Kingianin A: A New Natural Pentacyclic Compound from Endiandra kingiana

Kingianin A: A New Natural Pentacyclic Compound from Endiandra kingiana

A new natural pentacyclic compound, named kingianin A, was isolated as a racemic mixture from the barks of Endiandra kingiana (Lauraceae). Its structure was elucidated by comprehensive analysis of NMR spectroscopic data, X-ray crystallography, and ECD calculations. The pentacyclic skeleton may be fo...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2010-08, Vol.12 (16), p.3638-3641
Hauptverfasser: Leverrier, Aurélie, Dau, Marie Elise Tran Huu, Retailleau, Pascal, Awang, Khalijah, Guéritte, Françoise, Litaudon, Marc
Format: Artikel
Sprache:eng
Schlagworte:
Cellular Biology
Circular Dichroism
Crystallography, X-Ray
Lauraceae - chemistry
Life Sciences
Molecular Structure
Polycyclic Aromatic Hydrocarbons - chemistry
Polycyclic Aromatic Hydrocarbons - isolation & purification
Stereoisomerism
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 3641
container_issue 16
container_start_page 3638
container_title Organic letters
container_volume 12
creator Leverrier, Aurélie
Dau, Marie Elise Tran Huu
Retailleau, Pascal
Awang, Khalijah
Guéritte, Françoise
Litaudon, Marc
description A new natural pentacyclic compound, named kingianin A, was isolated as a racemic mixture from the barks of Endiandra kingiana (Lauraceae). Its structure was elucidated by comprehensive analysis of NMR spectroscopic data, X-ray crystallography, and ECD calculations. The pentacyclic skeleton may be formed by a Diels−Alder reaction between two monomers having a bicyclo[4.2.0]octadiene backbone formed by a stereospecific electrocyclization of a linear compound of polyketide origin.
doi_str_mv 10.1021/ol101427m
format Article
fullrecord <record><control><sourceid>proquest_hal_p</sourceid><recordid>TN_cdi_hal_primary_oai_HAL_hal_00521979v1</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>748946597</sourcerecordid><originalsourceid>FETCH-LOGICAL-a414t-c9293cda0ab3c933749c9388c04f82fa7ad271c2d3a06fc4d96f34205f9a87543</originalsourceid><addsrcrecordid>eNptkLFOwzAQhi0EoqUw8ALIC0IMBdtx4pgtqkqLqAoDzNbViSEliYudgPr2pEoJC9OdTt__SfcjdE7JDSWM3tqCEsqZKA_QkIYsGAsSssN-j8gAnXi_JoS2F3mMBowIwjmRQzR7zKu3HKq8wskdTvAy-8ZLqBsHBX7Oqhr0Vhe5xhNbbmxTpdg4W-JplbaZ1AH-6OJwio4MFD47288Rer2fvkzm48XT7GGSLMbAKa_HWjIZ6BQIrAItg0Bw2Y441oSbmBkQkDJBNUsDIJHRPJWRCTgjoZEQi5AHI3Tded-hUBuXl-C2ykKu5slC7W6kfZ1KIb9oy1517MbZzybztSpzr7OigCqzjVeCx5JHoRR_Vu2s9y4zvZoStatY9RW37MXe2qzKLO3J305b4LIDQHu1to2r2kL-Ef0A9Kd_0w</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>748946597</pqid></control><display><type>article</type><title>Kingianin A: A New Natural Pentacyclic Compound from Endiandra kingiana</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Leverrier, Aurélie ; Dau, Marie Elise Tran Huu ; Retailleau, Pascal ; Awang, Khalijah ; Guéritte, Françoise ; Litaudon, Marc</creator><creatorcontrib>Leverrier, Aurélie ; Dau, Marie Elise Tran Huu ; Retailleau, Pascal ; Awang, Khalijah ; Guéritte, Françoise ; Litaudon, Marc</creatorcontrib><description>A new natural pentacyclic compound, named kingianin A, was isolated as a racemic mixture from the barks of Endiandra kingiana (Lauraceae). Its structure was elucidated by comprehensive analysis of NMR spectroscopic data, X-ray crystallography, and ECD calculations. The pentacyclic skeleton may be formed by a Diels−Alder reaction between two monomers having a bicyclo[4.2.0]octadiene backbone formed by a stereospecific electrocyclization of a linear compound of polyketide origin.