Antileishmanial Metabolites from Geosmithia langdonii
Antileishmanial bioassay guided fractionation of Geosmithia langdonii has resulted in the isolation and identification of two new compounds (1 and 2) together with 10 known compounds (3–12). The structures of the isolated metabolites were elucidated based on comprehensive 1D and 2D NMR spectroscopic...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2014-09, Vol.77 (9), p.1987-1991 |
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| container_end_page | 1991 |
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| container_issue | 9 |
| container_start_page | 1987 |
| container_title | Journal of natural products (Washington, D.C.) |
| container_volume | 77 |
| creator | Malak, Lourin G Ibrahim, Mohamed Ali Bishay, Daoud W Abdel-baky, Afaf M Moharram, Ahmed M Tekwani, Babu Cutler, Stephen J Ross, Samir A |
| description | Antileishmanial bioassay guided fractionation of Geosmithia langdonii has resulted in the isolation and identification of two new compounds (1 and 2) together with 10 known compounds (3–12). The structures of the isolated metabolites were elucidated based on comprehensive 1D and 2D NMR spectroscopic data as well as mass spectrometry. The absolute configuration at C4, C5, and C6 of 2 was determined as R using a modified Mosher esterification method and NOESY correlations. The extracts and the isolated metabolites were evaluated for their antileishmanial activities. Compounds 3, 9, 11, and 12 were found to be active against Leishmania donovani with IC50 values of 6.9, 3.3, 8.5, and 9.2 μM, respectively, while compounds 1, 5, and 10 showed lower activities against L. donovani with IC50 values of 13.0, 47.3, and 34.0 μM, respectively. |
| doi_str_mv | 10.1021/np5000473 |
| format | Article |
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The structures of the isolated metabolites were elucidated based on comprehensive 1D and 2D NMR spectroscopic data as well as mass spectrometry. The absolute configuration at C4, C5, and C6 of 2 was determined as R using a modified Mosher esterification method and NOESY correlations. The extracts and the isolated metabolites were evaluated for their antileishmanial activities. Compounds 3, 9, 11, and 12 were found to be active against Leishmania donovani with IC50 values of 6.9, 3.3, 8.5, and 9.2 μM, respectively, while compounds 1, 5, and 10 showed lower activities against L. donovani with IC50 values of 13.0, 47.3, and 34.0 μM, respectively.</description><identifier>ISSN: 0163-3864</identifier><identifier>ISSN: 1520-6025</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np5000473</identifier><identifier>PMID: 25084548</identifier><language>eng</language><publisher>United States: American Chemical Society and American Society of Pharmacognosy</publisher><subject>Antineoplastic Agents, Phytogenic - chemistry ; antiparasitic properties ; Aspergillus fumigatus - drug effects ; Benzhydryl Compounds - chemistry ; Benzhydryl Compounds - isolation & purification ; Benzhydryl Compounds - pharmacology ; bioassays ; Candida - drug effects ; Cyclohexanones - chemistry ; Cyclohexanones - isolation & purification ; Cyclohexanones - pharmacology ; Escherichia coli - drug effects ; esterification ; fractionation ; Geosmithia ; Hypocreales - chemistry ; inhibitory concentration 50 ; Leishmania donovani ; Leishmania donovani - drug effects ; mass spectrometry ; metabolites ; Methicillin-Resistant Staphylococcus aureus - drug effects ; Microbial Sensitivity Tests ; Molecular Structure ; Mycobacterium avium Complex - drug effects ; nuclear magnetic resonance spectroscopy ; Plasmodium falciparum - drug effects ; Pseudomonas aeruginosa - drug effects ; Salicylates - chemistry ; Salicylates - isolation & purification ; Salicylates - pharmacology ; spectral analysis</subject><ispartof>Journal of natural products (Washington, D.C.), 2014-09, Vol.77 (9), p.1987-1991</ispartof><rights>Copyright © 2014 American Chemical Society and American Society of Pharmacognosy</rights><rights>Copyright © 2014 American Chemical Society and American Society of Pharmacognosy 2014 American Chemical Society and American Society of Pharmacognosy</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a504t-eb8906308a239d8cd1f11cbccbba3bb030c5e1d6af546804634bf874eb7d4ea23</citedby><cites>FETCH-LOGICAL-a504t-eb8906308a239d8cd1f11cbccbba3bb030c5e1d6af546804634bf874eb7d4ea23</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/np5000473$$EPDF$$P50$$Gacs$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np5000473$$EHTML$$P50$$Gacs$$Hfree_for_read</linktohtml><link.rule.ids>230,314,777,781,882,2752,27057,27905,27906,56719,56769</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25084548$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Malak, Lourin