Synthesis and antibacterial activity of ricinoleic acid glycosides
| Autor: | Kamlesh K. Bhutani, Ramakrishna Kuppala, Mugunthan Govindarajan, Neeraj K. Patel, K. P. Ravindranathan Kartha, Rushikesh Tambat, Hemraj Nandanwar |
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| Rok vydání: | 2016 |
| Předmět: |
0301 basic medicine
chemistry.chemical_classification biology Membrane permeability 010405 organic chemistry General Chemical Engineering Carboxylic acid Gram-positive bacteria Ricinoleic acid Glycoside General Chemistry biology.organism_classification 01 natural sciences Bacterial cell structure 0104 chemical sciences 03 medical and health sciences chemistry.chemical_compound 030104 developmental biology Biochemistry chemistry Micrococcus luteus Antibacterial activity |
| Zdroj: | RSC Advances. 6:3700-3713 |
| ISSN: | 2046-2069 |
| DOI: | 10.1039/c5ra20136e |
| Popis: | The antibacterial properties of twenty-eight novel ricinoleic acid glycosides synthesized by Koenigs–Knorr glycosylation are reported. Seven of them were found to show promising wide spectrum antibacterial activity against Gram positive bacteria of which two compounds, the mannopyranosyl- and the arabinofuranosyl derivatives, were proven effective against various non-clinical/clinical/NorA-overexpressed/resistant strains of Staphylococcus aureus as well as other Gram +ve bacteria such as Bacillus subtilis ATCC 6051 and Micrococcus luteus MTCC 2470. It was found that both the presence of the sugar and its structure are necessary and important for the compounds to be bioactive. The methyl ester protection of the carboxylic acid moiety of the ricinoleic acid unit was also found to be important for imparting good bioactivity to the molecule. Based on the membrane permeability and cell disintegration studies, these compounds are found to increase the bacterial cell membrane permeability, subsequently causing cell death. |
| Databáze: | OpenAIRE |
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