Diterpenes and sesquitrpenes from Mikania banisteriae

Two new ent-kaurane diterpenes, 18,19-diacetoxy-ent-kaur-16-ene and 17-oxo-ent-kaur-15(16)-en-18-oic acid, were isolated from the aerial parts of Mikania banisteriae, together with the known ent-kauranes ent-kaur-16-en-18-oic acid and ent-kaur-16-en-18-ol. The structures were established by mass spe...

Descripción completa

Detalles Bibliográficos
Autores: Lobitz, G. O., Tamayo Castillo, Giselle, Merfort, Irmgard
Tipo de recurso: artículo
Fecha de publicación:1997
País:Costa Rica
Institución:Universidad de Costa Rica
Repositorio:Kérwá
Idioma:inglés
OAI Identifier:oai:kerwa.ucr.ac.cr:10669/87845
Acceso en línea:https://www.sciencedirect.com/science/article/pii/S0031942297002288
https://hdl.handle.net/10669/87845
Access Level:acceso embargado
Palabra clave:Mikania banisteriae
Asteraceae
Diterpenes
Ent-kauranes
Sesquiterpenes
Eudesmane
Eudesmanolides
Biological studies
PHYTOCHEMISTRY
id CR_15a7c41de0996bec0a4da2e083f8ec37
oai_identifier_str oai:kerwa.ucr.ac.cr:10669/87845
network_acronym_str CR
network_name_str Costa Rica
repository_id_str
dc.title.es_ES.fl_str_mv Diterpenes and sesquitrpenes from Mikania banisteriae
title Diterpenes and sesquitrpenes from Mikania banisteriae
spellingShingle Diterpenes and sesquitrpenes from Mikania banisteriae
Lobitz, G. O.
Mikania banisteriae
Asteraceae
Diterpenes
Ent-kauranes
Sesquiterpenes
Eudesmane
Eudesmanolides
Biological studies
PHYTOCHEMISTRY
title_short Diterpenes and sesquitrpenes from Mikania banisteriae
title_full Diterpenes and sesquitrpenes from Mikania banisteriae
title_fullStr Diterpenes and sesquitrpenes from Mikania banisteriae
title_full_unstemmed Diterpenes and sesquitrpenes from Mikania banisteriae
title_sort Diterpenes and sesquitrpenes from Mikania banisteriae
dc.creator.none.fl_str_mv Lobitz, G. O.
Tamayo Castillo, Giselle
Merfort, Irmgard
author Lobitz, G. O.
author_facet Lobitz, G. O.
Tamayo Castillo, Giselle
Merfort, Irmgard
author_role author
author2 Tamayo Castillo, Giselle
Merfort, Irmgard
author2_role author
author
dc.subject.es_ES.fl_str_mv Mikania banisteriae
Asteraceae
Diterpenes
Ent-kauranes
Sesquiterpenes
Eudesmane
Eudesmanolides
Biological studies
PHYTOCHEMISTRY
topic Mikania banisteriae
Asteraceae
Diterpenes
Ent-kauranes
Sesquiterpenes
Eudesmane
Eudesmanolides
Biological studies
PHYTOCHEMISTRY
description Two new ent-kaurane diterpenes, 18,19-diacetoxy-ent-kaur-16-ene and 17-oxo-ent-kaur-15(16)-en-18-oic acid, were isolated from the aerial parts of Mikania banisteriae, together with the known ent-kauranes ent-kaur-16-en-18-oic acid and ent-kaur-16-en-18-ol. The structures were established by mass spectrometry, 1H NMR and partly 13C NMR spectroscopy. In addition, the sesquiterpene lactones eudesma-4(15),7(11)-dien-8β,12-olide and eudesma-4(15),7(11),8(9)-trien-12-olide as well as the sesquiterpenes 1β,6α-dihydroxyeudesm-4(15)-ene and caryophylleno-xide were identified by direct comparison (TLC, GC, GC-MS) with authentic samples. The chemotaxonomic significance is briefly discussed. ent-Kaur-16-en-18-oic acid and ent-kaur-16-en-19-oic acid showed no antifeedant, antimicrobial and antiinflammatory properties.
