Impact on cholinesterase-inhibition and in silico investigations of sesquiterpenoids from Amazonian Siparuna guianensis Aubl.

Martins, Regildo Max Gomes; Xavier, Francisco Humberto; Barros, Marcela Rodrigues; Menezes, Thaís Meira; Assis, Caio Rodrigo Dias; Melo, A.C. Goncalves Reis De; Veras, Bruno Oliveira de; Ferraz, Vany; Filho, Antônio Alves Melo; Yogui, Gilvan Takeshi; Bezerra, Ranilson S.; Seabra, Gustavo; Neves, Jorge Luiz; Tadei, Wanderli Pedro

doi:10.1016/j.saa.2021.119511

Cited by 10 publications

(8 citation statements)

References 22 publications

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“…(Siparunaceae), a well-known Amazonian medicinal plant. The essential oil of S. guianensis was shown to have strong cholinesterase inhibitory, anti-Alzheimer, and neuroprotective activities due to its content of shyobunone derivatives [ 21 ]. The presence of shyobunone isomers in the essential oil of the aerial parts of Daucus carota L. var.…”

Section: Resultsmentioning

confidence: 99%

Biological Activities of the Fruit Essential Oil, Fruit, and Root Extracts of Ferula drudeana Korovin, the Putative Anatolian Ecotype of the Silphion Plant

Tosun

Göğer

İşcan

et al. 2023

Plants

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In the present study, preliminary phytochemical investigations were performed on the fruit essential oil and antioxidant-rich methanolic extracts of the fruits and roots of Ferula drudeana, the putative Anatolian ecotype of the Silphion plant, to corroborate its medicinal plant potential and identify its unique characteristics amongst other Ferula species. The essential oil from the fruits of the endemic species Ferula drudeana collected from Aksaray was analyzed by GC and GC/MS. The main components of the oil were determined as shyobunone (44.2%) and 6-epishyobunone (12.6%). The essential oil of the fruits and various solvent extracts of the fruits and roots of F. drudeana were evaluated for their antibacterial and anticandidal activity using microbroth dilution methods. The essential oil of the fruits, methanol, and methylene chloride extracts of the fruits and roots showed weak to moderate inhibitory activity against all tested microorganisms with MIC values of 78–2000 µg/mL. However, the petroleum ether extract of the roots showed remarkable inhibitory activity against Candida krusei and Candida utilis with MIC values of 19.5 and 9.75 µg/mL, respectively. Furthermore, all the samples were tested for their antioxidant activities using DPPH• TLC spot testing, online HPLC–ABTS screening, and DPPH/ABTS radical scavenging activity assessment assays. Methanolic extracts of the fruits and roots showed strong antioxidant activity in both systems.

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Section: Resultsmentioning

confidence: 99%

Biological Activities of the Fruit Essential Oil, Fruit, and Root Extracts of Ferula drudeana Korovin, the Putative Anatolian Ecotype of the Silphion Plant

Tosun

Göğer

İşcan

et al. 2023

Plants

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“…In the absence of a crystal structure for the E. electricus AChE, the initial structure for this work was obtained by homology modeling using AChE from Tetronarce californica (PDB ID: 6EUC) as the template, as previously described and is detailed in the Supporting Information. For simulations in the presence of the substrate, the ATC substrate was inserted in the binding groove by docking with AutoDock Vina 4.2 .…”

Section: Methodsmentioning

confidence: 99%

Binding Mechanism between Acetylcholinesterase and Drugs Pazopanib and Lapatinib: Biochemical and Biophysical Studies

Menezes

Assis

Cintra

et al. 2021

ACS Chem. Neurosci.

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Tyrosine kinase inhibitors (TKIs) are antitumor compounds that prevent the phosphorylation of proteins in a biological environment. However, the multitarget performance of TKIs promotes them as possible candidates for drug repositioning. In this work, interaction and inhibition studies through spectroscopic and computational techniques to evaluate the binding effectiveness of lapatinib and pazopanib TKIs to acetylcholinesterase (AChE) are reported. The results indicated potent inhibition at the μM level. The types of inhibition were identified, with pazopanib acting through non-competitive inhibition and lapatinib through acompetitive inhibition. The fluorescence suppression studies indicate a static mechanism for lapatinib−AChE and pazopanib−AChE systems, with a binding constant in the order of 10 5 M −1 . The obtained thermodynamic parameters reveal interactions driven by van der Waals forces and hydrogen bonds in the lapatinib−AChE system (ΔH°and ΔS°< 0). In contrast, the pazopanib−AChE system shows positive ΔH°and ΔS°, characteristic of hydrophobic interactions. The Foster resonance energy transfer study supports the fluorescence studies performed. The 3D fluorescence studies suggest changes in the microenvironment of the tryptophan and tyrosine residues of the protein in contact with lapatinib and pazopanib. The results suggest effective inhibition and moderate interaction of the drugs with AChE, making them interesting for conducting more in-depth repositioning studies as AChE inhibitors.

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“…Also, spathulenol was identified with an amount lower than 3.87 % in the literature. [11,[20][21][22] Several factors may imply variations in the chemical composition of the essential oils, such as genetic factors, environmental characteristics of the collection sites, seasonality, and soil characteristics, which can be elements that alter the production of secondary metabolites in plant species, [23] these factors could explain the variability of constituents, their contents, and the presence and/or absence of some compounds in this work when compared to other studies.…”

Section: Yield and Chemical Composition Of Siparuna Guianensis Essent...mentioning

confidence: 99%

Siparuna guianensis Essential Oil Antitumoral Activity on Ehrlich Model and Its Effect on Oxidative Stress

Viana Barbosa,

Silva de Jesus,

Botelho Jerônimo

et al. 2023

Chemistry & Biodiversity

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This work aims to evaluate the chemical composition, in vitro antioxidant capacity, and in vivo antitumoral activity of S. guianensis essential oil against Ehrlich's ascitic carcinoma and the effects on oxidative stress. The animals (Mus musculus) received a daily dose of S. guianensis oil orally (100 mg/kg) for 9 days. The main constituents of essential oil were curzerenone (16.4±1.5 %), drimenol (13.7±0.2 %), and spathulenol (12.4±0.8 %). S. guianensis oil showed antioxidant activity, inhibiting 11.1 % of DPPH radicals (95.7 mgTE/g); and 15.5 % of the β‐carotene peroxidation. The group treated with S. guianensis showed a significant reduction in tumor cells (59.76±12.33) compared to the tumor group (96.88±19.15). Essential oil of S. guianensis decreased MDA levels and increased SOD levels in liver tissue. The essential oil of S. guianensis reduced oxidative stress, and showed antitumor and antioxidant activity, being characterized as a new chemical profile in the investigation of pathologies such as cancer.

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Impact on cholinesterase-inhibition and in silico investigations of sesquiterpenoids from Amazonian Siparuna guianensis Aubl.

Cited by 10 publications

References 22 publications

Biological Activities of the Fruit Essential Oil, Fruit, and Root Extracts of Ferula drudeana Korovin, the Putative Anatolian Ecotype of the Silphion Plant

Biological Activities of the Fruit Essential Oil, Fruit, and Root Extracts of Ferula drudeana Korovin, the Putative Anatolian Ecotype of the Silphion Plant

Binding Mechanism between Acetylcholinesterase and Drugs Pazopanib and Lapatinib: Biochemical and Biophysical Studies

Siparuna guianensis Essential Oil Antitumoral Activity on Ehrlich Model and Its Effect on Oxidative Stress

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