1,4-Dimethoxyglucobrassicin in Barbarea and 4-Hydroxyglucobrassicin in Arabidopsis and Brassica
A novel indole glucosinolate, 1,4-dimethoxyglucobrassicin (1,4-dimethoxyindol-3-ylmethylglucosinolate), was isolated as the desulfo derivative from roots of the P-type of Barbarea vulgaris ssp. arcuata, and its structure was determined by spectroscopy including 2D NMR spectroscopy. 4-Hydroxyglucobra...
Gespeichert in:
| Veröffentlicht in: | Journal of agricultural and food chemistry 2001-03, Vol.49 (3), p.1502-1507 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1507 |
|---|---|
| container_issue | 3 |
| container_start_page | 1502 |
| container_title | Journal of agricultural and food chemistry |
| container_volume | 49 |
| creator | Agerbirk, Niels Petersen, Bent Larsen Olsen, Carl Erik Halkier, Barbara Ann Nielsen, Jens Kvist |
| description | A novel indole glucosinolate, 1,4-dimethoxyglucobrassicin (1,4-dimethoxyindol-3-ylmethylglucosinolate), was isolated as the desulfo derivative from roots of the P-type of Barbarea vulgaris ssp. arcuata, and its structure was determined by spectroscopy including 2D NMR spectroscopy. 4-Hydroxyglucobrassicin (4-hydroxyindol-3-ylmethylglucosinolate) was isolated as the desulfo derivative from green siliques (fruits) of Arabidopsis thaliana and identified by comparison of its 1H NMR spectrum with the spectrum of the known desulfoglucosinolate from Brassica napus. The delayed elution of desulfo indole glucosinolates from the DEAE Sephadex column used in sample preparation was examined, and the diode-array UV spectra of desulfo indole glucosinolates were measured, to ensure a reliable determination of 1,4-dimethoxyglucobrassicin and 4-hydroxyglucobrassicin with the existing analysis method based on the HPLC of desulfoglucosinolates. 1,4-Dimethoxyglucobrassicin was not detected in 10 other Arabidopsis, Brassica, and Barbarea species, indicating an evolutionarily recent mutation in the indole glucosinolate biosynthesis in B. vulgaris ssp. arcuata type P. Keywords: Brassicaceae; Barbarea; Arabidopsis; Brassica; 1,4-dimethoxyindol-3-ylmethylglucosinolate; 1,4-dimethoxyglucobrassicin; 4-hydroxyindol-3-ylmethylglucosinolate; 4-hydroxyglucobrassicin; desulfoglucosinolate; indole phytoalexin; NMR; MS; UV; HPLC |
| doi_str_mv | 10.1021/jf001256r |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_77070393</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>77070393</sourcerecordid><originalsourceid>FETCH-LOGICAL-a377t-28024de9f8da6822c3bb5431264cdbf948f60c2e417cf9fbbb49f98a5a0c7bb73</originalsourceid><addsrcrecordid>eNpt0E1rGzEQBmARWmI3yaF_IBhKC4VuImlXK-lou01TSEjIB4FexEgrpXL3w5V2If73VbrGvRgG5vA-DMOL0HuCzwim5HzlMCaUleEATQmjOGOEiDdoilOYCVaSCXoX4wpjLBjHh2hCSE6oEOUUKfKlyL76xva_upfNcz2YTgeI0RvfztIsIGgIFmbQVrMiu9xUYa-bB9C-6tbRx390MYZwjN46qKM92e4j9Hjx7WF5mV3dfP-xnF9lkHPeZ1RgWlRWOlFBKSg1udasSE-Wham0k4VwJTbUFoQbJ53WupBOCmCADdea50fo03h3Hbo_g429anw0tq6htd0QFeeY41zmCX4eoQldjME6tQ6-gbBRBKvXNtWuzWRPt0cH3djqv9zWl8CHLYBooHYBWuPjzslclkwmlY3Kx96-7FIIv1XJc87Uw-29IosncSeuf6qL5D-OHkxUq24IbWpuz3t_AQKQl9s</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>77070393</pqid></control><display><type>article</type><title>1,4-Dimethoxyglucobrassicin in Barbarea and 4-Hydroxyglucobrassicin in Arabidopsis and Brassica</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Agerbirk, Niels ; Petersen, Bent Larsen ; Olsen, Carl Erik ; Halkier, Barbara Ann ; Nielsen, Jens Kvist</creator><creatorcontrib>Agerbirk, Niels ; Petersen, Bent Larsen ; Olsen, Carl Erik ; Halkier, Barbara Ann ; Nielsen, Jens Kvist</creatorcontrib><description>A novel indole glucosinolate, 1,4-dimethoxyglucobrassicin (1,4-dimethoxyindol-3-ylmethylglucosinolate), was isolated as the desulfo derivative from roots of the P-type of Barbarea vulgaris ssp. arcuata, and its structure was determined by spectroscopy including 2D NMR spectroscopy. 