Cytotoxic (9βH)-Pimarane and (9βH)-17-Norpimarane Diterpenes from the Tuber of Icacina trichantha
Three (9βH)‐pimaranes, 1, 2, and 3, and two (9βH)‐17‐norpimaranes, 4 and 5, belonging to a rare compound class in nature, were obtained from the tubers of Icacina trichantha for the first time. Compound 1 is a new natural product, and 2–5 have been previously reported. The structures were elucidated...
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| Veröffentlicht in: | Chemistry & biodiversity 2014-12, Vol.11 (12), p.1914-1922 |
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| container_issue | 12 |
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| container_title | Chemistry & biodiversity |
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| creator | Monday Onakpa, Michael Zhao, Ming Gödecke, Tanja Chen, Wei-Lun Che, Chun-Tao Santarsiero, Bernard D. Swanson, Steven M. Uzoma Asuzu, Isaac |
| description | Three (9βH)‐pimaranes, 1, 2, and 3, and two (9βH)‐17‐norpimaranes, 4 and 5, belonging to a rare compound class in nature, were obtained from the tubers of Icacina trichantha for the first time. Compound 1 is a new natural product, and 2–5 have been previously reported. The structures were elucidated based on NMR and MS data, and optical rotation values. The absolute configurations of (9βH)‐pimaranes were unambiguously established based on X‐ray crystallographic analysis. Full NMR signal assignments for the known compounds 2, 4, and 5, which were not available in previous publications, are also reported. All five isolates displayed cytotoxic activities on MDA‐MB‐435 cells (IC50 0.66–6.44 μM), while 2, 3, and 4 also exhibited cytotoxicities on HT‐29 cells (IC50 3.00–4.94 μM). |
| doi_str_mv | 10.1002/cbdv.201400151 |
| format | Article |
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Compound 1 is a new natural product, and 2–5 have been previously reported. The structures were elucidated based on NMR and MS data, and optical rotation values. The absolute configurations of (9βH)‐pimaranes were unambiguously established based on X‐ray crystallographic analysis. Full NMR signal assignments for the known compounds 2, 4, and 5, which were not available in previous publications, are also reported. All five isolates displayed cytotoxic activities on MDA‐MB‐435 cells (IC50 0.66–6.44 μM), while 2, 3, and 4 also exhibited cytotoxicities on HT‐29 cells (IC50 3.00–4.94 μM).</description><identifier>ISSN: 1612-1872</identifier><identifier>EISSN: 1612-1880</identifier><identifier>DOI: 10.1002/cbdv.201400151</identifier><identifier>PMID: 25491335</identifier><language>eng</language><publisher>Zürich: WILEY-VCH Verlag</publisher><subject>(9βH)-17-Norpimarane diterpenes ; (9βH)-Pimarane diterpenes ; Abietanes - isolation & purification ; Abietanes - pharmacology ; Cell Line, Tumor ; Cytotoxic activity ; Diterpenes ; Diterpenes - isolation & purification ; Diterpenes - pharmacology ; Humans ; Icacina trichantha ; Magnetic Resonance Spectroscopy ; Magnoliopsida - chemistry ; Models, Molecular ; X-Ray Diffraction</subject><ispartof>Chemistry & biodiversity, 2014-12, Vol.11 (12), p.1914-1922</ispartof><rights>Copyright © 2014 Verlag Helvetica Chimica Acta AG, Zürich</rights><rights>Copyright © 2014 Verlag Helvetica Chimica Acta AG, Zürich.</rights><rights>Copyright © 2014 Verlag Helvetica Chimica Acta AG, Zurich</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4111-b44139ca83ea23631db2ecb0b98dbc52bf446e689c85f9b840b2651435b2a183</citedby><cites>FETCH-LOGICAL-c4111-b44139ca83ea23631db2ecb0b98dbc52bf446e689c85f9b840b2651435b2a183</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fcbdv.201400151$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcbdv.201400151$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25491335$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Monday Onakpa, Michael</creatorcontrib><creatorcontrib>Zhao, Ming</creatorcontrib><creatorcontrib>Gödecke, Tanja</creatorcontrib><creatorcontrib>Chen, Wei-Lun</creatorcontrib><creatorcontrib>Che, Chun-Tao</creatorcontrib><creatorcontrib>Santarsiero, Bernard D.</creatorcontrib><creatorcontrib>Swanson, Steven M.