Structurally modified natural sesquiterpene lactones constitute effective and less toxic schistosomicidal compounds

Autor(es)

Sass, Daiane Cristina ^[1] ; Morais, Gustavo Oliveira ^[2] ; Crema Miranda, Ricardo Augusto ^[2] ; Magalhaes, Lizandra Guidi ^[2] ; Cunha, Wilson Roberto ^[2] ; dos Santos, Raquel Alves ^[2] ; Arakawa, Nilton Syogo ^[3] ; Da Costa, Fernando Batista ^[4] ; Constantino, Mauricio Gomes ^[1] ; Gomes Heleno, Vladimir Constantino ^[2]

Afiliação do(s) autor(es)

^[1] Univ Sao Paulo, Dept Quim, FFCLRP, BR-05508 Sao Paulo - Brazil

^[2] Univ Franca, Nucleo Pesquisas Ciencias Exatas & Tecnol, Franca - Brazil

^[3] Univ Estadual Londrina, Dept Ciencias Farmaceut, CCS, Londrina - Brazil

^[4] Univ Sao Paulo, Dept Ciencias Farmaceut, FCFRP, BR-05508 Sao Paulo - Brazil

• Tipo de documento: Artigo Científico
• Fonte: ORGANIC & BIOMOLECULAR CHEMISTRY; v. 12, n. 40, p. 7957-7964, 2014.
• Citações Web of Science: 6

Resumo

Sesquiterpene lactones are known to be active, but are also known to present high cytotoxicity. In the present work an evaluation of how slight structural alterations affect the cytotoxicity and the schistosomicidal activity of sesquiterpene lactones was undertaken. More specifically, we assessed the activity of budlein-A, a furanoheliangolide sesquiterpene lactone, and four of its derivatives. The structural modifications of budlein-A, presented in this work, diminished the cytotoxicity and changed the antiparasitary behavior of the molecule. They also provided data for a better understanding of the sesquiterpene lactone cytotoxicity. The establishment of the structures of three synthesized sesquiterpene lactones on the basis of NMR and HRESIMS data is also presented here. Complete and detailed H-1 and C-13 1D and 2D NMR data, with measurements of all J values and all multiplicities clarified, are presented for five sesquiterpene lactones for the first time. (AU)

• Processo FAPESP: 09/09491-1 - Modificação estrutural e estudos detalhados por RMN de produtos naturais de interesse biológico
• Beneficiário: Vladimir Constantino Gomes Heleno
• Modalidade de apoio: Auxílio à Pesquisa - Regular