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

被引：39

作者：

Majik, Mahesh S. ^{[1
]}

Naik, Deepak ^{[1
]}

Bhat, Chinmay ^{[2
]}

Tilve, Santosh ^{[2
]}

Tilvi, Supriya ^{[1
]}

D'Souza, Lisette ^{[1
]}

机构：

[1] CSIR Natl Inst Oceanog, Bioorgan Chem Lab, Panaji 403004, Goa, India

[2] Goa Univ, Dept Chem, Taleigao Plateau 403206, Goa, India

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2013年 / 23卷 / 08期

关键词：

Norbgugaine; QS inhibitor; Pseudomonas aeruginosa; Wittig reaction; Pyrrolidine alkaloid; BACTERIAL BIOFILMS; NATURAL-PRODUCTS; STEREOSELECTIVE-SYNTHESIS; ARISARUM-VULGARE; ANTIFUNGAL AGENT; ALKALOIDS; ANALOGS; PIPERIDINES; ENVIRONMENT; DRUGS;

D O I：

10.1016/j.bmcl.2013.02.051

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

(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%. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：2353 / 2356

页数：4

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