Chemical constituents isolated from the bark of Guatteria blepharophylla (Annonaceae) and their antiproliferative and antimicrobial activities

dc.creatorCosta, Emmanoel V.
dc.creatorMarques, Francisco de Assis
dc.creatorPinheiro, Maria Lúcia B.
dc.creatorBraga, Raquel M.
dc.creatorDelarmelina, Camila
dc.creatorDuarte, Marta Cristina T.
dc.creatorRuiz, Ana Lúcia T. G.
dc.creatorCarvalho, João Ernesto de
dc.creatorMaia, Beatriz H. L. N. S.
dc.date2011-06-01
dc.date2014-12-23T13:16:28Z
dc.date2015-11-26T11:51:56Z
dc.date2014-12-23T13:16:28Z
dc.date2015-11-26T11:51:56Z
dc.date.accessioned2018-03-28T20:55:11Z
dc.date.available2018-03-28T20:55:11Z
dc.identifierJournal of the Brazilian Chemical Society. Sociedade Brasileira de Química, v. 22, n. 6, p. 1111-1117, 2011.
dc.identifier0103-5053
dc.identifierS0103-50532011000600016
dc.identifier10.1590/S0103-50532011000600016
dc.identifierhttp://dx.doi.org/10.1590/S0103-50532011000600016
dc.identifierhttp://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532011000600016
dc.identifierhttp://www.repositorio.unicamp.br/jspui/handle/REPOSIP/36693
dc.identifierhttp://www.repositorio.unicamp.br/handle/REPOSIP/36693
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/36693
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1237413
dc.descriptionPhytochemical study of the bark of Guatteria blepharophylla (Mart.) Mart. afforded twelve compounds, namely two sesquiterpenes, caryophyllene oxide (1) and spathulenol (3), one xanthone, lichexanthone (2), a mixture of steroids, β-sitosterol (4), and stigmasterol (5), and seven isoquinoline alkaloids, O-methylmoschatoline (6), lysicamine (7), nornuciferine (8), liriodenine (9), isocoreximine (10), subsessiline (11), and isomoschatoline (12). Their structures were established on the basis of spectroscopic methods. Compounds 1-6, 11 and 12 were reported for the first time in this species. The 13C NMR (nuclear magnetic resonance) data for the compounds 11 and 12 are described for the first time in the literature. The antiproliferative activity against human tumour cell lines and antimicrobial activities were investigated for the major compounds. Compound 9 showed significant activity against cell lines of breast (MCF-7, Michigan Cancer Foundation-7), superior to the positive control doxorubicin. Compound 12 presented antifungal activity similar to the positive control nystatin against Candida albicans.
dc.descriptionO estudo fitoquímico das cascas de Guatteria blepharophylla (Mart.) Mart. forneceu 12 compostos, sendo dois sesquiterpenos, óxido de cariofileno (1) e espatulenol (3), uma xantona, liquexantona (2), uma mistura de esteróides, β-sitosterol (4) e estigmasterol (5), e sete alcalóides isoquinolínicos, O-metilmoschatolina (6), lysicamina (7), nornuciferina (8), liriodenina (9), isocoreximina (10), subsessilina (11) e isomoschatolina (12). Suas estruturas foram determinadas através de métodos espectroscópicos. Os compostos 1-6, 11 e 12 são reportados pela primeira vez nesta espécie. Os dados de RMN 13C (ressonância magnética nuclear) para os compostos 11 e 12 são descritos pela primeira vez na literatura. As atividades antiproliferativa em linhagens de células tumorais humanas e antimicrobiana foram investigadas para os compostos majoritários. O composto 9 mostrou significativa atividade contra linhagens de células de mama (MCF-7, Michigan Cancer Foundation-7), superior ao controle positivo doxorrubicina. O composto 12 apresentou atividade antifúngica similar ao controle positivo nistatina contra Candida albicans
dc.description1111
dc.description1117
dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.descriptionCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)
dc.languageen
dc.publisherSociedade Brasileira de Química
dc.relationJournal of the Brazilian Chemical Society
dc.rightsaberto
dc.sourceSciELO
dc.subjectGuatteria blepharophylla
dc.subjectantifungal and antiproliferative activities
dc.subjectalkaloids
dc.subjectterpenes
dc.subjectxanthone
dc.titleChemical constituents isolated from the bark of Guatteria blepharophylla (Annonaceae) and their antiproliferative and antimicrobial activities
dc.typeArtículos de revistas


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