Antimicrobial and antiparasitic (+)-trans-hexahydrodibenzopyrans and analogues from Machaerium multiflorum
Machaerium multiflorum yielded two additional new (+)-trans-hexahydrodibenzopyrans (HHDBP's), machaeriol C (1) and machaeriol D (2), and three new 5,6-seco-HHDBP's, machaeridiol A (3), machaeridiol B (4), and machaeridiol C (5). Their structures and stereochemistries were determined by 1D...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2003-06, Vol.66 (6), p.804-809 |
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| creator | Muhammad, I Li, X.C Jacob, M.R Tekwani, B.L Dunbar, D.C Ferreira, D |
| description | Machaerium multiflorum yielded two additional new (+)-trans-hexahydrodibenzopyrans (HHDBP's), machaeriol C (1) and machaeriol D (2), and three new 5,6-seco-HHDBP's, machaeridiol A (3), machaeridiol B (4), and machaeridiol C (5). Their structures and stereochemistries were determined by 1D and 2D NMR data, including HMBC, NOESY, and circular dichroism experiments. Machaeriol C (1) demonstrated in vitro antibacterial activity against Staphylococcus aureus (IC(50) 0.65 microg/mL) and methicillin-resistant S. aureus (MRSA) (IC(50) 0.70 microg/mL), while its corresponding 5,6-seco-analogues machaeridiol A (3) and machaeridiol B (4) showed antibacterial activity against S. aureus and MRSA (IC(50) 1.0-2.6 microg/mL) and antifungal activity against Candida albicans (IC(50), 2.0-3.5 microg/mL). In addition, machaeridiol B (4) demonstrated antiparasitic activities against Plasmodium falciparum D6 and W2 clones and Leishmania donavani with IC(50) values of 0.64, 0.22, and 0.9 microg/mL, respectively. |
| doi_str_mv | 10.1021/np030045o |
| format | Article |
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Their structures and stereochemistries were determined by 1D and 2D NMR data, including HMBC, NOESY, and circular dichroism experiments. Machaeriol C (1) demonstrated in vitro antibacterial activity against Staphylococcus aureus (IC(50) 0.65 microg/mL) and methicillin-resistant S. aureus (MRSA) (IC(50) 0.70 microg/mL), while its corresponding 5,6-seco-analogues machaeridiol A (3) and machaeridiol B (4) showed antibacterial activity against S. aureus and MRSA (IC(50) 1.0-2.6 microg/mL) and antifungal activity against Candida albicans (IC(50), 2.0-3.5 microg/mL). In addition, machaeridiol B (4) demonstrated antiparasitic activities against Plasmodium falciparum D6 and W2 clones and Leishmania donavani with IC(50) values of 0.64, 0.22, and 0.9 microg/mL, respectively.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np030045o</identifier><identifier>PMID: 12828466</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Animals ; Anti-Infective Agents - chemistry ; Anti-Infective Agents - isolation & purification ; Anti-Infective Agents - pharmacology ; antibacterial properties ; antifungal properties ; antimalarials ; Antimalarials - chemistry ; Antimalarials - isolation & purification ; Antimalarials - pharmacology ; Antiparasitic Agents - chemistry ; Antiparasitic Agents - isolation & purification ; Antiparasitic Agents - pharmacology ; bark ; benzene ; Benzopyrans - chemistry ; Benzopyrans - isolation & purification ; Benzopyrans - pharmacology ; Biological and medical sciences ; Candida albicans ; Candida albicans - drug effects ; carbon ; chemical structure ; circular dichroism spectroscopy ; Fabaceae - chemistry ; Faboideae ; General pharmacology ; heterocyclic compounds ; hexahydrodibenzopyran ; Inhibitory Concentration 50 ; Leishmania donovani ; Leishmania donovani - drug effects ; machaeridiols ; machaeriols ; Machaerium ; Machaerium multiflorum ; Medical sciences ; Methicillin Resistance ; Microbial Sensitivity Tests ; Molecular Structure ; Nuclear Magnetic Resonance, Biomolecular ; Peru ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; phytochemicals ; Plant Bark - drug effects ; plant extracts ; Plants, Medicinal - chemistry ; Plasmodium falciparum ; Plasmodium falciparum - drug effects ; protons ; pyrans ; spectral analysis ; Staphylococcus aureus ; Staphylococcus aureus - drug effects ; stems ; stereochemistry ; Stereoisomerism ; stilbenes ; styrene</subject><ispartof>Journal of natural products (Washington, D.C.), 2003-06, Vol.66 (6), p.804-809</ispartof><rights>2003 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=14924828$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12828466$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Muhammad, I</creatorcontrib><creatorcontrib>Li, X.C</creatorcontrib><creatorcontrib>Jacob, M.R</creatorcontrib><creatorcontrib>Tekwani, B.L</creatorcontrib><creatorcontrib>Dunbar, D.C</creatorcontrib><creatorcontrib>Ferreira, D</creatorcontrib><title>Antimicrobial and antiparasitic (+)-trans-hexahydrodibenzopyrans and analogues from Machaerium multiflorum</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Machaerium multiflorum yielded two additional new (+)-trans-hexahydrodibenzopyrans (HHDBP's), machaeriol C (1) and machaeriol D (2), and three new 5,6-seco-HHDBP's, machaeridiol A (3), machaeridiol B (4), and machaeridiol C (5). Their structures and stereochemistries were determined by 1D and 2D NMR data, including HMBC, NOESY, and circular dichroism experiments. Machaeriol C (1) demonstrated in vitro antibacterial activity against Staphylococcus aureus (IC(50) 0.65 microg/mL) and methicillin-resistant S. aureus (MRSA) (IC(50) 0.70 microg/mL), while its corresponding 5,6-seco-analogues machaeridiol A (3) and machaeridiol B (4) showed antibacterial activity against S. aureus and MRSA (IC(50) 1.0-2.6 microg/mL) and antifungal activity against Candida albicans (IC(50), 2.0-3.5 microg/mL). In addition, machaeridiol B (4) demonstrated antiparasitic activities against Plasmodium falciparum D6 and W2 clones and Leishmania donavani with IC(50) values of 0.64, 0.22, and 0.9 microg/mL, respectively.</description><subject>Animals</subject><subject>Anti-Infective Agents - chemistry</subject><subject>Anti-Infective Agents - isolation & purification</subject><subject>Anti-Infective Agents - pharmacology</subject><subject>antibacterial properties</subject><subject>antifungal properties</subject><subject>antimalarials</subject><subject>Antimalarials - chemistry</subject><subject>Antimalarials - isolation & purification</subject><subject>Antimalarials - pharmacology</subject><subject>Antiparasitic Agents - chemistry</subject><subject>Antiparasitic Agents - isolation & purification</subject><subject>Antiparasitic Agents - pharmacology</subject><subject>bark</subject><subject>benzene</subject><subject>Benzopyrans - chemistry</subject><subject>Benzopyrans - isolation & purification</subject><subject>Benzopyrans - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Candida albicans</subject><subject>Candida albicans - drug effects</subject><subject>carbon</subject><subject>chemical structure</subject><subject>circular dichroism spectroscopy</subject><subject>Fabaceae - chemistry</subject><subject>Faboideae</subject><subject>General pharmacology</subject><subject>heterocyclic compounds</subject><subject>hexahydrodibenzopyran</subject><subject>Inhibitory Concentration 50</subject><subject>Leishmania donovani</subject><subject>Leishmania donovani - drug effects</subject><subject>machaeridiols</subject><subject>machaeriols</subject><subject>Machaerium</subject><subject>Machaerium multiflorum</subject><subject>Medical sciences</subject><subject>Methicillin Resistance</subject><subject>Microbial Sensitivity Tests</subject><subject>Molecular Structure</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Peru</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>phytochemicals</subject><subject>Plant