Antimalarial β-Carboline and Indolactam Alkaloids from Marinactinospora thermotolerans, a Deep Sea Isolate
Four new β-carboline alkaloids, designated marinacarbolines A–D (1–4), two new indolactam alkaloids, 13-N-demethyl-methylpendolmycin (5) and methylpendolmycin-14-O-α-glucoside (6), and the three known compounds 1-acetyl-β-carboline (7), methylpendolmycin (8), and pendolmycin (9) were obtained from t...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2011-10, Vol.74 (10), p.2122-2127 |
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| creator | Huang, Hongbo Yao, Yueliang He, Zhengxiang Yang, Tingting Ma, Junying Tian, Xinpeng Li, Yayong Huang, Caiguo Chen, Xiaoping Li, Wenjun Zhang, Si Zhang, Changsheng Ju, Jianhua |
| description | Four new β-carboline alkaloids, designated marinacarbolines A–D (1–4), two new indolactam alkaloids, 13-N-demethyl-methylpendolmycin (5) and methylpendolmycin-14-O-α-glucoside (6), and the three known compounds 1-acetyl-β-carboline (7), methylpendolmycin (8), and pendolmycin (9) were obtained from the fermentation broth of Marinactinospora thermotolerans SCSIO 00652, a new actinomycete belonging to the family Nocardiopsaceae. Their structures were elucidated by extensive MS and 1D and 2D NMR spectroscopic data analyses. The structure of compound 1 was further confirmed by single-crystal X-ray crystallography. The new compounds 1–6 were inactive against a panel of eight tumor cell lines (IC50 > 50 μM) but exhibited antiplasmodial activities against Plasmodium falciparum lines 3D7 and Dd2, with IC50 values ranging from 1.92 to 36.03 μM. |
| doi_str_mv | 10.1021/np200399t |
| format | Article |
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Their structures were elucidated by extensive MS and 1D and 2D NMR spectroscopic data analyses. The structure of compound 1 was further confirmed by single-crystal X-ray crystallography. The new compounds 1–6 were inactive against a panel of eight tumor cell lines (IC50 > 50 μM) but exhibited antiplasmodial activities against Plasmodium falciparum lines 3D7 and Dd2, with IC50 values ranging from 1.92 to 36.03 μM.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np200399t</identifier><identifier>PMID: 21977916</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Northbrook, IL: American Chemical Society and American Society of Pharmacognosy</publisher><subject>Actinomycetales - chemistry ; Alkaloids - chemistry ; Alkaloids - isolation & purification ; Alkaloids - pharmacology ; Antimalarials - chemistry ; Antimalarials - isolation & purification ; Antimalarials - pharmacology ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - isolation & purification ; Antineoplastic Agents - pharmacology ; Applied microbiology ; Biological and medical sciences ; Carbolines - chemistry ; Carbolines - isolation & purification ; Carbolines - pharmacology ; Crystallography, X-Ray ; Drug Screening Assays, Antitumor ; Fundamental and applied biological sciences. Psychology ; Humans ; Marine Biology ; Microbiology ; Miscellaneous ; Molecular Structure ; Nuclear Magnetic Resonance, Biomolecular ; Plasmodium falciparum ; Plasmodium falciparum - drug effects</subject><ispartof>Journal of natural products (Washington, D.C.), 2011-10, Vol.74 (10), p.2122-2127</ispartof><rights>Copyright © 2011 American Chemical Society and American Society of