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dc.contributor.authorWALDREN, STEPHENen
dc.contributor.authorDE SOUSA MENEZES, FABIOen
dc.contributor.authorPARNELL, JOHNen
dc.date.accessioned2011-05-20T11:33:15Z
dc.date.available2011-05-20T11:33:15Z
dc.date.issued2011en
dc.date.submitted2011en
dc.identifier.citationNiko S. Radulović, Ana B. Miltojević, Michael McDermott, Steve Waldren, John Adrian Parnell, Mariana Martins Gomes Pinheiro, Patricia Dias Fernandes, Fabio de Sousa Menezes, Identification of a new antinociceptive alkaloid isopropyl N-methylanthranilate from the essential oil of Choisya ternata Kunth, Journal of Ethnopharmacology, 135, 3, 2011, 610-619en
dc.identifier.otherYen
dc.identifier.urihttp://hdl.handle.net/2262/55877
dc.descriptionPUBLISHEDen
dc.description.abstractEthnopharmacological relevance: Mexican people employed infusion of leaves of Choisya ternata Kunth for their antispasmodic and ?simulative properties? Aim of the study: In the present study the detailed GC and GC-MS analyses of the essential oil of Choisya ternata Kunth (Rutaceae) were performed. The presence of a minor constituent isopropyl N-methylanthranilate (1) was revealed among other identified volatiles. A synthesis of 1 was undertaken in order to corroborate this find and obtain gram quantities that would allow the testing of its biological activity (peripheral and central antinociceptive activity) Material and methods: The oils were investigated by GC and GC-MS. Synthesized compounds were spectrally characterized (UV-Vis, IR, 1D and 2D NMR, MS). The obtained synthetic samples of compounds were assayed for peripheral and central antinociceptive activity in two models (effects on acetic acid induced writhing in mice and the hot plate test for nociception). Results: Detailed GC and GC-MS analyses of the essential oil of Choisya ternata Kunth (Rutaceae) among 157 other identified volatiles revealed the presence of a minor constituent isopropyl N-methylanthranilate (1). Compound 1, named ternanthranin, is therefore detected as a natural product for the first time with a very restricted occurrence (samples of several citrus oils were screened for the presence of 1). The antinociceptive activities were assayed for ternanthtanin, the two other synthetic analogs, methyl and propyl N-methylanthranilate, as well as the essential oil and the crude ethanol extract of the leaves. The results clearly demonstrate a very high (even significant at 0.3 mg/kg) dose dependent activity for the anthranilates (and the extracts). Isopropyl N-methylanthranilate showed the highest, while methyl N-methylanthranilate showed the lowest activity (with the methyl ester at 3 mg/kg still better than acetylsalicylic acid, at 200 mg/kg, in the first, or comparable with morphine, at 5 mg/kg, in the second test). Conclusion: This study once again revealed that detailed investigations of plant species with ethnopharmacologically documented activity may yield new natural compounds?a new alkaloid (ternanthranin), a volatile simple anthranilate that can be considered responsible for the antinociceptive activity of the crude plant extracts. Keywords: Choisya ternata; essential oil; synthesis; esters of N-methylanthranilic acid; isopropyl N-methylanthranilate; peripheral and central antinociceptive activitie.en
dc.description.sponsorshipThe authors are grateful to the Botany Department, Faculty of Natural Sciences, Trinity College Dublin as well as to the Staff of the Botanic Gardens, TCD. The authors from Brazil thank the Conselho Nacional de Desenvolvimento Cientifico e Tecnologico (CNPq, grant support and fellowship to PDF), Fundac?o Carlos Chagas Filho de Apoio a Pesquisa do Estado do Rio de Janeiro (FAPERJ, grant support to PDF), and Conselho de Administrac?o de Pessoal de Ensino Superior (CAPES, fellowship to MMGP). FSM is grateful to the Start up grant No. 51002.516.R01336 from Trinity College Dublin. The authors from Serbia acknowledge funds received from the Ministry of Science and Technological Development of Serbia (Project 172061).en
dc.format.extent610-619en
dc.language.isoenen
dc.relation.ispartofseriesJournal of Ethnopharmacologyen
dc.relation.ispartofseries135en
dc.relation.ispartofseries3en
dc.rightsYen
dc.subjectPharmacologyen
dc.subjectChoisya ternataen
dc.titleIdentification of a new antinociceptive alkaloid isopropyl N-methylanthranilate from the essential oil of Choisya ternata Kunthen
dc.typeJournal Articleen
dc.type.supercollectionscholarly_publicationsen
dc.type.supercollectionrefereed_publicationsen
dc.identifier.peoplefinderurlhttp://people.tcd.ie/desouzafen
dc.identifier.peoplefinderurlhttp://people.tcd.ie/jparnellen
dc.identifier.peoplefinderurlhttp://people.tcd.ie/swaldrenen
dc.identifier.rssinternalid71884en
dc.subject.TCDThemeImmunology, Inflammation & Infectionen
dc.subject.TCDThemeInternational Developmenten
dc.identifier.rssurihttp://dx.doi.org/10.1016/j.jep.2011.03.035en


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