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

Author(s):Show less -

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]

Affiliation

^[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

• Document type: Journal article
• Source: Journal of the Brazilian Chemical Society; v. 31, n. 8, p. 1679-1689, AUG 2020.
• Web of Science Citations: 1

Abstract

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)

• FAPESP's process: 16/01232-0 - Copaifera oleoresins: development and validation of a HPLC-DAD analytical method and phytochemical study and in vitro antitumor evaluation of the main secondary metabolites obtained
• Grantee: Luiza Junqueira Carneiro
• Support Opportunities: Scholarships in Brazil - Doctorate (Direct)
• FAPESP's process: 11/13630-7 - Chemical and pharmacological validation of extracts and active compounds of Copaifera species
• Grantee: Jairo Kenupp Bastos
• Support Opportunities: Research Projects - Thematic Grants