Antimicrobial Compounds from the Australian Desert Plant Eremophila neglecta
A crude extract from the Australian desert plant Eremophila neglecta has recently been shown to possess antibacterial activity in a survey of candidate plants that may bear novel antimicrobial compounds. Bioassay-directed fractionation of the Et2O extract of E. neglecta using a broth microdilution a...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2007-09, Vol.70 (9), p.1439-1443 |
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| creator | Ndi, Chi P Semple, Susan J Griesser, Hans J Pyke, Simon M Barton, Mary D |
| description | A crude extract from the Australian desert plant Eremophila neglecta has recently been shown to possess antibacterial activity in a survey of candidate plants that may bear novel antimicrobial compounds. Bioassay-directed fractionation of the Et2O extract of E. neglecta using a broth microdilution assay led to the isolation of three new serrulatane-type diterpenoids, 2,19-diacetoxy-8-hydroxyserrulat-14-ene (2), 8,19-dihydroxyserrulat-14-ene (3), and 8-hydroxyserrulat-14-en-19-oic acid (4), and a known o-naphthoquinone commonly referred to as biflorin (5). The structures of 2–5 were determined using 1D and 2D NMR, FTIR, and high-resolution mass spectrometry. Compounds 3–5 showed antimicrobial activity against Gram-positive bacteria including Staphylococcus aureus, Streptococcus pyogenes, and S. pneumoniae. The minimum inhibitory concentrations (MICs) and the minimum bactericidal concentrations (MBCs) ranged from 6.5 to 101.6 µM and 12.7 to 202.9 µM, respectively. No activity was observed for these compounds against Gram-negative bacteria. |
| doi_str_mv | 10.1021/np070180r |
| format | Article |
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Bioassay-directed fractionation of the Et2O extract of E. neglecta using a broth microdilution assay led to the isolation of three new serrulatane-type diterpenoids, 2,19-diacetoxy-8-hydroxyserrulat-14-ene (2), 8,19-dihydroxyserrulat-14-ene (3), and 8-hydroxyserrulat-14-en-19-oic acid (4), and a known o-naphthoquinone commonly referred to as biflorin (5). The structures of 2–5 were determined using 1D and 2D NMR, FTIR, and high-resolution mass spectrometry. Compounds 3–5 showed antimicrobial activity against Gram-positive bacteria including Staphylococcus aureus, Streptococcus pyogenes, and S. pneumoniae. The minimum inhibitory concentrations (MICs) and the minimum bactericidal concentrations (MBCs) ranged from 6.5 to 101.6 µM and 12.7 to 202.9 µM, respectively. No activity was observed for these compounds against Gram-negative bacteria.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np070180r</identifier><identifier>PMID: 17844993</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Anti-Infective Agents - chemistry ; Anti-Infective Agents - isolation & purification ; Anti-Infective Agents - pharmacology ; antibacterial properties ; antimicrobial agents ; Australia ; bacterial infections ; Biological and medical sciences ; chemical structure ; Desert Climate ; Diterpenes - chemistry ; Diterpenes - isolation & purification ; Diterpenes - pharmacology ; diterpenoids ; Eremophila ; Eremophila neglecta ; Eremophila Plant - chemistry ; Escherichia coli ; General pharmacology ; Gram-Negative Bacteria - drug effects ; Gram-positive bacteria ; human health ; Medical sciences ; Microbial Sensitivity Tests ; minimum bactericidal concentrations ; Molecular Structure ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; phytochemicals ; Plant Leaves - chemistry ; Plants, Medicinal - chemistry ; Pseudomonas aeruginosa ; Salmonella typhimurium ; Scrophulariaceae ; serrulatane diterpene ; spectral analysis ; Staphylococcus aureus ; Staphylococcus aureus - drug effects ; stereochemistry ; Streptococcus pneumoniae ; Streptococcus pneumoniae - drug effects ; Streptococcus pyogenes ; Streptococcus pyogenes - drug effects ; xerophytes</subject><ispartof>Journal of natural products (Washington, D.C.), 2007-09, Vol.70 (9), p.1439-1443</ispartof><rights>Copyright © 2007 American Chemical Society and American Society of Pharmacognosy and STD NP</rights><rights>2008 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a351t-cd11a28fe6ccc2e07303d64031cdd57e9b1fee89e0022e0505a2c900e077a6e23</citedby><cites>FETCH-LOGICAL-a351t-cd11a28fe6ccc2e07303d64031cdd57e9b1fee89e0022e0505a2c900e077a6e23</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/np070180r$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np070180r$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56717,56767</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=19138271$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17844993$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ndi, Chi P</creatorcontrib><creatorcontrib>Semple, Susan