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Pyrrolizidine alkaloids and fatty acids from the endemic plant species Rindera umbellata and the effect of lindelofine-N-oxide on tubulin polymerization
The examination of the aerial parts, roots, and seeds of the endemic plant Rindera umbellata is reported in this paper for the first time. Phytochemical investigation of R. umbellata led to the isolation and characterization of ten pyrrolizidine alkaloids and eleven fatty acids in the form of trigly...
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Published in: | Molecules (Basel, Switzerland) Switzerland), 2013-09, Vol.18 (9), p.10694-10706 |
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creator | Mandić, Boris M Simić, Milena R Vučković, Ivan M Vujisić, Ljubodrag V Novaković, Miroslav M Trifunović, Snežana S Nikolić-Mandić, Snežana D Tešević, Vele V Vajs, Vlatka V Milosavljević, Slobodan M |
description | The examination of the aerial parts, roots, and seeds of the endemic plant Rindera umbellata is reported in this paper for the first time. Phytochemical investigation of R. umbellata led to the isolation and characterization of ten pyrrolizidine alkaloids and eleven fatty acids in the form of triglycerides. Pyrrolizidine alkaloids 1-9 were found in the aerial parts, 7 and 8 in the roots, and 6-10, together with eleven fatty acids, in the seeds of this plant species. The structures of compounds 1-10 were established based on spectroscopic studies (¹H- and ¹³C-NMR, 2D NMR, IR and CI-MS). After trans-esterification, methyl esters of the fatty acids were analyzed using GC-MS. The effect of lindelofine-N-oxide (7) on tubulin polymerization was determined. |
doi_str_mv | 10.3390/molecules180910694 |
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Phytochemical investigation of R. umbellata led to the isolation and characterization of ten pyrrolizidine alkaloids and eleven fatty acids in the form of triglycerides. Pyrrolizidine alkaloids 1-9 were found in the aerial parts, 7 and 8 in the roots, and 6-10, together with eleven fatty acids, in the seeds of this plant species. The structures of compounds 1-10 were established based on spectroscopic studies (¹H- and ¹³C-NMR, 2D NMR, IR and CI-MS). After trans-esterification, methyl esters of the fatty acids were analyzed using GC-MS. The effect of lindelofine-N-oxide (7) on tubulin polymerization was determined.</description><identifier>ISSN: 1420-3049</identifier><identifier>EISSN: 1420-3049</identifier><identifier>DOI: 10.3390/molecules180910694</identifier><identifier>PMID: 24005964</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>Animals ; Antineoplastic Agents - chemistry ; Boraginaceae - chemistry ; Cattle ; Cell cycle ; Electronic mail systems ; Fatty acids ; Fatty Acids - chemistry ; Fatty Acids - isolation & purification ; Flowers & plants ; Metabolites ; Natural products ; Pharmacy ; Phytochemicals ; Plant Components, Aerial - chemistry ; Plant Extracts - chemistry ; Plant Roots - chemistry ; Polymerization ; Protein Multimerization - drug effects ; pyrrolizidine alkaloids ; Pyrrolizidine Alkaloids - chemistry ; Pyrrolizidine Alkaloids - isolation & purification ; Rindera umbellata ; Seeds ; Seeds - chemistry ; Toxicity ; Tubulin - chemistry ; Tubulin Modulators - chemistry ; tubulin polymerization</subject><ispartof>Molecules (Basel, Switzerland), 2013-09, Vol.18 (9), p.10694-10706</ispartof><rights>Copyright MDPI AG 2013</rights><rights>2013 by the authors; licensee MDPI, Basel, Switzerland. 2013</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c496t-49c8cf7166f721a713dbfcc3ed55b23be63d56b564ec5bdcffb30c37700c3f0b3</citedby><cites>FETCH-LOGICAL-c496t-49c8cf7166f721a713dbfcc3ed55b23be63d56b564ec5bdcffb30c37700c3f0b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.proquest.com/docview/1532139335/fulltextPDF?pq-origsite=primo$$EPDF$$P50$$Gproquest$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/1532139335?pq-origsite=primo$$EHTML$$P50$$Gproquest$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,25753,27924,27925,37012,37013,44590,53791,53793,75126</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24005964$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Mandić, Boris M</creatorcontrib><creatorcontrib>Simić, Milena R</creatorcontrib><creatorcontrib>Vučković, Ivan M</creatorcontrib><creatorcontrib>Vujisić, Ljubodrag V</creatorcontrib><creatorcontrib>Novaković, Miroslav M</creatorcontrib><creatorcontrib>Trifunović, Snežana S</creatorcontrib><creatorcontrib>Nikolić-Mandić, Snežana