New prenylated metabolites of Deguelia longeracemosa and evaluation of their antimicrobial potential
Abstract The analysis of root extracts from DEGUELIA LONGERACEMOSA (Benth.) A.M.G. Azevedo yielded fifteen prenylated metabolites. Nine of them are novel, and their molecular structures were determined through spectral analyses (UV, IR, MS and NMR) as being five derivatives of 4-hydroxy-3-phenylcoum...
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description | Abstract
The analysis of root extracts from DEGUELIA LONGERACEMOSA (Benth.) A.M.G. Azevedo yielded fifteen prenylated metabolites. Nine of them are novel, and their molecular structures were determined through spectral analyses (UV, IR, MS and NMR) as being five derivatives of 4-hydroxy-3-phenylcoumarin: 4-hydroxy-3-(4′-hydroxyphenyl)-5-methoxy-6-(8′,9′-epoxy-9′-methylbutyl)-2′′,2′′-dimethylpyrano-(5′′,6′′:8,7)-coumarin; 4-hydroxy-3-(3′,4′-methylenedioxyphenyl)-5-methoxy-6-(3,3-dimethylallyl)-2′′,2′′-dimethypyrano-(5′′,6′′:8,7)-coumarin; 4-hydroxy-3-(3′-hydroxy-4′-methoxyphenyl)-5-methoxy-6-(3,3-dimethylallyl)-2′′,2′′-dimethylpyrano-(5′′,6′′:8,7)-coumarin; 4-hydroxy-3-(3′-hydroxy-4′-methoxyphenyl)-5-methoxy-2′′,2′′-dimethylpyrano-(5′′,6′′:6,7)-coumarin and 4-hydroxy-3-[4′-O-(3,3-dimethylallyl)phenyl]-5-methoxy-2′′,2′′-dimethylpyrano-(5′′,6′′:6,7)-coumarin, three derivatives of 1,2-diphenyl-1,2-ethanodione (α-oxodeoxybenzoin derivatives): 1-[6-hydroxy-2-methoxy-3-(3,3-dimethylallyl)-2′′,2′′-dimethylpyrano-(5′′,6′′:5,4)- ]-2-(4′-hydroxyphenyl)-1,2-ethanedione; 1-[6-hydroxy-2-methoxy-2′′,2′′-dimethylpyrano-(5′′,6′′:3,4)]-2-(4′-methoxyphenyl)-1,2-ethanedione; 1-[6-hydroxy-2-methoxy-2′′,2′′-dimethylpyrano-(5′′,6′′:3,4)]-2-(3′,4′-methylenedioxyphenyl)-1,2-ethanedione and one derivative of deoxybenzoin: 2,4′-dimethoxy-6-hydroxy-2′′,2′′-dimethylpyrano-(5′′,6′′:3,4)-deoxybenzoin. The antimicrobial activity of roots extracts and some isolated compounds was screened through bioautography against bacteria and fungi. |
doi_str_mv | 10.1055/s-2005-916232 |
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The analysis of root extracts from DEGUELIA LONGERACEMOSA (Benth.) A.M.G. Azevedo yielded fifteen prenylated metabolites. Nine of them are novel, and their molecular structures were determined through spectral analyses (UV, IR, MS and NMR) as being five derivatives of 4-hydroxy-3-phenylcoumarin: 4-hydroxy-3-(4′-hydroxyphenyl)-5-methoxy-6-(8′,9′-epoxy-9′-methylbutyl)-2′′,2′′-dimethylpyrano-(5′′,6′′:8,7)-coumarin; 4-hydroxy-3-(3′,4′-methylenedioxyphenyl)-5-methoxy-6-(3,3-dimethylallyl)-2′′,2′′-dimethypyrano-(5′′,6′′:8,7)-coumarin; 4-hydroxy-3-(3′-hydroxy-4′-methoxyphenyl)-5-methoxy-6-(3,3-dimethylallyl)-2′′,2′′-dimethylpyrano-(5′′,6′′:8,7)-coumarin; 4-hydroxy-3-(3′-hydroxy-4′-methoxyphenyl)-5-methoxy-2′′,2′′-dimethylpyrano-(5′′,6′′:6,7)-coumarin and 4-hydroxy-3-[4′-O-(3,3-dimethylallyl)phenyl]-5-methoxy-2′′,2′′-dimethylpyrano-(5′′,6′′:6,7)-coumarin, three derivatives of 1,2-diphenyl-1,2-ethanodione (α-oxodeoxybenzoin derivatives): 1-[6-hydroxy-2-methoxy-3-(3,3-dimethylallyl)-2′′,2′′-dimethylpyrano-(5′′,6′′:5,4)- ]-2-(4′-hydroxyphenyl)-1,2-ethanedione; 1-[6-hydroxy-2-methoxy-2′′,2′′-dimethylpyrano-(5′′,6′′:3,4)]-2-(4′-methoxyphenyl)-1,2-ethanedione; 1-[6-hydroxy-2-methoxy-2′′,2′′-dimethylpyrano-(5′′,6′′:3,4)]-2-(3′,4′-methylenedioxyphenyl)-1,2-ethanedione and one derivative of deoxybenzoin: 2,4′-dimethoxy-6-hydroxy-2′′,2′′-dimethylpyrano-(5′′,6′′:3,4)-deoxybenzoin. The antimicrobial activity of roots extracts and some isolated compounds was screened through bioautography against bacteria and fungi.