Pharmacognosy</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a377t-d924a67b8a01cbdafe4bf64d5152e66ffd21e7b8e5e2d698cc2f117726ccdb333</citedby><cites>FETCH-LOGICAL-a377t-d924a67b8a01cbdafe4bf64d5152e66ffd21e7b8e5e2d698cc2f117726ccdb333</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/np200399t$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np200399t$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=24741603$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21977916$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Huang, Hongbo</creatorcontrib><creatorcontrib>Yao, Yueliang</creatorcontrib><creatorcontrib>He, Zhengxiang</creatorcontrib><creatorcontrib>Yang, Tingting</creatorcontrib><creatorcontrib>Ma, Junying</creatorcontrib><creatorcontrib>Tian, Xinpeng</creatorcontrib><creatorcontrib>Li, Yayong</creatorcontrib><creatorcontrib>Huang, Caiguo</creatorcontrib><creatorcontrib>Chen, Xiaoping</creatorcontrib><creatorcontrib>Li, Wenjun</creatorcontrib><creatorcontrib>Zhang, Si</creatorcontrib><creatorcontrib>Zhang, Changsheng</creatorcontrib><creatorcontrib>Ju, Jianhua</creatorcontrib><title>Antimalarial β-Carboline and Indolactam Alkaloids from Marinactinospora thermotolerans, a Deep Sea Isolate</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Four new β-carboline alkaloids, designated marinacarbolines A–D (1–4), two new indolactam alkaloids, 13-N-demethyl-methylpendolmycin (5) and methylpendolmycin-14-O-α-glucoside (6), and the three known compounds 1-acetyl-β-carboline (7), methylpendolmycin (8), and pendolmycin (9) were obtained from the fermentation broth of Marinactinospora thermotolerans SCSIO 00652, a new actinomycete belonging to the family Nocardiopsaceae. Their structures were elucidated by extensive MS and 1D and 2D NMR spectroscopic data analyses. The structure of compound 1 was further confirmed by single-crystal X-ray crystallography. The new compounds 1–6 were inactive against a panel of eight tumor cell lines (IC50 > 50 μM) but exhibited antiplasmodial activities against Plasmodium falciparum lines 3D7 and Dd2, with IC50 values ranging from 1.92 to 36.03 μM.</description><subject>Actinomycetales - chemistry</subject><subject>Alkaloids - chemistry</subject><subject>Alkaloids - isolation & purification</subject><subject>Alkaloids - pharmacology</subject><subject>Antimalarials - chemistry</subject><subject>Antimalarials - isolation & purification</subject><subject>Antimalarials - pharmacology</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - isolation & purification</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Applied microbiology</subject><subject>Biological and medical sciences</subject><subject>Carbolines - chemistry</subject><subject>Carbolines - isolation & purification</subject><subject>Carbolines - pharmacology</subject><subject>Crystallography, X-Ray</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Humans</subject><subject>Marine Biology</subject><subject>Microbiology</subject><subject>Miscellaneous</subject><subject>Molecular Structure</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Plasmodium falciparum</subject><subject>Plasmodium falciparum - drug effects</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp90c1u1DAQB3CrArXbhQMvUPmCSiVC_ZHYm-NqaWGlIg7QczSxxyKtY6d29sBr9UF4Joy6bC-Ikw_zmxn5P4S84ewDZ4JfhkkwJtt2PiIL3ghWKSaaF2TBuJKVXKn6hJzmfMcKYm1zTE4Eb7VuuVqQ-3WYhxE8pAE8_fVYbSD10Q8BKQRLt8FGD2aGka79Pfg42ExdiiP9UjpCqQwh5ikmoPMPTGOco8cEIb-nQD8iTvQbAt3mMmTGV-SlA5_x9f5dktvrq--bz9XN10_bzfqmAqn1XNlW1KB0vwLGTW_BYd07VdumfA2Vcs4KjqWMDQqr2pUxwnGutVDG2F5KuSTnT3OnFB92mOduHLJB7yFg3OWuZZwxoRQv8t1_ZdlY16yRWhR68URNijkndN2USnDpZ8dZ9-cK3eEKxZ7tx-76Ee1B_o29gLd7ANmAdyUxM-RnV-uaKyafHZjc3cVdCiW3fyz8DXglnNY</recordid><startdate>20111028</startdate><enddate>20111028</enddate><creator>Huang, Hongbo</creator><creator>Yao, Yueliang</creator><creator>He, Zhengxiang</creator><creator>Yang, Tingting</creator><creator>Ma, Junying</creator><creator>Tian, Xinpeng</creator><creator>Li, Yayong</creator><creator>Huang, Caiguo</creator><creator>Chen, Xiaoping</creator><creator>Li, Wenjun</creator><creator>Zhang, Si</creator><creator>Zhang, Changsheng</creator><creator>Ju, Jianhua</creator><general>American Chemical Society and American Society of Pharmacognosy</general><general>American Society of