Cytotoxic sesquiterpene lactones from Campuloclinium macrocephalum (=Eupatorium macrocephalum)

Márcia R Pereira Cabral; Mariana Cecchetto; João M Batista Jr; Andrea N L Batista; Mary Ann Foglio; Ana Lúcia Tasca Gois Ruiz; Marta R Barrotto do Carmo; Willian Ferreira da Costa; Débora C Baldoqui; Maria H Sarragiotto

doi:10.1016/j.phytochem.2020.112469

Cytotoxic sesquiterpene lactones from Campuloclinium macrocephalum (=Eupatorium macrocephalum)

Phytochemistry. 2020 Nov:179:112469. doi: 10.1016/j.phytochem.2020.112469. Epub 2020 Aug 14.

Affiliations

¹ Departamento de Química, Universidade Estadual de Maringá, Av. Colombo 5790, 87020-900, Maringá, PR, Brazil.
² Faculdade de Ciências Farmacêuticas, Universidade Estadual de Campinas, R. Candido Portinari 200, Cidade Universitária, 13083871, Campinas, SP, Brazil.
³ Instituto de Ciência e Tecnologia, Universidade Federal de São Paulo, R. Talim 330, 12231-280, São José dos Campos, SP, Brazil.
⁴ Instituto de Química, Universidade Federal Fluminense, Outeiro de São João Batista s/n, 24020-141, Niterói, RJ, Brazil.
⁵ Departamento de Biologia Geral, Universidade Estadual de Ponta Grossa, Av. Carlos Cavalcanti, 4748, 84030-910, Ponta Grossa, PR, Brazil.
⁶ Departamento de Química, Universidade Estadual de Maringá, Av. Colombo 5790, 87020-900, Maringá, PR, Brazil. Electronic address: mhsarragiotto@uem.br.

PMID: 32805622
DOI: 10.1016/j.phytochem.2020.112469

Abstract

Three undescribed germacranolide sesquiterpene lactones, named macrocephalides A-C, along with known steroids, triterpenes and flavonoids were isolated from the aerial parts of Campuloclinium macrocephalum. The structures of the undescribed compounds were elucidated with basis on their 1D and 2D-NMR, and HR-ESI-MS data. Their absolute configurations were assigned by comparison of experimental and calculated electronic circular dichroism (ECD) spectra. Additionally, macrocephalides A-C were evaluated for their in vitro cytotoxic activities against nine human cancer cell lines. Macrocephalides A and B exhibited moderate to potent cytotoxic activity, inhibiting 50% of cell growth (GI₅₀) at concentrations ranging from 0.576 to 6.37 μM.

Keywords: Asteraceae; Campuloclinium macrocephalum; Cytotoxicity; Germacranolide; Sesquiterpene lactones.

MeSH terms

Asteraceae*
Cell Line, Tumor
Eupatorium*
Humans
Lactones / pharmacology
Molecular Structure
Phytochemicals
Sesquiterpenes* / pharmacology

Substances

Lactones
Phytochemicals
Sesquiterpenes