First Report on the Chemical Composition, Antioxidant Capacity, and Preliminary Toxicity to Artemia salina L. of Croton campinarensis Secco, A. Rosário & PE Berry (Euphorbiaceae) Essential Oil, and In Silico Study

Abstract

Croton campinarensis Secco, A. Rosário & PE Berry is an aromatic species recently discovered in the Amazon region. This study first reports the chemical profile, antioxidant capacity, and preliminary toxicity to A. salina Leach of the essential oil (EO) of this species. The phytochemical profile of the essential oil was analyzed by gas chromatography (GC/MS) and (GC-FID). The antioxidant capacity of the EO was measured by its inhibition of ABTS•+ and DPPH• radicals. Molecular modeling was used to evaluate the mode of interaction of the major compounds with acetylcholinesterase (AChE). The results indicate that the EO yield was 0.24%, and germacrene D (26.95%), bicyclogermacrene (17.08%), (E)-caryophyllene (17.06%), and δ-elemene (7.59%) were the major compounds of the EO sample. The EO showed a TEAC of 0.55 ± 0.04 mM·L−1 for the reduction of the ABTS•+ radical and 1.88 ± 0.08 mM·L−1 for the reduction of the DPPH• radical. Regarding preliminary toxicity, the EO was classified as toxic in the bioassay with A. salina (LC50 = 20.84 ± 4.84 µg·mL−1). Through molecular docking, it was found that the majority of the EO components were able to interact with the binding pocket of AChE, a molecular target related to toxicity evaluated in A. salina models; the main interactions were van der Waals and π-alkyl interactions.

Chemical Composition, Preliminary Toxicity, and Antioxidant Potential of Piper marginatum Sensu Lato Essential Oils and Molecular Modeling Study

“…The interaction between the molecules of natural origin and the molecular targets of pharmacological interest was effectively assessed using in silico methods [34]. The present research employed molecular docking to analyze the interaction of the principal compounds found in specific plant species with the binding pocket of AChE, which is a molecular target that is associated with toxicity and was previously investigated in A. salina models [34].…”

“…The interaction between the molecules of natural origin and the molecular targets of pharmacological interest was effectively assessed using in silico methods [34]. The present research employed molecular docking to analyze the interaction of the principal compounds found in specific plant species with the binding pocket of AChE, which is a molecular target that is associated with toxicity and was previously investigated in A. salina models [34]. Thus, we tested five major components such as (E)-Anethole, Isoosmorhizole, (E)-Isoosmorhizole, isomer-2-methoxy-4.5-Methylenedioxypropiophenone, and 2-Methoxy-4,5-(methylenedioxy)-propiophenone against the binding cavity of AChE (Figure 3).…”

“…To investigate how 5 compounds, (E)-Anethole, Isoosmorhizole, (E)-Isoosmorhizole, isomer-2-methoxy-4.5-Methylenedioxypropiophenone, and 2-Methoxy-4,5-(methylenedioxy)propiophenone), interact with the binding cavity of the acetylcholinesterase (AChE) protein, molecular docking was performed. The compounds were drawn using GaussView 6 and optimized via B3LYP/6-31G* using Gaussian quantum chemistry software 16 [34,65]. Glide software from Schrodinger, LLC, 2023 [66,67] was used for the docking process, with the crystal structure of the AChE obtained from the Protein Data Bank (https://www.rcsb.…”

“…While the A. salina lethality test is commonly used for preliminary toxicity screening, it is important to note that the results obtained from this test may not directly translate to the potential toxicity of essential oils in humans or other animals [30][31][32]; however, they can bring a potential toxicity perspective to natural products. Furthermore, the toxicity in A. salina may be related to the inhibition of acetylcholinesterase (AChE) [33], which is an enzyme that plays a crucial role in the termination of nerve impulse transmission by catalyzing the hydrolysis of the acetylcholine neurotransmitter; several studies reported AChE as a potential molecular target to cause the death of A. salina using molecular modeling, which can be a useful tool to analyze the potential interactions between the molecules present in essential oils and AChE [34].…”