Antibacterial hydroxycinnamic esters from Piper caninum from Paluma, North Queensland, Australia. The crystal and molecular structure of (+)-bornyl coumarate
Abstract The crude chloroform bark extract of PIPER CANINUM (Piperaceae) exhibits antibacterial activity against the Gram-positive bacteria, BACILLUS CEREUS, STAPHYLOCOCCUS AUREUS, and STREPTOCOCCUS PNEUMONIAE. The antibacterial agents in this extract have been isolated using bioactivity-directed ch...
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| Veröffentlicht in: | Planta medica 1999-12, Vol.65 (8), p.747-749 |
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| container_title | Planta medica |
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| creator | Setzer, W.N Setzer, M.C Bates, R.B Nakkiew, P Jackes, B.R Chen, L McFerrin, M.B Meehan, E.J |
| description | Abstract
The crude chloroform bark extract of PIPER CANINUM (Piperaceae) exhibits antibacterial activity against the Gram-positive bacteria, BACILLUS CEREUS, STAPHYLOCOCCUS AUREUS, and STREPTOCOCCUS PNEUMONIAE. The antibacterial agents in this extract have been isolated using bioactivity-directed chromatographic techniques and identified by NMR spectroscopy as (+)-bornyl P-coumarate and bornyl caffeate. A single-crystal X-ray structure has been carried out on (+)-bornyl P-coumarate. The compound crystallizes in the orthorhombic space group P2
1
2
1
2
1
(#19) with A = 12.659(4), B = 13.281(4), and C = 10.177(3) Å. Fullmatrix least-squares refinement converged at R = 0.047, and RW
= 0.058. |
| doi_str_mv | 10.1055/s-2006-960855 |
| format | Article |
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The crude chloroform bark extract of PIPER CANINUM (Piperaceae) exhibits antibacterial activity against the Gram-positive bacteria, BACILLUS CEREUS, STAPHYLOCOCCUS AUREUS, and STREPTOCOCCUS PNEUMONIAE. The antibacterial agents in this extract have been isolated using bioactivity-directed chromatographic techniques and identified by NMR spectroscopy as (+)-bornyl P-coumarate and bornyl caffeate. A single-crystal X-ray structure has been carried out on (+)-bornyl P-coumarate. The compound crystallizes in the orthorhombic space group P2
1
2
1
2
1
(#19) with A = 12.659(4), B = 13.281(4), and C = 10.177(3) Å. Fullmatrix least-squares refinement converged at R = 0.047, and RW
= 0.058.</description><identifier>ISSN: 0032-0943</identifier><identifier>EISSN: 1439-0221</identifier><identifier>DOI: 10.1055/s-2006-960855</identifier><identifier>PMID: 10630119</identifier><identifier>CODEN: PLMEAA</identifier><language>eng</language><publisher>Stuttgart: Thieme</publisher><subject>Anti-Bacterial Agents - chemistry ; antibacterial properties ; Bacillus cereus ; bark ; bioassays ; Biological and medical sciences ; chemical constituents of plants ; chemical structure ; coumaric acids ; Coumaric Acids - chemistry ; Esters ; fractionation ; General pharmacology ; Letters ; Medical sciences ; Models, Molecular ; Molecular Structure ; nuclear magnetic resonance spectroscopy ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; Piper ; Plants, Medicinal - chemistry ; spectral analysis ; Staphylococcus ; Staphylococcus aureus ; Streptococcus pneumoniae</subject><ispartof>Planta medica, 1999-12, Vol.65 (8), p.747-749</ispartof><rights>Georg Thieme Verlag Stuttgart · New York</rights><rights>2000 