Aurapten, a coumarin with growth inhibition against Leishmania major promastigotes
Autor(a) principal: | |
---|---|
Data de Publicação: | 2004 |
Outros Autores: | , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Brazilian Journal of Medical and Biological Research |
Texto Completo: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-879X2004001200010 |
Resumo: | Several natural compounds have been identified for the treatment of leishmaniasis. Among them are some alkaloids, chalcones, lactones, tetralones, and saponins. The new compound reported here, 7-geranyloxycoumarin, called aurapten, belongs to the chemical class of the coumarins and has a molecular weight of 298.37. The compund was extracted from the Rutaceae species Esenbeckia febrifuga and was purified from a hexane extract starting from 407.7 g of dried leaves and followed by four silica gel chromatographic fractionation steps using different solvents as the mobile phase. The resulting compound (47 mg) of shows significant growth inhibition with an LD50 of 30 µM against the tropical parasite Leishmania major, which causes severe clinical manifestations in humans and is endemic in the tropical and subtropical regions. In the present study, we investigated the atomic structure of aurapten in order to determine the existence of common structural motifs that might be related to other coumarins and potentially to other identified inhibitors of Leishmania growth and viability. This compound has a comparable inhibitory activity of other isolated molecules. The aurapten is a planar molecule constituted of an aromatic system with electron delocalization. A hydrophobic side chain consisting of ten carbon atoms with two double bonds and negative density has been identified and may be relevant for further compound synthesis. |
id |
ABDC-1_fb4180b7717abb6392b15efd3f347080 |
---|---|
oai_identifier_str |
oai:scielo:S0100-879X2004001200010 |
network_acronym_str |
ABDC-1 |
network_name_str |
Brazilian Journal of Medical and Biological Research |
repository_id_str |
|
spelling |
Aurapten, a coumarin with growth inhibition against Leishmania major promastigotesCoumarinAurapten (7-geranyloxycoumarin)X-raysLeishmaniaInhibitorSeveral natural compounds have been identified for the treatment of leishmaniasis. Among them are some alkaloids, chalcones, lactones, tetralones, and saponins. The new compound reported here, 7-geranyloxycoumarin, called aurapten, belongs to the chemical class of the coumarins and has a molecular weight of 298.37. The compund was extracted from the Rutaceae species Esenbeckia febrifuga and was purified from a hexane extract starting from 407.7 g of dried leaves and followed by four silica gel chromatographic fractionation steps using different solvents as the mobile phase. The resulting compound (47 mg) of shows significant growth inhibition with an LD50 of 30 µM against the tropical parasite Leishmania major, which causes severe clinical manifestations in humans and is endemic in the tropical and subtropical regions. In the present study, we investigated the atomic structure of aurapten in order to determine the existence of common structural motifs that might be related to other coumarins and potentially to other identified inhibitors of Leishmania growth and viability. This compound has a comparable inhibitory activity of other isolated molecules. The aurapten is a planar molecule constituted of an aromatic system with electron delocalization. A hydrophobic side chain consisting of ten carbon atoms with two double bonds and negative density has been identified and may be relevant for further compound synthesis.Associação Brasileira de Divulgação Científica2004-12-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-879X2004001200010Brazilian Journal of Medical and Biological Research v.37 n.12 2004reponame:Brazilian Journal of Medical and Biological Researchinstname:Associação Brasileira de Divulgação Científica (ABDC)instacron:ABDC10.1590/S0100-879X2004001200010info:eu-repo/semantics/openAccessNapolitano,H.B.Silva,M.Ellena,J.Rodrigues,B.D.G.Almeida,A.L.C.Vieira,P.C.Oliva,G.Thiemann,O.H.eng2004-11-17T00:00:00Zoai:scielo:S0100-879X2004001200010Revistahttps://www.bjournal.org/https://old.scielo.br/oai/scielo-oai.phpbjournal@terra.com.br||bjournal@terra.com.br1414-431X0100-879Xopendoar:2004-11-17T00:00Brazilian Journal of Medical and Biological Research - Associação Brasileira de Divulgação Científica (ABDC)false |
