Absolute Configuration of Actinophyllic Acid As Determined through Chiroptical Data
The absolute configuration of actinophyllic acid (−)-1, an alkaloid with an unprecedented 2,3,6,7,9,13c-hexahydro-1H-1,7,8-(methanetriyloxymethano)pyrrolo[1′,2′:1,2]azacino[4,3-b]indole-8(5H)-carboxylic acid skeleton isolated from Alstonia actinophylla, was determined through the study of its corres...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2009-03, Vol.72 (3), p.430-432 |
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| container_title | Journal of natural products (Washington, D.C.) |
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| creator | Taniguchi, Tohru Martin, Connor L Monde, Kenji Nakanishi, Koji Berova, Nina Overman, Larry E |
| description | The absolute configuration of actinophyllic acid (−)-1, an alkaloid with an unprecedented 2,3,6,7,9,13c-hexahydro-1H-1,7,8-(methanetriyloxymethano)pyrrolo[1′,2′:1,2]azacino[4,3-b]indole-8(5H)-carboxylic acid skeleton isolated from Alstonia actinophylla, was determined through the study of its corresponding methyl ester 2. Racemic 2 was separated into (+)-2 and (−)-2 enantiomers, and they were assigned unambiguously as 15S,16R,19R,20R,21S and 15R,16S,19S,20S,21R, respectively, by the use of optical rotation and electronic circular dichroism. Finally, (−)-2 was characterized as the methyl ester of naturally occurring (−)-1. The assigned 15R,16S,19S,20S,21R-configuration of (−)-1 is consistent with a proposed biosynthetic pathway. |
| doi_str_mv | 10.1021/np800665s |
| format | Article |
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Racemic 2 was separated into (+)-2 and (−)-2 enantiomers, and they were assigned unambiguously as 15S,16R,19R,20R,21S and 15R,16S,19S,20S,21R, respectively, by the use of optical rotation and electronic circular dichroism. Finally, (−)-2 was characterized as the methyl ester of naturally occurring (−)-1. The assigned 15R,16S,19S,20S,21R-configuration of (−)-1 is consistent with a proposed biosynthetic pathway.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np800665s</identifier><identifier>PMID: 19220031</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Northbrook, IL: American Chemical Society and American Society of Pharmacognosy</publisher><subject>actinophyllic acid ; Alkaloids - chemistry ; Alstonia ; Alstonia - chemistry ; Alstonia actinophylla ; Biological and medical sciences ; carboxypeptidases ; chemical structure ; enantiomers ; esters ; General pharmacology ; indole alkaloids ; Indole Alkaloids - chemistry ; Medical sciences ; Molecular Structure ; Nuclear Magnetic Resonance, Biomolecular ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; spectral analysis ; Stereoisomerism</subject><ispartof>Journal of natural products (Washington, D.C.), 2009-03, Vol.72 (3), p.430-432</ispartof><rights>Copyright © 2009 American Chemical Society and American Society of Pharmacognosy</rights><rights>2009 INIST-CNRS</rights><rights>2009 American Chemical Society and American Society of Pharmacognosy 2009</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a524t-4ac6c4e5b03810e1f964f646f6363a9198122b3b15eba5991dbe539baa646a293</citedby><cites>FETCH-LOGICAL-a524t-4ac6c4e5b03810e1f964f646f6363a9198122b3b15eba5991dbe539baa646a293</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/np800665s$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np800665s$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,776,780,881,2751,27055,27903,27904,56716,56766</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=21366887$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19220031$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Taniguchi, Tohru</creatorcontrib><creatorcontrib>Martin, Connor L</creatorcontrib><creatorcontrib>Monde, Kenji</creatorcontrib><creatorcontrib>Nakanishi, Koji</creatorcontrib><creatorcontrib>Berova, Nina</creatorcontrib><creatorcontrib>Overman, Larry E</creatorcontrib><title>Absolute Configuration of Actinophyllic Acid As Determined through Chiroptical Data</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>The absolute configuration of actinophyllic acid (−)-1, an alkaloid with an unprecedented 2,3,6,7,9,13c-hexahydro-1H-1,7,8-(methanetriyloxymethano)pyrrolo[1′,2′:1,2]azacino[4,3-b]indole-8(5H)-carboxylic acid skeleton isolated from Alstonia actinophylla, was determined through the study of its corresponding methyl ester 2. Racemic 2 was separated into (+)-2 and (−)-2 enantiomers, and they were assigned unambiguously as 15S,16R,19R,20R,21S and 15R,16S,19S,20S,21R, respectively, by the use of optical rotation and electronic circular dichroism. Finally, (−)-2 was characterized as the methyl ester of naturally occurring (−)-1. The assigned 15R,16S,19S,20S,21R-configuration of (−)-1 is consistent with a proposed biosynthetic pathway.