Terpenoids from Leaves of Guarea macrophylla Display In Vitro Cytotoxic Activity and Induce Apoptosis In Melanoma Cells

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dc.citation.issue16
dc.citation.volume83
dc.contributor.authorConserva, Geanne Alexandra A. [UNIFESP]
dc.contributor.authorGirola, Natalia [UNIFESP]
dc.contributor.authorFigueiredo, Carlos R. [UNIFESP]
dc.contributor.authorAzevedo, Ricardo A.
dc.contributor.authorMousdell, Sasha
dc.contributor.authorSartorelli, Patricia [UNIFESP]
dc.contributor.authorSoares, Marisi G.
dc.contributor.authorAntar, Guilherme M.
dc.contributor.authorLago, Joao Henrique G.
dc.coverageStuttgart
dc.date.accessioned2020-09-01T13:21:26Z
dc.date.available2020-09-01T13:21:26Z
dc.date.issued2017
dc.description.abstractGuarea macrophylla is a Brazilian plant species that has been used in folk medicine to treat a range of diseases. Our ongoing work focuses on the discovery of new bioactive natural products derived from Brazilian flora. The current study describes the identification of cytotoxic compounds from the EtOH extract of leaves from G. macrophylla using bioactivity-guided fractionation. This approach resulted in the isolation and characterization of four compounds: cycloart-23E-ene-3 beta,25-diol (1), (23S*,24S*)-dihydroxycicloart-25-en-3-one (2), isopimara-7,15-diene-2 alpha,3 beta-diol (3), and isopimara-7,15-dien-3 beta-ol (4), in which 2 and 3 are identified as new derivatives. In vitro assays were conducted to evaluate the cytotoxic activity of compounds 1-4 against a panel of cancer cell lines and to determine the possible mechanism(s) related to the activity of the compounds on B16F10Nex2 cells. The most active compound 1 induced cytotoxic effects on tumor cells, with IC50 values of 18.3, 52.1, and 58.9 mu M against HL-60, HeLa, and B16F10-Nex2 tumor cells, respectively. Furthermore, it was observed in melanoma cells that compound 1 induced several specific apoptotic hallmarks, such as morphological changes in the cell shape structure, nuclear DNA condensation, specific chromatin fragmentation, and disruption in the mitochondrial membrane potential, which are related to the intrinsic apoptotic pathway.en
dc.description.affiliationUniv Fed Sao Paulo, Inst Ciencias Ambientais Quim & Farmaceut, Sao Paulo, SP, Brazil
dc.description.affiliationUniv Fed ABC, Ctr Ciencias Nat & Humanas, Ave Estados 5001, BR-09210580 Santo Andre, SP, Brazil
dc.description.affiliationUniv Fed Sao Paulo, Dept Microbiol Imunol & Parasitol, Sao Paulo, SP, Brazil
dc.description.affiliationUniv Liverpool, Dept Mol & Clin Canc Med, Liverpool, Merseyside, England
dc.description.affiliationUniv Sao Paulo, Inst Ciencias Biomed, Lab Imunol Tumores, Sao Paulo, Brazil
dc.description.affiliationUniv Fed Alfenas, Inst Quim, Alfenas, MG, Brazil
dc.description.affiliationUniv Sao Paulo, Inst Biociencias, Dept Bot, Sao Paulo, Brazil
dc.description.affiliationUnifespUniv Fed Sao Paulo, Inst Ciencias Ambientais Quim & Farmaceut, Sao Paulo, SP, Brazil
dc.description.affiliationUnifespUniv Fed Sao Paulo, Dept Microbiol Imunol & Parasitol, Sao Paulo, SP, Brazil
dc.description.sourceWeb of Science
dc.description.sponsorshipFundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP)
dc.description.sponsorshipCNPq
dc.description.sponsorshipIDFAPESP: 2014/08961-2
dc.description.sponsorshipIDFAPESP: 2015/11936-5
dc.format.extent1289-1296
dc.identifierhttp://dx.doi.org/10.1055/s-0043-107241
dc.identifier.citationPlanta Medica. Stuttgart, v. 83, n. 16, p. 1289-1296, 2017.
dc.identifier.doi10.1055/s-0043-107241
dc.identifier.issn0032-0943
dc.identifier.urihttps://repositorio.unifesp.br/handle/11600/58263
dc.identifier.wosWOS:000415714600005
dc.language.isoeng
dc.publisherGeorg Thieme Verlag Kg
dc.relation.ispartofPlanta Medica
dc.rightsinfo:eu-repo/semantics/restrictedAccess
dc.subjectGuarea macrophyllaen
dc.subjectMeliaceaeen
dc.subjectcycloartane triterpeneen
dc.subjectisopimarane diterpeneen
dc.subjectcytotoxicityen
dc.subjectcancer cellsen
dc.subjectapoptosisen
dc.titleTerpenoids from Leaves of Guarea macrophylla Display In Vitro Cytotoxic Activity and Induce Apoptosis In Melanoma Cellsen
dc.typeinfo:eu-repo/semantics/article
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