Biosynthetic origin of 2-geranyl-1,4-naphthoquinone and its related anthraquinone in a Sesamum indicum hairy root culture
An isotope administration experiment with [1– 13C]glucose was conducted to clarify the biosynthetic origin of quinone derivatives produced by Sesamum indicum. [Display omitted] ► The geranyl group in geranylnaphthoquinone was formed via the MEP pathway. ► The ring moiety in geranylnaphthoquinone was...
Gespeichert in:
| Veröffentlicht in: | Phytochemistry (Oxford) 2011-06, Vol.72 (9), p.871-874 |
|---|---|
| Hauptverfasser: | , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 874 |
|---|---|
| container_issue | 9 |
| container_start_page | 871 |
| container_title | Phytochemistry (Oxford) |
| container_volume | 72 |
| creator | Furumoto, Toshio Hoshikuma, Arata |
| description | An isotope administration experiment with [1–
13C]glucose was conducted to clarify the biosynthetic origin of quinone derivatives produced by
Sesamum indicum.
[Display omitted]
► The geranyl group in geranylnaphthoquinone was formed via the MEP pathway. ► The ring moiety in geranylnaphthoquinone was formed via the shikimate pathway. ► Prenylation occurred at C-2 in 1,4-dihydroxy-2-naphthoate. ► Geranylnaphthoquinone and its related anthraquinone had the same biosynthetic origin.
In order to clarify the biosynthetic origin of 2-geranyl-1,4-naphthoquinone and its biogenetically related anthraquinone, which are possible intermediates of anthrasesamones, [1–
13C]glucose was administered to a hairy root culture of
Sesamum indicum. The labeling patterns of these quinone derivatives indicated that the naphthoquinone ring and geranyl side-chain of geranylnaphthoquinone were respectively biosynthesized through the shikimate and methylerythritol phosphate pathways, and that these quinone derivatives have the same biosynthetic origin. |
| doi_str_mv | 10.1016/j.phytochem.2011.03.012 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_907163106</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0031942211001488</els_id><sourcerecordid>1613949347</sourcerecordid><originalsourceid>FETCH-LOGICAL-c523t-8cde6a048d5e10b859c655632c9052b19ce6c63037ddc8f932af39c292ee93903</originalsourceid><addsrcrecordid>eNqFkUtv1DAQgC0EotvCX6C5IHogYcbOy8dS8ZIqcSg9W15nsvEqiRfbqZR_j6vdlhucRiN_M-OZj7FLhAIB60_74jCs0ZmBpoIDYgGiAOQv2AbbRuSiAXjJNgACc1lyfsbOQ9gDQFXV9Wt2xrFCFFhu2PrZurDOcaBoTea83dk5c33G8x15Pa9jjh_LfNaHIQ7u92JnN1Om5y6zMWSeRh2pS3kcvH56TQ10dkdBT8uUks6aFAdt_Zp552JmljEunt6wV70eA709xQt2__XLr5vv-e3Pbz9urm9zU3ER89Z0VGso264ihG1bSVOnLQQ3Eiq-RWmoNrUA0XSdaXspuO6FNFxyIikkiAv24dj34NMCFKKabDA0jnomtwQlocFaINSJvPoniTUKWUpRNgltjqjxLgRPvTp4O2m_KgT1aEjt1bMh9WhIgVDJUKp8dxqybCfqnuuelCTg_QnQweixTxaMDX-5kpeyrETiLo9cr53SO5-Y-7s0qQTAdKUGE3F9JCid98GSV8FYmg111pOJqnP2v9_9A8eovRY</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1613949347</pqid></control><display><type>article</type><title>Biosynthetic origin of 2-geranyl-1,4-naphthoquinone and its related anthraquinone in a Sesamum indicum hairy root culture</title><source>MEDLINE</source><source>Elsevier ScienceDirect Journals Complete</source><creator>Furumoto, Toshio ; Hoshikuma, Arata</creator><creatorcontrib>Furumoto, Toshio ; Hoshikuma, Arata</creatorcontrib><description>An isotope administration experiment with [1–
13C]glucose was conducted to clarify the biosynthetic origin of quinone derivatives produced by
Sesamum indicum.
[Display omitted]
► The geranyl group in geranylnaphthoquinone was formed via the MEP pathway. ► The ring moiety in geranylnaphthoquinone was formed via the shikimate pathway. ► Prenylation occurred at C-2 in 1,4-dihydroxy-2-naphthoate. ► Geranylnaphthoquinone and its related anthraquinone had the same biosynthetic origin.