D</creatorcontrib><creatorcontrib>Tešević, Vele V</creatorcontrib><creatorcontrib>Vajs, Vlatka V</creatorcontrib><creatorcontrib>Milosavljević, Slobodan M</creatorcontrib><title>Pyrrolizidine alkaloids and fatty acids from the endemic plant species Rindera umbellata and the effect of lindelofine-N-oxide on tubulin polymerization</title><title>Molecules (Basel, Switzerland)</title><addtitle>Molecules</addtitle><description>The examination of the aerial parts, roots, and seeds of the endemic plant Rindera umbellata is reported in this paper for the first time. Phytochemical investigation of R. umbellata led to the isolation and characterization of ten pyrrolizidine alkaloids and eleven fatty acids in the form of triglycerides. Pyrrolizidine alkaloids 1-9 were found in the aerial parts, 7 and 8 in the roots, and 6-10, together with eleven fatty acids, in the seeds of this plant species. The structures of compounds 1-10 were established based on spectroscopic studies (¹H- and ¹³C-NMR, 2D NMR, IR and CI-MS). After trans-esterification, methyl esters of the fatty acids were analyzed using GC-MS. The effect of lindelofine-N-oxide (7) on tubulin polymerization was determined.</description><subject>Animals</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Boraginaceae - chemistry</subject><subject>Cattle</subject><subject>Cell cycle</subject><subject>Electronic mail systems</subject><subject>Fatty acids</subject><subject>Fatty Acids - chemistry</subject><subject>Fatty Acids - isolation & purification</subject><subject>Flowers & plants</subject><subject>Metabolites</subject><subject>Natural products</subject><subject>Pharmacy</subject><subject>Phytochemicals</subject><subject>Plant Components, Aerial - chemistry</subject><subject>Plant Extracts - chemistry</subject><subject>Plant Roots - chemistry</subject><subject>Polymerization</subject><subject>Protein Multimerization - drug effects</subject><subject>pyrrolizidine alkaloids</subject><subject>Pyrrolizidine Alkaloids - chemistry</subject><subject>Pyrrolizidine Alkaloids - isolation & purification</subject><subject>Rindera umbellata</subject><subject>Seeds</subject><subject>Seeds - chemistry</subject><subject>Toxicity</subject><subject>Tubulin - chemistry</subject><subject>Tubulin Modulators - chemistry</subject><subject>tubulin polymerization</subject><issn>1420-3049</issn><issn>1420-3049</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>PIMPY</sourceid><sourceid>DOA</sourceid><recordid>eNplkstu1TAQhiMEoqXwAiyQJTZsAnbsOPEGCVVcKlWAEKwtX8atD04cbAdx-iQ8Lj7nlKqFjS8z_3xj_5qmeUrwS0oFfjXFAGYNkMmIBcFcsHvNMWEdbilm4v6t81HzKOcNxh1hpH_YHHUM415wdtz8_rxNKQZ_5a2fAanwXYXobUZqtsipUrZImd3dpTihcgkIZguTN2gJai4oL2A8ZPTF13BSaJ00hKCK2gP2eufAFBQdCjtNiK42aj-28Ze3gOKMyqrXmkJLDNsJkr9Sxcf5cfPAqZDhyfV-0nx79_br6Yf2_NP7s9M3561hgpeWCTMaNxDO3dARNRBqtTOGgu173VENnNqe654zML22xjlNsaHDgOvqsKYnzdmBa6PayCX5SaWtjMrLfSCmC6lS8SaAFDDqfjS12aAY7auBApuOjVSIYcQcV9brA2tZ9QTWwFySCnegdzOzv5QX8afkHRcj4xXw4hqQ4o8VcpGTz2Zn6AxxzZIwikc2jgOr0uf_SDdxTXO1SpKedoQKSvuq6g4qk2LOCdzNYwiWuyGS_w9RLXp2-xs3JX-nhv4BjoTIjg</recordid><startdate>20130903</startdate><enddate>20130903</enddate><creator>Mandić, Boris M</creator><creator>Simić, Milena R</creator><creator>Vučković, Ivan M</creator><creator>Vujisić, Ljubodrag V</creator><creator>Novaković, Miroslav M</creator><creator>Trifunović, Snežana S</creator><creator>Nikolić-Mandić, Snežana D</creator><creator>Tešević, Vele V</creator><creator>Vajs, Vlatka V</creator><creator>Milosavljević, Slobodan M</creator><general>MDPI AG</general><general>MDPI</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>3V.</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>K9.</scope><scope>M0S</scope><scope>M1P</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>7X8</scope><scope>5PM</scope><scope>DOA</scope></search><sort><creationdate>20130903</creationdate><title>Pyrrolizidine alkaloids and fatty acids from the endemic plant species Rindera umbellata and the effect of lindelofine-N-oxide on tubulin polymerization</title><author>Mandić, Boris M ; Simić, Milena R ; Vučković, Ivan M ; Vujisić, Ljubodrag V ; Novaković, Miroslav M ; Trifunović, Snežana S ; Nikolić-Mandić, Snežana D ; Tešević, Vele V ; Vajs, Vlatka V ; Milosavljević, Slobodan M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c496t-49c8cf7166f721a713dbfcc3ed55b23be63d56b564ec5bdcffb30c37700c3f0b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Animals</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Boraginaceae - chemistry</topic><topic>Cattle</topic><topic>Cell cycle</topic><topic>Electronic mail systems</topic><topic>Fatty