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Identifying three ecological chemotypes of Xanthium strumarium glandular trichomes using a combined NMR and LC-MS method
Xanthanolides, as the sesquiterpene lactones, are reportedly the major components for the pharmacological properties of X. strumarium L. species. Phytochemical studies indicated that the glandular structures on the surface of plant tissues would form the primary sites for the accumulation of this cl...
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Published in: | PloS one 2013-10, Vol.8 (10), p.e76621-e76621 |
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description | Xanthanolides, as the sesquiterpene lactones, are reportedly the major components for the pharmacological properties of X. strumarium L. species. Phytochemical studies indicated that the glandular structures on the surface of plant tissues would form the primary sites for the accumulation of this class of the compounds. As the interface between plants and their natural enemies, glandular trichomes may vary with respect to which of their chemicals are sequestered against different herbivores in different ecologies. However, to date, no data are available on the chemical characterisation of X. strumarium glandular cells. In this study, the trichome secretions of the X. strumarium species originating from nineteen unique areas across eleven provinces in China, were analysed by HPLC, LC-ESI-MS and NMR. For the first time three distinct chemotypes of X. strumarium glandular trichomes were discovered along with the qualitative and quantitative evaluations of their presence of xanthanolides; these were designated glandular cell Types I, II, and III, respectively. The main xanthanolides in Type I cells were 8-epi-xanthatin and xanthumin while no xanthatin was detected. Xanthatin, 8-epi-xanthatin, and xanthumin dominated in Type II cells with comparable levels of each being present. For Type III cells, significantly higher concentrations of 8-epi-xanthatin or xanthinosin (relative to xanthatin) were detected with xanthinosin only being observed in this type. Further research will focus on understanding the ecological and molecular mechanism causing these chemotype differences in X. strumarium glandular structures. |
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Phytochemical studies indicated that the glandular structures on the surface of plant tissues would form the primary sites for the accumulation of this class of the compounds. As the interface between plants and their natural enemies, glandular trichomes may vary with respect to which of their chemicals are sequestered against different herbivores in different ecologies. However, to date, no data are available on the chemical characterisation of X. strumarium glandular cells. In this study, the trichome secretions of the X. strumarium species originating from nineteen unique areas across eleven provinces in China, were analysed by HPLC, LC-ESI-MS and NMR. For the first time three distinct chemotypes of X. strumarium glandular trichomes were discovered along with the qualitative and quantitative evaluations of their presence of xanthanolides; these were designated glandular cell Types I, II, and III, respectively. The main xanthanolides in Type I cells were 8-epi-xanthatin and xanthumin while no xanthatin was detected. Xanthatin, 8-epi-xanthatin, and xanthumin dominated in Type II cells with comparable levels of each being present. For Type III cells, significantly higher concentrations of 8-epi-xanthatin or xanthinosin (relative to xanthatin) were detected with xanthinosin only being observed in this type. Further research will focus on understanding the ecological and molecular mechanism causing these chemotype differences in X. strumarium glandular structures.