</creatorcontrib><creatorcontrib>Uzoma Asuzu, Isaac</creatorcontrib><title>Cytotoxic (9βH)-Pimarane and (9βH)-17-Norpimarane Diterpenes from the Tuber of Icacina trichantha</title><title>Chemistry & biodiversity</title><addtitle>Chemistry & Biodiversity</addtitle><description>Three (9βH)‐pimaranes, 1, 2, and 3, and two (9βH)‐17‐norpimaranes, 4 and 5, belonging to a rare compound class in nature, were obtained from the tubers of Icacina trichantha for the first time. Compound 1 is a new natural product, and 2–5 have been previously reported. The structures were elucidated based on NMR and MS data, and optical rotation values. The absolute configurations of (9βH)‐pimaranes were unambiguously established based on X‐ray crystallographic analysis. Full NMR signal assignments for the known compounds 2, 4, and 5, which were not available in previous publications, are also reported. All five isolates displayed cytotoxic activities on MDA‐MB‐435 cells (IC50 0.66–6.44 μM), while 2, 3, and 4 also exhibited cytotoxicities on HT‐29 cells (IC50 3.00–4.94 μM).</description><subject>(9βH)-17-Norpimarane diterpenes</subject><subject>(9βH)-Pimarane diterpenes</subject><subject>Abietanes - isolation & purification</subject><subject>Abietanes - pharmacology</subject><subject>Cell Line, Tumor</subject><subject>Cytotoxic activity</subject><subject>Diterpenes</subject><subject>Diterpenes - isolation & purification</subject><subject>Diterpenes - pharmacology</subject><subject>Humans</subject><subject>Icacina trichantha</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Magnoliopsida - chemistry</subject><subject>Models, Molecular</subject><subject>X-Ray Diffraction</subject><issn>1612-1872</issn><issn>1612-1880</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkMtOGzEUhi1URCjtliUaqZuwmODjy4xnSQPlFgWoonZp2R6PMpCMU3umTV6LB-GZcBQSVd10Zeuc7_919CF0DHgAGJMzo8vfA4KBYQwc9tAhZEBSEAJ_2P1z0kMfQ3iKfJyLA9QjnBVAKT9EZrhqXeuWtUn6xevL9Wn6UM-VV41NVFNuZ5CnY-cX281F3Vq_sI0NSeXdPGmnNpl02vrEVcmNUaZuVNL62kxV007VJ7RfqVmwn9_fIzT5djkZXqej-6ub4fkoNQwAUs0Y0MIoQa0iNKNQamKNxroQpTac6IqxzGaiMIJXhRYMa5JxYJRrokDQI9Tf1C68-9XZ0Mp5HYydzeLJrgsSMsqjpRzjiH75B31ynW_icWuKZYUQlEZqsKGMdyF4W8mFXytYScBybV-u7cud_Rg4ea_t9NyWO3yrOwLFBvhTz-zqP3Vy-PXix9_l6SZbh9Yud1nln2WW05zLn-Mr-chux_j24bu8o29fWp7J</recordid><startdate>201412</startdate><enddate>201412</enddate><creator>Monday Onakpa, Michael</creator><creator>Zhao, Ming</creator><creator>Gödecke, Tanja</creator><creator>Chen, Wei-Lun</creator><creator>Che, Chun-Tao</creator><creator>Santarsiero, Bernard D.</creator><creator>Swanson, Steven M.</creator><creator>Uzoma Asuzu, Isaac</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</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>7QO</scope><scope>7TM</scope><scope>8FD</scope><scope>FR3</scope><scope>K9.</scope><scope>M7N</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>201412</creationdate><title>Cytotoxic (9βH)-Pimarane and (9βH)-17-Norpimarane Diterpenes from the Tuber of Icacina trichantha</title><author>Monday Onakpa, Michael ; 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Compound 1 is a new natural product, and 2–5 have been previously reported. The structures were elucidated based on NMR and MS data, and optical rotation values. The absolute configurations of (9βH)‐pimaranes were unambiguously established based on X‐ray crystallographic analysis. Full NMR signal assignments for the known compounds 2, 4, and 5, which were not available in previous publications, are also reported. All five isolates displayed cytotoxic activities on MDA‐MB‐435 cells (IC50 0.66–6.44 μM), while 2, 3, and 4 also exhibited cytotoxicities on HT‐29 cells (IC50 3.00–4.94 μM).</abstract><cop>Zürich</cop><pub>WILEY-VCH Verlag</pub><pmid>25491335</pmid><doi>10.1002/cbdv.201400151</doi><tpages>9</tpages></addata></record> |
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| subjects | (9βH)-17-Norpimarane diterpenes (9βH)-Pimarane diterpenes Abietanes - isolation & purification Abietanes - pharmacology Cell Line, Tumor Cytotoxic activity Diterpenes Diterpenes - isolation & purification Diterpenes - pharmacology Humans Icacina trichantha Magnetic Resonance Spectroscopy Magnoliopsida - chemistry Models, Molecular X-Ray Diffraction |
| title | Cytotoxic (9βH)-Pimarane and (9βH)-17-Norpimarane Diterpenes from the Tuber of Icacina trichantha |
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