publishDate 1997
dc.date.issued.none.fl_str_mv 1997
dc.date.accessioned.none.fl_str_mv 2022-12-01T20:16:50Z
dc.date.available.none.fl_str_mv 2022-12-01T20:16:50Z
dc.type.es_ES.fl_str_mv artículo original
dc.type.none.fl_str_mv http://purl.org/coar/resource_type/c_2df8fbb1
info:eu-repo/semantics/article
format article
dc.identifier.citation.es_ES.fl_str_mv https://www.sciencedirect.com/science/article/pii/S0031942297002288
dc.identifier.issn.none.fl_str_mv 0031-9422
dc.identifier.uri.none.fl_str_mv https://hdl.handle.net/10669/87845
dc.identifier.doi.none.fl_str_mv 10.1016/S0031-9422(97)00228-8
url https://www.sciencedirect.com/science/article/pii/S0031942297002288
https://hdl.handle.net/10669/87845
identifier_str_mv 0031-9422
10.1016/S0031-9422(97)00228-8
dc.language.iso.es_ES.fl_str_mv eng
language eng
dc.rights.none.fl_str_mv acceso embargado
http://purl.org/coar/access_right/c_f1cf
info:eu-repo/semantics/embargoedAccess
rights_invalid_str_mv acceso embargado
http://purl.org/coar/access_right/c_f1cf
eu_rights_str_mv embargoedAccess
dc.source.es_ES.fl_str_mv Phytochemistry; Vol. 21 Núm. 6: 1997 pp.1868-1870.
dc.source.none.fl_str_mv reponame:Kérwá
instname:Universidad de Costa Rica
instacron:UCR
instname_str Universidad de Costa Rica
instacron_str UCR
institution UCR
reponame_str Kérwá
collection Kérwá
bitstream.url.fl_str_mv https://www.kerwa.ucr.ac.cr/bitstreams/116a7aad-fd91-4eec-af5a-f8de19a425e8/download
https://www.kerwa.ucr.ac.cr/bitstreams/aaae2bd2-6fe9-4904-95bd-0b59ce617861/download
https://www.kerwa.ucr.ac.cr/bitstreams/0fc58f63-c51a-499b-b2be-5afa79bcdae4/download
https://www.kerwa.ucr.ac.cr/bitstreams/86bb8275-1731-4e13-bce7-c0f80d3bc6c3/download
bitstream.checksum.fl_str_mv 44ae5839bc6497e3c892c5ee8e4284f1
255f530431d1f7aa6f4ca07a0a1f2884
e28e1fc759c4622b7b6e7b925d42cb0c
54629df637bb9e07019ddf93028dd960
bitstream.checksumAlgorithm.fl_str_mv MD5
MD5
MD5
MD5
repository.name.fl_str_mv Kérwá - Universidad de Costa Rica
repository.mail.fl_str_mv meilyn.garro@ucr.ac.cr
_version_ 1849325628227059712
spelling Lobitz, G. O.388d6ff4-665a-4745-a5aa-07030648d477Tamayo Castillo, Giselle610169ed-cccd-4ad0-8df7-5849f7b8fd1f600Merfort, Irmgarde4467de7-9fde-41f9-aefb-28f7ca7fb1096002022-12-01T20:16:50Z2022-12-01T20:16:50Z1997https://www.sciencedirect.com/science/article/pii/S00319422970022880031-9422https://hdl.handle.net/10669/8784510.1016/S0031-9422(97)00228-8Two new ent-kaurane diterpenes, 18,19-diacetoxy-ent-kaur-16-ene and 17-oxo-ent-kaur-15(16)-en-18-oic acid, were isolated from the aerial parts of Mikania banisteriae, together with the known ent-kauranes ent-kaur-16-en-18-oic acid and ent-kaur-16-en-18-ol. The structures were established by mass spectrometry, 