</description><identifier>ISSN: 1932-6203</identifier><identifier>EISSN: 1932-6203</identifier><identifier>DOI: 10.1371/journal.pone.0076621</identifier><identifier>PMID: 24098541</identifier><language>eng</language><publisher>United States: Public Library of Science</publisher><subject>Animals ; Antineoplastic Agents, Phytogenic ; Artemisia annua ; Asteraceae ; Biosynthesis ; Botanical gardens ; Chromatography, High Pressure Liquid ; Ecological effects ; Furans - isolation & purification ; Germplasm ; Herbivores ; Herbivory - physiology ; High-performance liquid chromatography ; Laboratories ; Lactones ; Lactones - isolation & purification ; Leaves ; Liquid chromatography ; Localization ; Magnetic Resonance Spectroscopy ; Mass spectrometry ; Metabolism ; Metabolites ; Molecular chains ; Molecular physics ; Natural enemies ; NMR ; Nuclear magnetic resonance ; Pharmacology ; Physics ; Physiological aspects ; Plant tissues ; Ruminants - physiology ; Secretions ; Seeds ; Sesquiterpene lactones ; Sesquiterpenes - isolation & purification ; Spectrometry, Mass, Electrospray Ionization ; Staphylococcus infections ; Trichomes ; Trichomes - chemistry ; Trichomes - classification ; Trichomes - cytology ; Trichomes - immunology ; Xanthium ; Xanthium - chemistry ; Xanthium - immunology ; Xanthium spinosum ; Xanthium strumarium</subject><ispartof>PloS one, 2013-10, Vol.8 (10), p.e76621-e76621</ispartof><rights>COPYRIGHT 2013 Public Library of Science</rights><rights>2013 Chen et al. This is an open-access article distributed under the terms of the Creative Commons Attribution License: https://creativecommons.org/licenses/by/4.0/ (the “License”), which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited. Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>2013 Chen et al 2013 Chen et al</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c692t-9e48f10c1f52315b1a68ee19b06163cc0ca31093dc737db72294324fa7ee69e63</citedby><cites>FETCH-LOGICAL-c692t-9e48f10c1f52315b1a68ee19b06163cc0ca31093dc737db72294324fa7ee69e63</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.proquest.com/docview/1439076510/fulltextPDF?pq-origsite=primo$$EPDF$$P50$$Gproquest$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/1439076510?pq-origsite=primo$$EHTML$$P50$$Gproquest$$Hfree_for_read</linktohtml><link.rule.ids>230,314,724,777,781,882,25734,27905,27906,36993,36994,44571,53772,53774,74875</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24098541$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><contributor>Bundy, Jacob Guy</contributor><creatorcontrib>Chen, Fangfang</creatorcontrib><creatorcontrib>Hao, Fuhua</creatorcontrib><creatorcontrib>Li, Changfu</creatorcontrib><creatorcontrib>Gou, Junbo</creatorcontrib><creatorcontrib>Lu, Dayan</creatorcontrib><creatorcontrib>Gong, Fujun</creatorcontrib><creatorcontrib>Tang, Huiru</creatorcontrib><creatorcontrib>Zhang, Yansheng</creatorcontrib><title>Identifying three ecological chemotypes of Xanthium strumarium glandular trichomes using a combined NMR and LC-MS method</title><title>PloS one</title><addtitle>PLoS One</addtitle><description>Xanthanolides, as the sesquiterpene lactones, are reportedly the major components for the pharmacological properties of X. strumarium L. species. Phytochemical studies indicated that the glandular structures on the surface of plant tissues would form the primary sites for the accumulation of this class of the compounds. As the interface between plants and their natural enemies, glandular trichomes may vary with respect to which of their chemicals are sequestered against different herbivores in different ecologies. However, to date, no data are available on the chemical characterisation of X. strumarium glandular cells. In this study, the trichome secretions of the X. strumarium species originating from nineteen unique areas across eleven provinces in China, were analysed by HPLC, LC-ESI-MS and NMR. For the first time three distinct chemotypes of X. strumarium glandular trichomes were discovered along with the qualitative and quantitative evaluations of their presence of xanthanolides; these were designated glandular cell Types I, II, and III, respectively. The main xanthanolides in Type I cells were 8-epi-xanthatin and xanthumin while no xanthatin was detected. Xanthatin, 8-epi-xanthatin, and xanthumin dominated in Type II cells with comparable levels of each being present. For Type III cells, significantly higher concentrations of 8-epi-xanthatin or xanthinosin (relative to xanthatin) were detected with xanthinosin only being observed in this type. Further research will focus on understanding the ecological and molecular mechanism causing these chemotype differences in X. strumarium glandular structures.