Chemical Evaluation, Phytotoxic Potential, and In Silico Study of Essential Oils from Leaves of Guatteria schomburgkiana Mart. and Xylopia frutescens Aubl. (Annonaceae) from the Brazilian Amazon

Molecules. 2023 Mar 14;28(6):2633. doi: 10.3390/molecules28062633.

Abstract

The essential oils (EOs) of Guatteria schomburgkiana (Gsch) and Xylopia frutescens (Xfru) (Annonaceae) were obtained by hydrodistillation, and their chemical composition was evaluated by gas chromatography-mass spectrometry (GC/MS). Herbicide activity was measured by analyzing the seed germination percentage and root and hypocotyl elongation of two invasive species: Mimosa pudica and Senna obtusifolia. The highest yield was obtained for the EO of Xfru (1.06%). The chemical composition of Gsch was characterized by the presence of the oxygenated sesquiterpenes spathulenol (22.40%) and caryophyllene oxide (14.70%). Regarding the EO of Xfru, the hydrocarbon monoterpenes α-pinene (35.73%) and β-pinene (18.90%) were the components identified with the highest concentrations. The germination of seeds of S. obtusifolia (13.33 ± 5.77%) showed higher resistance than that of seeds of M. pudica (86.67 ± 5.77%). S. obtusifolia was also more sensitive to the EO of Xfru in terms of radicle (55.22 ± 2.72%) and hypocotyl (71.12 ± 3.80%) elongation, while M. pudica showed greater sensitivity to the EO of Gsch. To screen the herbicidal activity, the molecular docking study of the major and potent compounds was performed against 4-hydroxyphenylpyruvate dioxygenase (HPPD) protein. Results showed good binding affinities and attributed the strongest inhibitory activity to δ-cadinene for the target protein. This work contributes to the study of the herbicidal properties of the EOs of species of Annonaceae from the Amazon region.

Keywords: Amazonian essential oils; caryophyllene oxide; molecular modeling; phytotoxicity; spathulenol; α-pinene; β-pinene.

MeSH terms

  • Annonaceae* / chemistry
  • Brazil
  • Guatteria* / chemistry
  • Molecular Docking Simulation
  • Oils, Volatile* / chemistry
  • Plant Leaves / chemistry
  • Xylopia* / chemistry

Substances

  • Oils, Volatile

Grants and funding

This research received no external funding. The APC was funded by Universidade Federal do Pará, Pró-Reitoria de Pesquisa e Pós-Graduação (PROPESP), Edital 02/2023-PAPQ/PROPESP.