Cholinesterase inhibitors assessment of aporphine alkaloids from Annona crassiflora and molecular docking studies

Barbosa, Marília Fontes; Justino, Allisson Benatti; Martins, Mário Machado; Belaz, K. R. A.; Ferreira, Francis Barbosa; Oliveira, Ronaldo Junio de; Danuello, Amanda; Espíndola, Foued Salmen; Pivatto, Marcos

doi:10.1016/j.bioorg.2021.105593

Cited by 8 publications

(8 citation statements)

References 42 publications

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“…The stephalagine was purified by semi-preparative HPLC on RP-C 18 and structurally characterized by high-resolution mass spectrometry, with electrospray ionization (HR-ESI-MS) and nuclear magnetic resonance (NMR) techniques, for the first time by Pereira et al [ 29 ]. Additionally, recent studies have reported the presence of stephalagine in araticum peel and pulp [ 14 , 26 , 27 , 28 , 30 ], indicating that this compound is present in more than a fraction of the fruit. Stephalagine, an aporphine alkaloid, has demonstrated anti-obesity, antinociceptive, and anti-edematogenic effects, suggesting its use as a new potential drug [ 28 , 29 ].…”

Section: Bioactive Compounds Found In Araticum Fruit Partsmentioning

confidence: 99%

“…In addition to stephalagine, other alkaloids, such as xylopine, romucosine, asimilobine, roemerine, nornuciferine, N -methylcoclaurine, guattescidine, actinodaphnine, isoboldine, and N -methyllaurotetanine, have been identified in araticum pulp [ 14 , 22 ]. Several studies demonstrated the presence of liriodenine, atherospermidine, isopiline, isoboldine, isocorydine, anonaine, xylopine, nuciferine, liriodenine, atherospermidine, reticuline, roemerine, nornuciferine, N -methylcoclaurine, guattescidine, actinodaphnine, and N -methyllaurotetanine in the araticum peel [ 22 , 26 , 30 ]. As mentioned above, there is a significant interest in isolating and purifying alkaloids from araticum pulp and its byproduct (peel), which can serve as potential sources for obtaining alkaloids for the pharmaceutical industry.…”

Section: Bioactive Compounds Found In Araticum Fruit Partsmentioning

confidence: 99%

“…This extract inhibited 45% of acetylcholinesterase (AChE) activity at 1.5 mg/mL. Likewise, Barbosa et al [ 26 ] studied the effect of ethanolic extract from araticum peel, its alkaloidal fraction (dichloromethane fraction), and isolated alkaloids against AChE and butyrylcholinesterase (BChE) enzymes. Ethanolic extract and alkaloidal fraction displayed a low anticholinesterase activity, whereas isolated alkaloids (stephalagine, liriodenine, and atherospermidine) strongly inhibited the AChE and BChE enzymes.…”

Section: Biological Activities Reported In Araticum Fruit Partsmentioning

confidence: 99%

“…On the other hand, liriodenine showed the highest AChE inhibitory activity with an IC 50 value (2.7 µg/mL) very close to the positive control galantamine (IC 50 value of 1.5 µg/mL). Phenolic compounds and alkaloids can interact with active sites of cholinesterase enzymes (e.g., enzyme catalytic sites), delaying or inhibiting their catalytic activities [ 26 , 70 ]. In another study, Lucas dos Santos et al [ 54 ] verified that the treatment with aqueous extract from araticum pulp (1 mg/mL) can reduce the juglone-induced oxidative stress in wild-type (N2) strains of Caenorhabditis elegans (enhanced survival rates (32.2% survival) when compared to the control group (5.5% survival)) and paralysis in CL2006 strains of C. elegans expressing the Aβ1–42 peptide in muscle tissue (decreased the mean of worms paralyzed 10 h after treatment by 13.4%).…”

Section: Biological Activities Reported In Araticum Fruit Partsmentioning

confidence: 99%

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Scientific Advances in the Last Decade on the Recovery, Characterization, and Functionality of Bioactive Compounds from the Araticum Fruit (Annona crassiflora Mart.)

Arruda

Borsoi

Andrade

et al. 2023

Plants

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Araticum (Annona crassiflora Mart.) is a native and endemic species to Brazilian Cerrado whose fruits have high sensorial, nutritional, bioactive, and economic potential. Its use in local folk medicine, associated with recent scientific findings, has attracted growing interest from different industrial sectors. Therefore, understanding the scientific advances achieved so far and identifying gaps to be filled is essential to direct future studies and transform accumulated knowledge into innovative technologies and products. In this review, we summarize the phytochemical composition, bioactivities, and food products from araticum fruit that have been reported in the scientific literature over the past 10 years. The compiled data showed that araticum fruit parts contain a wide range of bioactive compounds, particularly phenolic compounds, alkaloids, annonaceous acetogenins, carotenoids, phytosterols, and tocols. These phytochemicals contribute to different biological activities verified in araticum fruit extracts/fractions, including antioxidant, anti-inflammatory, anti-Alzheimer, anticancer, antidiabetic, anti-obesity, antidyslipidemic, antinociceptive, hepatoprotective, healing of the cutaneous wound, antibacterial, and insecticide effects. Despite the promising findings, further studies—particularly toxicological (especially, with byproducts), pre-clinical, and clinical trials—must be conducted to confirm these biological effects in humans and assure the safety and well-being of consumers.

