Synthesis, Anti‐inflammatory, and Arginase Inhibitory Activity of Piceatannol and Its Analogs

Abstract

The present study describes the synthesis of piceatannol (2) and its analogs (3–8) using Wittig‐Horner reaction, Colvin rearrangement, and Sonogashira reaction as key steps and also evaluation of their inhibitory potency on the production of inflammatory mediator nitric oxide (NO) in lipopolysaccharide (LPS)‐induced RAW‐264.7 macrophages. Three compounds 7 (90.1%), 8 (60.8%), and 6 (55.2%) were found to potently inhibit NO production induced by LPS without affecting the viability of RAW‐264.7 cells. In addition, their Arginase I and II inhibition activity was also evaluated. In this study, three compounds, i.e., compounds 2–4 were showed good inhibition activity to both arginase I and II. Of the synthesized compounds, compound 2 exhibited maximum inhibitory activity of 28% (arginase I) and 26% (arginase II) at 10 μM concentration followed by compounds 3 and 4 of 20 and 22% to arginase I, 22 and 23% to arginase II, respectively.

Piceatannol Protects Human Retinal Pigment Epithelial Cells against Hydrogen Peroxide Induced Oxidative Stress and Apoptosis through Modulating PI3K/Akt Signaling Pathway

“…Piceatannol (3,3′,4,5′-trans-tetrahydroxystilbene) is a natural stilbene found in fruits [8], seeds [9], and wine [10]. Piceatannol has been reported to have several beneficial properties, such as anti-oxidation [11], anti-inflammation [12], and neuroprotective activity [13]. The number and substituted position of hydroxys make piceatannol more preferentially active than other natural stilbene, such as resveratrol and oxyresveratrol [11].…”

Piceatannol Alleviates Deoxynivalenol-Induced Damage in Intestinal Epithelial Cells via Inhibition of the NF-κB Pathway

“…PIC is similar to resveratrol (RES) and shares similar biological activities. It has been shown to possess various beneficial properties, including antioxidation, anti-inflammation, and neuroprotective activities [ 19 , 20 , 21 ]. Li’s research demonstrated that PIC could suppress inflammation induced by tumor necrosis factor-alpha (TNF-α) [ 22 ].…”