Subincanadines A−C, Novel Quaternary Indole Alkaloids from Aspidosperma subincanum
Three novel quaternary indole alkaloids with an unprecedented 1-azoniatricyclo[4.3.3.0(1,5)]undecane moiety, subincanadines A-C (1-3), as well as two new indole alkaloids with a 1-azabicyclo[5.2.2]undecane moiety, subincanadines D (4) and E (5), and a new indole alkaloid with a 1-azabicyclo[4.3.1]de...
Gespeichert in:
| Veröffentlicht in: | Journal of organic chemistry 2002-09, Vol.67 (18), p.6449-6455 |
|---|---|
| Hauptverfasser: | , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 6455 |
|---|---|
| container_issue | 18 |
| container_start_page | 6449 |
| container_title | Journal of organic chemistry |
| container_volume | 67 |
| creator | KOBAYASHI, Jun'ichi SEKIGUCHI, Mitsuhiro SHIMAMOTO, Sayaka SHIGEMORI, Hideyuki ISHIYAMA, Haruaki OHSAKI, Ayumi |
| description | Three novel quaternary indole alkaloids with an unprecedented 1-azoniatricyclo[4.3.3.0(1,5)]undecane moiety, subincanadines A-C (1-3), as well as two new indole alkaloids with a 1-azabicyclo[5.2.2]undecane moiety, subincanadines D (4) and E (5), and a new indole alkaloid with a 1-azabicyclo[4.3.1]decane moiety, subincanadine F (6), have been isolated from the barks of Aspidosperma subincanum Mart, and the structures of 1-6 and the stereochemistry of 1-3 were elucidated by spectroscopic data and chemical means. |
| doi_str_mv | 10.1021/jo025854b |
| format | Article |
| fullrecord | <record><control><sourceid>istex_pubme</sourceid><recordid>TN_cdi_pubmed_primary_12201766</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>ark_67375_TPS_ZXDQJ7FH_Z</sourcerecordid><originalsourceid>FETCH-LOGICAL-i275t-72e517fe5948a05ef3b57fe9c5e6ddc25c8e3b1a4fed8f7ca439448815e579d53</originalsourceid><addsrcrecordid>eNpFz81Kw0AQB_BFFFurB19A9uLN6H5NdnMs1dpKUUsrSC9hk93Atvki24i-gWcf0Scx0KpzGYb58WcGoXNKrilh9GZdEQYKRHKA-hQYCcKIiEPUJ4SxgLOQ99CJ92vSFQAcox5ljFAZhn20XLSJK1NdauNK6_Hw-_NrdIUfqzeb43mrt7YpdfOBp6WpcouH-UbnlTMeZ01V4KGvnal8bZtCY79PaotTdJTp3NuzfR-gl_HdcjQJZk_309FwFjgmYRtIZoHKzEIklCZgM55AN0Yp2NCYlEGqLE-oFpk1KpOpFjwSQikKFmRkgA_QxS63bpPCmrhuXNEdG_--14HLPdA-1XnW6DJ1_t9xFQkWqc4FO-f81r7_7XWziUPJJcTL50W8er2dP8jxJF7xH1qJbtw</addsrcrecordid><sourcetype>Index Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Subincanadines A−C, Novel Quaternary Indole Alkaloids from Aspidosperma subincanum</title><source>MEDLINE</source><source>ACS Publications</source><creator>KOBAYASHI, Jun'ichi ; SEKIGUCHI, Mitsuhiro ; SHIMAMOTO, Sayaka ; SHIGEMORI, Hideyuki ; ISHIYAMA, Haruaki ; OHSAKI, Ayumi</creator><creatorcontrib>KOBAYASHI, Jun'ichi ; SEKIGUCHI, Mitsuhiro ; SHIMAMOTO, Sayaka ; SHIGEMORI, Hideyuki ; ISHIYAMA, Haruaki ; OHSAKI, Ayumi</creatorcontrib><description>Three novel quaternary indole alkaloids with an unprecedented 1-azoniatricyclo[4.3.3.0(1,5)]undecane moiety, subincanadines A-C (1-3), as well as two new indole alkaloids with a 1-azabicyclo[5.2.2]undecane moiety, subincanadines D (4) and E (5), and a new indole alkaloid with a 1-azabicyclo[4.3.1]decane moiety, subincanadine F (6), have been isolated from the barks of Aspidosperma subincanum Mart, and the structures of 1-6 and the stereochemistry of 1-3 were elucidated by spectroscopic data and chemical means.