title: Synthesis of (R)-norbgugaine and its potential as quorum sensing inhibitor against Pseudomonas aeruginosa.
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%.
authors.affiliation: Bio-organic Chemistry Laboratory, CSIR - National Institute of Oceanography, Dona-Paula, Goa 403 004, India. majikms@gmail.com
authors.forename: Mahesh S
authors.initials: MS
authors.lastname: Majik
authors.forename: Deepak
authors.initials: D
authors.lastname: Naik
authors.forename: Chinmay
authors.initials: C
authors.lastname: Bhat
authors.forename: Santosh
authors.initials: S
authors.lastname: Tilve
authors.forename: Supriya
authors.initials: S
authors.lastname: Tilvi
authors.forename: Lisette
authors.initials: L
authors.lastname: D'Souza
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry; D029064:Araceae / Q000737:chemistry; D011550:Pseudomonas aeruginosa / Q000187:drug effects* / Q000502:physiology; D011759:Pyrrolidines / Q000138:chemical synthesis / Q000737:chemistry*; D053038:Quorum Sensing / Q000187:drug effects* / Q000502:physiology; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D000900:Anti-Bacterial Agents; D011759:Pyrrolidines; C118087:bgugaine