G</creatorcontrib><creatorcontrib>Ibrahim, Mohamed Ali</creatorcontrib><creatorcontrib>Bishay, Daoud W</creatorcontrib><creatorcontrib>Abdel-baky, Afaf M</creatorcontrib><creatorcontrib>Moharram, Ahmed M</creatorcontrib><creatorcontrib>Tekwani, Babu</creatorcontrib><creatorcontrib>Cutler, Stephen J</creatorcontrib><creatorcontrib>Ross, Samir A</creatorcontrib><title>Antileishmanial Metabolites from Geosmithia langdonii</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. 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Compounds 3, 9, 11, and 12 were found to be active against Leishmania donovani with IC50 values of 6.9, 3.3, 8.5, and 9.2 μM, respectively, while compounds 1, 5, and 10 showed lower activities against L. donovani with IC50 values of 13.0, 47.3, and 34.0 μM, respectively.</description><subject>Antineoplastic Agents, Phytogenic - chemistry</subject><subject>antiparasitic properties</subject><subject>Aspergillus fumigatus - drug effects</subject><subject>Benzhydryl Compounds - chemistry</subject><subject>Benzhydryl Compounds - isolation & purification</subject><subject>Benzhydryl Compounds - pharmacology</subject><subject>bioassays</subject><subject>Candida - drug effects</subject><subject>Cyclohexanones - chemistry</subject><subject>Cyclohexanones - isolation & purification</subject><subject>Cyclohexanones - pharmacology</subject><subject>Escherichia coli - drug effects</subject><subject>esterification</subject><subject>fractionation</subject><subject>Geosmithia</subject><subject>Hypocreales - chemistry</subject><subject>inhibitory concentration 50</subject><subject>Leishmania donovani</subject><subject>Leishmania donovani - drug effects</subject><subject>mass spectrometry</subject><subject>metabolites</subject><subject>Methicillin-Resistant Staphylococcus aureus - drug effects</subject><subject>Microbial Sensitivity Tests</subject><subject>Molecular Structure</subject><subject>Mycobacterium avium Complex - drug effects</subject><subject>nuclear magnetic resonance spectroscopy</subject><subject>Plasmodium falciparum - drug effects</subject><subject>Pseudomonas aeruginosa - drug effects</subject><subject>Salicylates - chemistry</subject><subject>Salicylates - isolation & purification</subject><subject>Salicylates - pharmacology</subject><subject>spectral analysis</subject><issn>0163-3864</issn><issn>1520-6025</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>N~.</sourceid><sourceid>EIF</sourceid><recordid>eNqFkU1LAzEQhoMotlYP_gHZi6CH1cnmY9OLUIpWoeJFzyHJZtuU3U3d7Ar-e1Nai4LgaQ7zzMPMvAidY7jBkOHbZs0AgObkAA0xyyDlkLFDNATMSUoEpwN0EsIqMgTG7BgNMgaCMiqGiE2azlXWhWWtGqeq5Nl2SvvKdTYkZevrZGZ9qF23dCqpVLMofOPcKToqVRXs2a6O0NvD_ev0MZ2_zJ6mk3mqGNAutVqMgRMQKiPjQpgClxgbbYzWimgdtzHM4oKrklEugHJCdSlyanVeUBuHRuhu6133uraFsU3XqkquW1er9lN65eTvTuOWcuE_JMU5J2MSBVc7Qevfexs6WbtgbBUvsb4PMtv8hHOciX9RzCIHOeQb6_UWNa0PobXlfiMMcpOI3CcS2YufJ-zJ7wgicLkFlAly5fu2iR_9Q_QFApOSWg</recordid><startdate>20140926</startdate><enddate>20140926</enddate><creator>Malak, Lourin G</creator><creator>Ibrahim, Mohamed Ali</creator><creator>Bishay, Daoud W</creator><creator>Abdel-baky, Afaf M</creator><creator>Moharram, Ahmed M</creator><creator>Tekwani, Babu</creator><creator>Cutler, Stephen J</creator><creator>Ross, Samir A</creator><general>American Chemical Society and American Society of Pharmacognosy</general><scope>N~.</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><scope>7S9</scope><scope>L.6</scope><scope>5PM</scope></search><sort><creationdate>20140926</creationdate><title>Antileishmanial Metabolites from Geosmithia langdonii</title><author>Malak, Lourin G ; Ibrahim, Mohamed Ali ; Bishay, Daoud W ; Abdel-baky, Afaf M ; Moharram, Ahmed M ; Tekwani, Babu ; Cutler, Stephen J ; Ross, Samir A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a504t-eb8906308a239d8cd1f11cbccbba3bb030c5e1d6af546804634bf874eb7d4ea23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Antineoplastic Agents, Phytogenic - chemistry</topic><topic>antiparasitic properties</topic><topic>Aspergillus fumigatus - drug effects</topic><topic>Benzhydryl Compounds - chemistry</topic><topic>Benzhydryl Compounds - isolation & purification</topic><topic>Benzhydryl Compounds - pharmacology</topic><topic>bioassays</topic><topic>Candida - drug