</description><subject>Animals</subject><subject>Antineoplastic Agents, Phytogenic</subject><subject>Artemisia annua</subject><subject>Asteraceae</subject><subject>Biosynthesis</subject><subject>Botanical gardens</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Ecological effects</subject><subject>Furans - isolation & purification</subject><subject>Germplasm</subject><subject>Herbivores</subject><subject>Herbivory - physiology</subject><subject>High-performance liquid chromatography</subject><subject>Laboratories</subject><subject>Lactones</subject><subject>Lactones - isolation & purification</subject><subject>Leaves</subject><subject>Liquid chromatography</subject><subject>Localization</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mass spectrometry</subject><subject>Metabolism</subject><subject>Metabolites</subject><subject>Molecular chains</subject><subject>Molecular physics</subject><subject>Natural enemies</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Pharmacology</subject><subject>Physics</subject><subject>Physiological aspects</subject><subject>Plant tissues</subject><subject>Ruminants - physiology</subject><subject>Secretions</subject><subject>Seeds</subject><subject>Sesquiterpene lactones</subject><subject>Sesquiterpenes - isolation & purification</subject><subject>Spectrometry, Mass, Electrospray Ionization</subject><subject>Staphylococcus infections</subject><subject>Trichomes</subject><subject>Trichomes - chemistry</subject><subject>Trichomes - classification</subject><subject>Trichomes - cytology</subject><subject>Trichomes - immunology</subject><subject>Xanthium</subject><subject>Xanthium - chemistry</subject><subject>Xanthium - immunology</subject><subject>Xanthium spinosum</subject><subject>Xanthium strumarium</subject><issn>1932-6203</issn><issn>1932-6203</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>PIMPY</sourceid><sourceid>DOA</sourceid><recordid>eNqNk12L1DAUhoso7rr6D0QDgujFjEmTpu2NsAx-DMy6sKviXUjT0zZD28wmqez8e1Onu0xlL6QXCclz3nPOm54oeknwktCUfNiawfayXe5MD0uMU85j8ig6JTmNFzzG9PHR_iR65twW44RmnD-NTmKG8yxh5DS6XZfQe13tdV8j31gABMq0ptZKtkg10Bm_34FDpkK_ZO8bPXTIeTt00o7bupV9ObTSIm-1akwX0MGNYhIp0xW6hxJ9u7hCAUOb1eLiGnXgG1M-j55UsnXwYlrPoh-fP31ffV1sLr-sV-ebheJ57Bc5sKwiWJEqiSlJCiJ5BkDyAnPCqVJYSUpwTkuV0rQs0jjOGY1ZJVMAngOnZ9Hrg-6uNU5MpjlBGM2DZwnBgVgfiNLIrdhZHVrbCyO1-HtgbC2k9Vq1IOKkUiXHXKmQg6hS8oKlGcukoqTMGAlaH6dsQ9FBqYK3VrYz0flNrxtRm9-CplmWxmMx7yYBa24GcF502ilog81ghrFuRhkO1tCAvvkHfbi7iaplaED3lQl51SgqzsfaWUwwC9TyASp8JXRahT-s0uF8FvB-FhAYD7e-loNzYn199f_s5c85-_aIbUC2vnGmHbw2vZuD7AAqa5yzUN2bTLAYB-TODTEOiJgGJIS9On6g-6C7iaB_ACT2CxY</recordid><startdate>20131002</startdate><enddate>20131002</enddate><creator>Chen, Fangfang</creator><creator>Hao, Fuhua</creator><creator>Li, Changfu</creator><creator>Gou, Junbo</creator><creator>Lu, Dayan</creator><creator>Gong, Fujun</creator><creator>Tang, Huiru</creator><creator>Zhang, Yansheng</creator><general>Public Library of Science</general><general>Public Library of Science (PLoS)</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>IOV</scope><scope>ISR</scope><scope>3V.</scope><scope>7QG</scope><scope>7QL</scope><scope>7QO</scope><scope>7RV</scope><scope>7SN</scope><scope>7SS</scope><scope>7T5</scope><scope>7TG</scope><scope>7TM</scope><scope>7U9</scope><scope>7X2</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8AO</scope><scope>8C1</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AEUYN</scope><scope>AFKRA</scope><scope>ARAPS</scope><scope>ATCPS</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>BHPHI</scope><scope>C1K</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>FR3</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>H94</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>KB.</scope><scope>KB0</scope><scope>KL.