J</creatorcontrib><creatorcontrib>Griesser, Hans J</creatorcontrib><creatorcontrib>Pyke, Simon M</creatorcontrib><creatorcontrib>Barton, Mary D</creatorcontrib><title>Antimicrobial Compounds from the Australian Desert Plant Eremophila neglecta</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>A crude extract from the Australian desert plant Eremophila neglecta has recently been shown to possess antibacterial activity in a survey of candidate plants that may bear novel antimicrobial compounds. Bioassay-directed fractionation of the Et2O extract of E. neglecta using a broth microdilution assay led to the isolation of three new serrulatane-type diterpenoids, 2,19-diacetoxy-8-hydroxyserrulat-14-ene (2), 8,19-dihydroxyserrulat-14-ene (3), and 8-hydroxyserrulat-14-en-19-oic acid (4), and a known o-naphthoquinone commonly referred to as biflorin (5). The structures of 2–5 were determined using 1D and 2D NMR, FTIR, and high-resolution mass spectrometry. Compounds 3–5 showed antimicrobial activity against Gram-positive bacteria including Staphylococcus aureus, Streptococcus pyogenes, and S. pneumoniae. The minimum inhibitory concentrations (MICs) and the minimum bactericidal concentrations (MBCs) ranged from 6.5 to 101.6 µM and 12.7 to 202.9 µM, respectively. No activity was observed for these compounds against Gram-negative bacteria.</description><subject>Anti-Infective Agents - chemistry</subject><subject>Anti-Infective Agents - isolation & purification</subject><subject>Anti-Infective Agents - pharmacology</subject><subject>antibacterial properties</subject><subject>antimicrobial agents</subject><subject>Australia</subject><subject>bacterial infections</subject><subject>Biological and medical sciences</subject><subject>chemical structure</subject><subject>Desert Climate</subject><subject>Diterpenes - chemistry</subject><subject>Diterpenes - isolation & purification</subject><subject>Diterpenes - pharmacology</subject><subject>diterpenoids</subject><subject>Eremophila</subject><subject>Eremophila neglecta</subject><subject>Eremophila Plant - chemistry</subject><subject>Escherichia coli</subject><subject>General pharmacology</subject><subject>Gram-Negative Bacteria - drug effects</subject><subject>Gram-positive bacteria</subject><subject>human health</subject><subject>Medical sciences</subject><subject>Microbial Sensitivity Tests</subject><subject>minimum bactericidal concentrations</subject><subject>Molecular Structure</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>phytochemicals</subject><subject>Plant Leaves - chemistry</subject><subject>Plants, Medicinal - chemistry</subject><subject>Pseudomonas aeruginosa</subject><subject>Salmonella typhimurium</subject><subject>Scrophulariaceae</subject><subject>serrulatane diterpene</subject><subject>spectral analysis</subject><subject>Staphylococcus aureus</subject><subject>Staphylococcus aureus - drug effects</subject><subject>stereochemistry</subject><subject>Streptococcus pneumoniae</subject><subject>Streptococcus pneumoniae - drug effects</subject><subject>Streptococcus pyogenes</subject><subject>Streptococcus pyogenes - drug effects</subject><subject>xerophytes</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0U1v1DAQBmALgehSOPAHIBeQOATGdpzYx9W2BaStqNQPuFmzzqR1SeLUTiT678lqV90LEicf5tGM5x3G3nL4zEHwL_0AFXAN8RlbcCUgL0Go52wBvJS51GVxxF6ldA8AEox6yY54pYvCGLlg62U_-s67GDYe22wVuiFMfZ2yJoYuG-8oW05pjNh67LMTShTH7KLFfsxOI3VhuPMtZj3dtuRGfM1eNNgmerN_j9n12enV6lu-_vH1-2q5zlEqPuau5hyFbqh0zgmCSoKsywIkd3WtKjIb3hBpQwBiLitQKJwBmGWFJQl5zD7u-g4xPEyURtv55Kid_0VhSrbUcru1_i_kpjKqLPgMP-3gHERKkRo7RN9hfLQc7DZj-5TxbN_tm06bjuqD3Ic6gw97gMlh20TsnU8HZ7jUotoOzXfOp5H-PNUx_rZlJStlry4u7c2vm_Of58WJ3W7zfucbDBZv49zz-lIAlwCaF0bAYTK6ZO_DFPv5DP9Y4S9P8Kfl</recordid><startdate>200709</startdate><enddate>200709</enddate><creator>Ndi, Chi P</creator><creator>Semple, Susan J</creator><creator>Griesser, Hans J</creator><creator>Pyke, Simon M</creator><creator>Barton, Mary D</creator><general>American Chemical Society</general><general>American Society of Pharmacognosy</general><scope>FBQ</scope><scope>BSCLL</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>7T7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>200709</creationdate><title>Antimicrobial Compounds from the Australian Desert Plant Eremophila neglecta</title><author>Ndi, Chi P ; Semple, Susan J ; Griesser, Hans J ; Pyke, Simon M ; Barton, Mary D</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a351t-cd11a28fe6ccc2e07303d64031cdd57e9b1fee89e0022e0505a2c900e077a6e23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Anti-Infective Agents - chemistry</topic><topic>Anti-Infective Agents - isolation & purification</topic><topic>Anti-Infective Agents - pharmacology</topic><topic>antibacterial properties</topic><topic>antimicrobial agents</topic><topic>Australia</topic><topic>bacterial