</description><identifier>ISSN: 0032-0943</identifier><identifier>EISSN: 1439-0221</identifier><identifier>DOI: 10.1055/s-2005-916232</identifier><identifier>PMID: 16557478</identifier><identifier>CODEN: PLMEAA</identifier><language>eng</language><publisher>Stuttgart: Thieme</publisher><subject>Anti-Infective Agents - administration & dosage ; Anti-Infective Agents - chemistry ; Anti-Infective Agents - pharmacology ; Anti-Infective Agents - therapeutic use ; antibacterial properties ; antifungal properties ; Biological and medical sciences ; chemical structure ; Deguelia ; Deguelia longeracemosa ; General pharmacology ; Gram-Negative Bacteria - drug effects ; Gram-Positive Bacteria - drug effects ; human health ; Humans ; isoflavonoids ; Medical sciences ; Microbial Sensitivity Tests ; Millettia - metabolism ; Mitosporic Fungi - drug effects ; Original Paper ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; Phytotherapy ; plant extracts ; Plant Extracts - administration & dosage ; Plant Extracts - chemistry ; Plant Extracts - pharmacology ; Plant Extracts - therapeutic use ; Plant Roots ; Protein Prenylation ; spectral analysis</subject><ispartof>Planta medica, 2006-03, Vol.72 (4), p.358-363</ispartof><rights>Georg Thieme Verlag KG Stuttgart · New York</rights><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c344t-400403ef14d512987c8b1e8eda38ecabd379b0527b0aa49348bf937cfbcd1f983</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-2005-916232.pdf$$EPDF$$P50$$Gthieme$$H</linktopdf><linktohtml>$$Uhttps://www.thieme-connect.de/products/ejournals/html/10.1055/s-2005-916232$$EHTML$$P50$$Gthieme$$H</linktohtml><link.rule.ids>314,776,780,3005,27901,27902,54534,54535</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17616868$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16557478$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Magalhaes, A.F</creatorcontrib><creatorcontrib>Tozzi, A.M.G.A</creatorcontrib><creatorcontrib>Magalhaes, E.G</creatorcontrib><creatorcontrib>Souza-Neta, L.C</creatorcontrib><title>New prenylated metabolites of Deguelia longeracemosa and evaluation of their antimicrobial potential</title><title>Planta medica</title><addtitle>Planta Med</addtitle><description>Abstract
The analysis of root extracts from DEGUELIA LONGERACEMOSA (Benth.) A.M.G. Azevedo yielded fifteen prenylated metabolites. Nine of them are novel, and their molecular structures were determined through spectral analyses (UV, IR, MS and NMR) as being five derivatives of 4-hydroxy-3-phenylcoumarin: 4-hydroxy-3-(4′-hydroxyphenyl)-5-methoxy-6-(8′,9′-epoxy-9′-methylbutyl)-2′′,2′′-dimethylpyrano-(5′′,6′′:8,7)-coumarin; 4-hydroxy-3-(3′,4′-methylenedioxyphenyl)-5-methoxy-6-(3,3-dimethylallyl)-2′′,2′′-dimethypyrano-(5′′,6′′:8,7)-coumarin; 4-hydroxy-3-(3′-hydroxy-4′-methoxyphenyl)-5-methoxy-6-(3,3-dimethylallyl)-2′′,2′′-dimethylpyrano-(5′′,6′′:8,7)-coumarin; 4-hydroxy-3-(3′-hydroxy-4′-methoxyphenyl)-5-methoxy-2′′,2′′-dimethylpyrano-(5′′,6′′:6,7)-coumarin and 4-hydroxy-3-[4′-O-(3,3-dimethylallyl)phenyl]-5-methoxy-2′′,2′′-dimethylpyrano-(5′′,6′′:6,7)-coumarin, three derivatives of 1,2-diphenyl-1,2-ethanodione (α-oxodeoxybenzoin derivatives): 1-[6-hydroxy-2-methoxy-3-(3,3-dimethylallyl)-2′′,2′′-dimethylpyrano-(5′′,6′′:5,4)- ]-2-(4′-hydroxyphenyl)-1,2-ethanedione; 1-[6-hydroxy-2-methoxy-2′′,2′′-dimethylpyrano-(5′′,6′′:3,4)]-2-(4′-methoxyphenyl)-1,2-ethanedione; 1-[6-hydroxy-2-methoxy-2′′,2′′-dimethylpyrano-(5′′,6′′:3,4)]-2-(3′,4′-methylenedioxyphenyl)-1,2-ethanedione and one derivative of deoxybenzoin: 2,4′-dimethoxy-6-hydroxy-2′′,2′′-dimethylpyrano-(5′′,6′′:3,4)-deoxybenzoin. The antimicrobial activity of roots extracts and some isolated compounds was screened through bioautography against bacteria and fungi.