A novel eudesmol derivative from the leaf essential oil of Guatteria friesiana (Annonaceae) and evaluation of the antinociceptive activity

Author:

Costa Emmanoel V.1,Alencar Menezes Leociley R.2,Dutra Lívia M.23,Pinheiro Maria Lúcia B.1,Lavor Érica M.3,Silva Mariana G.3,Alves Cristiane dos S. C.3,Almeida Jackson R. G. S.3,da Silva Felipe Moura A.1,Koolen Hector H. F.4,Barison Andersson2

Affiliation:

1. Department of Chemistry , Federal University of Amazonas , Manaus , Amazonas , 69080-900 , Brazil

2. NMR Center, Federal University of Paraná , Curitiba , Paraná , 81531-990 , Brazil

3. Center for Studies and Research of Medicinal Plants (NEPLAME), Federal University of San Francisco Valley , Petrolina , Pernambuco , 56304-205 , Brazil

4. Dempster Mass Spectrometry Group, Amazonas State University , Manaus , Amazonas , 69065-001 , Brazil

Abstract

Abstract In the present study, it was evaluated the chemical composition and the antinociceptive activity of the essential oil obtained from the leaves of Guatteria friesiana. Seven compounds corresponding to 96.2% of the crude essential oil were identified. The main components identified were the mixture of β-eudesmol and α-eudesmol (58.1%), and γ-eudesmol (16.8%). A new α-eudesmol derivative, named 5-hydroxy-α-eudesmol, was isolated together with the known compounds β-eudesmol and a mixture of α-eudesmol, β-eudesmol and γ-eudesmol of the essential oil. The chemical structures were determined by 1D and 2D NMR, and MS experiments. Essential oil has significant antinociceptive properties, which are related probably with the involvement of the opioid receptors and K+-ATP channels.

Funder

Conselho Nacional de Desenvolvimento Científico e Tecnológico

Coordenação de Aperfeiçoamento de Pessoal de Nível Superior

Financiadora de Estudos e Projetos

Instituto Nacional de Pesquisas da Amazônia

Publisher

Walter de Gruyter GmbH

Subject

General Biochemistry, Genetics and Molecular Biology

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