Synthesis and antibacterial properties of 2,3-dideoxyglucosides of terpene alcohols and phenols

Essential oils and their oxygenated terpene constituents possess potent antimicrobial properties. In the present study, a facile synthetic route to the 2,3-dideoxy 1-O-glucosides of important phenols and terpene alcohols in excellent yields (85-96%) has been delineated. Studies on their antimicrobial action against four food-borne pathogens - Bacillus cereus, Staphylococcus aureus, Escherichia coli and Yersinia enterocolitica - demonstrated that the zone of inhibition, in general, was higher for the 2,3-unsaturated 1-O-glucoside derivatives (1b-6b) and the corresponding saturated glucosides (1c-5c) when compared to the parent alcohols/phenols (1-6). The minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) values for these derivatives too were generally lower than those of the parent compounds. Furthermore, the time-kill and bacteriolysis assays too demonstrated the greater antimicrobial potential of the derivatives. The 2,3-dideoxy 1-O-glucosides of phenols and terpene alcohols were more effective in their antimicrobial action than the corresponding parent compounds. The study indicated that these novel derivatives can find useful application in control of food-related pathogenic microbes in foods. (C) 2015 Elsevier Ltd. All rights reserved.