Ruthenium Chloride—Induced Oxidative Cyclization of Trans-Resveratrol to (±)-ε-Viniferin and Antimicrobial and Antibiofilm Activity Against Streptococcus pneumoniae
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 wer...
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Frontiers Media S.A.
2019-08-01
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| Series: | Frontiers in Pharmacology |
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| Online Access: | https://www.frontiersin.org/article/10.3389/fphar.2019.00890/full |
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| author | Mukesh Kumar Yadav Mukesh Kumar Yadav Karabasappa Mailar Jagadeesh Nagarajappa Masagalli Sung-Won Chae Jae-Jun Song Won Jun Choi |
| author_facet | Mukesh Kumar Yadav Mukesh Kumar Yadav Karabasappa Mailar Jagadeesh Nagarajappa Masagalli Sung-Won Chae Jae-Jun Song Won Jun Choi |
| author_sort | Mukesh Kumar Yadav |
| collection | DOAJ |
| description | 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 antibacterial and antibiofilm activity against Gram-positive bacteria Streptococcus pneumoniae. The minimum inhibitory concentrations (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. 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. |
| first_indexed | 2024-12-12T02:27:13Z |
| format | Article |
| id | doaj.art-b0385ecbb7fb401c8db6232fc152587a |
| institution | Directory Open Access Journal |
| issn | 1663-9812 |
| language | English |
| last_indexed | 2024-12-12T02:27:13Z |
| publishDate | 2019-08-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Pharmacology |
| spelling | doaj.art-b0385ecbb7fb401c8db6232fc152587a2022-12-22T00:41:31ZengFrontiers Media S.A.Frontiers in Pharmacology1663-98122019-08-011010.3389/fphar.2019.00890460873Ruthenium Chloride—Induced Oxidative Cyclization of Trans-Resveratrol to (±)-ε-Viniferin and Antimicrobial and Antibiofilm Activity Against Streptococcus pneumoniaeMukesh Kumar Yadav0Mukesh Kumar Yadav1Karabasappa Mailar2Jagadeesh Nagarajappa Masagalli3Sung-Won ChaeJae-Jun Song4Won Jun Choi5Department of Otorhinolaryngology–Head and Neck Surgery, Korea University Guro Hospital, Seoul, South KoreaInstitute for Medical Device Clinical Trials, Korea University College of Medicine, Seoul, South KoreaCollege of Pharmacy and Integrated Research Institute for Drug Development, Dongguk University, Seoul, South KoreaCollege of Pharmacy and Integrated Research Institute for Drug Development, Dongguk University, Seoul, South KoreaDepartment of Otorhinolaryngology–Head and Neck Surgery, Korea University Guro Hospital, Seoul, South KoreaCollege of Pharmacy and Integrated Research Institute for Drug Development, Dongguk University, Seoul, South KoreaPolyphenol 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 antibacterial and antibiofilm activity against Gram-positive bacteria Streptococcus pneumoniae. The minimum inhibitory concentrations (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. 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.https://www.frontiersin.org/article/10.3389/fphar.2019.00890/fullε-viniferinantimicobacterialantibiofilmStreptococcus pneumoniaecell membrane |
| spellingShingle | Mukesh Kumar Yadav Mukesh Kumar Yadav Karabasappa Mailar Jagadeesh Nagarajappa Masagalli Sung-Won Chae Jae-Jun Song Won Jun Choi Ruthenium Chloride—Induced Oxidative Cyclization of Trans-Resveratrol to (±)-ε-Viniferin and Antimicrobial and Antibiofilm Activity Against Streptococcus pneumoniae Frontiers in Pharmacology ε-viniferin antimicobacterial antibiofilm Streptococcus pneumoniae cell membrane |
| title | Ruthenium Chloride—Induced Oxidative Cyclization of Trans-Resveratrol to (±)-ε-Viniferin and Antimicrobial and Antibiofilm Activity Against Streptococcus pneumoniae |
| title_full | Ruthenium Chloride—Induced Oxidative Cyclization of Trans-Resveratrol to (±)-ε-Viniferin and Antimicrobial and Antibiofilm Activity Against Streptococcus pneumoniae |
| title_fullStr | Ruthenium Chloride—Induced Oxidative Cyclization of Trans-Resveratrol to (±)-ε-Viniferin and Antimicrobial and Antibiofilm Activity Against Streptococcus pneumoniae |
| title_full_unstemmed | Ruthenium Chloride—Induced Oxidative Cyclization of Trans-Resveratrol to (±)-ε-Viniferin and Antimicrobial and Antibiofilm Activity Against Streptococcus pneumoniae |
| title_short | Ruthenium Chloride—Induced Oxidative Cyclization of Trans-Resveratrol to (±)-ε-Viniferin and Antimicrobial and Antibiofilm Activity Against Streptococcus pneumoniae |
| title_sort | ruthenium chloride induced oxidative cyclization of trans resveratrol to ε viniferin and antimicrobial and antibiofilm activity against streptococcus pneumoniae |
| topic | ε-viniferin antimicobacterial antibiofilm Streptococcus pneumoniae cell membrane |
| url | https://www.frontiersin.org/article/10.3389/fphar.2019.00890/full |
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