Prenylated Stilbenoids Affect Inflammation by Inhibiting the
NF-kappa B/AP-1 Signaling Pathway and Cyclooxygenases and
Lipoxygenase

J 2019

Prenylated Stilbenoids Affect Inflammation by Inhibiting the NF-kappa B/AP-1 Signaling Pathway and Cyclooxygenases and Lipoxygenase

HOŠEK, Jan; Veronika LELÁKOVÁ; Pavel BOBÁĽ; Hana PÍŽOVÁ; Markéta GAZDOVÁ et al.

Základní údaje

Originální název

Prenylated Stilbenoids Affect Inflammation by Inhibiting the NF-kappa B/AP-1 Signaling Pathway and Cyclooxygenases and Lipoxygenase

Autoři

Vydání

Journal of Natural Products, Washington, American Chemical Society, 2019, 0163-3864

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

30104 Pharmacology and pharmacy

Utajení

není předmětem státního či obchodního tajemství

Impakt faktor

Impact factor: 3.782

Označené pro přenos do RIV

Organizační jednotka

Farmaceutická fakulta

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 23. 2. 2021 14:23, PharmDr. Milan Malaník, Ph.D.

Anotace

V originále

Stilbenoids are important components of foods (e.g., peanuts, grapes, various edible berries), beverages (wine, white tea), and medicinal plants. Many publications have described the anti-inflammatory potential of stilbenoids, including the widely known trans-resveratrol and its analogues. However, comparatively little information is available regarding the activity of their prenylated derivatives. One new prenylated stilbenoid (2) was isolated from Artocarpus altilis and characterized structurally based on 1D and 2D NMR analysis and HRMS. Three other prenylated stilbenoids were prepared synthetically (9-11). Their antiphlogistic potential was determined by testing them together with known natural prenylated stilbenoids from Macaranga siamensis and Artocarpus heterophyllus in both cell-free and cell assays. The inhibition of 5-lipoxygenase (5-LOX) was also shown by simulated molecular docking for the most active stilbenoids in order to elucidate the mode of interaction between these compounds and the enzyme. Their effects on the pro-inflammatory nuclear factor-kappa B (NF-kappa B) and the activator protein 1 (AP-1) signaling pathway were also analyzed. The THP1-XBlue-MD2-CD14 cell line was used as a model for determining their anti-inflammatory potential, and lipopolysaccharide (LPS) stimulation of Toll-like receptor 4 induced a signaling cascade leading to the activation of NF-kappa B/AP-1. The ability of prenylated stilbenoids to attenuate the production of pro-inflammatory cytokines tumor necrosis factor-alpha (TNF-alpha) and interleukin-1 beta (IL-1 beta) was further evaluated using LPS-stimulated THP-1 macrophages.

Citovat

HOŠEK, Jan; Veronika LELÁKOVÁ; Pavel BOBÁĽ; Hana PÍŽOVÁ; Markéta GAZDOVÁ; Milan MALANÍK; K JAKUBCZYK; O. VESELY; P. LANDA; V. TEMML; D. SCHUSTER; V. PRACHYAWARAKORN; P. PAILEE; G. REN; F. ZPURNY; M. ORAVEC a Karel ŠMEJKAL. Prenylated Stilbenoids Affect Inflammation by Inhibiting the NF-kappa B/AP-1 Signaling Pathway and Cyclooxygenases and Lipoxygenase. Journal of Natural Products. Washington: American Chemical Society, 2019, roč. 82, č. 7, s. 1839-1848. ISSN 0163-3864. Dostupné z: https://doi.org/10.1021/acs.jnatprod.9b00081.