In order to clarify the biosynthetic origin of 2-geranyl-1,4-naphthoquinone and its biogenetically related anthraquinone, which are possible intermediates of anthrasesamones, [1–
13C]glucose was administered to a hairy root culture of
Sesamum indicum. The labeling patterns of these quinone derivatives indicated that the naphthoquinone ring and geranyl side-chain of geranylnaphthoquinone were respectively biosynthesized through the shikimate and methylerythritol phosphate pathways, and that these quinone derivatives have the same biosynthetic origin.</description><identifier>ISSN: 0031-9422</identifier><identifier>EISSN: 1873-3700</identifier><identifier>DOI: 10.1016/j.phytochem.2011.03.012</identifier><identifier>PMID: 21511314</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Anthraquinone ; Anthraquinones - metabolism ; Anthrasesamone ; Biological and medical sciences ; Biosynthesis ; Carbon Isotopes - analysis ; Chemical constitution ; Fundamental and applied biological sciences. Psychology ; glucose ; Methylerythritol phosphate pathway ; Molecular Structure ; Naphthoquinone ; Naphthoquinones - metabolism ; Pedaliaceae ; phosphates ; Plant physiology and development ; Plant Roots - metabolism ; Prenylation ; roots ; Sesame ; Sesamum - metabolism ; Sesamum indicum ; Tissue Culture Techniques</subject><ispartof>Phytochemistry (Oxford), 2011-06, Vol.72 (9), p.871-874</ispartof><rights>2011 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2011 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c523t-8cde6a048d5e10b859c655632c9052b19ce6c63037ddc8f932af39c292ee93903</citedby><cites>FETCH-LOGICAL-c523t-8cde6a048d5e10b859c655632c9052b19ce6c63037ddc8f932af39c292ee93903</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.phytochem.2011.03.012$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>315,781,785,3551,27929,27930,46000</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=24249453$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21511314$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Furumoto, Toshio</creatorcontrib><creatorcontrib>Hoshikuma, Arata</creatorcontrib><title>Biosynthetic origin of 2-geranyl-1,4-naphthoquinone and its related anthraquinone in a Sesamum indicum hairy root culture</title><title>Phytochemistry (Oxford)</title><addtitle>Phytochemistry</addtitle><description>An isotope administration experiment with [1–
13C]glucose was conducted to clarify the biosynthetic origin of quinone derivatives produced by
Sesamum indicum.
[Display omitted]
► The geranyl group in geranylnaphthoquinone was formed via the MEP pathway. ► The ring moiety in geranylnaphthoquinone was formed via the shikimate pathway. ► Prenylation occurred at C-2 in 1,4-dihydroxy-2-naphthoate. ► Geranylnaphthoquinone and its related anthraquinone had the same biosynthetic origin.
In order to clarify the biosynthetic origin of 2-geranyl-1,4-naphthoquinone and its biogenetically related anthraquinone, which are possible intermediates of anthrasesamones, [1–
13C]glucose was administered to a hairy root culture of
Sesamum indicum. The labeling patterns of these quinone derivatives indicated that the naphthoquinone ring and geranyl side-chain of geranylnaphthoquinone were respectively biosynthesized through the shikimate and methylerythritol phosphate pathways, and that these quinone derivatives have the same biosynthetic origin.</description><subject>Anthraquinone</subject><subject>Anthraquinones - metabolism</subject><subject>Anthrasesamone</subject><subject>Biological and medical sciences</subject><subject>Biosynthesis</subject><subject>Carbon Isotopes - analysis</subject><subject>Chemical constitution</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>glucose</subject><subject>Methylerythritol phosphate pathway</subject><subject>Molecular Structure</subject><subject>Naphthoquinone</subject><subject>Naphthoquinones - metabolism</subject><subject>Pedaliaceae</subject><subject>phosphates</subject><subject>Plant physiology and development</subject><subject>Plant Roots - metabolism</subject><subject>Prenylation</subject><subject>roots</subject><subject>Sesame</subject><subject>Sesamum - metabolism</subject><subject>Sesamum indicum</subject><subject>Tissue Culture Techniques</subject><issn>0031-9422</issn><issn>1873-3700</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkUtv1DAQgC0EotvCX6C5IHogYcbOy8dS8ZIqcSg9W15nsvEqiRfbqZR_j6vdlhucRiN_M-OZj7FLhAIB60_74jCs0ZmBpoIDYgGiAOQv2AbbRuSiAXjJNgACc1lyfsbOQ9gDQFXV9Wt2xrFCFFhu2PrZurDOcaBoTea83dk5c33G8x15Pa9jjh_LfNaHIQ7u92JnN1Om5y6zMWSeRh2pS3kcvH56TQ10dkdBT8uUks6aFAdt_Zp552JmljEunt6wV70eA709xQt2__XLr5vv-e3Pbz9urm9zU3ER89Z0VGso264ihG1bSVOnLQQ3Eiq-RWmoNrUA0XSdaXspuO6FNFxyIikkiAv24dj34NMCFKKabDA0jnomtwQlocFaINSJvPoniTUKWUpRNgltjqjxLgRPvTp4O2m_KgT1aEjt1bMh9WhIgVDJUKp8dxqybCfqnuuelCTg_QnQweixTxaMDX-5kpeyrETiLo9cr53SO5-Y-7s0qQTAdKUGE3F9JCid98GSV8FYmg111pOJqnP2v9_9A8eovRY</recordid><startdate>20110601</startdate><enddate>20110601</enddate><creator>Furumoto, Toshio</creator><creator>Hoshikuma, Arata</creator><general>Elsevier