Ruthenium Chloride-Induced Oxidative Cyclization of Trans-Resveratrol to (±)-Viniferin and Antimicrobial and Antibiofilm Activity against Streptococcus pneumoniae

Mukesh Kumar Yadav, Karabasappa Mailar, Jagadeesh Nagarajappa Masagalli, Sung Won Chae, Jae-Jun Song, Won Jun Choi

Research output: Contribution to journalArticle

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)-viniferin (3) as a minor product. Synthesized viniferin compounds and standard viniferin were analyzed for antibacterial and antibiofilm activity against Gram-positive bacteria Streptococcus pneumoniae. The minimum inhibitory concentrations (MICs) of (±)-ϵ-viniferin (2) and standard viniferin were 20 um. However, the MICs of (±)-(E)-viniferin (3) and compound 8 were 40 um. 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. Scanning electron microscope (SEM) analysis and live/ dead biofilm staining of pre-established biofilms revealed that viniferin treatment disrupts membrane integrity of biofilm bacteria. Crystal violet absorption, total protein, and DNA and RNA release revealed that viniferin alters bacterial cell permeability, eventually killing bacteria.

Original languageEnglish
Article number890
JournalFrontiers in Pharmacology
Volume10
Issue numberJULY
DOIs
Publication statusPublished - 2019 Jan 1

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Cyclization
Biofilms
Streptococcus pneumoniae
Microbial Sensitivity Tests
Bacteria
Gentian Violet
Phytochemicals
Gram-Positive Bacteria
Polyphenols
ruthenium chloride
resveratrol
Permeability
RNA
Electrons
Staining and Labeling
Membranes
DNA
Proteins

Keywords

  • Antibiofilm
  • Antimicobacterial
  • Cell membrane
  • E-viniferin
  • Streptococcus pneumoniae

ASJC Scopus subject areas

  • Pharmacology
  • Pharmacology (medical)

Cite this

Ruthenium Chloride-Induced Oxidative Cyclization of Trans-Resveratrol to (±)-Viniferin and Antimicrobial and Antibiofilm Activity against Streptococcus pneumoniae. / Yadav, Mukesh Kumar; Mailar, Karabasappa; Masagalli, Jagadeesh Nagarajappa; Chae, Sung Won; Song, Jae-Jun; Choi, Won Jun.

In: Frontiers in Pharmacology, Vol. 10, No. JULY, 890, 01.01.2019.

Research output: Contribution to journalArticle

Yadav, Mukesh Kumar ; Mailar, Karabasappa ; Masagalli, Jagadeesh Nagarajappa ; Chae, Sung Won ; Song, Jae-Jun ; Choi, Won Jun. / Ruthenium Chloride-Induced Oxidative Cyclization of Trans-Resveratrol to (±)-Viniferin and Antimicrobial and Antibiofilm Activity against Streptococcus pneumoniae. In: Frontiers in Pharmacology. 2019 ; Vol. 10, No. JULY.
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