AUTHOR=Yadav Mukesh Kumar , Mailar Karabasappa , Nagarajappa Masagalli Jagadeesh , Chae Sung-Won , Song Jae-Jun , Choi Won Jun TITLE=Ruthenium Chloride—Induced Oxidative Cyclization of Trans-Resveratrol to (±)-ε-Viniferin and Antimicrobial and Antibiofilm Activity Against Streptococcus pneumoniae JOURNAL=Frontiers in Pharmacology VOLUME=Volume 10 - 2019 YEAR=2019 URL=https://www.frontiersin.org/journals/pharmacology/articles/10.3389/fphar.2019.00890 DOI=10.3389/fphar.2019.00890 ISSN=1663-9812 ABSTRACT=Polyphenol, ε-viniferin (2) is a protective phytochemical found in several plant families. Here, we report a simple and effective method for the synthesis of (±)-ε-viniferin (2) as major product and (±)-(E)-ω-viniferin (3) as a minor product. Synthesized viniferin compounds and standard viniferin were analyzed for anti-bacterial and anti-biofilm activity against Gram positive bacteria Streptococcus pneumoniae. The MICs of (±)-ε-viniferin (2) and standard viniferin were 20 µm. However, the MICs of (±)-(E)-ω-viniferin (3) and compound 8 were 40 µm. Although viniferin significantly (p<0.05) reduced pre-established in-vitro biofilms and killed bacteria within the biofilm, it was unable to prevent biofilm formation at sub-MIC concentrations. The time kill experiment revealed that viniferin killed bacteria and reduced 2.8 log10 bacteria at 2×MIC concentration after 24 h. SEM analysis and live/dead biofilm staining of pre-established biofilms revealed that viniferin treatment disrupt membrane integrity of biofilm bacteria. Crystal violet absorption, total protein, DNA and RNA release revealed that viniferin alters bacterial cell permeability, eventually kill bacteria.