</description><subject>Anti-Infective Agents - administration & dosage</subject><subject>Anti-Infective Agents - chemistry</subject><subject>Anti-Infective Agents - pharmacology</subject><subject>Anti-Infective Agents - therapeutic use</subject><subject>antibacterial properties</subject><subject>antifungal properties</subject><subject>Biological and medical sciences</subject><subject>chemical structure</subject><subject>Deguelia</subject><subject>Deguelia longeracemosa</subject><subject>General pharmacology</subject><subject>Gram-Negative Bacteria - drug effects</subject><subject>Gram-Positive Bacteria - drug effects</subject><subject>human health</subject><subject>Humans</subject><subject>isoflavonoids</subject><subject>Medical sciences</subject><subject>Microbial Sensitivity Tests</subject><subject>Millettia - metabolism</subject><subject>Mitosporic Fungi - drug effects</subject><subject>Original Paper</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Phytotherapy</subject><subject>plant extracts</subject><subject>Plant Extracts - administration & dosage</subject><subject>Plant Extracts - chemistry</subject><subject>Plant Extracts - pharmacology</subject><subject>Plant Extracts - therapeutic use</subject><subject>Plant Roots</subject><subject>Protein Prenylation</subject><subject>spectral analysis</subject><issn>0032-0943</issn><issn>1439-0221</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpF0U1v1DAQBmALgehSOHKFXOBEyvgjcXJE5aNIFT1Az9bYmWxdOfFiO6D-exLtokojjTR6NNLMy9hrDhccmuZjrgVAU_e8FVI8YTuuZF-DEPwp2wFIUUOv5Bl7kfM9AFc9wHN2xtum0Up3Ozb8oL_VIdH8ELDQUE1U0MbgC-UqjtVn2i8UPFYhzntK6GiKGSuch4r-YFiw-DhvsNyRT-u8-Mm7FK3HUB1ioXWA4SV7NmLI9OrUz9nt1y-_Lq_q65tv3y8_XddOKlVqBaBA0sjV0HDRd9p1llNHA8qOHNpB6t5CI7QFRNVL1dmxl9qN1g187Dt5zt4f9x5S_L1QLmby2VEIOFNcsmm17mTTbPDNCS52osEckp8wPZj_f1nBuxPA7DCMCWfn86PTLW-7dnMfjq7ceZrI3MclzeuJhoPZ4jHZbPGYYzwrf3vkI0aD-7SuvP0pgEvgoLeS_wBlVIn2</recordid><startdate>20060301</startdate><enddate>20060301</enddate><creator>Magalhaes, A.F</creator><creator>Tozzi, A.M.G.A</creator><creator>Magalhaes, E.G</creator><creator>Souza-Neta, L.C</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>7X8</scope></search><sort><creationdate>20060301</creationdate><title>New prenylated metabolites of Deguelia longeracemosa and evaluation of their antimicrobial potential</title><author>Magalhaes, A.F ; Tozzi, A.M.G.A ; Magalhaes, E.G ; Souza-Neta, L.C</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c344t-400403ef14d512987c8b1e8eda38ecabd379b0527b0aa49348bf937cfbcd1f983</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Anti-Infective Agents - administration & dosage</topic><topic>Anti-Infective Agents - chemistry</topic><topic>Anti-Infective Agents - pharmacology</topic><topic>Anti-Infective Agents - therapeutic use</topic><topic>antibacterial properties</topic><topic>antifungal properties</topic><topic>Biological and medical sciences</topic><topic>chemical structure</topic><topic>Deguelia</topic><topic>Deguelia longeracemosa</topic><topic>General pharmacology</topic><topic>Gram-Negative Bacteria - drug effects</topic><topic>Gram-Positive Bacteria - drug effects</topic><topic>human health</topic><topic>Humans</topic><topic>isoflavonoids</topic><topic>Medical sciences</topic><topic>Microbial Sensitivity Tests</topic><topic>Millettia - metabolism</topic><topic>Mitosporic Fungi - drug effects</topic><topic>Original Paper</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Phytotherapy</topic><topic>plant extracts</topic><topic>Plant Extracts - administration & dosage</topic><topic>Plant Extracts - chemistry</topic><topic>Plant Extracts - pharmacology</topic><topic>Plant Extracts - therapeutic use</topic><topic>Plant