</scope><scope>L6V</scope><scope>LK8</scope><scope>M0K</scope><scope>M0S</scope><scope>M1P</scope><scope>M7N</scope><scope>M7P</scope><scope>M7S</scope><scope>NAPCQ</scope><scope>P5Z</scope><scope>P62</scope><scope>P64</scope><scope>PATMY</scope><scope>PDBOC</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>PTHSS</scope><scope>PYCSY</scope><scope>RC3</scope><scope>7X8</scope><scope>5PM</scope><scope>DOA</scope></search><sort><creationdate>20131002</creationdate><title>Identifying three ecological chemotypes of Xanthium strumarium glandular trichomes using a combined NMR and LC-MS method</title><author>Chen, Fangfang ; Hao, Fuhua ; Li, Changfu ; Gou, Junbo ; Lu, Dayan ; Gong, Fujun ; Tang, Huiru ; Zhang, Yansheng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c692t-9e48f10c1f52315b1a68ee19b06163cc0ca31093dc737db72294324fa7ee69e63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Animals</topic><topic>Antineoplastic Agents, Phytogenic</topic><topic>Artemisia annua</topic><topic>Asteraceae</topic><topic>Biosynthesis</topic><topic>Botanical gardens</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Ecological effects</topic><topic>Furans - isolation & purification</topic><topic>Germplasm</topic><topic>Herbivores</topic><topic>Herbivory - physiology</topic><topic>High-performance liquid chromatography</topic><topic>Laboratories</topic><topic>Lactones</topic><topic>Lactones - isolation & purification</topic><topic>Leaves</topic><topic>Liquid chromatography</topic><topic>Localization</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mass spectrometry</topic><topic>Metabolism</topic><topic>Metabolites</topic><topic>Molecular chains</topic><topic>Molecular physics</topic><topic>Natural enemies</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Pharmacology</topic><topic>Physics</topic><topic>Physiological aspects</topic><topic>Plant tissues</topic><topic>Ruminants - physiology</topic><topic>Secretions</topic><topic>Seeds</topic><topic>Sesquiterpene lactones</topic><topic>Sesquiterpenes - isolation & purification</topic><topic>Spectrometry, Mass, Electrospray Ionization</topic><topic>Staphylococcus infections</topic><topic>Trichomes</topic><topic>Trichomes - chemistry</topic><topic>Trichomes - classification</topic><topic>Trichomes - cytology</topic><topic>Trichomes - immunology</topic><topic>Xanthium</topic><topic>Xanthium - chemistry</topic><topic>Xanthium - immunology</topic><topic>Xanthium spinosum</topic><topic>Xanthium strumarium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chen, Fangfang</creatorcontrib><creatorcontrib>Hao, Fuhua</creatorcontrib><creatorcontrib>Li, Changfu</creatorcontrib><creatorcontrib>Gou, Junbo</creatorcontrib><creatorcontrib>Lu, Dayan</creatorcontrib><creatorcontrib>Gong, Fujun</creatorcontrib><creatorcontrib>Tang, Huiru</creatorcontrib><creatorcontrib>Zhang, Yansheng</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Gale In Context: Opposing Viewpoints</collection><collection>Gale In Context: Science</collection><collection>ProQuest Central (Corporate)</collection><collection>Animal Behavior Abstracts</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Biotechnology Research Abstracts</collection><collection>ProQuest Nursing and Allied Health Journals</collection><collection>Ecology Abstracts</collection><collection>Entomology Abstracts (Full archive)</collection><collection>Immunology Abstracts</collection><collection>Meteorological & Geoastrophysical Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>Agricultural Science Collection</collection><collection>ProQuest Health and Medical</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>ProQuest Pharma Collection</collection><collection>ProQuest Public Health Database</collection><collection>Technology Research Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>ProQuest Natural Science Collection</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central (Alumni)</collection><collection>ProQuest One Sustainability</collection><collection>ProQuest Central</collection><collection>Advanced Technologies & Aerospace Collection</collection><collection>Agricultural & Environmental Science Collection</collection><collection>ProQuest Central Essentials</collection><collection>Biological Science Collection</collection><collection>AUTh Library subscriptions: ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest Natural Science Collection</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central</collection><collection>Engineering Research