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Sesquiterpene Lactones from Calea pinnatifida: Absolute Configuration and Structural Requirements for Antitumor Activity

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Autor(es):
Caldas, Lhais Araujo [1] ; Rodrigues, Mariana T. [2] ; Batista, Andrea N. L. [3, 4] ; Batista, Jr., Joao M. [3] ; Lago, Joao H. G. [5] ; Ferreira, Marcelo J. P. [6] ; Rubio, Ileana G. S. [1, 2] ; Sartorelli, Patricia [1]
Número total de Autores: 8
Afiliação do(s) autor(es):
[1] Univ Fed Sao Paulo, Inst Ciencias Ambientais Quim & Farmaceut, BR-09972270 Diadema, SP - Brazil
[2] Univ Fed Sao Paulo, Programa Posgrad Biol Estrutural & Func, BR-04021001 Sao Paulo, SP - Brazil
[3] Univ Fed Sao Paulo, Inst Ciencia Tecnol, BR-12231280 Sao Jose Dos Campos, SP - Brazil
[4] Univ Fed Fluminense, Insitituto Quim, BR-24020141 Niteroi, RJ - Brazil
[5] Univ Fed ABC, Ctr Ciencias Nat & Humanas, BR-09210180 Santo Andre, SP - Brazil
[6] Univ Sao Paulo, Inst Biociencias, Dept Bot, BR-05508090 Sao Paulo, SP - Brazil
Número total de Afiliações: 6
Tipo de documento: Artigo Científico
Fonte: Molecules; v. 25, n. 13 JUL 2020.
Citações Web of Science: 0
Resumo

This work describes the chromatographic fractionation of the aerial parts of Calea pinnatifida and the structural characterization and determination of the absolute configuration of the isolated compounds as well as their antitumor potential. The HPLC fractionation of the CH2Cl2 phase of the MeOH extract from the leaves of C. pinnatifida led to the isolation of two related sesquiterpene lactones (STLs): calein C (1) and calealactone B (2). Additionally, during the purification process, a derivative of calein C (3) was formed as a product of the Michael addition of MeOH. The structures of Compounds 1-3 were established based on spectroscopic and spectrometric data, while the absolute stereochemistry was established by vibrational circular dichroism. In order to evaluate the effect of the conjugated double bonds on the cytotoxic activity of STLs, Compounds 1-3 were tested against anaplastic (KTC-2) and papillary (TPC-1) thyroid carcinoma cells. Calein C was the most active of the STLs, and displayed activity against both KTC-2 and TPC-1. On the other hand, the calein C derivative (3) was the least cytotoxic of all the compounds tested. These results are promising and suggest the importance of studying sesquiterpene lactones isolated from C. pinnatifida in terms of antitumor activity, especially considering the effects of alpha,beta-unsaturated carbonyl systems. (AU)

Processo FAPESP: 20/05741-2 - Lactonas sesquiterpênicas de Calea pinnatifida: configuração absoluta e requisitos estruturais para atividade anti-tumoral
Beneficiário:Patricia Sartorelli
Linha de fomento: Auxílio à Pesquisa - Publicações científicas - Artigo
Processo FAPESP: 16/24985-4 - Estudo da composição química de fungos e plantas da Mata Atlântica visando o potencial antitumoral, antiparasitário e antimicrobiano
Beneficiário:Patricia Sartorelli
Linha de fomento: Auxílio à Pesquisa - Regular
Processo FAPESP: 14/25222-9 - Espectroscopia quiróptica vibracional na caracterização estereoquímica de pequenas moléculas e macromoléculas
Beneficiário:João Marcos Batista Junior
Linha de fomento: Auxílio à Pesquisa - Apoio a Jovens Pesquisadores