pyrimidine-β-carboline and other alkaloids from Annona foetida with antileishmanial activity
Bioassay-guided fractionation of the bark extract of Annona foetida afforded a new antileishmanial pyrimidine-beta-carboline alkaloid, N-hydroxyannomontine (1), together with the previously reported annomontine (2), O-methylmoschatoline (3), and liriodenine (4). The structure of compound 1 was estab...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2006-02, Vol.69 (2), p.292-294 |
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| creator | Costa, E.V Pinheiro, M.L.B Xavier, C.M Silva, J.R.A Amaral, A.C.F Souza, A.D.L Barison, A Campos, F.R Ferreira, A.G Machado, G.M.C |
| description | Bioassay-guided fractionation of the bark extract of Annona foetida afforded a new antileishmanial pyrimidine-beta-carboline alkaloid, N-hydroxyannomontine (1), together with the previously reported annomontine (2), O-methylmoschatoline (3), and liriodenine (4). The structure of compound 1 was established on the basis of extensive 1D and 2D NMR and MS analyses. This is the third reported pyrimidine-beta-carboline-type alkaloid and is particularly important for Annona genus chemotaxonomy. In addition, all compounds exhibit in vitro antileishmanial activity against promastigote forms of Leishmania braziliensis. Compounds 2 and 4 showed better activity than compounds 1 and 3 against L. braziliensis. Compound 2 was not active against L. guyanensis. |
| doi_str_mv | 10.1021/np050422s |
| format | Article |
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The structure of compound 1 was established on the basis of extensive 1D and 2D NMR and MS analyses. This is the third reported pyrimidine-beta-carboline-type alkaloid and is particularly important for Annona genus chemotaxonomy. In addition, all compounds exhibit in vitro antileishmanial activity against promastigote forms of Leishmania braziliensis. Compounds 2 and 4 showed better activity than compounds 1 and 3 against L. braziliensis. Compound 2 was not active against L. guyanensis.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np050422s</identifier><identifier>PMID: 16499336</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>alkaloids ; Alkaloids - chemistry ; Alkaloids - isolation & purification ; Alkaloids - pharmacology ; Animals ; Annona ; Annona - chemistry ; Annona foetida ; Antiprotozoal Agents - chemistry ; Antiprotozoal Agents - isolation & purification ; Antiprotozoal Agents - pharmacology ; Biological and medical sciences ; Brazil ; Carbolines - chemistry ; Carbolines - isolation & purification ; Carbolines - pharmacology ; chemical structure ; General pharmacology ; Leishmania - drug effects ; Leishmania braziliensis ; Lishmania guyanensis ; Medical sciences ; Molecular Structure ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; Plants, Medicinal - chemistry ; pyrimidine-beta-carboline ; pyrimidines ; Pyrimidines - chemistry ; Pyrimidines - isolation & purification ; Pyrimidines - pharmacology ; spectral analysis ; stereochemistry</subject><ispartof>Journal of natural products (Washington, D.C.), 2006-02, Vol.69 (2), p.292-294</ispartof><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17581629$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16499336$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Costa, E.V</creatorcontrib><creatorcontrib>Pinheiro, M.L.B</creatorcontrib><creatorcontrib>Xavier, C.M</creatorcontrib><creatorcontrib>Silva, J.R.A</creatorcontrib><creatorcontrib>Amaral, A.C.F</creatorcontrib><creatorcontrib>Souza, A.D.L</creatorcontrib><creatorcontrib>Barison, A</creatorcontrib><creatorcontrib>Campos, F.R</creatorcontrib><creatorcontrib>Ferreira, A.G</creatorcontrib><creatorcontrib>Machado, G.M.C</creatorcontrib><title>pyrimidine-β-carboline and other alkaloids from Annona foetida with antileishmanial activity</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Bioassay-guided