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol101427m</identifier><identifier>PMID: 20704409</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Cellular Biology ; Circular Dichroism ; Crystallography, X-Ray ; Lauraceae - chemistry ; Life Sciences ; Molecular Structure ; Polycyclic Aromatic Hydrocarbons - chemistry ; Polycyclic Aromatic Hydrocarbons - isolation &amp; purification ; Stereoisomerism</subject><ispartof>Organic letters, 2010-08, Vol.12 (16), p.3638-3641</ispartof><rights>Copyright © 2010 American Chemical Society</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a414t-c9293cda0ab3c933749c9388c04f82fa7ad271c2d3a06fc4d96f34205f9a87543</citedby><cites>FETCH-LOGICAL-a414t-c9293cda0ab3c933749c9388c04f82fa7ad271c2d3a06fc4d96f34205f9a87543</cites><orcidid>0000-0003-3995-519X ; 0000-0002-0877-8234</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ol101427m$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol101427m$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,780,784,885,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20704409$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-00521979$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Leverrier, Aurélie</creatorcontrib><creatorcontrib>Dau, Marie Elise Tran Huu</creatorcontrib><creatorcontrib>Retailleau, Pascal</creatorcontrib><creatorcontrib>Awang, Khalijah</creatorcontrib><creatorcontrib>Guéritte, Françoise</creatorcontrib><creatorcontrib>Litaudon, Marc</creatorcontrib><title>Kingianin A: A New Natural Pentacyclic Compound from Endiandra kingiana</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>A new natural pentacyclic compound, named kingianin A, was isolated as a racemic mixture from the barks of Endiandra kingiana (Lauraceae). Its structure was elucidated by comprehensive analysis of NMR spectroscopic data, X-ray crystallography, and ECD calculations. The pentacyclic skeleton may be formed by a Diels−Alder reaction between two monomers having a bicyclo[4.2.0]octadiene backbone formed by a stereospecific electrocyclization of a linear compound of polyketide origin.</description><subject>Cellular Biology</subject><subject>Circular Dichroism</subject><subject>Crystallography, X-Ray</subject><subject>Lauraceae - chemistry</subject><subject>Life Sciences</subject><subject>Molecular Structure</subject><subject>Polycyclic Aromatic Hydrocarbons - chemistry</subject><subject>Polycyclic Aromatic Hydrocarbons - isolation &amp; purification</subject><subject>Stereoisomerism</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkLFOwzAQhi0EoqUw8ALIC0IMBdtx4pgtqkqLqAoDzNbViSEliYudgPr2pEoJC9OdTt__SfcjdE7JDSWM3tqCEsqZKA_QkIYsGAsSssN-j8gAnXi_JoS2F3mMBowIwjmRQzR7zKu3HKq8wskdTvAy-8ZLqBsHBX7Oqhr0Vhe5xhNbbmxTpdg4W-JplbaZ1AH-6OJwio4MFD47288Rer2fvkzm48XT7GGSLMbAKa_HWjIZ6BQIrAItg0Bw2Y441oSbmBkQkDJBNUsDIJHRPJWRCTgjoZEQi5AHI3Tded-hUBuXl-C2ykKu5slC7W6kfZ1KIb9oy1517MbZzybztSpzr7OigCqzjVeCx5JHoRR_Vu2s9y4zvZoStatY9RW37MXe2qzKLO3J305b4LIDQHu1to2r2kL-Ef0A9Kd_0w</recordid><startdate>20100820</startdate><enddate>20100820</enddate><creator>Leverrier, Aurélie</creator><creator>Dau, Marie Elise Tran Huu</creator><creator>Retailleau, Pascal</creator><creator>Awang, Khalijah</creator><creator>Guéritte, Françoise</creator><creator>Litaudon, Marc</creator><general>American Chemical Society</general><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>1XC</scope><orcidid>https://orcid.org/0000-0003-3995-519X</orcidid><orcidid>https://orcid.org/0000-0002-0877-8234</orcidid></search><sort><creationdate>20100820</creationdate><title>Kingianin A: A New Natural Pentacyclic