Bark - drug effects</subject><subject>plant extracts</subject><subject>Plants, Medicinal - chemistry</subject><subject>Plasmodium falciparum</subject><subject>Plasmodium falciparum - drug effects</subject><subject>protons</subject><subject>pyrans</subject><subject>spectral analysis</subject><subject>Staphylococcus aureus</subject><subject>Staphylococcus aureus - drug effects</subject><subject>stems</subject><subject>stereochemistry</subject><subject>Stereoisomerism</subject><subject>stilbenes</subject><subject>styrene</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpF0M1u1DAQAGALUdFt4cALQC4gEAqM7dixj9WWUqTyp7aCWzRx7K5LEgc7kbo8fY12gYM1kueb0cwQ8pTCWwqMvhsn4ACVCA_IigoGpQQmHpIVUMlLrmR1SI5SugXITItH5JAyxVQl5YrcnoyzH7yJofXYFzh2-c1-wojJz94Ur968LueIYyo39g432y6Gzrd2_B2m7Z_vfQn24WaxqXAxDMUnNBu00S9DMSz97F0f4jI8JgcO-2Sf7OMxuT57f7U-Ly--fPi4PrkoHecwl10tmHBaa0UNmrwfU4bySgiN0LZS1EyytlZSKeda2XEuwVQaOieZMQIsPyYvd32nGH7lmeZm8MnYvsfRhiU1VCnKuOYZPtvDpR1s10zRDxi3zd_rZPBiDzAZ7F3e1_j031WaVZlmV-6cT7O9-5fH-LORNa9Fc_X1svn8TX9fn2re_Mj--c47DA3exNzz-pIB5UBBaKEovwdzmow-</recordid><startdate>20030601</startdate><enddate>20030601</enddate><creator>Muhammad, I</creator><creator>Li, X.C</creator><creator>Jacob, M.R</creator><creator>Tekwani, B.L</creator><creator>Dunbar, D.C</creator><creator>Ferreira, 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>7T7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20030601</creationdate><title>Antimicrobial and antiparasitic (+)-trans-hexahydrodibenzopyrans and analogues from Machaerium multiflorum</title><author>Muhammad, I ; Li, X.C ; Jacob, M.R ; Tekwani, B.L ; Dunbar, D.C ; Ferreira, D</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-f330t-d7525f99981cac10228c134559a0bb657262b78688ffb6d3360c490df62cc50e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Animals</topic><topic>Anti-Infective Agents - chemistry</topic><topic>Anti-Infective Agents - isolation & purification</topic><topic>Anti-Infective Agents - pharmacology</topic><topic>antibacterial properties</topic><topic>antifungal properties</topic><topic>antimalarials</topic><topic>Antimalarials - chemistry</topic><topic>Antimalarials - isolation & purification</topic><topic>Antimalarials - pharmacology</topic><topic>Antiparasitic Agents - chemistry</topic><topic>Antiparasitic Agents - isolation & purification</topic><topic>Antiparasitic Agents - pharmacology</topic><topic>bark</topic><topic>benzene</topic><topic>Benzopyrans - chemistry</topic><topic>Benzopyrans - isolation & purification</topic><topic>Benzopyrans - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Candida albicans</topic><topic>Candida albicans - drug effects</topic><topic>carbon</topic><topic>chemical structure</topic><topic>circular dichroism spectroscopy</topic><topic>Fabaceae - chemistry</topic><topic>Faboideae</topic><topic>General pharmacology</topic><topic>heterocyclic compounds</topic><topic>hexahydrodibenzopyran</topic><topic>Inhibitory Concentration 50</topic><topic>Leishmania donovani</topic><topic>Leishmania donovani - drug effects</topic><topic>machaeridiols</topic><topic>machaeriols</topic><topic>Machaerium</topic><topic>Machaerium multiflorum</topic><topic>Medical sciences</topic><topic>Methicillin Resistance</topic><topic>Microbial Sensitivity Tests</topic><topic>Molecular Structure</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Peru</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>phytochemicals</topic><topic>Plant Bark - drug effects</topic><topic>plant extracts</topic><topic>Plants, Medicinal - chemistry</topic><topic>Plasmodium falciparum</topic><topic>Plasmodium falciparum - drug effects</topic><topic>protons</topic><topic>pyrans</topic><topic>spectral analysis</topic><topic>Staphylococcus aureus</topic><topic>Staphylococcus aureus - drug