1H NMR and partly 13C NMR spectroscopy. In addition, the sesquiterpene lactones eudesma-4(15),7(11)-dien-8β,12-olide and eudesma-4(15),7(11),8(9)-trien-12-olide as well as the sesquiterpenes 1β,6α-dihydroxyeudesm-4(15)-ene and caryophylleno-xide were identified by direct comparison (TLC, GC, GC-MS) with authentic samples. The chemotaxonomic significance is briefly discussed. ent-Kaur-16-en-18-oic acid and ent-kaur-16-en-19-oic acid showed no antifeedant, antimicrobial and antiinflammatory properties.Institut für Pharmazeutische Chemie//IPC/AlemaniaUniversität Düsseldorf//HHU/AlemaniaUniversidad Nacional//UNA/Costa RicaInstitut für Pharmazeutische Biologie//IPB/AlemaniaUniversity of Würzburg//JMU/AlemaniaShanghai Institute of Materia Medica///ChinaUCR::Vicerrectoría de Docencia::Ciencias Básicas::Facultad de Ciencias::Escuela de Químicaengacceso embargadohttp://purl.org/coar/access_right/c_f1cfinfo:eu-repo/semantics/embargoedAccessPhytochemistry; Vol. 21 Núm. 6: 1997 pp.1868-1870.reponame:Kérwáinstname:Universidad de Costa Ricainstacron:UCRMikania banisteriaeAsteraceaeDiterpenesEnt-kauranesSesquiterpenesEudesmaneEudesmanolidesBiological studiesPHYTOCHEMISTRYDiterpenes and sesquitrpenes from Mikania banisteriaeartículo originalhttp://purl.org/coar/resource_type/c_2df8fbb1info:eu-repo/semantics/articleLICENSElicense.txtlicense.txttext/plain; charset=utf-83585https://www.kerwa.ucr.ac.cr/bitstreams/116a7aad-fd91-4eec-af5a-f8de19a425e8/download44ae5839bc6497e3c892c5ee8e4284f1MD52ORIGINAL16-Mikania_banisterae_Phytochemistry_1997_46_161.pdf16-Mikania_banisterae_Phytochemistry_1997_46_161.pdfArtículo principalapplication/pdf222445https://www.kerwa.ucr.ac.cr/bitstreams/aaae2bd2-6fe9-4904-95bd-0b59ce617861/download255f530431d1f7aa6f4ca07a0a1f2884MD51TEXT16-Mikania_banisterae_Phytochemistry_1997_46_161.pdf.txt16-Mikania_banisterae_Phytochemistry_1997_46_161.pdf.txtExtracted texttext/plain13682https://www.kerwa.ucr.ac.cr/bitstreams/0fc58f63-c51a-499b-b2be-5afa79bcdae4/downloade28e1fc759c4622b7b6e7b925d42cb0cMD53THUMBNAIL16-Mikania_banisterae_Phytochemistry_1997_46_161.pdf.jpg16-Mikania_banisterae_Phytochemistry_1997_46_161.pdf.jpgIM Thumbnailimage/jpeg9970https://www.kerwa.ucr.ac.cr/bitstreams/86bb8275-1731-4e13-bce7-c0f80d3bc6c3/download54629df637bb9e07019ddf93028dd960MD5410669/878452024-06-21 10:04:27.838embargo2150-12-01oai:kerwa.ucr.ac.cr:10669/87845https://www.kerwa.ucr.ac.crInstitucionalhttp://www.kerwa.ucr.ac.crUniversidadhttp://www.ucr.ac.crhttps://kerwa.ucr.ac.cr/oai/requestmeilyn.garro@ucr.ac.crCosta RicaNo aplicaNo aplicaNo aplicaopendoar:18712025-03-29T18:04:33.092Kérwá - Universidad de Costa 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
score 15.812455