4-Hydroxyglucobrassicin (4-hydroxyindol-3-ylmethylglucosinolate) was isolated as the desulfo derivative from green siliques (fruits) of Arabidopsis thaliana and identified by comparison of its 1H NMR spectrum with the spectrum of the known desulfoglucosinolate from Brassica napus. The delayed elution of desulfo indole glucosinolates from the DEAE Sephadex column used in sample preparation was examined, and the diode-array UV spectra of desulfo indole glucosinolates were measured, to ensure a reliable determination of 1,4-dimethoxyglucobrassicin and 4-hydroxyglucobrassicin with the existing analysis method based on the HPLC of desulfoglucosinolates. 1,4-Dimethoxyglucobrassicin was not detected in 10 other Arabidopsis, Brassica, and Barbarea species, indicating an evolutionarily recent mutation in the indole glucosinolate biosynthesis in B. vulgaris ssp. arcuata type P. Keywords: Brassicaceae; Barbarea; Arabidopsis; Brassica; 1,4-dimethoxyindol-3-ylmethylglucosinolate; 1,4-dimethoxyglucobrassicin; 4-hydroxyindol-3-ylmethylglucosinolate; 4-hydroxyglucobrassicin; desulfoglucosinolate; indole phytoalexin; NMR; MS; UV; HPLC</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf001256r</identifier><identifier>PMID: 11312886</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Agronomy. Soil science and plant productions ; Arabidopsis - chemistry ; Biological and medical sciences ; Brassica - chemistry ; Brassicaceae - chemistry ; Chemical constitution ; Economic plant physiology ; Fundamental and applied biological sciences. Psychology ; Glucosinolates ; Indoles - chemistry ; Indoles - isolation & purification ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; Molecular Conformation ; Molecular Structure ; Monosaccharides - chemistry ; Monosaccharides - isolation & purification ; Plant physiology and development ; Vegetables - chemistry</subject><ispartof>Journal of agricultural and food chemistry, 2001-03, Vol.49 (3), p.1502-1507</ispartof><rights>Copyright © 2001 American Chemical Society</rights><rights>2001 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a377t-28024de9f8da6822c3bb5431264cdbf948f60c2e417cf9fbbb49f98a5a0c7bb73</citedby><cites>FETCH-LOGICAL-a377t-28024de9f8da6822c3bb5431264cdbf948f60c2e417cf9fbbb49f98a5a0c7bb73</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/jf001256r$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf001256r$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56716,56766</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=939659$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11312886$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Agerbirk, Niels</creatorcontrib><creatorcontrib>Petersen, Bent Larsen</creatorcontrib><creatorcontrib>Olsen, Carl Erik</creatorcontrib><creatorcontrib>Halkier, Barbara Ann</creatorcontrib><creatorcontrib>Nielsen, Jens Kvist</creatorcontrib><title>1,4-Dimethoxyglucobrassicin in Barbarea and 4-Hydroxyglucobrassicin in Arabidopsis and Brassica</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>A novel indole glucosinolate, 1,4-dimethoxyglucobrassicin (1,4-dimethoxyindol-3-ylmethylglucosinolate), was isolated as the desulfo derivative from roots of the P-type of Barbarea vulgaris ssp. arcuata, and its structure was determined by spectroscopy including 2D NMR spectroscopy. 4-Hydroxyglucobrassicin (4-hydroxyindol-3-ylmethylglucosinolate) was isolated as the desulfo derivative from green siliques (fruits) of Arabidopsis thaliana and identified by comparison of its 1H NMR spectrum with the spectrum of the known desulfoglucosinolate from Brassica napus. The delayed elution of desulfo indole glucosinolates from the DEAE Sephadex column used in sample preparation was examined, and the diode-array UV spectra of desulfo indole glucosinolates were measured, to ensure a reliable determination of 1,4-dimethoxyglucobrassicin and 4-hydroxyglucobrassicin with the existing analysis method based on the HPLC of desulfoglucosinolates. 