Complete assignments of NMR data and assessment of trypanocidal activity of new eremantholide C derivatives
Chemical transformations of eremantholide C (1), a sesquiterpene lactone that was isolated from Lychnophora trichocarpha Spreng. led to five new derivatives: 1′,2′- epoxyeremantholide C (2), 5-n-propylamine-4,5-dihydro-1′,2′-epoxyeremantholide C (3), 5-n-propylammonium-4,5-dihydro-1′,2′-epoxyeremantholide C chloride (4), 5-n-propylammonium-4,5-dihydroeremantolide C chloride (5) and 16-O-ethyleremantholide C (6). The structures of all these derivatives were assigned on the basis of IR, MS, 1H and 13C NMR data by 1D and 2D techniques. Eremantholide C and the derivatives 2, 4 and 5 were evaluated against trypomastigotes Y and CL strains of Trypanosoma cruzi. Eremantholide C completely inhibited the growth of both the parasites strains while all derivatives were partially active against the CL strain and inactive against the Y strain.
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2014
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oai:scielo:S0001-376520140004015632015-10-27Complete assignments of NMR data and assessment of trypanocidal activity of new eremantholide C derivativesSAÚDE-GUIMARÃES,DÊNIA A.RASLAN,DÉLIO S.CHIARI,EGLEROLIVEIRA,ALAÍDE B. DE Eremantholide C derivatives Lychnophora trichocarpha NMR sesquiterpene lactones trypanocidal activity Chemical transformations of eremantholide C (1), a sesquiterpene lactone that was isolated from Lychnophora trichocarpha Spreng. led to five new derivatives: 1′,2′- epoxyeremantholide C (2), 5-n-propylamine-4,5-dihydro-1′,2′-epoxyeremantholide C (3), 5-n-propylammonium-4,5-dihydro-1′,2′-epoxyeremantholide C chloride (4), 5-n-propylammonium-4,5-dihydroeremantolide C chloride (5) and 16-O-ethyleremantholide C (6). The structures of all these derivatives were assigned on the basis of IR, MS, 1H and 13C NMR data by 1D and 2D techniques. Eremantholide C and the derivatives 2, 4 and 5 were evaluated against trypomastigotes Y and CL strains of Trypanosoma cruzi. Eremantholide C completely inhibited the growth of both the parasites strains while all derivatives were partially active against the CL strain and inactive against the Y strain.info:eu-repo/semantics/openAccessAcademia Brasileira de CiênciasAnais da Academia Brasileira de Ciências v.86 n.4 20142014-12-01info:eu-repo/semantics/articletext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0001-37652014000401563en10.1590/0001-3765201420140167 |
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SAÚDE-GUIMARÃES,DÊNIA A. RASLAN,DÉLIO S. CHIARI,EGLER OLIVEIRA,ALAÍDE B. DE |
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SAÚDE-GUIMARÃES,DÊNIA A. RASLAN,DÉLIO S. CHIARI,EGLER OLIVEIRA,ALAÍDE B. DE Complete assignments of NMR data and assessment of trypanocidal activity of new eremantholide C derivatives |
author_facet |
SAÚDE-GUIMARÃES,DÊNIA A. RASLAN,DÉLIO S. CHIARI,EGLER OLIVEIRA,ALAÍDE B. DE |
author_sort |
SAÚDE-GUIMARÃES,DÊNIA A. |
title |
Complete assignments of NMR data and assessment of trypanocidal activity of new eremantholide C derivatives |
title_short |
Complete assignments of NMR data and assessment of trypanocidal activity of new eremantholide C derivatives |
title_full |
Complete assignments of NMR data and assessment of trypanocidal activity of new eremantholide C derivatives |
title_fullStr |
Complete assignments of NMR data and assessment of trypanocidal activity of new eremantholide C derivatives |
title_full_unstemmed |
Complete assignments of NMR data and assessment of trypanocidal activity of new eremantholide C derivatives |
title_sort |
complete assignments of nmr data and assessment of trypanocidal activity of new eremantholide c derivatives |
description |
Chemical transformations of eremantholide C (1), a sesquiterpene lactone that was isolated from Lychnophora trichocarpha Spreng. led to five new derivatives: 1′,2′- epoxyeremantholide C (2), 5-n-propylamine-4,5-dihydro-1′,2′-epoxyeremantholide C (3), 5-n-propylammonium-4,5-dihydro-1′,2′-epoxyeremantholide C chloride (4), 5-n-propylammonium-4,5-dihydroeremantolide C chloride (5) and 16-O-ethyleremantholide C (6). The structures of all these derivatives were assigned on the basis of IR, MS, 1H and 13C NMR data by 1D and 2D techniques. Eremantholide C and the derivatives 2, 4 and 5 were evaluated against trypomastigotes Y and CL strains of Trypanosoma cruzi. Eremantholide C completely inhibited the growth of both the parasites strains while all derivatives were partially active against the CL strain and inactive against the Y strain. |
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Academia Brasileira de Ciências |
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2014 |
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http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0001-37652014000401563 |
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