Synthesis of (R)-norbgugaine and its potential as quorum sensing inhibitor against Pseudomonas aeruginosa |
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Authors: | Mahesh S Majik Deepak Naik Chinmay Bhat Santosh Tilve Supriya Tilvi Lisette D’Souza |
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Institution: | 1. Bio-organic Chemistry Laboratory, CSIR – National Institute of Oceanography, Dona-Paula, Goa 403 004, India;2. Department of Chemistry, Goa University, Taleigao Plateau, Goa 403 206, India |
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Abstract: | (R)-Bgugaine is a natural pyrrolidine alkaloid from Arisarum vulgare, which shows antifungal and antibacterial activity. In this Letter, we have accomplished the simple synthesis of norbgugaine (demethylated form of natural bgugaine) employing Wittig olefination and cat. hydrogenation as the key steps and its biological studies are reported for the first time. The synthesized norbgugaine was evaluated for inhibition of quorum sensing mediated virulence factors (motility, biofilm formation, pyocyanin pigmentation, rhamnolipid production and LasA protease) in Pseudomonas aeruginosa wherein swarming motility is reduced by 95%, and biofilm formation by 83%. |
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