Triterpenes from maytenus macrocarpa and evaluation of their anti-hiv activity

Detalhes bibliográficos
Autor(a) principal: Piacente, Sonia
Data de Publicação: 2006
Outros Autores: Dos Santos, Lourdes Campaner [UNESP], Mahmood, Naheed, Pizza, Cosimo
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UNESP
Texto Completo: http://dx.doi.org/10.1177/1934578x0600101201
http://hdl.handle.net/11449/219466
Resumo: A set of pentacyclic triterpenes has been isolated from the bark of Maytenus macrocarpa (Celastraceae). It includes two new olean-12-ene derivatives, namely 3β, 22α-dihydroxy-olean-12-en-30-oic acid (1) and 22α-hydroxy-olean-12-en-3-oxo-30-oic acid (2), and the new urs-12-ene derivative 3-(E)-coumaroyluvaol (7), along with 10 known compounds possessing olean-12- ene, urs-12-ene, lupane and friedelane skeletons. The structures have been elucidated by extensive spectroscopic methods including 1D- and 2D-NMR experiments, as well as ESI-MS analysis. All isolated compounds were tested for anti-HIV activity in C8166 cells infected with HIV-1MN. The most active compound was 22α-hydroxy-12-en-3-oxo-29-oic acid (triterpenonic acid A, 4), with an EC50 value of 1 μg/mL and a selectivity index of 35.
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spelling Triterpenes from maytenus macrocarpa and evaluation of their anti-hiv activityAnti-HIV activityCelastraceaeMaytenus macrocarpaPentacyclic triterpenesA set of pentacyclic triterpenes has been isolated from the bark of Maytenus macrocarpa (Celastraceae). It includes two new olean-12-ene derivatives, namely 3β, 22α-dihydroxy-olean-12-en-30-oic acid (1) and 22α-hydroxy-olean-12-en-3-oxo-30-oic acid (2), and the new urs-12-ene derivative 3-(E)-coumaroyluvaol (7), along with 10 known compounds possessing olean-12- ene, urs-12-ene, lupane and friedelane skeletons. The structures have been elucidated by extensive spectroscopic methods including 1D- and 2D-NMR experiments, as well as ESI-MS analysis. All isolated compounds were tested for anti-HIV activity in C8166 cells infected with HIV-1MN. The most active compound was 22α-hydroxy-12-en-3-oxo-29-oic acid (triterpenonic acid A, 4), with an EC50 value of 1 μg/mL and a selectivity index of 35.Dipartimento di Scienze Farmaceutiche University of Salerno, via Ponte Don Melillo, 84084 Fisciano SalernoInstituto de Quimica UNESP, CP335, CEP, 14801-970 Araraquara, SPRetroscreen Ltd Academic Virology London Hospital, 64 Turner Street, London E1 2ADInstituto de Quimica UNESP, CP335, CEP, 14801-970 Araraquara, SPUniversity of SalernoUniversidade Estadual Paulista (UNESP)London HospitalPiacente, SoniaDos Santos, Lourdes Campaner [UNESP]Mahmood, NaheedPizza, Cosimo2022-04-28T18:55:44Z2022-04-28T18:55:44Z2006-01-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article1073-1078http://dx.doi.org/10.1177/1934578x0600101201Natural Product Communications, v. 1, n. 12, p. 1073-1078, 2006.1555-94751934-578Xhttp://hdl.handle.net/11449/21946610.1177/1934578x06001012012-s2.0-48149086277Scopusreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengNatural Product Communicationsinfo:eu-repo/semantics/openAccess2022-04-28T18:55:44Zoai:repositorio.unesp.br:11449/219466Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462022-04-28T18:55:44Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false
dc.title.none.fl_str_mv Triterpenes from maytenus macrocarpa and evaluation of their anti-hiv activity
title Triterpenes from maytenus macrocarpa and evaluation of their anti-hiv activity
spellingShingle Triterpenes from maytenus macrocarpa and evaluation of their anti-hiv activity
Piacente, Sonia
Anti-HIV activity
Celastraceae
Maytenus macrocarpa
Pentacyclic triterpenes
title_short Triterpenes from maytenus macrocarpa and evaluation of their anti-hiv activity
title_full Triterpenes from maytenus macrocarpa and evaluation of their anti-hiv activity
title_fullStr Triterpenes from maytenus macrocarpa and evaluation of their anti-hiv activity
title_full_unstemmed Triterpenes from maytenus macrocarpa and evaluation of their anti-hiv activity
title_sort Triterpenes from maytenus macrocarpa and evaluation of their anti-hiv activity
author Piacente, Sonia
author_facet Piacente, Sonia
Dos Santos, Lourdes Campaner [UNESP]
Mahmood, Naheed
Pizza, Cosimo
author_role author
author2 Dos Santos, Lourdes Campaner [UNESP]
Mahmood, Naheed
Pizza, Cosimo
author2_role author
author
author
dc.contributor.none.fl_str_mv University of Salerno
Universidade Estadual Paulista (UNESP)
London Hospital
dc.contributor.author.fl_str_mv Piacente, Sonia
Dos Santos, Lourdes Campaner [UNESP]
Mahmood, Naheed
Pizza, Cosimo
dc.subject.por.fl_str_mv Anti-HIV activity
Celastraceae
Maytenus macrocarpa
Pentacyclic triterpenes
topic Anti-HIV activity
Celastraceae
Maytenus macrocarpa
Pentacyclic triterpenes
description A set of pentacyclic triterpenes has been isolated from the bark of Maytenus macrocarpa (Celastraceae). It includes two new olean-12-ene derivatives, namely 3β, 22α-dihydroxy-olean-12-en-30-oic acid (1) and 22α-hydroxy-olean-12-en-3-oxo-30-oic acid (2), and the new urs-12-ene derivative 3-(E)-coumaroyluvaol (7), along with 10 known compounds possessing olean-12- ene, urs-12-ene, lupane and friedelane skeletons. The structures have been elucidated by extensive spectroscopic methods including 1D- and 2D-NMR experiments, as well as ESI-MS analysis. All isolated compounds were tested for anti-HIV activity in C8166 cells infected with HIV-1MN. The most active compound was 22α-hydroxy-12-en-3-oxo-29-oic acid (triterpenonic acid A, 4), with an EC50 value of 1 μg/mL and a selectivity index of 35.
publishDate 2006
dc.date.none.fl_str_mv 2006-01-01
2022-04-28T18:55:44Z
2022-04-28T18:55:44Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://dx.doi.org/10.1177/1934578x0600101201
Natural Product Communications, v. 1, n. 12, p. 1073-1078, 2006.
1555-9475
1934-578X
http://hdl.handle.net/11449/219466
10.1177/1934578x0600101201
2-s2.0-48149086277
url http://dx.doi.org/10.1177/1934578x0600101201
http://hdl.handle.net/11449/219466
identifier_str_mv Natural Product Communications, v. 1, n. 12, p. 1073-1078, 2006.
1555-9475
1934-578X
10.1177/1934578x0600101201
2-s2.0-48149086277
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Natural Product Communications
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 1073-1078
dc.source.none.fl_str_mv Scopus
reponame:Repositório Institucional da UNESP
instname:Universidade Estadual Paulista (UNESP)
instacron:UNESP
instname_str Universidade Estadual Paulista (UNESP)
instacron_str UNESP
institution UNESP
reponame_str Repositório Institucional da UNESP
collection Repositório Institucional da UNESP
repository.name.fl_str_mv Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)
repository.mail.fl_str_mv
_version_ 1797790114684862464

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