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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Veröffentlicht in:Planta medica 2006-03, Vol.72 (4), p.358-363
Hauptverfasser: Magalhaes, A.F, Tozzi, A.M.G.A, Magalhaes, E.G, Souza-Neta, L.C
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creator Magalhaes, A.F
Tozzi, A.M.G.A
Magalhaes, E.G
Souza-Neta, L.C
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.
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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. 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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 &amp; 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 &amp; 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 &amp; 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 &amp; 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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ispartof Planta medica, 2006-03, Vol.72 (4), p.358-363
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language eng
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source MEDLINE; Thieme Connect Journals
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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