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c379t-149ddc254d4451b3f5d81822bccfd9f859c4256530e2926e39d65bd62236a90c3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-2006-960855.pdf$$EPDF$$P50$$Gthieme$$H</linktopdf><link.rule.ids>314,776,780,3004,3005,27901,27902,54534</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=1211608$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/10630119$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Setzer, W.N</creatorcontrib><creatorcontrib>Setzer, M.C</creatorcontrib><creatorcontrib>Bates, R.B</creatorcontrib><creatorcontrib>Nakkiew, P</creatorcontrib><creatorcontrib>Jackes, B.R</creatorcontrib><creatorcontrib>Chen, L</creatorcontrib><creatorcontrib>McFerrin, M.B</creatorcontrib><creatorcontrib>Meehan, E.J</creatorcontrib><title>Antibacterial hydroxycinnamic esters from Piper caninum from Paluma, North Queensland, Australia. The crystal and molecular structure of (+)-bornyl coumarate</title><title>Planta medica</title><addtitle>Planta Med</addtitle><description>Abstract
The crude chloroform bark extract of PIPER CANINUM (Piperaceae) exhibits antibacterial activity against the Gram-positive bacteria, BACILLUS CEREUS, STAPHYLOCOCCUS AUREUS, and STREPTOCOCCUS PNEUMONIAE. The antibacterial agents in this extract have been isolated using bioactivity-directed chromatographic techniques and identified by NMR spectroscopy as (+)-bornyl P-coumarate and bornyl caffeate. A single-crystal X-ray structure has been carried out on (+)-bornyl P-coumarate. The compound crystallizes in the orthorhombic space group P2
1
2
1
2
1
(#19) with A = 12.659(4), B = 13.281(4), and C = 10.177(3) Å. Fullmatrix least-squares refinement converged at R = 0.047, and RW
= 0.058.</description><subject>Anti-Bacterial Agents - chemistry</subject><subject>antibacterial properties</subject><subject>Bacillus cereus</subject><subject>bark</subject><subject>bioassays</subject><subject>Biological and medical sciences</subject><subject>chemical constituents of plants</subject><subject>chemical structure</subject><subject>coumaric acids</subject><subject>Coumaric Acids - chemistry</subject><subject>Esters</subject><subject>fractionation</subject><subject>General pharmacology</subject><subject>Letters</subject><subject>Medical sciences</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>nuclear magnetic resonance spectroscopy</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Piper</subject><subject>Plants, Medicinal - chemistry</subject><subject>spectral analysis</subject><subject>Staphylococcus</subject><subject>Staphylococcus aureus</subject><subject>Streptococcus pneumoniae</subject><issn>0032-0943</issn><issn>1439-0221</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1999</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kU1vVCEUhonR2Gl16VZZGKNxbj3AhQ7LSeNX0vgR2zXhAteh4cIIl8T5Mf2v0txJdOOKhPPkgfe8CD0jcE6A83elowCikwI2nD9AK9Iz2QGl5CFaATDagezZCTot5RaA9BLgMTohIBgQIlfobhtnP2gzu-x1wLuDzen3wfgY9eQNdqUNCh5zmvA3v3cZGx19rNPxSoc66TX-kvK8w9-rc7EEHe0ab2uZsw5en-PrncMmH8rc_G2GpxScqUFn3JBq5podTiN-_fZNN6QcDwGb1KxZz-4JejTqUNzT43mGbj68v7781F19_fj5cnvVGXYh567FstZQ3tu-52RgI7cbsqF0MGa0ctxwaXrKBWfgqKTCMWkFH6yglAktwbAz9Grx7nP6VVtoNfliXGhZXKpFCcmkoBeygd0CmpxKyW5U--zbXw-KgLrvQxV134da-mj886O4DpOz_9BLAQ14eQR0MTqMWUfjy1-OEtJMDVsv2LzzbnLqNtUc20b---yLBR91UvpnbsabHxQIAyoZ73vB_gBXuatV</recordid><startdate>19991201</startdate><enddate>19991201</enddate><creator>Setzer, W.N</creator><creator>Setzer, M.C</creator><creator>Bates, R.B</creator><creator>Nakkiew, P</creator><creator>Jackes, B.R</creator><creator>Chen, L</creator><creator>McFerrin, M.B</creator><creator>Meehan, E.J</creator><general>Thieme</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>7X8</scope></search><sort><creationdate>19991201</creationdate><title>Antibacterial hydroxycinnamic esters from Piper caninum from Paluma, North Queensland, Australia. The crystal and molecular structure of (+)-bornyl coumarate</title><author>Setzer, W.N ; Setzer, M.C ; Bates, R.B ; Nakkiew, P ; Jackes, B.R ; Chen, L ; McFerrin, M.B ; Meehan, E.J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c379t-149ddc254d4451b3f5d81822bccfd9f859c4256530e2926e39d65bd62236a90c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1999</creationdate><topic>Anti-Bacterial Agents - chemistry</topic><topic>antibacterial properties</topic><topic>Bacillus cereus</topic><topic>bark</topic><topic>bioassays</topic><topic>Biological and medical sciences</topic><topic>chemical constituents of plants</topic><topic>chemical structure</topic><topic>coumaric acids</topic><topic>Coumaric Acids - chemistry</topic><topic>Esters</topic><topic>fractionation</topic><topic>General pharmacology</topic><topic>Letters</topic><topic>Medical sciences</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>nuclear magnetic resonance spectroscopy</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Piper</topic><topic>Plants, Medicinal - chemistry</topic><topic>spectral analysis</topic><topic>Staphylococcus</topic><topic>Staphylococcus aureus</topic><topic>Streptococcus pneumoniae</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Setzer, W.N</creatorcontrib><creatorcontrib>Setzer, M.C</creatorcontrib><creatorcontrib>Bates, R.B</creatorcontrib><creatorcontrib>Nakkiew, P</creatorcontrib><creatorcontrib>Jackes, B.R</creatorcontrib><creatorcontrib>Chen, L</creatorcontrib><creatorcontrib>McFerrin, M.B</creatorcontrib><creatorcontrib>Meehan, E.J</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>MEDLINE - Academic</collection><jtitle>Planta medica</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Setzer, W.N</au><au>Setzer, M.C</au><au>Bates, R.B</au><au>Nakkiew, P</au><au>Jackes, B.R</au><au>Chen, L</au><au>McFerrin, M.B</au><au>Meehan, E.J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Antibacterial hydroxycinnamic esters from Piper caninum from Paluma, North Queensland, Australia. The crystal and molecular structure of (+)-bornyl coumarate</atitle><jtitle>Planta medica</jtitle><addtitle>Planta Med</addtitle><date>1999-12-01</date><risdate>1999</risdate><volume>65</volume><issue>8</issue><spage>747</spage><epage>749</epage><pages>747-749</pages><issn>0032-0943</issn><eissn>1439-0221</eissn><coden>PLMEAA</coden><abstract>Abstract
The crude chloroform bark extract of PIPER CANINUM (Piperaceae) exhibits antibacterial activity against the Gram-positive bacteria, BACILLUS CEREUS, STAPHYLOCOCCUS AUREUS, and STREPTOCOCCUS PNEUMONIAE. The antibacterial agents in this extract have been isolated using bioactivity-directed chromatographic techniques and identified by NMR spectroscopy as (+)-bornyl P-coumarate and bornyl caffeate. A single-crystal X-ray structure has been carried out on (+)-bornyl P-coumarate. The compound crystallizes in the orthorhombic space group P2
1
2
1
2
1
(#19) with A = 12.659(4), B = 13.281(4), and C = 10.177(3) Å. Fullmatrix least-squares refinement converged at R = 0.047, and RW
= 0.058.</abstract><cop>Stuttgart</cop><cop>New York, NY</cop><pub>Thieme</pub><pmid>10630119</pmid><doi>10.1055/s-2006-960855</doi><tpages>3</tpages></addata></record> |
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| subjects | Anti-Bacterial Agents - chemistry antibacterial properties Bacillus cereus bark bioassays Biological and medical sciences chemical constituents of plants chemical structure coumaric acids Coumaric Acids - chemistry Esters fractionation General pharmacology Letters Medical sciences Models, Molecular Molecular Structure nuclear magnetic resonance spectroscopy Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Piper Plants, Medicinal - chemistry spectral analysis Staphylococcus Staphylococcus aureus Streptococcus pneumoniae |
| title | Antibacterial hydroxycinnamic esters from Piper caninum from Paluma, North Queensland, Australia. The crystal and molecular structure of (+)-bornyl coumarate |
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