Cholinesterase-inhibitory effect and in silico analysis of alkaloids from bulbs of Hieronymiella species

Ortiz, Javier E.; Garro, Adriana; Pigni, Natalia B.; Agüero, María Belén; Roitman, Gustavo Germán; Slanis, Alberto C.; Enriz, Ricardo D.; Feresin, Gabriela Egly; Tapia, Aníbal Alejandro

doi:10.1016/j.phymed.2017.12.020

Cited by 29 publications

(19 citation statements)

References 35 publications

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“…The respective ρ (r) values obtained for each interaction indicate that such interactions are strong enough to stabilize very well this molecular complex. This result is in agreement with previously reported experimental and theoretical results [31,32]. Comparing the molecular graph of galantamine-AChE complex with that obtained for compound 3 (Figure 4a), it is possible to observe that the interactions with Trp84 and Ser122 are maintained.…”

Section: Qtaim Analysissupporting

confidence: 92%

“…These results can be very well appreciated in the analysis per residue which has been performed for the different compounds ( Figure 2). We have previously reported that the main interactions that stabilize the galantamine complex with AChE are these with the following amino acids from the active site of the enzyme: Trp84, Gly118, Ser122, Glu199, Phe330 and His440 [32]. These interactions can be observed in the residue analysis obtained for galantamine ( Figure 2a) which is very similar to that reported in the reference [32].…”

Section: Molecular Modellingsupporting

confidence: 85%

“…The combined analysis using a docking study and MD simulations predicts that the carbamates 1-16 reported here bind in the same region of the active site of AChE to that reported for galantamine [31,32] (Figure 1); however, MD simulations indicate that these molecules are arranged spatially in a slightly different way. Therefore, these carbamates bind to some of the same amino acids of the galantamine binding site, but also to the others.…”

Section: Molecular Modellingsupporting

confidence: 52%

“…We have previously reported that the main interactions that stabilize the galantamine complex with AChE are these with the following amino acids from the active site of the enzyme: Trp84, Gly118, Ser122, Glu199, Phe330 and His440 [32]. These interactions can be observed in the residue analysis obtained for galantamine ( Figure 2a) which is very similar to that reported in the reference [32]. The histograms shown in Figure 2b-d are those obtained for compounds 3, 5 and 6, respectively, whereas the histogram of compound 2 is reported in Supplementary Material ( Figure S1).…”

Section: Molecular Modellingmentioning

confidence: 99%

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Arylaminopropanone Derivatives as Potential Cholinesterase Inhibitors: Synthesis, Docking Study and Biological Evaluation

et al. 2020

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Neurodegenerative diseases in which the decrease of the acetylcholine is observed are growing worldwide. In the present study, a series of new arylaminopropanone derivatives with N-phenylcarbamate moiety (1–16) were prepared as potential acetylcholinesterase and butyrylcholinesterase inhibitors. In vitro enzyme assays were performed; the results are expressed as a percentage of inhibition and the IC50 values. The inhibitory activities were compared with reference drugs galantamine and rivastigmine showing piperidine derivatives (1–3) as the most potent. A possible mechanism of action for these compounds was determined from a molecular modelling study by using combined techniques of docking, molecular dynamics simulations and quantum mechanics calculations.

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Section: Qtaim Analysissupporting

confidence: 92%

Section: Molecular Modellingsupporting

confidence: 85%

Section: Molecular Modellingsupporting

confidence: 52%

Section: Molecular Modellingmentioning

confidence: 99%

See 2 more Smart Citations

Arylaminopropanone Derivatives as Potential Cholinesterase Inhibitors: Synthesis, Docking Study and Biological Evaluation

et al. 2020

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“…Alkaloids have diverse biological activities, which are mainly related to its ability to inhibit enzymes [35], i.e., acetylcholinesterase [36] and its effects to induce apoptosis [37]. The pharmacological effects of isoquinolinic alkaloids such as its anti-Alzheimer [38], antiinflammatory, antiprotozoal [39], antimicrobial, and anticancer activities [40].…”

Section: Cytotoxicitymentioning

confidence: 99%

In Vitro Anti-Inflammatory and Cytotoxicity of Crinum X Amabile Grown in Ecuador

Vinueza

Santiago

Pilco

et al. 2018

Asian J Pharm Clin Res

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Objective: The aim of this research was to assess the in vitro anti-inflammatory activity and cytotoxicity of the methanolic extract and total alkaloid extract obtained from leaves and bulbs of Crinum x amabile (CA) growing in Ecuador.Methods: Methanolic extracts of dry powered leaves and bulbs of CA obtained by cold maceration method were subjected to preliminary phytochemical screening. Total alkaloid extracts of leaves and bulbs of CA were obtained by conventional extraction of alkaloids base with an organic solvent. Furthermore, the anti-inflammatory activity and cytotoxicity of the four extracts were investigated by in vitro isolated neutrophils model using stable tetrazolium salt (WST-1).Results: Phytochemical analysis of methanolic extracts revealed the major classes of phytochemicals such as alkaloids, flavonoids, tannins, triterpenes, and steroids, but no proteins or saponins could be detected on leaves extract. Extracts obtained from bulbs both methanolic and total alkaloids of CA show an interesting anti-inflammatory activity, although it was not significant compared to the standard anti-inflammatory drug, aspirin. Cytotoxicity of bulb alkaloid extract was lower compared with all of the other extracts.Conclusion: Based on the results of this research, it could be concluded that CA is a very interesting source of natural anti-inflammatory compounds (especially alkaloids) which could be used to prevent many chronic disorders. Further, phytochemical studies are necessary to identify the chemical compounds responsible for the significant anti-inflammatory activity showed.

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Clinanthus microstephium, an Amaryllidaceae Species with Cholinesterase Inhibitor Alkaloids: Structure−Activity Analysis of Haemanthamine Skeleton Derivatives

Adessi

Borioni

Pigni

et al. 2019

Chemistry & Biodiversity

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Plants of the Amaryllidaceae family are well-known (not only) for their ornamental value but also for the alkaloids they produce. In this report, the first phytochemical study of Clinanthus genus was carried out. The chemical composition of alkaloid fractions from Clinanthus microstephus was analyzed by GC-MS and NMR. Seven known compounds belonging to three structural types of Amaryllidaceae alkaloids were identified. An epimeric mixture of a haemanthamine-type compound (6-hydroxymaritidine) was tested as an inhibitor against acetyl and butyryl cholinesterase enzymes (AChE and BChE, respectively), two enzymes relevant in the treatment of Alzheimer's Disease, with good results. Structure-activity relationships through molecular docking studies with this alkaloid and other structurally related compounds were discussed.

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Cholinesterase-inhibitory effect and in silico analysis of alkaloids from bulbs of Hieronymiella species

Cited by 29 publications

References 35 publications

Arylaminopropanone Derivatives as Potential Cholinesterase Inhibitors: Synthesis, Docking Study and Biological Evaluation

Arylaminopropanone Derivatives as Potential Cholinesterase Inhibitors: Synthesis, Docking Study and Biological Evaluation

In Vitro Anti-Inflammatory and Cytotoxicity of Crinum X Amabile Grown in Ecuador

Clinanthus microstephium, an Amaryllidaceae Species with Cholinesterase Inhibitor Alkaloids: Structure−Activity Analysis of Haemanthamine Skeleton Derivatives

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