dc.title.none.fl_str_mv |
Aurapten, a coumarin with growth inhibition against Leishmania major promastigotes |
title |
Aurapten, a coumarin with growth inhibition against Leishmania major promastigotes |
spellingShingle |
Aurapten, a coumarin with growth inhibition against Leishmania major promastigotes Napolitano,H.B. Coumarin Aurapten (7-geranyloxycoumarin) X-rays Leishmania Inhibitor |
title_short |
Aurapten, a coumarin with growth inhibition against Leishmania major promastigotes |
title_full |
Aurapten, a coumarin with growth inhibition against Leishmania major promastigotes |
title_fullStr |
Aurapten, a coumarin with growth inhibition against Leishmania major promastigotes |
title_full_unstemmed |
Aurapten, a coumarin with growth inhibition against Leishmania major promastigotes |
title_sort |
Aurapten, a coumarin with growth inhibition against Leishmania major promastigotes |
author |
Napolitano,H.B. |
author_facet |
Napolitano,H.B. Silva,M. Ellena,J. Rodrigues,B.D.G. Almeida,A.L.C. Vieira,P.C. Oliva,G. Thiemann,O.H. |
author_role |
author |
author2 |
Silva,M. Ellena,J. Rodrigues,B.D.G. Almeida,A.L.C. Vieira,P.C. Oliva,G. Thiemann,O.H. |
author2_role |
author author author author author author author |
dc.contributor.author.fl_str_mv |
Napolitano,H.B. Silva,M. Ellena,J. Rodrigues,B.D.G. Almeida,A.L.C. Vieira,P.C. Oliva,G. Thiemann,O.H. |
dc.subject.por.fl_str_mv |
Coumarin Aurapten (7-geranyloxycoumarin) X-rays Leishmania Inhibitor |
topic |
Coumarin Aurapten (7-geranyloxycoumarin) X-rays Leishmania Inhibitor |
description |
Several natural compounds have been identified for the treatment of leishmaniasis. Among them are some alkaloids, chalcones, lactones, tetralones, and saponins. The new compound reported here, 7-geranyloxycoumarin, called aurapten, belongs to the chemical class of the coumarins and has a molecular weight of 298.37. The compund was extracted from the Rutaceae species Esenbeckia febrifuga and was purified from a hexane extract starting from 407.7 g of dried leaves and followed by four silica gel chromatographic fractionation steps using different solvents as the mobile phase. The resulting compound (47 mg) of shows significant growth inhibition with an LD50 of 30 µM against the tropical parasite Leishmania major, which causes severe clinical manifestations in humans and is endemic in the tropical and subtropical regions. In the present study, we investigated the atomic structure of aurapten in order to determine the existence of common structural motifs that might be related to other coumarins and potentially to other identified inhibitors of Leishmania growth and viability. This compound has a comparable inhibitory activity of other isolated molecules. The aurapten is a planar molecule constituted of an aromatic system with electron delocalization. A hydrophobic side chain consisting of ten carbon atoms with two double bonds and negative density has been identified and may be relevant for further compound synthesis. |
publishDate |
2004 |
dc.date.none.fl_str_mv |
2004-12-01 |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-879X2004001200010 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-879X2004001200010 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.1590/S0100-879X2004001200010 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
text/html |
dc.publisher.none.fl_str_mv |
Associação Brasileira de Divulgação Científica |
publisher.none.fl_str_mv |
Associação Brasileira de Divulgação Científica |
dc.source.none.fl_str_mv |
Brazilian Journal of Medical and Biological Research v.37 n.12 2004 reponame:Brazilian Journal of Medical and Biological Research instname:Associação Brasileira de Divulgação Científica (ABDC) instacron:ABDC |
instname_str |
Associação Brasileira de Divulgação Científica (ABDC) |
instacron_str |
ABDC |
institution |
ABDC |
reponame_str |
Brazilian Journal of Medical and Biological Research |
collection |
Brazilian Journal of Medical and Biological Research |
repository.name.fl_str_mv |
Brazilian Journal of Medical and Biological Research - Associação Brasileira de Divulgação Científica (ABDC) |
repository.mail.fl_str_mv |
bjournal@terra.com.br||bjournal@terra.com.br |
_version_ |
1754302933441183744 |