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Section: Bioactive Compounds Found In Araticum Fruit Partsmentioning

confidence: 99%

Section: Bioactive Compounds Found In Araticum Fruit Partsmentioning

confidence: 99%

Section: Biological Activities Reported In Araticum Fruit Partsmentioning

confidence: 99%

Section: Biological Activities Reported In Araticum Fruit Partsmentioning

confidence: 99%

See 2 more Smart Citations

Scientific Advances in the Last Decade on the Recovery, Characterization, and Functionality of Bioactive Compounds from the Araticum Fruit (Annona crassiflora Mart.)

Arruda

Borsoi

Andrade

et al. 2023

Plants

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“…This fact is in a good agreement with the Gibbs free energies of binding in protein–ligand complexes found here by MD simulations for 1 and 3 . The aporphine alkaloids may inhibit both AChE and BChE; preferential activity toward one enzyme or another strongly depends on a particular alkaloid structure [ 76 , 77 ].…”

Section: Resultsmentioning

confidence: 99%

In Vitro and In Silico Evaluation of Cholinesterase Inhibition by Alkaloids Obtained from Branches of Abuta panurensis Eichler

et al. 2022

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Alkaloids are natural products known as ethnobotanicals that have attracted increasing attention due to a wide range of their pharmacological properties. In this study, cholinesterase inhibitors were obtained from branches of Abuta panurensis Eichler (Menispermaceae), an endemic species from the Amazonian rainforest. Five alkaloids were isolated, and their structure was elucidated by a combination of 1D and 2D 1H and 13C NMR spectroscopy, HPLC-MS, and high-resolution MS: Lindoldhamine isomer m/z 569.2674 (1), stepharine m/z 298.1461 (2), palmatine m/z 352.1616 (3), 5-N-methylmaytenine m/z 420.2669 (4) and the N-trans-feruloyltyramine m/z 314.1404 (5). The compounds 1, 3, and 5 were isolated from A. panurensis for the first time. Interaction of the above-mentioned alkaloids with acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes was investigated in silico by molecular docking and molecular dynamics. The molecules under investigation were able to bind effectively with the active sites of the AChE and BChE enzymes. The compounds 1–4 demonstrated in vitro an inhibitory effect on acetylcholinesterase with IC50 values in the range of 19.55 µM to 61.24 µM. The data obtained in silico corroborate the results of AChE enzyme inhibition.

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Application of effect‐directed analysis using TLC–bioautography for rapid isolation and identification of antidiabetic compounds from the leaves of Annona cherimola Mill.

Galarce‐Bustos,

Obregón,

Vallejos‐Almirall

et al. 2023

Phytochemical Analysis

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IntroductionType 2 diabetes mellitus is a globally prevalent chronic disease characterised by hyperglycaemia and oxidative stress. The search for new natural bioactive compounds that contribute to controlling this condition and the application of analytical methodologies that facilitate rapid detection and identification are important challenges for science. Annona cherimola Mill. is an important source of aporphine alkaloids with many bioactivities.ObjectiveThe aim of this study is to isolate and identify antidiabetic compounds from alkaloid extracts with α‐glucosidase and α‐amylase inhibitory activity from A. cherimola Mill. leaves using an effect‐directed analysis by thin‐layer chromatography (TLC)–bioautography.MethodologyGuided fractionation for α‐glucosidase and α‐amylase inhibitors in leaf extracts was done using TLC–bioassays. The micro‐preparative TLC was used to isolate the active compounds, and the identification was performed by mass spectrometry associated with web‐based molecular networks. Additionally, in vitro estimation of the inhibitory activity and antioxidant capacity was performed in the isolated compounds.ResultsFive alkaloids (liriodenine, dicentrinone, N‐methylnuciferine, anonaine, and moupinamide) and two non‐alkaloid compounds (3‐methoxybenzenepropanoic acid and methylferulate) with inhibitory activity were isolated and identified using a combination of simple methodologies. Anonaine, moupinamide, and methylferulate showed promising results with an outstanding inhibitory activity against both enzymes and antioxidant capacity that could contribute to controlling redox imbalance.ConclusionsThese high‐throughput methodologies enabled a rapid isolation and identification of seven compounds with potential antidiabetic activity. To our knowledge, the estimated inhibitory activity of dicentrinone, N‐methylnuciferine, and anonaine against α‐glucosidase and α‐amylase is reported here for the first time.

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Cholinesterase inhibitors assessment of aporphine alkaloids from Annona crassiflora and molecular docking studies

Cited by 8 publications

References 42 publications

Scientific Advances in the Last Decade on the Recovery, Characterization, and Functionality of Bioactive Compounds from the Araticum Fruit (Annona crassiflora Mart.)

Scientific Advances in the Last Decade on the Recovery, Characterization, and Functionality of Bioactive Compounds from the Araticum Fruit (Annona crassiflora Mart.)

In Vitro and In Silico Evaluation of Cholinesterase Inhibition by Alkaloids Obtained from Branches of Abuta panurensis Eichler

Application of effect‐directed analysis using TLC–bioautography for rapid isolation and identification of antidiabetic compounds from the leaves of Annona cherimola Mill.

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