Antioxidant Activity of Selected Stilbenoid Derivatives in a Cellular Model System

Abstract

The stilbenoids, a group of naturally occurring phenolic compounds, are found in a variety of plants, including some berries that are used as food or for medicinal purposes. They are known to be beneficial for human health as anti-inflammatory, chemopreventive, and antioxidative agents. We have investigated a group of 19 stilbenoid substances in vitro using a cellular model of THP-1 macrophage-like cells and pyocyanin-induced oxidative stress to evaluate their antioxidant or pro-oxidant properties. Then we have determined any effects that they might have on the expression of the enzymes catalase, glutathione peroxidase, and heme oxygenase-1, and their effects on the activation of Nrf2. The experimental results showed that these stilbenoids could affect the formation of reactive oxygen species in a cellular model, producing either an antioxidative or pro-oxidative effect, depending on the structure pinostilbene (2) worked as a pro-oxidant and also decreased expression of catalase in the cell culture. Piceatannol (4) had shown reactive oxygen species (ROS) scavenging activity, whereas isorhapontigenin (18) had a mild direct antioxidant effect and activated Nrf2-antioxidant response element (ARE) system and elevated expression of Nrf2 and catalase. Their effects shown on cells in vitro warrant their further study in vivo.

Antioxidative Activity of 1,3,5-Triazine Analogues Incorporating Aminobenzene Sulfonamide, Aminoalcohol/Phenol, Piperazine, Chalcone, or Stilbene Motifs

“…Structural Motif (26)(27)(28)(29)(30)(31)(32) Step 1: Starting dichlorotriazinyl benzene sulfonamide (1 mmol) was dissolved in 10 mL of DMF. One mmol of solid anhydrous potassium carbonate was added in small portions, and the mixture was stirred for 10 min.…”

“…They might have an effect on the production of catalase, heme oxygenase-1, and glutathione peroxidase enzymes. Depending on their molecular structure, they can produce antioxidative but also pro-oxidative effects [31]. Resveratrol (stilbene analogue; see Figure 1f) is an example of phenolic antioxidant, which serves in medicine as an adjuvant treatment of cardiovascular diseases, metabolic syndrome, type 2 diabetes, and inflammatory diseases [4].…”

More Than Resveratrol: New Insights into Stilbene-Based Compounds

“…Other studies, including the research with 19 stilbenoids, on human monocytic THP-1 cell line (THP1-XBlue™-MD2-CD14) and human hepatoma cell line (HepG2), showed that ISO has mild antioxidant activity compared to piceatannol. Interestingly, ISO activated the increased expression of the nuclear factor erythroid 2-related factor 2 (Nrf2), the transcription factor that controls the expression of genes encoding cytoprotective enzymes and protein [55].…”

Stilbenoids: chemistry, occurrence, bioavailability and health effects—a review

“…Stilbenoids and related compounds are produced by plants for antifungal and antibacterial purposes. Nineteen stilbenoid derivatives were tested in a cellular model system, some of which exhibited antioxidant properties while others were pro-oxidative (Treml et al, 2019). Among these, resveratrol was found to have direct scavenging effect on reactive oxygen species (ROS) (Akinwumi et al, 2018).…”

“…Stilbenoids have been of interest due to their antioxidant (Oh and Shahidi, 2017;Oh et al, 2019;Treml et al, 2019), anti-inflammatory (Leláková et al, 2019;Hošek et al, 2019), anticancer (Cuzick et al, 2015) cardioprotective (Zamora-Ros et al, 2012), anti-Alzheimer's (Moussa et al, 2017), and anti-diabetic (Banaszewska et al, 2016) activities. In addition, resveratrol, for example, has a higher lipophilicity compared to other phenolic compounds, which may lead to its better cell permeability (Neves et al, 2013).…”