Compounds of Alpinia katsumadai as potential efflux inhibitors in Mycobacterium smegmatis
Efflux pumps are one of the well established mechanisms that contribute to antibiotic resistance in bacteria, such as mycobacteria. As a result, the identification of efflux pump inhibitors is an attractive target in antimicrobial therapy. The isolated compounds, three diarylheptanoids, trans,trans-...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2012-04, Vol.20 (8), p.2701-2706 |
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| creator | Gröblacher, Barbara Kunert, Olaf Bucar, Franz |
| description | Efflux pumps are one of the well established mechanisms that contribute to antibiotic resistance in bacteria, such as mycobacteria. As a result, the identification of efflux pump inhibitors is an attractive target in antimicrobial therapy. The isolated compounds, three diarylheptanoids, trans,trans-1,7-diphenylhepta-4,6-dien-3-one (1), (5R)-trans-1,7-diphenyl-5-hydroxyhept-6-en-3-one (2), (3S,5S)-trans-1,7-diphenylhept-1-ene-3,5-diol (3) and the flavonoid pinocembrin (4), from Alpinia katsumadai, Zingiberaceae, were examined for their antimycobacterial activity and their synergistic effects with different antibiotics against M. smegmatis mc2 155. Furthermore, these compounds were evaluated as potential EtBr efflux inhibitors. Although they showed weak antimycobacterial activities (MIC⩾64mg/L), especially compound 1 revealed a significant activity on the EtBr accumulation and efflux as well as a synergistic effect in combination with rifampicin. |
| doi_str_mv | 10.1016/j.bmc.2012.02.039 |
| format | Article |
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As a result, the identification of efflux pump inhibitors is an attractive target in antimicrobial therapy. The isolated compounds, three diarylheptanoids, trans,trans-1,7-diphenylhepta-4,6-dien-3-one (1), (5R)-trans-1,7-diphenyl-5-hydroxyhept-6-en-3-one (2), (3S,5S)-trans-1,7-diphenylhept-1-ene-3,5-diol (3) and the flavonoid pinocembrin (4), from Alpinia katsumadai, Zingiberaceae, were examined for their antimycobacterial activity and their synergistic effects with different antibiotics against M. smegmatis mc2 155. Furthermore, these compounds were evaluated as potential EtBr efflux inhibitors. Although they showed weak antimycobacterial activities (MIC⩾64mg/L), especially compound 1 revealed a significant activity on the EtBr accumulation and efflux as well as a synergistic effect in combination with rifampicin.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2012.02.039</identifier><identifier>PMID: 22459211</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Alpinia ; Alpinia - chemistry ; antibacterial properties ; Antibiotic resistance ; Antibiotics ; Antibiotics, Antitubercular - chemistry ; Antibiotics, Antitubercular - isolation & purification ; Antibiotics, Antitubercular - pharmacology ; Antimicrobial agents ; Antitubercular Agents - chemistry ; Antitubercular Agents - isolation & purification ; Antitubercular Agents - pharmacology ; bacteria ; Biological and medical sciences ; chemistry ; Diarylheptanoids ; Diarylheptanoids - chemistry ; Diarylheptanoids - isolation & purification ; Diarylheptanoids - pharmacology ; drug therapy ; Efflux pumps ; Fatty acids ; Flavonoids ; General pharmacology ; MDR resistance ; Medical sciences ; Microbial Sensitivity Tests ; Minimum inhibitory concentration ; Molecular Structure ; Mycobacteria ; Mycobacterium smegmatis ; Mycobacterium smegmatis - drug effects ; Mycobacterium smegmatis - growth & development ; Pharmacognosy. 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As a result, the identification of efflux pump inhibitors is an attractive target in antimicrobial therapy. The isolated compounds, three diarylheptanoids, trans,trans-1,7-diphenylhepta-4,6-dien-3-one (1), (5R)-trans-1,7-diphenyl-5-hydroxyhept-6-en-3-one (2), (3S,5S)-trans-1,7-diphenylhept-1-ene-3,5-diol (3) and the flavonoid pinocembrin (4), from Alpinia katsumadai, Zingiberaceae, were examined for their antimycobacterial activity and their synergistic effects with different antibiotics against M. smegmatis mc2 155. Furthermore, these compounds were evaluated as potential EtBr efflux inhibitors. Although they showed weak antimycobacterial activities (MIC⩾64mg/L), especially compound 1 revealed a significant activity on the EtBr accumulation and efflux as well as a synergistic effect in combination with rifampicin.