Database</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>SciTech Premium Collection</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Materials Science Database</collection><collection>Nursing & Allied Health Database (Alumni Edition)</collection><collection>Meteorological & Geoastrophysical Abstracts - 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Academic</collection><collection>PubMed Central (Full Participant titles)</collection><collection>DOAJ Directory of Open Access Journals</collection><jtitle>PloS one</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chen, Fangfang</au><au>Hao, Fuhua</au><au>Li, Changfu</au><au>Gou, Junbo</au><au>Lu, Dayan</au><au>Gong, Fujun</au><au>Tang, Huiru</au><au>Zhang, Yansheng</au><au>Bundy, Jacob Guy</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Identifying three ecological chemotypes of Xanthium strumarium glandular trichomes using a combined NMR and LC-MS method</atitle><jtitle>PloS one</jtitle><addtitle>PLoS One</addtitle><date>2013-10-02</date><risdate>2013</risdate><volume>8</volume><issue>10</issue><spage>e76621</spage><epage>e76621</epage><pages>e76621-e76621</pages><issn>1932-6203</issn><eissn>1932-6203</eissn><abstract>Xanthanolides, as the sesquiterpene lactones, are reportedly the major components for the pharmacological properties of X. strumarium L. species. Phytochemical studies indicated that the glandular structures on the surface of plant tissues would form the primary sites for the accumulation of this class of the compounds. As the interface between plants and their natural enemies, glandular trichomes may vary with respect to which of their chemicals are sequestered against different herbivores in different ecologies. However, to date, no data are available on the chemical characterisation of X. strumarium glandular cells. In this study, the trichome secretions of the X. strumarium species originating from nineteen unique areas across eleven provinces in China, were analysed by HPLC, LC-ESI-MS and NMR. For the first time three distinct chemotypes of X. strumarium glandular trichomes were discovered along with the qualitative and quantitative evaluations of their presence of xanthanolides; these were designated glandular cell Types I, II, and III, respectively. The main xanthanolides in Type I cells were 8-epi-xanthatin and xanthumin while no xanthatin was detected. Xanthatin, 8-epi-xanthatin, and xanthumin dominated in Type II cells with comparable levels of each being present. For Type III cells, significantly higher concentrations of 8-epi-xanthatin or xanthinosin (relative to xanthatin) were detected with xanthinosin only being observed in this type. Further research will focus on understanding the ecological and molecular mechanism causing these chemotype differences in X. strumarium glandular structures.</abstract><cop>United States</cop><pub>Public Library of Science</pub><pmid>24098541</pmid><doi>10.1371/journal.pone.0076621</doi><tpages>e76621</tpages><oa>free_for_read</oa></addata></record> |
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subjects | Animals Antineoplastic Agents, Phytogenic Artemisia annua Asteraceae Biosynthesis Botanical gardens Chromatography, High Pressure Liquid Ecological effects Furans - isolation & purification Germplasm Herbivores Herbivory - physiology High-performance liquid chromatography Laboratories Lactones Lactones - isolation & purification Leaves Liquid chromatography Localization Magnetic Resonance Spectroscopy Mass spectrometry Metabolism Metabolites Molecular chains Molecular physics Natural enemies NMR Nuclear magnetic resonance Pharmacology Physics Physiological aspects Plant tissues Ruminants - physiology Secretions Seeds Sesquiterpene lactones Sesquiterpenes - isolation & purification Spectrometry, Mass, Electrospray Ionization Staphylococcus infections Trichomes Trichomes - chemistry Trichomes - classification Trichomes - cytology Trichomes - immunology Xanthium Xanthium - chemistry Xanthium - immunology Xanthium spinosum Xanthium strumarium |
title | Identifying three ecological chemotypes of Xanthium strumarium glandular trichomes using a combined NMR and LC-MS method |
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