Synthesis and quorum sensing inhibitory activity of key phenolic compounds of ginger and their derivatives.

Vijendra Kumar, N. and Pushpa, S. Murthy and Manjunatha, J. R. and Bettadaiah, B. K. (2014) Synthesis and quorum sensing inhibitory activity of key phenolic compounds of ginger and their derivatives. Food Chemistry, 159. pp. 451-457.

PDF Food Chemistry, Volume 159, 15 September 2014, Pages 451-457.pdf - Published Version Restricted to Registered users only Download (841kB)

Abstract

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 500 ppm. [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 (1H NMR and 13C 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.

Item Type:	Article
Uncontrolled Keywords:	Quorum sensing inhibitory activity, [6]-Gingerol [6]-Shogaol, Zingerone, [6]-Azashogaol and isoxazoline derivative
Subjects:	600 Technology > 08 Food technology > 30 Spices/Condiments
Divisions:	Plantation Products Spices and Flavour Technology
Depositing User:	Food Sci. & Technol. Information Services
Date Deposited:	27 May 2014 12:04
Last Modified:	27 May 2014 12:04
URI:	http://ir.cftri.res.in/id/eprint/11575

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