Design, synthesis, and antiviral activity of novel rutin derivatives containing 1, 4-pentadien-3-one moiety

•Novel rutin analogs were synthesized.•The synthesized compounds showed good antiviral activities.•The EC50 value of 7r was 394.78 μg/mL against cucumber mosaic virus.•Preliminary SAR was analyzed.

Rutin (compound 5) and some compounds (compounds 1–4 and 6) were isolated from Artemisia princeps Pamp (A. princeps Pamp.) and a series of novel rutin derivatives containing 1,4-pentadien-3-one moiety were designed and synthesized. The target compounds were characterized by proton nuclear magnetic resonance spectroscopy (1H NMR), carbon nuclear magnetic resonance spectroscopy (13C NMR), and ESI-MS. Bioassay results indicated that some of the compounds showed good to excellent antiviral activities against tobacco mosaic virus (TMV) and cucumber mosaic virus (CMV) at 500 μg/mL in vivo. The 50% effective concentrations (EC50) of the compound 7r against CMV was 394.78 μg/mL, which was better than that of Ningnanmycin (432.22 μg/mL). These results indicated that novel rutin derivatives containing 1,4-pentadien-3-one moiety can effectively control CMV.

Graphical abstractNovel rutin derivatives containing a 1,4-pentadien-3-one moiety were synthesized and evaluated for their antiviral activities. Compounds showed good activities against tobacco mosaic virus and cucumber mosaic virus.Figure optionsDownload full-size imageDownload as PowerPoint slide