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Synthesis and antibacterial activity of ricinoleic acid glycosides
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 ar...
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| Published in: | RSC advances 2016-01, Vol.6 (5), p.37-3713 |
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| Main Authors: | , , , , , , |
| Format: | Article |
| Language: | English |
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| cites | cdi_FETCH-LOGICAL-c319t-d4b9c732a0460ea4cbd3c7d61b1cb45994d0cbdea17bcf60e7d5eb934f7f04d63 |
| container_end_page | 3713 |
| container_issue | 5 |
| container_start_page | 37 |
| container_title | RSC advances |
| container_volume | 6 |
| creator | Kuppala, Ramakrishna Govindarajan, Mugunthan Tambat, Rushikesh Patel, Neeraj Nandanwar, Hemraj Bhutani, Kamlesh K Kartha, K. P. Ravindranathan |
| description | 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.
The antibacterial properties of twenty-eight novel ricinoleic acid glycosides synthesized by Koenigs-Knorr glycosylation are reported. |
| doi_str_mv | 10.1039/c5ra20136e |
| format | article |
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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.
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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.
The antibacterial properties of twenty-eight novel ricinoleic acid glycosides synthesized by Koenigs-Knorr glycosylation are reported.</description><subject>Antibacterial properties</subject><subject>Bacillus subtilis</subject><subject>Bacteria</subject><subject>Derivatives</subject><subject>Esters</subject><subject>Glycosides</subject><subject>Membranes</subject><subject>Micrococcus luteus</subject><subject>Permeability</subject><subject>Ricinoleic acid</subject><subject>Staphylococcus aureus</subject><issn>2046-2069</issn><issn>2046-2069</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqNkEtLAzEUhYMoWGo37oVZijCad8yylvqAguBjPSQ3GY1MZ2oyFebfmzqiLr1wuYfDx-VwEDom-Jxgpi9AREMxYdLvoQnFXJYUS73_Rx-iWUpvOI8UhEoyQVePQ9u_-hRSYVqXtw_WQO9jME2RRfgI_VB0dREDhLZrfIBsB1e8NAN0KTifjtBBbZrkZ993ip6vl0-L23J1f3O3mK9KYET3peNWg2LU5DDYGw7WMVBOEkvAcqE1dzh73hBloc6IcsJbzXitasydZFN0Ov7dxO5961NfrUMC3zSm9d02VeSSKk0VxuI_qBCSCbpDz0YUYpdS9HW1iWFt4lARXO1qrRbiYf5V6zLDJyMcE_xwv7WzTwKzdHg</recordid><startdate>20160101</startdate><enddate>20160101</enddate><creator>Kuppala, Ramakrishna</creator><creator>Govindarajan, Mugunthan</creator><creator>Tambat, Rushikesh</creator><creator>Patel, Neeraj</creator><creator>Nandanwar, Hemraj</creator><creator>Bhutani, Kamlesh K</creator><creator>Kartha, K. P. Ravindranathan</creator><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7QL</scope><scope>C1K</scope></search><sort><creationdate>20160101</creationdate><title>Synthesis and antibacterial activity of ricinoleic acid glycosides</title><author>Kuppala, Ramakrishna ; Govindarajan, Mugunthan ; Tambat, Rushikesh ; Patel, Neeraj ; Nandanwar, Hemraj ; Bhutani, Kamlesh K ; Kartha, K. P. Ravindranathan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c319t-d4b9c732a0460ea4cbd3c7d61b1cb45994d0cbdea17bcf60e7d5eb934f7f04d63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Antibacterial properties</topic><topic>Bacillus subtilis</topic><topic>Bacteria</topic><topic>Derivatives</topic><topic>Esters</topic><topic>Glycosides</topic><topic>Membranes</topic><topic>Micrococcus luteus</topic><topic>Permeability</topic><topic>Ricinoleic acid</topic><topic>Staphylococcus aureus</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kuppala, Ramakrishna</creatorcontrib><creatorcontrib>Govindarajan, Mugunthan</creatorcontrib><creatorcontrib>Tambat, Rushikesh</creatorcontrib><creatorcontrib>Patel, Neeraj</creatorcontrib><creatorcontrib>Nandanwar, Hemraj</creatorcontrib><creatorcontrib>Bhutani, Kamlesh K</creatorcontrib><creatorcontrib>Kartha, K. P. Ravindranathan</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Environmental Sciences and Pollution Management</collection><jtitle>RSC advances</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kuppala, Ramakrishna</au><au>Govindarajan, Mugunthan</au><au>Tambat, Rushikesh</au><au>Patel, Neeraj</au><au>Nandanwar, Hemraj</au><au>Bhutani, Kamlesh K</au><au>Kartha, K. P. Ravindranathan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and antibacterial activity of ricinoleic acid glycosides</atitle><jtitle>RSC advances</jtitle><date>2016-01-01</date><risdate>2016</risdate><volume>6</volume><issue>5</issue><spage>37</spage><epage>3713</epage><pages>37-3713</pages><issn>2046-2069</issn><eissn>2046-2069</eissn><abstract>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.
The antibacterial properties of twenty-eight novel ricinoleic acid glycosides synthesized by Koenigs-Knorr glycosylation are reported.</abstract><doi>10.1039/c5ra20136e</doi><tpages>14</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2046-2069 |
| ispartof | RSC advances, 2016-01, Vol.6 (5), p.37-3713 |
| issn | 2046-2069 2046-2069 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1827927005 |
| source | Royal Society of Chemistry |
| subjects | Antibacterial properties Bacillus subtilis Bacteria Derivatives Esters Glycosides Membranes Micrococcus luteus Permeability Ricinoleic acid Staphylococcus aureus |
| title | Synthesis and antibacterial activity of ricinoleic acid glycosides |
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