1,4-Dimethoxyglucobrassicin was not detected in 10 other Arabidopsis, Brassica, and Barbarea species, indicating an evolutionarily recent mutation in the indole glucosinolate biosynthesis in B. vulgaris ssp. arcuata type P. Keywords: Brassicaceae; Barbarea; Arabidopsis; Brassica; 1,4-dimethoxyindol-3-ylmethylglucosinolate; 1,4-dimethoxyglucobrassicin; 4-hydroxyindol-3-ylmethylglucosinolate; 4-hydroxyglucobrassicin; desulfoglucosinolate; indole phytoalexin; NMR; MS; UV; HPLC</description><subject>Agronomy. Soil science and plant productions</subject><subject>Arabidopsis - chemistry</subject><subject>Biological and medical sciences</subject><subject>Brassica - chemistry</subject><subject>Brassicaceae - chemistry</subject><subject>Chemical constitution</subject><subject>Economic plant physiology</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Glucosinolates</subject><subject>Indoles - chemistry</subject><subject>Indoles - isolation & purification</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mass Spectrometry</subject><subject>Molecular Conformation</subject><subject>Molecular Structure</subject><subject>Monosaccharides - chemistry</subject><subject>Monosaccharides - isolation & purification</subject><subject>Plant physiology and development</subject><subject>Vegetables - chemistry</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0E1rGzEQBmARWmI3yaF_IBhKC4VuImlXK-lou01TSEjIB4FexEgrpXL3w5V2If73VbrGvRgG5vA-DMOL0HuCzwim5HzlMCaUleEATQmjOGOEiDdoilOYCVaSCXoX4wpjLBjHh2hCSE6oEOUUKfKlyL76xva_upfNcz2YTgeI0RvfztIsIGgIFmbQVrMiu9xUYa-bB9C-6tbRx390MYZwjN46qKM92e4j9Hjx7WF5mV3dfP-xnF9lkHPeZ1RgWlRWOlFBKSg1udasSE-Wham0k4VwJTbUFoQbJ53WupBOCmCADdea50fo03h3Hbo_g429anw0tq6htd0QFeeY41zmCX4eoQldjME6tQ6-gbBRBKvXNtWuzWRPt0cH3djqv9zWl8CHLYBooHYBWuPjzslclkwmlY3Kx96-7FIIv1XJc87Uw-29IosncSeuf6qL5D-OHkxUq24IbWpuz3t_AQKQl9s</recordid><startdate>20010301</startdate><enddate>20010301</enddate><creator>Agerbirk, Niels</creator><creator>Petersen, Bent Larsen</creator><creator>Olsen, Carl Erik</creator><creator>Halkier, Barbara Ann</creator><creator>Nielsen, Jens Kvist</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><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20010301</creationdate><title>1,4-Dimethoxyglucobrassicin in Barbarea and 4-Hydroxyglucobrassicin in Arabidopsis and Brassica</title><author>Agerbirk, Niels ; Petersen, Bent Larsen ; Olsen, Carl Erik ; Halkier, Barbara Ann ; Nielsen, Jens Kvist</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a377t-28024de9f8da6822c3bb5431264cdbf948f60c2e417cf9fbbb49f98a5a0c7bb73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>Agronomy. Soil science and plant productions</topic><topic>Arabidopsis - chemistry</topic><topic>Biological and medical sciences</topic><topic>Brassica - chemistry</topic><topic>Brassicaceae - chemistry</topic><topic>Chemical constitution</topic><topic>Economic plant physiology</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Glucosinolates</topic><topic>Indoles - chemistry</topic><topic>Indoles - isolation & purification</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mass Spectrometry</topic><topic>Molecular Conformation</topic><topic>Molecular Structure</topic><topic>Monosaccharides - chemistry</topic><topic>Monosaccharides - isolation & purification</topic><topic>Plant physiology and development</topic><topic>Vegetables - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Agerbirk, Niels</creatorcontrib><creatorcontrib>Petersen, Bent Larsen</creatorcontrib><creatorcontrib>Olsen, Carl Erik</creatorcontrib><creatorcontrib>Halkier, Barbara