@article{1726950,
   author = {Hošek, Jan and Leláková, Veronika and Bobáľ, Pavel and Pížová, Hana and Gazdová, Markéta and Malaník, Milan and Jakubczyk, K and Vesely, O. and Landa, P. and Temml, V. and Schuster, D. and Prachyawarakorn, V. and Pailee, P. and Ren, G. and Zpurny, F. and Oravec, M. and Šmejkal, Karel},
   article_location = {Washington},
   article_number = {7},
   doi = {https://doi.org/10.1021/acs.jnatprod.9b00081},
   language = {eng},
   issn = {0163-3864},
   journal = {Journal of Natural Products},
   title = {Prenylated Stilbenoids Affect Inflammation by Inhibiting the NF-kappa B/AP-1 Signaling Pathway and Cyclooxygenases and Lipoxygenase},
   volume = {82},
   year = {2019}
}

TY  - JOUR
ID  - 1726950
AU  - Hošek, Jan - Leláková, Veronika - Bobáľ, Pavel - Pížová, Hana - Gazdová, Markéta - Malaník, Milan - Jakubczyk, K - Vesely, O. - Landa, P. - Temml, V. - Schuster, D. - Prachyawarakorn, V. - Pailee, P. - Ren, G. - Zpurny, F. - Oravec, M. - Šmejkal, Karel
PY  - 2019
TI  - Prenylated Stilbenoids Affect Inflammation by Inhibiting the NF-kappa B/AP-1 Signaling Pathway and Cyclooxygenases and Lipoxygenase
JF  - Journal of Natural Products
VL  - 82
IS  - 7
SP  - 1839-1848
EP  - 1839-1848
PB  - American Chemical Society
SN  - 01633864
N2  - Stilbenoids are important components of foods (e.g., peanuts, grapes, various edible berries), beverages (wine, white tea), and medicinal plants. Many publications have described the anti-inflammatory potential of stilbenoids, including the widely known trans-resveratrol and its analogues. However, comparatively little information is available regarding the activity of their prenylated derivatives. One new prenylated stilbenoid (2) was isolated from Artocarpus altilis and characterized structurally based on 1D and 2D NMR analysis and HRMS. Three other prenylated stilbenoids were prepared synthetically (9-11). Their antiphlogistic potential was determined by testing them together with known natural prenylated stilbenoids from Macaranga siamensis and Artocarpus heterophyllus in both cell-free and cell assays. The inhibition of 5-lipoxygenase (5-LOX) was also shown by simulated molecular docking for the most active stilbenoids in order to elucidate the mode of interaction between these compounds and the enzyme. Their effects on the pro-inflammatory nuclear factor-kappa B (NF-kappa B) and the activator protein 1 (AP-1) signaling pathway were also analyzed. The THP1-XBlue-MD2-CD14 cell line was used as a model for determining their anti-inflammatory potential, and lipopolysaccharide (LPS) stimulation of Toll-like receptor 4 induced a signaling cascade leading to the activation of NF-kappa B/AP-1. The ability of prenylated stilbenoids to attenuate the production of pro-inflammatory cytokines tumor necrosis factor-alpha (TNF-alpha) and interleukin-1 beta (IL-1 beta) was further evaluated using LPS-stimulated THP-1 macrophages.
ER  -

HOŠEK, Jan; Veronika LELÁKOVÁ; Pavel BOBÁĽ; Hana PÍŽOVÁ; Markéta GAZDOVÁ; Milan MALANÍK; K JAKUBCZYK; O. VESELY; P. LANDA; V. TEMML; D. SCHUSTER; V. PRACHYAWARAKORN; P. PAILEE; G. REN; F. ZPURNY; M. ORAVEC a Karel ŠMEJKAL. Prenylated Stilbenoids Affect Inflammation by Inhibiting the NF-kappa B/AP-1 Signaling Pathway and Cyclooxygenases and Lipoxygenase. \textit{Journal of Natural Products}. Washington: American Chemical Society, 2019, roč.~82, č.~7, s.~1839-1848. ISSN~0163-3864. Dostupné z: https://doi.org/10.1021/acs.jnatprod.9b00081.

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