acids</topic><topic>Fatty Acids - chemistry</topic><topic>Fatty Acids - isolation & purification</topic><topic>Flowers & plants</topic><topic>Metabolites</topic><topic>Natural products</topic><topic>Pharmacy</topic><topic>Phytochemicals</topic><topic>Plant Components, Aerial - chemistry</topic><topic>Plant Extracts - chemistry</topic><topic>Plant Roots - chemistry</topic><topic>Polymerization</topic><topic>Protein Multimerization - drug effects</topic><topic>pyrrolizidine alkaloids</topic><topic>Pyrrolizidine Alkaloids - chemistry</topic><topic>Pyrrolizidine Alkaloids - isolation & purification</topic><topic>Rindera umbellata</topic><topic>Seeds</topic><topic>Seeds - chemistry</topic><topic>Toxicity</topic><topic>Tubulin - chemistry</topic><topic>Tubulin Modulators - chemistry</topic><topic>tubulin polymerization</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mandić, Boris M</creatorcontrib><creatorcontrib>Simić, Milena R</creatorcontrib><creatorcontrib>Vučković, Ivan M</creatorcontrib><creatorcontrib>Vujisić, Ljubodrag V</creatorcontrib><creatorcontrib>Novaković, Miroslav M</creatorcontrib><creatorcontrib>Trifunović, Snežana S</creatorcontrib><creatorcontrib>Nikolić-Mandić, Snežana D</creatorcontrib><creatorcontrib>Tešević, Vele V</creatorcontrib><creatorcontrib>Vajs, Vlatka V</creatorcontrib><creatorcontrib>Milosavljević, Slobodan M</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>ProQuest Central (Alumni)</collection><collection>ProQuest Central</collection><collection>ProQuest Central Essentials</collection><collection>AUTh Library subscriptions: ProQuest Central</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>PML(ProQuest Medical Library)</collection><collection>ProQuest Publicly Available Content database</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><collection>Directory of Open Access Journals</collection><jtitle>Molecules (Basel, Switzerland)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mandić, Boris M</au><au>Simić, Milena R</au><au>Vučković, Ivan M</au><au>Vujisić, Ljubodrag V</au><au>Novaković, Miroslav M</au><au>Trifunović, Snežana S</au><au>Nikolić-Mandić, Snežana D</au><au>Tešević, Vele V</au><au>Vajs, Vlatka V</au><au>Milosavljević, Slobodan M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Pyrrolizidine alkaloids and fatty acids from the endemic plant species Rindera umbellata and the effect of lindelofine-N-oxide on tubulin polymerization</atitle><jtitle>Molecules (Basel, Switzerland)</jtitle><addtitle>Molecules</addtitle><date>2013-09-03</date><risdate>2013</risdate><volume>18</volume><issue>9</issue><spage>10694</spage><epage>10706</epage><pages>10694-10706</pages><issn>1420-3049</issn><eissn>1420-3049</eissn><abstract>The examination of the aerial parts, roots, and seeds of the endemic plant Rindera umbellata is reported in this paper for the first time. Phytochemical investigation of R. umbellata led to the isolation and characterization of ten pyrrolizidine alkaloids and eleven fatty acids in the form of triglycerides. Pyrrolizidine alkaloids 1-9 were found in the aerial parts, 7 and 8 in the roots, and 6-10, together with eleven fatty acids, in the seeds of this plant species. The structures of compounds 1-10 were established based on spectroscopic studies (¹H- and ¹³C-NMR, 2D NMR, IR and CI-MS). After trans-esterification, methyl esters of the fatty acids were analyzed using GC-MS. The effect of lindelofine-N-oxide (7) on tubulin polymerization was determined.</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>24005964</pmid><doi>10.3390/molecules180910694</doi><tpages>13</tpages><oa>free_for_read</oa></addata></record> |
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subjects | Animals Antineoplastic Agents - chemistry Boraginaceae - chemistry Cattle Cell cycle Electronic mail systems Fatty acids Fatty Acids - chemistry Fatty Acids - isolation & purification Flowers & plants Metabolites Natural products Pharmacy Phytochemicals Plant Components, Aerial - chemistry Plant Extracts - chemistry Plant Roots - chemistry Polymerization Protein Multimerization - drug effects pyrrolizidine alkaloids Pyrrolizidine Alkaloids - chemistry Pyrrolizidine Alkaloids - isolation & purification Rindera umbellata Seeds Seeds - chemistry Toxicity Tubulin - chemistry Tubulin Modulators - chemistry tubulin polymerization |
title | Pyrrolizidine alkaloids and fatty acids from the endemic plant species Rindera umbellata and the effect of lindelofine-N-oxide on tubulin polymerization |
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