effects</topic><topic>Cyclohexanones - chemistry</topic><topic>Cyclohexanones - isolation & purification</topic><topic>Cyclohexanones - pharmacology</topic><topic>Escherichia coli - drug effects</topic><topic>esterification</topic><topic>fractionation</topic><topic>Geosmithia</topic><topic>Hypocreales - chemistry</topic><topic>inhibitory concentration 50</topic><topic>Leishmania donovani</topic><topic>Leishmania donovani - drug effects</topic><topic>mass spectrometry</topic><topic>metabolites</topic><topic>Methicillin-Resistant Staphylococcus aureus - drug effects</topic><topic>Microbial Sensitivity Tests</topic><topic>Molecular Structure</topic><topic>Mycobacterium avium Complex - drug effects</topic><topic>nuclear magnetic resonance spectroscopy</topic><topic>Plasmodium falciparum - drug effects</topic><topic>Pseudomonas aeruginosa - drug effects</topic><topic>Salicylates - chemistry</topic><topic>Salicylates - isolation & purification</topic><topic>Salicylates - pharmacology</topic><topic>spectral analysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Malak, Lourin G</creatorcontrib><creatorcontrib>Ibrahim, Mohamed Ali</creatorcontrib><creatorcontrib>Bishay, Daoud W</creatorcontrib><creatorcontrib>Abdel-baky, Afaf M</creatorcontrib><creatorcontrib>Moharram, Ahmed M</creatorcontrib><creatorcontrib>Tekwani, Babu</creatorcontrib><creatorcontrib>Cutler, Stephen J</creatorcontrib><creatorcontrib>Ross, Samir A</creatorcontrib><collection>American Chemical Society (ACS) Open Access</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><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Malak, Lourin G</au><au>Ibrahim, Mohamed Ali</au><au>Bishay, Daoud W</au><au>Abdel-baky, Afaf M</au><au>Moharram, Ahmed M</au><au>Tekwani, Babu</au><au>Cutler, Stephen J</au><au>Ross, Samir A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Antileishmanial Metabolites from Geosmithia langdonii</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2014-09-26</date><risdate>2014</risdate><volume>77</volume><issue>9</issue><spage>1987</spage><epage>1991</epage><pages>1987-1991</pages><issn>0163-3864</issn><issn>1520-6025</issn><eissn>1520-6025</eissn><abstract>Antileishmanial bioassay guided fractionation of Geosmithia langdonii has resulted in the isolation and identification of two new compounds (1 and 2) together with 10 known compounds (3–12). The structures of the isolated metabolites were elucidated based on comprehensive 1D and 2D NMR spectroscopic data as well as mass spectrometry. The absolute configuration at C4, C5, and C6 of 2 was determined as R using a modified Mosher esterification method and NOESY correlations. The extracts and the isolated metabolites were evaluated for their antileishmanial activities. Compounds 3, 9, 11, and 12 were found to be active against Leishmania donovani with IC50 values of 6.9, 3.3, 8.5, and 9.2 μM, respectively, while compounds 1, 5, and 10 showed lower activities against L. donovani with IC50 values of 13.0, 47.3, and 34.0 μM, respectively.</abstract><cop>United States</cop><pub>American Chemical Society and American Society of Pharmacognosy</pub><pmid>25084548</pmid><doi>10.1021/np5000473</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0163-3864 |
| ispartof | Journal of natural products (Washington, D.C.), 2014-09, Vol.77 (9), p.1987-1991 |
| issn | 0163-3864 1520-6025 1520-6025 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_4176393 |
| source | MEDLINE; ACS Publications |
| subjects | Antineoplastic Agents, Phytogenic - chemistry antiparasitic properties Aspergillus fumigatus - drug effects Benzhydryl Compounds - chemistry Benzhydryl Compounds - isolation & purification Benzhydryl Compounds - pharmacology bioassays Candida - drug effects Cyclohexanones - chemistry Cyclohexanones - isolation & purification Cyclohexanones - pharmacology Escherichia coli - drug effects esterification fractionation Geosmithia Hypocreales - chemistry inhibitory concentration 50 Leishmania donovani Leishmania donovani - drug effects mass spectrometry metabolites Methicillin-Resistant Staphylococcus aureus - drug effects Microbial Sensitivity Tests Molecular Structure Mycobacterium avium Complex - drug effects nuclear magnetic resonance spectroscopy Plasmodium falciparum - drug effects Pseudomonas aeruginosa - drug effects Salicylates - chemistry Salicylates - isolation & purification Salicylates - pharmacology spectral analysis |
| title | Antileishmanial Metabolites from Geosmithia langdonii |
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