Copaifera multijuga, Copaifera pubiflora and Copaifera trapezifolia Oleoresins: Chemical Characterization and in vitro Cytotoxic Potential against Tumoral Cell Lines

Autor(es):Mostrar menos -

Carneiro, Luiza J. ^[1] ; Tasso, Thercius O. ^[1] ; Santos, Mario F. C. ^[1] ; Goulart, Mirian O. ^[1] ; dos Santos, Raquel ^[1] ; Bastos, Jairo K. ^[2] ; da Silva, Jonas J. M. ^{[2, 3]} ; Crotti, Antonio E. M. ^[3] ; Parreira, Renato L. T. ^[1] ; Orenha, Renato P. ^[1] ; Veneziani, Rodrigo C. S. ^[1] ; Ambrosio, Sergio R. ^[1]

Afiliação do(s) autor(es)

^[1] Univ Franca, Nucleo Pesquisa Ciencias Exatas & Tecnol, Av Dr Armando de Salles Oliveira 201, BR-14404600 Franca, SP - Brazil

^[2] Univ Sao Paulo, Fac Ciencias Farmaceut Ribeirao Preto, Dept Fis & Quim, Av Cafe S-N, BR-14040903 Ribeirao Preto, SP - Brazil

^[3] Univ Sao Paulo, Dept Quim, Fac Filosofia Ciencias & Letras Ribeirao Preto, Av Cafe S-N, BR-14040903 Ribeirao Preto, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: Journal of the Brazilian Chemical Society; v. 31, n. 8, p. 1679-1689, AUG 2020.
• Citações Web of Science: 1

Resumo

Copaifera species (Fabaceae) comprises approximately 70 species of large trees, from which 16 can be found in Brazil. The oleoresins obtained from their trunk are widely used in Brazilian folk medicine, which display important antitumoral potential. Chemically, these oleoresins are mainly composed of a mixture of sesquiterpenes and diterpenes. In this paper we are describing the isolation and identification of 12 already known terpenes from oleoresins obtained from three different Copaifera species (C. multijuga, C. pubiflora and C. trapezifolia) and 2 novel diterpenes (ent-16-hidroxy-3,13 clerodadien-15,18-dioic acid and ent-labda-5,13-dien-15-oic acid) from C. trapezifolia. Both new compounds were identified by nuclear magnetic resonance (NMR) spectroscopic (1H and 13C NMR, correlation 1H-1H (COSY), heteronuclear multiple quantum coherence (HMQC) and heteronuclear multiple bond correlation (HMBC)) and by high-resolution electrospray ionization mass spectrometry (HR-ESIMS) analyses. The cytotoxic potential of these oleoresins, their main non-volatile compounds and their volatile compound fractions were evaluated against a panel of tumoral (MCF-7, ACP01, A549, HeLa) and normal cell lines (MCF-10A, GM07492-A) through XTT (tetrazolium salt) and SRB (sulforhodamine B) assays. The novel diterpene ent-labda-5,13-dien-15-oic acid displayed relevant cytotoxic effect against most of the cancer cell lines with mean inhibitory concentration (IC50) values ranging from 3.57 ± 1.12 to 22.56 ± 1.03 µg mL-1, and a high selectivity level in both assays. (AU)

• Processo FAPESP: 16/01232-0 - Oleorresinas de Copaifera: desenvolvimento e validação de metodologia analítica por CLAE-DAD e estudo fitoquímico e antitumoral in vitro dos principais metabólitos secundários isolados
• Beneficiário: Luiza Junqueira Carneiro
• Modalidade de apoio: Bolsas no Brasil - Doutorado Direto
• Processo FAPESP: 11/13630-7 - Validação química e farmacológica de extratos e princípios ativos de espécies de Copaifera
• Beneficiário: Jairo Kenupp Bastos
• Modalidade de apoio: Auxílio à Pesquisa - Temático