</description><subject>actinophyllic acid</subject><subject>Alkaloids - chemistry</subject><subject>Alstonia</subject><subject>Alstonia - chemistry</subject><subject>Alstonia actinophylla</subject><subject>Biological and medical sciences</subject><subject>carboxypeptidases</subject><subject>chemical structure</subject><subject>enantiomers</subject><subject>esters</subject><subject>General pharmacology</subject><subject>indole alkaloids</subject><subject>Indole Alkaloids - chemistry</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>spectral analysis</subject><subject>Stereoisomerism</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0U1rGzEQBmBRGhon7aF_oN1LCDlso4-VvLoEjPNVCOSQ5ixmZcmrsJa2kjaQfx8FG6eFnMSgh3eGGYS-E_yLYErO_dhiLARPn9CMcIprgSn_jGaYCFazVjSH6CilJ4wxw5J_QYdEUloKMkMPiy6FYcqmWgZv3XqKkF3wVbDVQmfnw9i_DIPTpXKrapGqS5NN3DhvVlXuY5jWfbXsXQxjdhqG6hIyfEUHFoZkvu3eY_R4ffVneVvf3d_8Xi7uauC0yXUDWujG8A6zlmBDrBSNFY2wggkGksiWUNqxjnDTAZeSrDrDmewACgIq2TG62OaOU7cxK218jjCoMboNxBcVwKn_f7zr1To8KyollZyVgNNdQAx_J5Oy2rikzTCAN2FKas6YkHNJ2iLPtlLHkFI0dt-FYPV2A7W_QbE__h3rXe6WXsDJDkAqO7MRvHZp7yhhQrTtvLifW2chKFjHYh4fKCbs7a60bfB7EuiknsIUfdn3ByO9AqyjpJU</recordid><startdate>20090327</startdate><enddate>20090327</enddate><creator>Taniguchi, Tohru</creator><creator>Martin, Connor L</creator><creator>Monde, Kenji</creator><creator>Nakanishi, Koji</creator><creator>Berova, Nina</creator><creator>Overman, Larry E</creator><general>American Chemical Society and American Society of Pharmacognosy</general><general>American Society of Pharmacognosy</general><scope>FBQ</scope><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>7X8</scope><scope>5PM</scope></search><sort><creationdate>20090327</creationdate><title>Absolute Configuration of Actinophyllic Acid As Determined through Chiroptical Data</title><author>Taniguchi, Tohru ; Martin, Connor L ; Monde, Kenji ; Nakanishi, Koji ; Berova, Nina ; Overman, Larry E</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a524t-4ac6c4e5b03810e1f964f646f6363a9198122b3b15eba5991dbe539baa646a293</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>actinophyllic acid</topic><topic>Alkaloids - chemistry</topic><topic>Alstonia</topic><topic>Alstonia - chemistry</topic><topic>Alstonia actinophylla</topic><topic>Biological and medical sciences</topic><topic>carboxypeptidases</topic><topic>chemical structure</topic><topic>enantiomers</topic><topic>esters</topic><topic>General pharmacology</topic><topic>indole alkaloids</topic><topic>Indole Alkaloids - chemistry</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>spectral analysis</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Taniguchi, Tohru</creatorcontrib><creatorcontrib>Martin, Connor L</creatorcontrib><creatorcontrib>Monde, Kenji</creatorcontrib><creatorcontrib>Nakanishi, Koji</creatorcontrib><creatorcontrib>Berova, Nina</creatorcontrib><creatorcontrib>Overman, Larry E</creatorcontrib><collection>AGRIS</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>CrossRef</collection><collection>MEDLINE - 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>Taniguchi, Tohru</au><au>Martin, Connor L</au><au>Monde, Kenji</au><au>Nakanishi, Koji</au><au>Berova, Nina</au><au>Overman, Larry E</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Absolute Configuration of Actinophyllic Acid As Determined through Chiroptical Data</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2009-03-27</date><risdate>2009</risdate><volume>72</volume><issue>3</issue><spage>430</spage><epage>432</epage><pages>430-432</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>The absolute configuration of actinophyllic acid (−)-1, an alkaloid with an unprecedented 2,3,6,7,9,13c-hexahydro-1H-1,7,8-(methanetriyloxymethano)pyrrolo[1′,2′:1,2]azacino[4,3-b]indole-8(5H)-carboxylic acid skeleton isolated from Alstonia actinophylla, was determined through the study of its corresponding methyl ester 2. Racemic 2 was separated into (+)-2 and (−)-2 enantiomers, and they were assigned unambiguously as 15S,16R,19R,20R,21S and 15R,16S,19S,20S,21R, respectively, by the use of optical rotation and electronic circular dichroism. Finally, (−)-2 was characterized as the methyl ester of naturally occurring (−)-1. The assigned 15R,16S,19S,20S,21R-configuration of (−)-1 is consistent with a proposed biosynthetic pathway.</abstract><cop>Northbrook, IL</cop><pub>American Chemical Society and American Society of Pharmacognosy</pub><pmid>19220031</pmid><doi>10.1021/np800665s</doi><tpages>3</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Journal of natural products (Washington, D.C.), 2009-03, Vol.72 (3), p.430-432 |
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| source | MEDLINE; American Chemical Society Publications |
| subjects | actinophyllic acid Alkaloids - chemistry Alstonia Alstonia - chemistry Alstonia actinophylla Biological and medical sciences carboxypeptidases chemical structure enantiomers esters General pharmacology indole alkaloids Indole Alkaloids - chemistry Medical sciences Molecular Structure Nuclear Magnetic Resonance, Biomolecular Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments spectral analysis Stereoisomerism |
| title | Absolute Configuration of Actinophyllic Acid As Determined through Chiroptical Data |
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