Ex vivo inhibition of PGE2 formation in human blood by four bicyclico [3.2.1] octane neolignans isolated from Aniba firmula bark, two with unusual structural pattern

Abstract

The phytochemical investigation of the stem bark crude extract of Aniba firmula (Lauraceae) led to the isolation of undescribed bicyclic [3.2.1] octane neolignans, 1 and 2, characterized by unusual bicyclic patterns and two other known bicyclic neolignans 3 and 4. Anti-inflammatory bicyclic [3.2.1] octane neolignans metabolites were previously reported in the literature, and the A. firmula stands out in the Lauraceae family as a source of potentially bioactive compounds. Thus, herein the anti-inflammatory potential of four isolated compounds from A. firmula was accessed via an ex vivo anti-inflammatory model that included plasmatic quantification of the prostaglandin E2 (PGE2) inflammatory mediator. Compounds 2 and 3 exhibited significant anti-inflammatory activity by inhibiting the production of PGE2 in plasma samples, thus by interference with the cyclooxygenase (COX) inflammatory pathway. Therefore, these findings demonstrate that the bicyclic octane neolignan classes [3.2.1] can present anti-inflammatory potential.

Graphical Abstract

Keywords:

• Neolignan
• Aniba firmula
• prostaglandin E2
• bicyclic [3.2.1] octane

Acknowledgements

The authors thank the National Council for Science and Technology (Conselho Nacional de Desenvolvimento Científico e Tecnológico – CNPq, grant number 406837/2021-0 and 316204/2021-8) and the Coordination for the Improvement of Higher Education Personnel (Coordenação de Aperfeiçoamento de Pessoal de Nível Superior – CAPES, finance code 001). We also thank Minas Gerais Research Funding Foundation (Fundação de Amparo à Pesquisa do Estado de Minas Gerais – FAPEMIG, grant numbers APQ-02353-17, APQ-00207-18) for financial support, the researchers from Natural Products and Organic Synthesis Research Group (GEAPS-CNPq-UFES) and the São Paulo Research Foundation, Brazil-FAPESP (2018/25010-2 and 2018/05080-6).

Declaration of competing interest

The authors declare no conflict of interest.

Additional information

Funding

This work was supported by São Paulo Research Foundation (FAPESP).