104797},
   doi = {http://dx.doi.org/10.1016/j.bioorg.2021.104797},
   keywords = {Antiproliferative activity; Cytotoxic activity; Flavonoid; Geranyl; Paulownia tomentosa; Prenyl; THP-1 cell line},
   language = {eng},
   issn = {0045-2068},
   journal = {Bioorganic Chemistry},
   title = {Antiproliferative and cytotoxic activities of C-Geranylated flavonoids from Paulownia tomentosa Steud. Fruit},
   url = {https://www.sciencedirect.com/science/article/pii/S0045206821001747?via%3Dihub},
   volume = {111},
   year = {2021}
}

TY  - JOUR
ID  - 1757217
AU  - Molčanová, Lenka - Kauerová, Tereza - Dall'Acqua, S. - Marsik, P. - Kollár, Peter - Šmejkal, Karel
PY  - 2021
TI  - Antiproliferative and cytotoxic activities of C-Geranylated flavonoids from Paulownia tomentosa Steud. Fruit
JF  - Bioorganic Chemistry
VL  - 111
IS  - 104797
SP  - 1-12
EP  - 1-12
PB  - ACADEMIC PRESS INC ELSEVIER SCIENCE
SN  - 00452068
KW  - Antiproliferative activity
KW  - Cytotoxic activity
KW  - Flavonoid
KW  - Geranyl
KW  - Paulownia tomentosa
KW  - Prenyl
KW  - THP-1 cell line
UR  - https://www.sciencedirect.com/science/article/pii/S0045206821001747?via%3Dihub
N2  - Prenylated or geranylated flavonoids have been studied for their promising antiproliferative and cytotoxic activities. Twelve natural geranylated flavonoids (1-12) were isolated from the fruit of Paulownia tomentosa Steud. Their structures were elucidated using UV and IR spectroscopy, mass spectrometry, and 1D and 2D NMR spectroscopy. The absolute configurations were determined using NMR and circular dichroism. Seven of the compounds were characterized as new geranylated derivatives isolated from a natural source for the first time, namely 3 '-O-methyl-5 '-hydroxyisodiplacone (3), paulodiplacone A (5), tomentone II (6), tomentone B (7), tomentodiplacone P (8), paulodiplacone B (9), and tomentoflavone A (12). After 24 h of incubation at concentrations in the range 1-30 mu M, the isolated compounds were tested for their antiproliferative and cytotoxic potentials against the human monocytic leukaemia cell line THP-1, using WST-1 and LDH assays, respectively. Almost all of the test compounds induced a concentration-dependent reduction in the metabolic activity of THP-1 cells and a concentration-dependent reduction in the cell viability. Diplacone (1) was the most potent antiproliferative and cytotoxic agent (IC50 9.31 +/- 0.72 mu M, LC50 18.01 +/- 1.19 mu M). 3 '-O-Methyl-5 '-hydroxydiplacone (2) showed relatively strong antiproliferative effect (IC50 12.61 +/- 0.90 mu M) and weaker cytotoxic activity (LC50 > 30 mu M), indicating that it may serve as a potential lead compound for further testing. The structure-activity relationship for the 12 isolated compounds is discussed.
ER  -

MOLČANOVÁ, Lenka, Tereza KAUEROVÁ, S. DALL'ACQUA, P. MARSIK, Peter KOLLÁR a Karel ŠMEJKAL. Antiproliferative and cytotoxic activities of C-Geranylated flavonoids from Paulownia tomentosa Steud. Fruit. \textit{Bioorganic Chemistry}. SAN DIEGO: ACADEMIC PRESS INC ELSEVIER SCIENCE, 2021, roč.~111, č.~104797, s.~1-12. ISSN~0045-2068. Dostupné z: https://dx.doi.org/10.1016/j.bioorg.2021.104797.

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