effects</topic><topic>stems</topic><topic>stereochemistry</topic><topic>Stereoisomerism</topic><topic>stilbenes</topic><topic>styrene</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Muhammad, I</creatorcontrib><creatorcontrib>Li, X.C</creatorcontrib><creatorcontrib>Jacob, M.R</creatorcontrib><creatorcontrib>Tekwani, B.L</creatorcontrib><creatorcontrib>Dunbar, D.C</creatorcontrib><creatorcontrib>Ferreira, 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>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><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Muhammad, I</au><au>Li, X.C</au><au>Jacob, M.R</au><au>Tekwani, B.L</au><au>Dunbar, D.C</au><au>Ferreira, D</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Antimicrobial and antiparasitic (+)-trans-hexahydrodibenzopyrans and analogues from Machaerium multiflorum</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2003-06-01</date><risdate>2003</risdate><volume>66</volume><issue>6</issue><spage>804</spage><epage>809</epage><pages>804-809</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>Machaerium multiflorum yielded two additional new (+)-trans-hexahydrodibenzopyrans (HHDBP's), machaeriol C (1) and machaeriol D (2), and three new 5,6-seco-HHDBP's, machaeridiol A (3), machaeridiol B (4), and machaeridiol C (5). Their structures and stereochemistries were determined by 1D and 2D NMR data, including HMBC, NOESY, and circular dichroism experiments. Machaeriol C (1) demonstrated in vitro antibacterial activity against Staphylococcus aureus (IC(50) 0.65 microg/mL) and methicillin-resistant S. aureus (MRSA) (IC(50) 0.70 microg/mL), while its corresponding 5,6-seco-analogues machaeridiol A (3) and machaeridiol B (4) showed antibacterial activity against S. aureus and MRSA (IC(50) 1.0-2.6 microg/mL) and antifungal activity against Candida albicans (IC(50), 2.0-3.5 microg/mL). In addition, machaeridiol B (4) demonstrated antiparasitic activities against Plasmodium falciparum D6 and W2 clones and Leishmania donavani with IC(50) values of 0.64, 0.22, and 0.9 microg/mL, respectively.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>12828466</pmid><doi>10.1021/np030045o</doi><tpages>6</tpages></addata></record> |
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| subjects | Animals Anti-Infective Agents - chemistry Anti-Infective Agents - isolation & purification Anti-Infective Agents - pharmacology antibacterial properties antifungal properties antimalarials Antimalarials - chemistry Antimalarials - isolation & purification Antimalarials - pharmacology Antiparasitic Agents - chemistry Antiparasitic Agents - isolation & purification Antiparasitic Agents - pharmacology bark benzene Benzopyrans - chemistry Benzopyrans - isolation & purification Benzopyrans - pharmacology Biological and medical sciences Candida albicans Candida albicans - drug effects carbon chemical structure circular dichroism spectroscopy Fabaceae - chemistry Faboideae General pharmacology heterocyclic compounds hexahydrodibenzopyran Inhibitory Concentration 50 Leishmania donovani Leishmania donovani - drug effects machaeridiols machaeriols Machaerium Machaerium multiflorum Medical sciences Methicillin Resistance Microbial Sensitivity Tests Molecular Structure Nuclear Magnetic Resonance, Biomolecular Peru Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments phytochemicals Plant Bark - drug effects plant extracts Plants, Medicinal - chemistry Plasmodium falciparum Plasmodium falciparum - drug effects protons pyrans spectral analysis Staphylococcus aureus Staphylococcus aureus - drug effects stems stereochemistry Stereoisomerism stilbenes styrene |
| title | Antimicrobial and antiparasitic (+)-trans-hexahydrodibenzopyrans and analogues from Machaerium multiflorum |
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