Oxidative functionalization of a halimane diterpenoid achieved by fungal transformation

Página do item simplificado
dc.contributor.authorMonteiro, Afif Felix [UNESP]
dc.contributor.authorRighetto, Gabriela Marinho
dc.contributor.authorSimões, Laura Vilar [UNESP]
dc.contributor.authorAlmeida, Larissa Costa de
dc.contributor.authorCosta-Lotufo, Letícia Veras
dc.contributor.authorCamargo, Ilana Lopes Baratella da Cunha
dc.contributor.authorCastro-Gamboa, Ian [UNESP]
dc.contributor.institutionUniversidade Estadual Paulista (Unesp)
dc.contributor.institutionUniversidade de São Paulo (USP)
dc.date.accessioned2019-10-06T15:33:59Z
dc.date.available2019-10-06T15:33:59Z
dc.date.issued2019-05-01
dc.description.abstractRegio and stereoselective activation of sp 3 C–H bonds remain one of the major advantages of biocatalysis over traditional chemocatalytic methods. Herein, we describe the oxy-functionalization of halimane diterpenoid 1 by whole cells of three filamentous fungi, aiming to obtain derivatives with desirable biological properties. After incubating 1 with Fusarium oxysporum, Myrothecium verrucaria, and Rhinocladiella similis at different concentrations and incubation times, four known (3, 5, 6, and 7) and three new (2, 4, and 8) halimane derivatives were obtained and characterized. F. oxysporum catalyzed the hydroxylation of positions C-2 (2) and C-7 (4), while R. similis simultaneously mediated the 2-oxo-functionalization and the hydration of 13,14-(C–C)double bond belonging to an α,β-unsaturated carbonyl system (8). Compounds 1–7 were non-cytotoxic against HCT-116 and MCF-7 cancer cell lines at tested concentrations. However, substrate 1 displayed moderate reduction ability against biofilm produced by Staphylococcus epidermidis ATCC35984 (84% at 1.6 mM), and this effect was retained to some extent by derivatives 4 and 7. These results emphasize the prominent potential of filamentous fungi associated with the microbiota of medicinal plants as versatile catalysts for singularly useful reactions through their complex enzymatic machinery, as well as the high susceptibility of halimane-diterpenoid substrates.en
dc.description.affiliationNúcleo de Bioensaios Biossíntese e Ecofisiologia de Produtos Naturais (NuBBE) Universidade Estadual Paulista (UNESP) Instituto de Química Departamento de Química Orgância, Francisco Degni, 55
dc.description.affiliationSão Carlos Institute of Physics University of São Paulo, PO Box 369
dc.description.affiliationUniversidade de São Paulo (USP) Instituto de Ciências Biomédicas, Av. Lineu Prestes, 1524
dc.description.affiliationUnespNúcleo de Bioensaios Biossíntese e Ecofisiologia de Produtos Naturais (NuBBE) Universidade Estadual Paulista (UNESP) Instituto de Química Departamento de Química Orgância, Francisco Degni, 55
dc.description.sponsorshipCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)
dc.description.sponsorshipConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.description.sponsorshipFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.description.sponsorshipIdCAPES: Finance code 001
dc.description.sponsorshipIdCAPES: PROEX – 1427484
dc.format.extent550-556
dc.identifierhttp://dx.doi.org/10.1016/j.bioorg.2019.02.021
dc.identifier.citationBioorganic Chemistry, v. 86, p. 550-556.
dc.identifier.doi10.1016/j.bioorg.2019.02.021
dc.identifier.issn1090-2120
dc.identifier.issn0045-2068
dc.identifier.scopus2-s2.0-85061701206
dc.identifier.urihttp://hdl.handle.net/11449/187367
dc.language.isoeng
dc.relation.ispartofBioorganic Chemistry
dc.rights.accessRightsAcesso aberto
dc.sourceScopus
dc.subjectBiofilm reduction
dc.subjectC–H oxidation
dc.subjectDouble-bond hydration
dc.subjectHalimane diterpenoid
dc.subjectMicrobial transformation
dc.titleOxidative functionalization of a halimane diterpenoid achieved by fungal transformationen
dc.typeArtigo

Arquivos

Coleções

Artigos