Compound from Endiandra kingiana</title><author>Leverrier, Aurélie ; Dau, Marie Elise Tran Huu ; Retailleau, Pascal ; Awang, Khalijah ; Guéritte, Françoise ; Litaudon, Marc</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a414t-c9293cda0ab3c933749c9388c04f82fa7ad271c2d3a06fc4d96f34205f9a87543</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Cellular Biology</topic><topic>Circular Dichroism</topic><topic>Crystallography, X-Ray</topic><topic>Lauraceae - chemistry</topic><topic>Life Sciences</topic><topic>Molecular Structure</topic><topic>Polycyclic Aromatic Hydrocarbons - chemistry</topic><topic>Polycyclic Aromatic Hydrocarbons - isolation &amp; purification</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Leverrier, Aurélie</creatorcontrib><creatorcontrib>Dau, Marie Elise Tran Huu</creatorcontrib><creatorcontrib>Retailleau, Pascal</creatorcontrib><creatorcontrib>Awang, Khalijah</creatorcontrib><creatorcontrib>Guéritte, Françoise</creatorcontrib><creatorcontrib>Litaudon, Marc</creatorcontrib><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>Hyper Article en Ligne (HAL)</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Leverrier, Aurélie</au><au>Dau, Marie Elise Tran Huu</au><au>Retailleau, Pascal</au><au>Awang, Khalijah</au><au>Guéritte, Françoise</au><au>Litaudon, Marc</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Kingianin A: A New Natural Pentacyclic Compound from Endiandra kingiana</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2010-08-20</date><risdate>2010</risdate><volume>12</volume><issue>16</issue><spage>3638</spage><epage>3641</epage><pages>3638-3641</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>A new natural pentacyclic compound, named kingianin A, was isolated as a racemic mixture from the barks of Endiandra kingiana (Lauraceae). Its structure was elucidated by comprehensive analysis of NMR spectroscopic data, X-ray crystallography, and ECD calculations. The pentacyclic skeleton may be formed by a Diels−Alder reaction between two monomers having a bicyclo[4.2.0]octadiene backbone formed by a stereospecific electrocyclization of a linear compound of polyketide origin.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>20704409</pmid><doi>10.1021/ol101427m</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0003-3995-519X</orcidid><orcidid>https://orcid.org/0000-0002-0877-8234</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2010-08, Vol.12 (16), p.3638-3641
issn 1523-7060
1523-7052
language eng
recordid cdi_hal_primary_oai_HAL_hal_00521979v1
source MEDLINE; American Chemical Society Journals
subjects Cellular Biology
Circular Dichroism
Crystallography, X-Ray
Lauraceae - chemistry
Life Sciences
Molecular Structure
Polycyclic Aromatic Hydrocarbons - chemistry
Polycyclic Aromatic Hydrocarbons - isolation & purification
Stereoisomerism
title Kingianin A: A New Natural Pentacyclic Compound from Endiandra kingiana
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-29T21%3A13%3A55IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_hal_p&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Kingianin%20A:%20A%20New%20Natural%20Pentacyclic%20Compound%20from%20Endiandra%20kingiana&rft.jtitle=Organic%20letters&rft.au=Leverrier,%20Aure%CC%81lie&rft.date=2010-08-20&rft.volume=12&rft.issue=16&rft.spage=3638&rft.epage=3641&rft.pages=3638-3641&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol101427m&rft_dat=%3Cproquest_hal_p%3E748946597%3C/proquest_hal_p%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=748946597&rft_id=info:pmid/20704409&rfr_iscdi=true