fractionation of the bark extract of Annona foetida afforded a new antileishmanial pyrimidine-beta-carboline alkaloid, N-hydroxyannomontine (1), together with the previously reported annomontine (2), O-methylmoschatoline (3), and liriodenine (4). The structure of compound 1 was established on the basis of extensive 1D and 2D NMR and MS analyses. This is the third reported pyrimidine-beta-carboline-type alkaloid and is particularly important for Annona genus chemotaxonomy. In addition, all compounds exhibit in vitro antileishmanial activity against promastigote forms of Leishmania braziliensis. Compounds 2 and 4 showed better activity than compounds 1 and 3 against L. braziliensis. Compound 2 was not active against L. guyanensis.</description><subject>alkaloids</subject><subject>Alkaloids - chemistry</subject><subject>Alkaloids - isolation & purification</subject><subject>Alkaloids - pharmacology</subject><subject>Animals</subject><subject>Annona</subject><subject>Annona - chemistry</subject><subject>Annona foetida</subject><subject>Antiprotozoal Agents - chemistry</subject><subject>Antiprotozoal Agents - isolation & purification</subject><subject>Antiprotozoal Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Brazil</subject><subject>Carbolines - chemistry</subject><subject>Carbolines - isolation & purification</subject><subject>Carbolines - pharmacology</subject><subject>chemical structure</subject><subject>General pharmacology</subject><subject>Leishmania - drug effects</subject><subject>Leishmania braziliensis</subject><subject>Lishmania guyanensis</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Plants, Medicinal - chemistry</subject><subject>pyrimidine-beta-carboline</subject><subject>pyrimidines</subject><subject>Pyrimidines - chemistry</subject><subject>Pyrimidines - isolation & purification</subject><subject>Pyrimidines - pharmacology</subject><subject>spectral analysis</subject><subject>stereochemistry</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0MFu1DAQBmALUdGlcOAFIBe4pYzt2LGPVaFLpSIQ3XJD0SR2WFPH3tpZYF-LB-GZamkXOHIajeab0egn5BmFUwqMvg4bENAwlh-QBRUMaglMPCQLoJLXXMnmmDzO-RsAcNDiETmmstGac7kgXza75CZnXLD171_1gKmPvjQVBlPFeW1Thf4WfXQmV2OKU3UWQgxYjdHOzmD1w83rgmfnrcvrCYNDX-Ewu-9u3j0hRyP6bJ8e6gm5uXi7On9XX31YXp6fXdUjl-1cc6O5sNSovu-RIbDGUlA914oyg7QFpqU1ijYDIFUIhsmBcisbJVpVED8hr_Z3NynebW2eu8nlwXqPwcZt7mQrtdCt-C-kmrNWM1Xg8wPc9pM13aakhGnX_UmugJcHgHlAPyYMg8v_XCsUlUwXV--dy7P9-XeO6bZ8xVvRrT5ed-rT8vPF-zerbln8i70fMXb4NZWbN9cMKAcKUrCycw-Qj5VW</recordid><startdate>20060201</startdate><enddate>20060201</enddate><creator>Costa, E.V</creator><creator>Pinheiro, M.L.B</creator><creator>Xavier, C.M</creator><creator>Silva, J.R.A</creator><creator>Amaral, A.C.F</creator><creator>Souza, A.D.L</creator><creator>Barison, A</creator><creator>Campos, F.R</creator><creator>Ferreira, A.G</creator><creator>Machado, G.M.C</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>M7N</scope><scope>7X8</scope></search><sort><creationdate>20060201</creationdate><title>pyrimidine-β-carboline and other alkaloids from Annona foetida with antileishmanial activity</title><author>Costa, E.V ; Pinheiro, M.L.B ; Xavier, C.M ; Silva, J.R.A ; Amaral, A.C.F ; Souza, A.D.L ; Barison, A ; Campos, F.R ; Ferreira, A.G ; Machado, G.M.C</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-f367t-3d935e1d8bbba2a024e108b39812da170296ed814c0a18a0d26c13e6485789813</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>alkaloids</topic><topic>Alkaloids - chemistry</topic><topic>Alkaloids - isolation & purification</topic><topic>Alkaloids - pharmacology</topic><topic>Animals</topic><topic>Annona</topic><topic>Annona - chemistry</topic><topic>Annona foetida</topic><topic>Antiprotozoal Agents - chemistry</topic><topic>Antiprotozoal Agents - isolation & purification</topic><topic>Antiprotozoal Agents - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Brazil</topic><topic>Carbolines - chemistry</topic><topic>Carbolines - isolation & purification</topic><topic>Carbolines - pharmacology</topic><topic>chemical structure</topic><topic>General pharmacology</topic><topic>Leishmania - drug effects</topic><topic>Leishmania braziliensis</topic><topic>Lishmania guyanensis</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Plants, Medicinal - chemistry</topic><topic>pyrimidine-beta-carboline</topic><topic>pyrimidines</topic><topic>Pyrimidines - chemistry</topic><topic>Pyrimidines - isolation & purification</topic><topic>Pyrimidines - pharmacology</topic><topic>spectral analysis</topic><topic>stereochemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Costa, E.V</creatorcontrib><creatorcontrib>Pinheiro, M.L.B</creatorcontrib><creatorcontrib>Xavier, C.M</creatorcontrib><creatorcontrib>Silva, J.R.A</creatorcontrib><creatorcontrib>Amaral, A.C.F</creatorcontrib><creatorcontrib>Souza, A.D.L</creatorcontrib><creatorcontrib>Barison, A</creatorcontrib><creatorcontrib>Campos, F.R</creatorcontrib><creatorcontrib>Ferreira, A.G</creatorcontrib><creatorcontrib>Machado, G.M.C</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>Algology Mycology and Protozoology Abstracts (Microbiology C)</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>Costa, E.V</au><au>Pinheiro, M.L.B</au><au>Xavier, C.M</au><au>Silva, J.R.A</au><au>Amaral, A.C.F</au><au>Souza, A.D.L</au><au>Barison, A</au><au>Campos, F.R</au><au>Ferreira, A.G</au><au>Machado, G.M.C</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>pyrimidine-β-carboline and other alkaloids from Annona foetida with antileishmanial activity</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2006-02-01</date><risdate>2006</risdate><volume>69</volume><issue>2</issue><spage>292</spage><epage>294</epage><pages>292-294</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>Bioassay-guided fractionation of the bark extract of Annona foetida afforded a new antileishmanial pyrimidine-beta-carboline alkaloid, N-hydroxyannomontine (1), together with the previously reported annomontine (2), O-methylmoschatoline (3), and liriodenine (4). The structure of compound 1 was established on the basis of extensive 1D and 2D NMR and MS analyses. This is the third reported pyrimidine-beta-carboline-type alkaloid and is particularly important for Annona genus chemotaxonomy. In addition, all compounds exhibit in vitro antileishmanial activity against promastigote forms of Leishmania braziliensis. Compounds 2 and 4 showed better activity than compounds 1 and 3 against L. braziliensis. Compound 2 was not active against L. guyanensis.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>16499336</pmid><doi>10.1021/np050422s</doi><tpages>3</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Journal of natural products (Washington, D.C.), 2006-02, Vol.69 (2), p.292-294 |
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| subjects | alkaloids Alkaloids - chemistry Alkaloids - isolation & purification Alkaloids - pharmacology Animals Annona Annona - chemistry Annona foetida Antiprotozoal Agents - chemistry Antiprotozoal Agents - isolation & purification Antiprotozoal Agents - pharmacology Biological and medical sciences Brazil Carbolines - chemistry Carbolines - isolation & purification Carbolines - pharmacology chemical structure General pharmacology Leishmania - drug effects Leishmania braziliensis Lishmania guyanensis Medical sciences Molecular Structure Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Plants, Medicinal - chemistry pyrimidine-beta-carboline pyrimidines Pyrimidines - chemistry Pyrimidines - isolation & purification Pyrimidines - pharmacology spectral analysis stereochemistry |
| title | pyrimidine-β-carboline and other alkaloids from Annona foetida with antileishmanial activity |
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