Synthesis of (R)-norbgugaine and its potential as quorum sensing inhibitor against Pseudomonas aeruginosa

(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 ste...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2013-04, Vol.23 (8), p.2353-2356
Main Authors: Majik, Mahesh S., Naik, Deepak, Bhat, Chinmay, Tilve, Santosh, Tilvi, Supriya, D’Souza, Lisette
Format: Article
Language:English
Subjects:
Alkaloids - chemical synthesis
Alkaloids - chemistry
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
antibacterial properties
Araceae - chemistry
Arisarum
Arisarum vulgare
bacterial motility
biofilm
hydrogenation
Norbgugaine
pigmentation
proteinases
Pseudomonas aeruginosa
Pseudomonas aeruginosa - drug effects
Pseudomonas aeruginosa - physiology
pyocyanin
Pyrrolidine alkaloid
Pyrrolidines - chemical synthesis
Pyrrolidines - chemistry
QS inhibitor
quorum sensing
Quorum Sensing - drug effects
Quorum Sensing - physiology
Stereoisomerism
virulence
Wittig reaction
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Summary:(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%.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2013.02.051