infections</topic><topic>Biological and medical sciences</topic><topic>chemical structure</topic><topic>Desert Climate</topic><topic>Diterpenes - chemistry</topic><topic>Diterpenes - isolation & purification</topic><topic>Diterpenes - pharmacology</topic><topic>diterpenoids</topic><topic>Eremophila</topic><topic>Eremophila neglecta</topic><topic>Eremophila Plant - chemistry</topic><topic>Escherichia coli</topic><topic>General pharmacology</topic><topic>Gram-Negative Bacteria - drug effects</topic><topic>Gram-positive bacteria</topic><topic>human health</topic><topic>Medical sciences</topic><topic>Microbial Sensitivity Tests</topic><topic>minimum bactericidal concentrations</topic><topic>Molecular Structure</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>phytochemicals</topic><topic>Plant Leaves - chemistry</topic><topic>Plants, Medicinal - chemistry</topic><topic>Pseudomonas aeruginosa</topic><topic>Salmonella typhimurium</topic><topic>Scrophulariaceae</topic><topic>serrulatane diterpene</topic><topic>spectral analysis</topic><topic>Staphylococcus aureus</topic><topic>Staphylococcus aureus - drug effects</topic><topic>stereochemistry</topic><topic>Streptococcus pneumoniae</topic><topic>Streptococcus pneumoniae - drug effects</topic><topic>Streptococcus pyogenes</topic><topic>Streptococcus pyogenes - drug effects</topic><topic>xerophytes</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ndi, Chi P</creatorcontrib><creatorcontrib>Semple, Susan J</creatorcontrib><creatorcontrib>Griesser, Hans J</creatorcontrib><creatorcontrib>Pyke, Simon M</creatorcontrib><creatorcontrib>Barton, Mary D</creatorcontrib><collection>AGRIS</collection><collection>Istex</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>Industrial and Applied Microbiology Abstracts (Microbiology A)</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>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ndi, Chi P</au><au>Semple, Susan J</au><au>Griesser, Hans J</au><au>Pyke, Simon M</au><au>Barton, Mary D</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Antimicrobial Compounds from the Australian Desert Plant Eremophila neglecta</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2007-09</date><risdate>2007</risdate><volume>70</volume><issue>9</issue><spage>1439</spage><epage>1443</epage><pages>1439-1443</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>A crude extract from the Australian desert plant Eremophila neglecta has recently been shown to possess antibacterial activity in a survey of candidate plants that may bear novel antimicrobial compounds. Bioassay-directed fractionation of the Et2O extract of E. neglecta using a broth microdilution assay led to the isolation of three new serrulatane-type diterpenoids, 2,19-diacetoxy-8-hydroxyserrulat-14-ene (2), 8,19-dihydroxyserrulat-14-ene (3), and 8-hydroxyserrulat-14-en-19-oic acid (4), and a known o-naphthoquinone commonly referred to as biflorin (5). The structures of 2–5 were determined using 1D and 2D NMR, FTIR, and high-resolution mass spectrometry. Compounds 3–5 showed antimicrobial activity against Gram-positive bacteria including Staphylococcus aureus, Streptococcus pyogenes, and S. pneumoniae. The minimum inhibitory concentrations (MICs) and the minimum bactericidal concentrations (MBCs) ranged from 6.5 to 101.6 µM and 12.7 to 202.9 µM, respectively. No activity was observed for these compounds against Gram-negative bacteria.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>17844993</pmid><doi>10.1021/np070180r</doi><tpages>5</tpages></addata></record> |
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| subjects | Anti-Infective Agents - chemistry Anti-Infective Agents - isolation & purification Anti-Infective Agents - pharmacology antibacterial properties antimicrobial agents Australia bacterial infections Biological and medical sciences chemical structure Desert Climate Diterpenes - chemistry Diterpenes - isolation & purification Diterpenes - pharmacology diterpenoids Eremophila Eremophila neglecta Eremophila Plant - chemistry Escherichia coli General pharmacology Gram-Negative Bacteria - drug effects Gram-positive bacteria human health Medical sciences Microbial Sensitivity Tests minimum bactericidal concentrations Molecular Structure Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments phytochemicals Plant Leaves - chemistry Plants, Medicinal - chemistry Pseudomonas aeruginosa Salmonella typhimurium Scrophulariaceae serrulatane diterpene spectral analysis Staphylococcus aureus Staphylococcus aureus - drug effects stereochemistry Streptococcus pneumoniae Streptococcus pneumoniae - drug effects Streptococcus pyogenes Streptococcus pyogenes - drug effects xerophytes |
| title | Antimicrobial Compounds from the Australian Desert Plant Eremophila neglecta |
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