A novel eudesmol derivative from the leaf essential oil of Guatteria friesiana (Annonaceae) and evaluation of the antinociceptive activity
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Emmanoel V. Costa
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Leociley R. Alencar Menezes
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.
Funding source: Conselho Nacional de Desenvolvimento Científico e Tecnológico
Award Identifier / Grant number: Unassigned
Funding source: Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
Award Identifier / Grant number: Unassigned
Funding source: Financiadora de Estudos e Projetos
Award Identifier / Grant number: Unassigned
Funding source: Instituto Nacional de Pesquisas da Amazônia
Award Identifier / Grant number: Unassigned
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Author contributions: EVC, LRAM, and LMD were responsible for the phytochemical study. HHFK and FMAS was responsible mass spectrometry analysis. EVC, LRAM, LMD, MLBP and AB were responsible for the structural elucidation of the compounds. EML, MGS and JRGSA were responsible by the pharmacological tests. EVC, LRAM, LMD, CSCA, HHFK and JRGSA contributed to the discussion of the results, revised all text, and improved the language of the manuscript. EVC and JRGSA supervised the work and contributed to critical reading of the manuscript. All the authors have read the final manuscript and approved the submission.
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Research funding: The authors would like to thank Brazilian agencies Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq), Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES), Financiadora de Estudos e Projetos (FINEP) for financial support and fellowships, and Instituto Nacional de Pesquisas da Amazônia (INPA) for the high-resolution mass spectrometry analysis.
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Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
References
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Supplementary Material
The online version of this article offers supplementary material (https://doi.org/10.1515/znc-2022-0059).
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Articles in the same Issue
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Articles in the same Issue
- Frontmatter
- Research Articles
- A novel eudesmol derivative from the leaf essential oil of Guatteria friesiana (Annonaceae) and evaluation of the antinociceptive activity
- Chemical constituents of Desmodium triflorum and their antifungal activity against various phytopathogenic fungi
- Exploring phytochemical constituents of Achillea arabica Kotschy. ethanolic flower extract by LC-MS/MS and its possible antioxidant and antidiabetic effects in diabetic rats
- Chemical constituents from Ficus sur Forssk (Moraceae)
- In vitro acetylcholinesterase, tyrosinase inhibitory potentials of secondary metabolites from Euphorbia schimperiana and Euphorbia balsamifera
- Furoquinoline and bisindole alkaloids from the roots of Teclea nobilis and their in-silico molecular docking analysis
- Limonoids and insecticidal activity on Spodoptera frugiperda (J.E. Smith) (Lepidoptera: Noctuidae) of Trichilia catigua A. Juss. (Meliaceae)
- Tissue specific changes of phytochemicals, antioxidant, antidiabetic and anti-inflammatory activities of tea [Camellia sinensis (L.)] extracted with different solvents
- Anonazepine, a new alkaloid from the leaves of Annona muricata (Annonaceae)
- Two new natural products from Portulaca oleracea L. and their bioactivities