</description><subject>Alpinia</subject><subject>Alpinia - chemistry</subject><subject>antibacterial properties</subject><subject>Antibiotic resistance</subject><subject>Antibiotics</subject><subject>Antibiotics, Antitubercular - chemistry</subject><subject>Antibiotics, Antitubercular - isolation & purification</subject><subject>Antibiotics, Antitubercular - pharmacology</subject><subject>Antimicrobial agents</subject><subject>Antitubercular Agents - chemistry</subject><subject>Antitubercular Agents - isolation & purification</subject><subject>Antitubercular Agents - pharmacology</subject><subject>bacteria</subject><subject>Biological and medical sciences</subject><subject>chemistry</subject><subject>Diarylheptanoids</subject><subject>Diarylheptanoids - chemistry</subject><subject>Diarylheptanoids - isolation & purification</subject><subject>Diarylheptanoids - pharmacology</subject><subject>drug therapy</subject><subject>Efflux pumps</subject><subject>Fatty acids</subject><subject>Flavonoids</subject><subject>General pharmacology</subject><subject>MDR resistance</subject><subject>Medical sciences</subject><subject>Microbial Sensitivity Tests</subject><subject>Minimum inhibitory concentration</subject><subject>Molecular Structure</subject><subject>Mycobacteria</subject><subject>Mycobacterium smegmatis</subject><subject>Mycobacterium smegmatis - drug effects</subject><subject>Mycobacterium smegmatis - growth & development</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Plant Extracts - chemistry</subject><subject>Plant Extracts - isolation & purification</subject><subject>Plant Extracts - pharmacology</subject><subject>rifampicin</subject><subject>Rifampin</subject><subject>Seeds - chemistry</subject><subject>synergism</subject><subject>transporters</subject><subject>Zingiberaceae</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp90E1v1DAQBmALUdGl8AO4QC4ILln8ETu2OFUrPiq14gA9cLImzrh4SeJgJ4j--7raBW6VRhofnhmPXkJeMLpllKl3-203ui2njG9pKWEekQ1rVFMLYdhjsqFG6Zpqo07J05z3lFLeGPaEnHLeSMMZ25DvuzjOcZ36XEVfnQ9zmAJUP2HJ6wg9hApyNccFpyXAUKH3w_qnCtOP0IUlplye1dWtix24BVNYxyqPeDPCEvIzcuJhyPj82M_I9ccP33af68svny5255e1a4RZ6gZboAZ0h53vpKMUoFWspwZ5543wTnmpVe9MQ50TDpTRwDXTUvStQOPFGXlz2Dun-GvFvNgxZIfDABPGNVtjuOa65brItw_KkinjTOq2KZQdqEsx54TezimMkG4LunfK7m3J3t5nb2kpYcrMy-P6tRux_zfxN-wCXh8BZAeDTzC5kP87qaVsNS_u1cF5iBZuUjHXX8tPkpYDaVlXxPuDwBLs74DJZhdwctiHhG6xfQwPHHoHtfyrbQ</recordid><startdate>20120415</startdate><enddate>20120415</enddate><creator>Gröblacher, Barbara</creator><creator>Kunert, Olaf</creator><creator>Bucar, Franz</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>FBQ</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QL</scope><scope>7QO</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20120415</creationdate><title>Compounds of Alpinia katsumadai as potential efflux inhibitors in Mycobacterium smegmatis</title><author>Gröblacher, Barbara ; Kunert, Olaf ; Bucar, Franz</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c439t-4e7a09a8bebfb5c00aa761d09e2bf93fc6f586dc940cc3ca698a281853d73e9f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Alpinia</topic><topic>Alpinia - chemistry</topic><topic>antibacterial properties</topic><topic>Antibiotic resistance</topic><topic>Antibiotics</topic><topic>Antibiotics, Antitubercular - chemistry</topic><topic>Antibiotics, Antitubercular - isolation & purification</topic><topic>Antibiotics, Antitubercular - pharmacology</topic><topic>Antimicrobial agents</topic><topic>Antitubercular Agents - chemistry</topic><topic>Antitubercular Agents - isolation & purification</topic><topic>Antitubercular Agents - pharmacology</topic><topic>bacteria</topic><topic>Biological and medical sciences</topic><topic>chemistry</topic><topic>Diarylheptanoids</topic><topic>Diarylheptanoids - chemistry</topic><topic>Diarylheptanoids - isolation & purification</topic><topic>Diarylheptanoids - pharmacology</topic><topic>drug therapy</topic><topic>Efflux pumps</topic><topic>Fatty acids</topic><topic>Flavonoids</topic><topic>General pharmacology</topic><topic>MDR resistance</topic><topic>Medical sciences</topic><topic>Microbial Sensitivity Tests</topic><topic>Minimum inhibitory concentration</topic><topic>Molecular Structure</topic><topic>Mycobacteria</topic><topic>Mycobacterium smegmatis</topic><topic>Mycobacterium smegmatis - drug effects</topic><topic>Mycobacterium smegmatis - growth & development</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Plant Extracts - chemistry</topic><topic>Plant Extracts - isolation & purification</topic><topic>Plant Extracts - pharmacology</topic><topic>rifampicin</topic><topic>Rifampin</topic><topic>Seeds - chemistry</topic><topic>synergism</topic><topic>transporters</topic><topic>Zingiberaceae</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gröblacher, Barbara</creatorcontrib><creatorcontrib>Kunert, Olaf</creatorcontrib><creatorcontrib>Bucar, Franz</creatorcontrib><collection>AGRIS</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gröblacher, Barbara</au><au>Kunert, Olaf</au><au>Bucar, Franz</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Compounds of Alpinia katsumadai as potential efflux inhibitors in Mycobacterium smegmatis</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2012-04-15</date><risdate>2012</risdate><volume>20</volume><issue>8</issue><spage>2701</spage><epage>2706</epage><pages>2701-2706</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>Efflux pumps are one of the well established mechanisms that contribute to antibiotic resistance in bacteria, such as mycobacteria. As a result, the identification of efflux pump inhibitors is an attractive target in antimicrobial therapy. The isolated compounds, three diarylheptanoids, trans,trans-1,7-diphenylhepta-4,6-dien-3-one (1), (5R)-trans-1,7-diphenyl-5-hydroxyhept-6-en-3-one (2), (3S,5S)-trans-1,7-diphenylhept-1-ene-3,5-diol (3) and the flavonoid pinocembrin (4), from Alpinia katsumadai, Zingiberaceae, were examined for their antimycobacterial activity and their synergistic effects with different antibiotics against M. smegmatis mc2 155. Furthermore, these compounds were evaluated as potential EtBr efflux inhibitors. Although they showed weak antimycobacterial activities (MIC⩾64mg/L), especially compound 1 revealed a significant activity on the EtBr accumulation and efflux as well as a synergistic effect in combination with rifampicin.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>22459211</pmid><doi>10.1016/j.bmc.2012.02.039</doi><tpages>6</tpages></addata></record> |
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| ispartof | Bioorganic & medicinal chemistry, 2012-04, Vol.20 (8), p.2701-2706 |
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| subjects | Alpinia Alpinia - chemistry antibacterial properties Antibiotic resistance Antibiotics Antibiotics, Antitubercular - chemistry Antibiotics, Antitubercular - isolation & purification Antibiotics, Antitubercular - pharmacology Antimicrobial agents Antitubercular Agents - chemistry Antitubercular Agents - isolation & purification Antitubercular Agents - pharmacology bacteria Biological and medical sciences chemistry Diarylheptanoids Diarylheptanoids - chemistry Diarylheptanoids - isolation & purification Diarylheptanoids - pharmacology drug therapy Efflux pumps Fatty acids Flavonoids General pharmacology MDR resistance Medical sciences Microbial Sensitivity Tests Minimum inhibitory concentration Molecular Structure Mycobacteria Mycobacterium smegmatis Mycobacterium smegmatis - drug effects Mycobacterium smegmatis - growth & development Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Plant Extracts - chemistry Plant Extracts - isolation & purification Plant Extracts - pharmacology rifampicin Rifampin Seeds - chemistry synergism transporters Zingiberaceae |
| title | Compounds of Alpinia katsumadai as potential efflux inhibitors in Mycobacterium smegmatis |
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