Ann</creatorcontrib><creatorcontrib>Nielsen, Jens Kvist</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><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Agerbirk, Niels</au><au>Petersen, Bent Larsen</au><au>Olsen, Carl Erik</au><au>Halkier, Barbara Ann</au><au>Nielsen, Jens Kvist</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>1,4-Dimethoxyglucobrassicin in Barbarea and 4-Hydroxyglucobrassicin in Arabidopsis and Brassica</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2001-03-01</date><risdate>2001</risdate><volume>49</volume><issue>3</issue><spage>1502</spage><epage>1507</epage><pages>1502-1507</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>A novel indole glucosinolate, 1,4-dimethoxyglucobrassicin (1,4-dimethoxyindol-3-ylmethylglucosinolate), was isolated as the desulfo derivative from roots of the P-type of Barbarea vulgaris ssp. arcuata, and its structure was determined by spectroscopy including 2D NMR spectroscopy. 4-Hydroxyglucobrassicin (4-hydroxyindol-3-ylmethylglucosinolate) was isolated as the desulfo derivative from green siliques (fruits) of Arabidopsis thaliana and identified by comparison of its 1H NMR spectrum with the spectrum of the known desulfoglucosinolate from Brassica napus. The delayed elution of desulfo indole glucosinolates from the DEAE Sephadex column used in sample preparation was examined, and the diode-array UV spectra of desulfo indole glucosinolates were measured, to ensure a reliable determination of 1,4-dimethoxyglucobrassicin and 4-hydroxyglucobrassicin with the existing analysis method based on the HPLC of desulfoglucosinolates. 1,4-Dimethoxyglucobrassicin was not detected in 10 other Arabidopsis, Brassica, and Barbarea species, indicating an evolutionarily recent mutation in the indole glucosinolate biosynthesis in B. vulgaris ssp. arcuata type P. Keywords: Brassicaceae; Barbarea; Arabidopsis; Brassica; 1,4-dimethoxyindol-3-ylmethylglucosinolate; 1,4-dimethoxyglucobrassicin; 4-hydroxyindol-3-ylmethylglucosinolate; 4-hydroxyglucobrassicin; desulfoglucosinolate; indole phytoalexin; NMR; MS; UV; HPLC</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>11312886</pmid><doi>10.1021/jf001256r</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0021-8561 |
| ispartof | Journal of agricultural and food chemistry, 2001-03, Vol.49 (3), p.1502-1507 |
| issn | 0021-8561 1520-5118 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_77070393 |
| source | MEDLINE; American Chemical Society Journals |
| subjects | Agronomy. Soil science and plant productions Arabidopsis - chemistry Biological and medical sciences Brassica - chemistry Brassicaceae - chemistry Chemical constitution Economic plant physiology Fundamental and applied biological sciences. Psychology Glucosinolates Indoles - chemistry Indoles - isolation & purification Magnetic Resonance Spectroscopy Mass Spectrometry Molecular Conformation Molecular Structure Monosaccharides - chemistry Monosaccharides - isolation & purification Plant physiology and development Vegetables - chemistry |
| title | 1,4-Dimethoxyglucobrassicin in Barbarea and 4-Hydroxyglucobrassicin in Arabidopsis and Brassica |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-26T15%3A19%3A28IST&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=1,4-Dimethoxyglucobrassicin%20in%20Barbarea%20and%204-Hydroxyglucobrassicin%20in%20Arabidopsis%20and%20Brassica&rft.jtitle=Journal%20of%20agricultural%20and%20food%20chemistry&rft.au=Agerbirk,%20Niels&rft.date=2001-03-01&rft.volume=49&rft.issue=3&rft.spage=1502&rft.epage=1507&rft.pages=1502-1507&rft.issn=0021-8561&rft.eissn=1520-5118&rft.coden=JAFCAU&rft_id=info:doi/10.1021/jf001256r&rft_dat=%3Cproquest_cross%3E77070393%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=77070393&rft_id=info:pmid/11312886&rfr_iscdi=true |