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Chem Biodivers. 2019 May;16(5):e1800644. doi: 10.1002/cbdv.201800644. Epub 2019 Apr 25.

Structural Characterization and Biological Evaluation of 18-Nor-ent-labdane Diterpenoids from Grazielia gaudichaudeana.

Author information

1
Departamento de Química, Universidade Estadual de Maringá, Av. Colombo 5790, 87020-900, Maringá, Paraná, Brazil.
2
Programa de Pós-Graduação em Ciências Farmacêuticas, Universidade Estadual de Maringá, Av. Colombo 5790, 87020-900 Maringá, Paraná, Brazil.
3
Programa de Pós-Graduação em Ciências Biológicas, Universidade Estadual de Maringá, Av. Colombo 5790, 87020-900, Maringá, Paraná, Brazil.
4
Centro Pluridisciplinar de Pesquisas Químicas, Biológicas e Agrícolas (CPQBA), Universidade Estadual de Campinas, 13083-970 Campinas, São Paulo, Brazil.
5
Departamento de Química, Universidade Federal de Santa Maria, Caixa Postal 5031, 97105-970, Santa Maria, Rio Grande do Sul, Brazil.
6
Departamento de Biologia Geral, Universidade Estadual de Ponta Grossa, Av. Carlos Cavalcanti, 4748, 84030-910, Ponta Grossa, Paraná, Brazil.

Abstract

The phytochemical investigation of Grazielia gaudichaudeana aerial parts yielded 15 compounds, including diterpenes, triterpenes, sterols and flavonoids. With exception to ent-kaurenoic acid diterpenes, the compounds isolated are being described for the first time in this species. Some unusual 1 H-NMR chemical shifts of 18-nor-ent-labdane (7-9) led us carry out a conformational analysis by theoretical calculations in order to support the experimental data. Moreover, due to the limitation of studies focused on pharmacological potential of Grazielia gaudichaudeana, the present study was carried out to investigate the antioxidant, antiproliferative, antiviral, antileishmanial and antimicrobial activities from the extract, fractions and isolated compounds obtained from this species. Ethyl acetate fraction showed significant activity in the antiproliferative assay, with GI50 range of 3.9 to 27.2 μg mL-1 . Dichloromethane fraction, rich in diterpenoids, inhibited all human tumor cell lines tested, and the nor-labdane 7 showed potent cytotoxic activity against glioma and ovary cancer cell lines.

KEYWORDS:

Asteraceae; Grazielia gaudichaudeana; antiproliferative assays; conformational analysis; cytotoxic activity; labdane diterpenoids; phytochemistry

PMID:
30843651
DOI:
10.1002/cbdv.201800644
[Indexed for MEDLINE]

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