Roots</topic><topic>Protein Prenylation</topic><topic>spectral analysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Magalhaes, A.F</creatorcontrib><creatorcontrib>Tozzi, A.M.G.A</creatorcontrib><creatorcontrib>Magalhaes, E.G</creatorcontrib><creatorcontrib>Souza-Neta, L.C</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>MEDLINE - Academic</collection><jtitle>Planta medica</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Magalhaes, A.F</au><au>Tozzi, A.M.G.A</au><au>Magalhaes, E.G</au><au>Souza-Neta, L.C</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>New prenylated metabolites of Deguelia longeracemosa and evaluation of their antimicrobial potential</atitle><jtitle>Planta medica</jtitle><addtitle>Planta Med</addtitle><date>2006-03-01</date><risdate>2006</risdate><volume>72</volume><issue>4</issue><spage>358</spage><epage>363</epage><pages>358-363</pages><issn>0032-0943</issn><eissn>1439-0221</eissn><coden>PLMEAA</coden><abstract>Abstract
The analysis of root extracts from DEGUELIA LONGERACEMOSA (Benth.) A.M.G. Azevedo yielded fifteen prenylated metabolites. Nine of them are novel, and their molecular structures were determined through spectral analyses (UV, IR, MS and NMR) as being five derivatives of 4-hydroxy-3-phenylcoumarin: 4-hydroxy-3-(4′-hydroxyphenyl)-5-methoxy-6-(8′,9′-epoxy-9′-methylbutyl)-2′′,2′′-dimethylpyrano-(5′′,6′′:8,7)-coumarin; 4-hydroxy-3-(3′,4′-methylenedioxyphenyl)-5-methoxy-6-(3,3-dimethylallyl)-2′′,2′′-dimethypyrano-(5′′,6′′:8,7)-coumarin; 4-hydroxy-3-(3′-hydroxy-4′-methoxyphenyl)-5-methoxy-6-(3,3-dimethylallyl)-2′′,2′′-dimethylpyrano-(5′′,6′′:8,7)-coumarin; 4-hydroxy-3-(3′-hydroxy-4′-methoxyphenyl)-5-methoxy-2′′,2′′-dimethylpyrano-(5′′,6′′:6,7)-coumarin and 4-hydroxy-3-[4′-O-(3,3-dimethylallyl)phenyl]-5-methoxy-2′′,2′′-dimethylpyrano-(5′′,6′′:6,7)-coumarin, three derivatives of 1,2-diphenyl-1,2-ethanodione (α-oxodeoxybenzoin derivatives): 1-[6-hydroxy-2-methoxy-3-(3,3-dimethylallyl)-2′′,2′′-dimethylpyrano-(5′′,6′′:5,4)- ]-2-(4′-hydroxyphenyl)-1,2-ethanedione; 1-[6-hydroxy-2-methoxy-2′′,2′′-dimethylpyrano-(5′′,6′′:3,4)]-2-(4′-methoxyphenyl)-1,2-ethanedione; 1-[6-hydroxy-2-methoxy-2′′,2′′-dimethylpyrano-(5′′,6′′:3,4)]-2-(3′,4′-methylenedioxyphenyl)-1,2-ethanedione and one derivative of deoxybenzoin: 2,4′-dimethoxy-6-hydroxy-2′′,2′′-dimethylpyrano-(5′′,6′′:3,4)-deoxybenzoin. The antimicrobial activity of roots extracts and some isolated compounds was screened through bioautography against bacteria and fungi.</abstract><cop>Stuttgart</cop><cop>New York, NY</cop><pub>Thieme</pub><pmid>16557478</pmid><doi>10.1055/s-2005-916232</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record> |
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subjects | Anti-Infective Agents - administration & dosage Anti-Infective Agents - chemistry Anti-Infective Agents - pharmacology Anti-Infective Agents - therapeutic use antibacterial properties antifungal properties Biological and medical sciences chemical structure Deguelia Deguelia longeracemosa General pharmacology Gram-Negative Bacteria - drug effects Gram-Positive Bacteria - drug effects human health Humans isoflavonoids Medical sciences Microbial Sensitivity Tests Millettia - metabolism Mitosporic Fungi - drug effects Original Paper Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Phytotherapy plant extracts Plant Extracts - administration & dosage Plant Extracts - chemistry Plant Extracts - pharmacology Plant Extracts - therapeutic use Plant Roots Protein Prenylation spectral analysis |
title | New prenylated metabolites of Deguelia longeracemosa and evaluation of their antimicrobial potential |
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