Synthesis, Anti-inflammatory, and Arginase Inhibitory Activity of Piceatannol and Its Analogs: Synthesis and Activity of Piceatannol Derivatives

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 mu M concentration followed by compounds 3 and 4 of 20 and 22% to arginase I, 22 and 23% to arginase II, respectively.