Pharmacognosy</general><scope>IQODW</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>8FD</scope><scope>C1K</scope><scope>F1W</scope><scope>FR3</scope><scope>H95</scope><scope>H97</scope><scope>H99</scope><scope>L.F</scope><scope>L.G</scope><scope>M7N</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20111028</creationdate><title>Antimalarial β-Carboline and Indolactam Alkaloids from Marinactinospora thermotolerans, a Deep Sea Isolate</title><author>Huang, Hongbo ; Yao, Yueliang ; He, Zhengxiang ; Yang, Tingting ; Ma, Junying ; Tian, Xinpeng ; Li, Yayong ; Huang, Caiguo ; Chen, Xiaoping ; Li, Wenjun ; Zhang, Si ; Zhang, Changsheng ; Ju, Jianhua</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a377t-d924a67b8a01cbdafe4bf64d5152e66ffd21e7b8e5e2d698cc2f117726ccdb333</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Actinomycetales - chemistry</topic><topic>Alkaloids - chemistry</topic><topic>Alkaloids - isolation & purification</topic><topic>Alkaloids - pharmacology</topic><topic>Antimalarials - chemistry</topic><topic>Antimalarials - isolation & purification</topic><topic>Antimalarials - pharmacology</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - isolation & purification</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Applied microbiology</topic><topic>Biological and medical sciences</topic><topic>Carbolines - chemistry</topic><topic>Carbolines - isolation & purification</topic><topic>Carbolines - pharmacology</topic><topic>Crystallography, X-Ray</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Fundamental and applied biological sciences. 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Nat. Prod</addtitle><date>2011-10-28</date><risdate>2011</risdate><volume>74</volume><issue>10</issue><spage>2122</spage><epage>2127</epage><pages>2122-2127</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>Four new β-carboline alkaloids, designated marinacarbolines A–D (1–4), two new indolactam alkaloids, 13-N-demethyl-methylpendolmycin (5) and methylpendolmycin-14-O-α-glucoside (6), and the three known compounds 1-acetyl-β-carboline (7), methylpendolmycin (8), and pendolmycin (9) were obtained from the fermentation broth of Marinactinospora thermotolerans SCSIO 00652, a new actinomycete belonging to the family Nocardiopsaceae. Their structures were elucidated by extensive MS and 1D and 2D NMR spectroscopic data analyses. The structure of compound 1 was further confirmed by single-crystal X-ray crystallography. The new compounds 1–6 were inactive against a panel of eight tumor cell lines (IC50 > 50 μM) but exhibited antiplasmodial activities against Plasmodium falciparum lines 3D7 and Dd2, with IC50 values ranging from 1.92 to 36.03 μM.</abstract><cop>Northbrook, IL</cop><pub>American Chemical Society and American Society of Pharmacognosy</pub><pmid>21977916</pmid><doi>10.1021/np200399t</doi><tpages>6</tpages></addata></record> |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Actinomycetales - chemistry Alkaloids - chemistry Alkaloids - isolation & purification Alkaloids - pharmacology Antimalarials - chemistry Antimalarials - isolation & purification Antimalarials - pharmacology Antineoplastic Agents - chemistry Antineoplastic Agents - isolation & purification Antineoplastic Agents - pharmacology Applied microbiology Biological and medical sciences Carbolines - chemistry Carbolines - isolation & purification Carbolines - pharmacology Crystallography, X-Ray Drug Screening Assays, Antitumor Fundamental and applied biological sciences. Psychology Humans Marine Biology Microbiology Miscellaneous Molecular Structure Nuclear Magnetic Resonance, Biomolecular Plasmodium falciparum Plasmodium falciparum - drug effects |
| title | Antimalarial β-Carboline and Indolactam Alkaloids from Marinactinospora thermotolerans, a Deep Sea Isolate |
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