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo025854b</identifier><identifier>PMID: 12201766</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Alcaloids ; Analytical, structural and metabolic biochemistry ; Aspidosperma - chemistry ; Biological and medical sciences ; Brazil ; Fundamental and applied biological sciences. Psychology ; Heterocyclic compounds, pigments ; Indole Alkaloids - chemistry ; Indole Alkaloids - isolation & purification ; Inhibitory Concentration 50 ; Molecular Conformation ; Molecular Structure ; Nuclear Magnetic Resonance, Biomolecular ; Other biological molecules ; Oxidation-Reduction ; Plant Bark - chemistry ; Plants, Medicinal - chemistry</subject><ispartof>Journal of organic chemistry, 2002-09, Vol.67 (18), p.6449-6455</ispartof><rights>2003 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=13894298$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12201766$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>KOBAYASHI, Jun'ichi</creatorcontrib><creatorcontrib>SEKIGUCHI, Mitsuhiro</creatorcontrib><creatorcontrib>SHIMAMOTO, Sayaka</creatorcontrib><creatorcontrib>SHIGEMORI, Hideyuki</creatorcontrib><creatorcontrib>ISHIYAMA, Haruaki</creatorcontrib><creatorcontrib>OHSAKI, Ayumi</creatorcontrib><title>Subincanadines A−C, Novel Quaternary Indole Alkaloids from Aspidosperma subincanum</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>Three novel quaternary indole alkaloids with an unprecedented 1-azoniatricyclo[4.3.3.0(1,5)]undecane moiety, subincanadines A-C (1-3), as well as two new indole alkaloids with a 1-azabicyclo[5.2.2]undecane moiety, subincanadines D (4) and E (5), and a new indole alkaloid with a 1-azabicyclo[4.3.1]decane moiety, subincanadine F (6), have been isolated from the barks of Aspidosperma subincanum Mart, and the structures of 1-6 and the stereochemistry of 1-3 were elucidated by spectroscopic data and chemical means.</description><subject>Alcaloids</subject><subject>Analytical, structural and metabolic biochemistry</subject><subject>Aspidosperma - chemistry</subject><subject>Biological and medical sciences</subject><subject>Brazil</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Heterocyclic compounds, pigments</subject><subject>Indole Alkaloids - chemistry</subject><subject>Indole Alkaloids - isolation & purification</subject><subject>Inhibitory Concentration 50</subject><subject>Molecular Conformation</subject><subject>Molecular Structure</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Other biological molecules</subject><subject>Oxidation-Reduction</subject><subject>Plant Bark - chemistry</subject><subject>Plants, Medicinal - chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFz81Kw0AQB_BFFFurB19A9uLN6H5NdnMs1dpKUUsrSC9hk93Atvki24i-gWcf0Scx0KpzGYb58WcGoXNKrilh9GZdEQYKRHKA-hQYCcKIiEPUJ4SxgLOQ99CJ92vSFQAcox5ljFAZhn20XLSJK1NdauNK6_Hw-_NrdIUfqzeb43mrt7YpdfOBp6WpcouH-UbnlTMeZ01V4KGvnal8bZtCY79PaotTdJTp3NuzfR-gl_HdcjQJZk_309FwFjgmYRtIZoHKzEIklCZgM55AN0Yp2NCYlEGqLE-oFpk1KpOpFjwSQikKFmRkgA_QxS63bpPCmrhuXNEdG_--14HLPdA-1XnW6DJ1_t9xFQkWqc4FO-f81r7_7XWziUPJJcTL50W8er2dP8jxJF7xH1qJbtw</recordid><startdate>20020906</startdate><enddate>20020906</enddate><creator>KOBAYASHI, Jun'ichi</creator><creator>SEKIGUCHI, Mitsuhiro</creator><creator>SHIMAMOTO, Sayaka</creator><creator>SHIGEMORI, Hideyuki</creator><creator>ISHIYAMA, Haruaki</creator><creator>OHSAKI, Ayumi</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope></search><sort><creationdate>20020906</creationdate><title>Subincanadines A−C, Novel Quaternary Indole Alkaloids from Aspidosperma subincanum</title><author>KOBAYASHI, Jun'ichi ; SEKIGUCHI, Mitsuhiro ; SHIMAMOTO, Sayaka ; SHIGEMORI, Hideyuki ; ISHIYAMA, Haruaki ; OHSAKI, Ayumi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-i275t-72e517fe5948a05ef3b57fe9c5e6ddc25c8e3b1a4fed8f7ca439448815e579d53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>Alcaloids</topic><topic>Analytical, structural and metabolic biochemistry</topic><topic>Aspidosperma - chemistry</topic><topic>Biological