Synthesis and quorum sensing inhibitory activity of key phenolic compounds of ginger and their derivatives.
Phenolic components of ginger (Zingiber officinale Roscoe) viz. [6]-gingerol, [6]-shogaol and zingerone exhibited quorum sensing inhibitory activity (QSI) against Chromobacterium violaceum and Pseudomonas aeruginosa. The inhibitory activity of all the compounds was studied by zone inhibition, pyocyanin, and violacein assay. All the compounds displayed good inhibition at 500ppm. [6]-Azashogaol, a new derivative of [6]-shogaol has been synthesized by Beckmann rearrangement of its oxime in the presence of ZnCl2. The structure elucidation of this new derivative was carried out by 1D ((1)H NMR and (13)C NMR) and 2D-NMR (COSY, HSQC and NOESY) spectral studies. This compound showed good QSI activity against P. aeruginosa. An isoxazoline derivative of [6]-gingerol was prepared and it exhibited good QSI activity. Present study illustrated that, the phenolic compounds of ginger and their derivatives form a class of compounds with promising QSI activity.
Plantation Products, Spices and Flavour Technology Department, CSIR-Central Food Technological Research Institute, Mysore 570 020, India.
N Vijendra
NV
Kumar
Plantation Products, Spices and Flavour Technology Department, CSIR-Central Food Technological Research Institute, Mysore 570 020, India.
Pushpa S
PS
Murthy
Plantation Products, Spices and Flavour Technology Department, CSIR-Central Food Technological Research Institute, Mysore 570 020, India.
J R
JR
Manjunatha
Plantation Products, Spices and Flavour Technology Department, CSIR-Central Food Technological Research Institute, Mysore 570 020, India. Electronic address: bettadaiah@cftri.res.in.
B K
BK
Bettadaiah
D002396:Catechols / Q000737:chemistry; D002861:Chromobacterium / Q000187:drug effects*; D005233:Fatty Alcohols / Q000737:chemistry; D020939:Zingiber officinale / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry; D009822:Oils, Volatile / Q000737:chemistry; D010636:Phenols / Q000737:chemistry; D010936:Plant Extracts / Q000737:chemistry*; D011550:Pseudomonas aeruginosa / Q000187:drug effects*; D011710:Pyocyanine / Q000737:chemistry; D053038:Quorum Sensing / Q000187:drug effects*
D002396:Catechols; D005233:Fatty Alcohols; D007211:Indoles; D009822:Oils, Volatile; D010636:Phenols; D010936:Plant Extracts; C040115:shogaol; C007845:gingerol; D011710:Pyocyanine; C063155:violacein
Quorum sensing inhibitory activity; Zingerone; [6]-Azashogaol and isoxazoline derivative; [6]-Gingerol; [6]-Shogaol