2. Academic Validation
  3. Prenylated Stilbenoids Affect Inflammation by Inhibiting the NF-κB/AP-1 Signaling Pathway and Cyclooxygenases and Lipoxygenase

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

  • J Nat Prod. 2019 Jul 26;82(7):1839-1848. doi: 10.1021/acs.jnatprod.9b00081.
Jan Hošek,  Veronika Leláková,  Pavel Bobál,  Hana Pížová,  Markéta Gazdová,  Milan Malaník,  Karolina Jakubczyk 1,  Ondřej Veselý 1 2,  Přemysl Landa 1,  Veronika Temml 3,  Daniela Schuster 4,  Vilailak Prachyawarakorn 5,  Phanruethai Pailee 5,  Gang Ren 6,  Filip Zpurný 7,  Michal Oravec 8,  Karel Šmejkal
Affiliations

Affiliations

  • 1 Laboratory of Plant Biotechnologies, Institute of Experimental Botany , Czech Academy of Sciences , Rozvojová 263 , 16502 Prague , Czech Republic.
  • 2 Department of Quality of Agricultural Products, Faculty of Agrobiology, Food and Natural Resources , Czech University of Life Sciences Prague , Kamýcká 129 , 16521 Prague 6-Suchdol , Czech Republic.
  • 3 Department of Pharmacy/Pharmacognosy and Center for Molecular Biosciences (CMBI) , University of Innsbruck , Innrain 80-82 , 6020 Innsbruck , Austria.
  • 4 Institute of Pharmacy, Department of Pharmaceutical and Medicinal Chemistry , Paracelsus Medical University Salzburg , Strubergasse 21 , 2020 Salzburg , Austria.
  • 5 Chulabhorn Research Institute , Kamphaeng Phet 6 Road , Laksi, Bangkok 10210 , Thailand.
  • 6 Research Center of Natural Resources of Chinese Medicinal Materials and Ethnic Medicine , Jiangxi University of Traditional Chinese Medicine , Nanchang 330004 , People's Republic of China.
  • 7 Botanical Garden Teplice , J. Suka 1388/18 , 41501 Teplice , Czech Republic.
  • 8 Global Change Research Institute of the Czech Academy of Sciences , Bělidla 986/4a , 60300 Brno , Czech Republic.
PMID: 31268709 DOI: 10.1021/acs.jnatprod.9b00081
Abstract

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-κB (NF-κB) 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-κB/AP-1. The ability of prenylated stilbenoids to attenuate the production of pro-inflammatory cytokines tumor necrosis factor-α (TNF-α) and interleukin-1β (IL-1β) was further evaluated using LPS-stimulated THP-1 macrophages.

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