and medical sciences</topic><topic>Brazil</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Heterocyclic compounds, pigments</topic><topic>Indole Alkaloids - chemistry</topic><topic>Indole Alkaloids - isolation & purification</topic><topic>Inhibitory Concentration 50</topic><topic>Molecular Conformation</topic><topic>Molecular Structure</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Other biological molecules</topic><topic>Oxidation-Reduction</topic><topic>Plant Bark - chemistry</topic><topic>Plants, Medicinal - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>KOBAYASHI, Jun'ichi</creatorcontrib><creatorcontrib>SEKIGUCHI, Mitsuhiro</creatorcontrib><creatorcontrib>SHIMAMOTO, Sayaka</creatorcontrib><creatorcontrib>SHIGEMORI, Hideyuki</creatorcontrib><creatorcontrib>ISHIYAMA, Haruaki</creatorcontrib><creatorcontrib>OHSAKI, Ayumi</creatorcontrib><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><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>KOBAYASHI, Jun'ichi</au><au>SEKIGUCHI, Mitsuhiro</au><au>SHIMAMOTO, Sayaka</au><au>SHIGEMORI, Hideyuki</au><au>ISHIYAMA, Haruaki</au><au>OHSAKI, Ayumi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Subincanadines A−C, Novel Quaternary Indole Alkaloids from Aspidosperma subincanum</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2002-09-06</date><risdate>2002</risdate><volume>67</volume><issue>18</issue><spage>6449</spage><epage>6455</epage><pages>6449-6455</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>Three novel quaternary indole alkaloids with an unprecedented 1-azoniatricyclo[4.3.3.0(1,5)]undecane moiety, subincanadines A-C (1-3), as well as two new indole alkaloids with a 1-azabicyclo[5.2.2]undecane moiety, subincanadines D (4) and E (5), and a new indole alkaloid with a 1-azabicyclo[4.3.1]decane moiety, subincanadine F (6), have been isolated from the barks of Aspidosperma subincanum Mart, and the structures of 1-6 and the stereochemistry of 1-3 were elucidated by spectroscopic data and chemical means.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>12201766</pmid><doi>10.1021/jo025854b</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2002-09, Vol.67 (18), p.6449-6455 |
| issn | 0022-3263 1520-6904 |
| language | eng |
| recordid | cdi_pubmed_primary_12201766 |
| source | MEDLINE; ACS Publications |
| subjects | Alcaloids Analytical, structural and metabolic biochemistry Aspidosperma - chemistry Biological and medical sciences Brazil Fundamental and applied biological sciences. Psychology Heterocyclic compounds, pigments Indole Alkaloids - chemistry Indole Alkaloids - isolation & purification Inhibitory Concentration 50 Molecular Conformation Molecular Structure Nuclear Magnetic Resonance, Biomolecular Other biological molecules Oxidation-Reduction Plant Bark - chemistry Plants, Medicinal - chemistry |
| title | Subincanadines A−C, Novel Quaternary Indole Alkaloids from Aspidosperma subincanum |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-06T07%3A57%3A27IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-istex_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Subincanadines%20A%E2%88%92C,%20Novel%20Quaternary%20Indole%20Alkaloids%20from%20Aspidosperma%20subincanum&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=KOBAYASHI,%20Jun'ichi&rft.date=2002-09-06&rft.volume=67&rft.issue=18&rft.spage=6449&rft.epage=6455&rft.pages=6449-6455&rft.issn=0022-3263&rft.eissn=1520-6904&rft.coden=JOCEAH&rft_id=info:doi/10.1021/jo025854b&rft_dat=%3Cistex_pubme%3Eark_67375_TPS_ZXDQJ7FH_Z%3C/istex_pubme%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/12201766&rfr_iscdi=true |