Ltd</general><general>Elsevier</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>F1W</scope><scope>H95</scope><scope>L.G</scope></search><sort><creationdate>20110601</creationdate><title>Biosynthetic origin of 2-geranyl-1,4-naphthoquinone and its related anthraquinone in a Sesamum indicum hairy root culture</title><author>Furumoto, Toshio ; Hoshikuma, Arata</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c523t-8cde6a048d5e10b859c655632c9052b19ce6c63037ddc8f932af39c292ee93903</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Anthraquinone</topic><topic>Anthraquinones - metabolism</topic><topic>Anthrasesamone</topic><topic>Biological and medical sciences</topic><topic>Biosynthesis</topic><topic>Carbon Isotopes - analysis</topic><topic>Chemical constitution</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>glucose</topic><topic>Methylerythritol phosphate pathway</topic><topic>Molecular Structure</topic><topic>Naphthoquinone</topic><topic>Naphthoquinones - metabolism</topic><topic>Pedaliaceae</topic><topic>phosphates</topic><topic>Plant physiology and development</topic><topic>Plant Roots - metabolism</topic><topic>Prenylation</topic><topic>roots</topic><topic>Sesame</topic><topic>Sesamum - metabolism</topic><topic>Sesamum indicum</topic><topic>Tissue Culture Techniques</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Furumoto, Toshio</creatorcontrib><creatorcontrib>Hoshikuma, Arata</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>ASFA: Aquatic Sciences and Fisheries Abstracts</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) 1: Biological Sciences & Living Resources</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) Professional</collection><jtitle>Phytochemistry (Oxford)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Furumoto, Toshio</au><au>Hoshikuma, Arata</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Biosynthetic origin of 2-geranyl-1,4-naphthoquinone and its related anthraquinone in a Sesamum indicum hairy root culture</atitle><jtitle>Phytochemistry (Oxford)</jtitle><addtitle>Phytochemistry</addtitle><date>2011-06-01</date><risdate>2011</risdate><volume>72</volume><issue>9</issue><spage>871</spage><epage>874</epage><pages>871-874</pages><issn>0031-9422</issn><eissn>1873-3700</eissn><abstract>An isotope administration experiment with [1–
13C]glucose was conducted to clarify the biosynthetic origin of quinone derivatives produced by
Sesamum indicum.
[Display omitted]
► The geranyl group in geranylnaphthoquinone was formed via the MEP pathway. ► The ring moiety in geranylnaphthoquinone was formed via the shikimate pathway. ► Prenylation occurred at C-2 in 1,4-dihydroxy-2-naphthoate. ► Geranylnaphthoquinone and its related anthraquinone had the same biosynthetic origin.
In order to clarify the biosynthetic origin of 2-geranyl-1,4-naphthoquinone and its biogenetically related anthraquinone, which are possible intermediates of anthrasesamones, [1–
13C]glucose was administered to a hairy root culture of
Sesamum indicum. The labeling patterns of these quinone derivatives indicated that the naphthoquinone ring and geranyl side-chain of geranylnaphthoquinone were respectively biosynthesized through the shikimate and methylerythritol phosphate pathways, and that these quinone derivatives have the same biosynthetic origin.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>21511314</pmid><doi>10.1016/j.phytochem.2011.03.012</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0031-9422 |
| ispartof | Phytochemistry (Oxford), 2011-06, Vol.72 (9), p.871-874 |
| issn | 0031-9422 1873-3700 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_907163106 |
| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | Anthraquinone Anthraquinones - metabolism Anthrasesamone Biological and medical sciences Biosynthesis Carbon Isotopes - analysis Chemical constitution Fundamental and applied biological sciences. Psychology glucose Methylerythritol phosphate pathway Molecular Structure Naphthoquinone Naphthoquinones - metabolism Pedaliaceae phosphates Plant physiology and development Plant Roots - metabolism Prenylation roots Sesame Sesamum - metabolism Sesamum indicum Tissue Culture Techniques |
| title | Biosynthetic origin of 2-geranyl-1,4-naphthoquinone and its related anthraquinone in a Sesamum indicum hairy root culture |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-13T22%3A06%3A39IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Biosynthetic%20origin%20of%202-geranyl-1,4-naphthoquinone%20and%20its%20related%20anthraquinone%20in%20a%20Sesamum%20indicum%20hairy%20root%20culture&rft.jtitle=Phytochemistry%20(Oxford)&rft.au=Furumoto,%20Toshio&rft.date=2011-06-01&rft.volume=72&rft.issue=9&rft.spage=871&rft.epage=874&rft.pages=871-874&rft.issn=0031-9422&rft.eissn=1873-3700&rft_id=info:doi/10.1016/j.phytochem.2011.03.012&rft_dat=%3Cproquest_cross%3E1613949347%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1613949347&rft_id=info:pmid/21511314&rft_els_id=S0031942211001488&rfr_iscdi=true |