Acetylcholinesterase inhibitory activities and bioguided fractionation of the Ocotea percoriacea extracts: HPLC-DAD-MS/MS characterization and molecular modeling of their alkaloids in the active fraction

Cassiano, Dayse Santos Almeida; Reis, Isabella Mary Alves; Estrela, Isabela de Oliveira; Freitas, Humberto Fonseca de; Pita, Samuel Silva da Rocha; David, Jorge; Branco, Alexsandro

doi:10.1016/j.compbiolchem.2019.107129

Cited by 17 publications

(10 citation statements)

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“…The enzyme hydrolyzes the active neurotransmitter acetylcholine into the inactive compounds choline and acetic acid. Currently, against Alzheimer's disease, drug research and development are based on the cholinergic hypothesis that supports the cognition improvement by the regulation of the synthesis and release of acetylcholine in the brain [5].…”

Section: Introductionmentioning

confidence: 99%

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Application of HPLC-DAD for In Vitro Investigation of Acetylcholinesterase Inhibition Activity of Selected Isoquinoline Alkaloids from Sanguinaria canadensis Extracts

Tuzimski

Petruczynik

2021

Molecules

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Isoquinoline alkaloids may have a wide range of pharmacological activities. Some of them have acetylcholinesterase activity inhibition. Nowadays, neurodegenerative disorders such as Alzheimer’s disease have become a serious public health problem. Searching for new effective compounds with inhibited acetylcholinesterase activity is one of the most significant challenges of modern scientific research. The aim of this study was the in vitro investigation of acetylcholinesterase activity inhibition of extracts obtained from Sanguinaria canadensis collected before, during and after flowering. The acetylcholinesterase activity inhibition of these extracts has not been previously tested. The aim was also to quantify selected alkaloids in the investigated extracts by high performance liquid chromatography (HPLC). The analyses of alkaloid content were performed using HPLC in reversed phase (RP) mode using Polar RP column and mobile phase containing acetonitrile, water and ionic liquid (IL). The acetylcholinesterase activity inhibition of the tested plant extracts and respective alkaloid standards were examined using high performance liquid chromatography with diode-array detector (HPLC-DAD) for the quantification of 5-thio-2-nitro-benzoic acid, which is the product of the reaction between the thiocholine (product of the hydrolysis of acetylthiocholine reaction) with Ellman reagent. The application of the HPLC method allowed for elimination of absorption of interfering components, for example, alkaloids such as sanguinarine and berberine. It is revealed that the HPLC method can be successfully used for the evaluation of the acetylcholinesterase inhibitory activity in samples such as plant extracts, especially those containing colored components adsorbing at wavelength in the range 405–412 nm. The acetylcholinesterase inhibition activity synergy of pairs of alkaloid standards and mixture of all investigated alkaloids was also determined. Most investigated alkaloids and all Sanguinaria canadensis extracts exhibited very high acetylcholinesterase activity inhibition. IC50 values obtained for alkaloid standards were from 0.36 for berberine to 23.13 µg/mL for protopine and from 61.24 to 89.14 µg/mL for Sanguinaria canadensis extracts. Our investigations demonstrated that these plant extracts can be recommended for further in vivo experiments to confirm their acetylcholinesterase activity inhibition.

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Section: Introductionmentioning

confidence: 99%

“…Among plant-derived cholinesterase inhibitors, alkaloids are regarded as the strongest acetylcholinesterase inhibitors. This activity is exhibited by some alkaloids, for example, Amarylidaceae alkaloids [5][6][7], isoquinoline alkaloids [5,8], and indole alkaloids [9].…”

Section: Introductionmentioning

confidence: 99%

Application of HPLC-DAD for In Vitro Investigation of Acetylcholinesterase Inhibition Activity of Selected Isoquinoline Alkaloids from Sanguinaria canadensis Extracts

Tuzimski

Petruczynik

2021

Molecules

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“…Species of this genus are known for producing a variety of secondary metabolites, with neolignans, aporphine and benzylisoquinoline‐type alkaloids as the most representative classes 2,3 . A wide range of biological activities from Ocotea species has been described in the literature, including acaricide, 4,5 antiproliferative, 6 anti‐inflammatory 7 and the inhibition of acetylcholinesterase (AChE) 8 …”

Section: Introductionmentioning

confidence: 99%

Rapid structural characterisation of benzylisoquinoline and aporphine alkaloids from Ocotea spixiana acaricide extract by HPTLC‐DESI‐MSⁿ

Conceição

Reis

Cerqueira

et al. 2020

Phytochemical Analysis

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Introduction: Lauraceae alkaloids are a structurally diverse class of plant specialised secondary metabolites that play an important role in modern pharmacotherapy, being useful as well as model compounds for the development of synthetic analogues. However, alkaloids characterisation is challenging due to low concentrations, the complexity of plant extracts, and long processes for accurate structural determinations. Objective: The use of high-performance thin layer chromatography coupled with desorption electrospray ionisation multistage mass spectrometry (HPTLC DESI-MS n) as a fast tool to identify alkaloids present in Ocotea spixiana extract and evaluate the extract's acaricide activity. Methods: Ocotea spixiana twigs were extracted by conventional liquid-liquid partitioning. HPTLC analysis of the ethyl acetate extract was performed to separate isobaric alkaloids prior to DESI-MS n analysis, performed from MS 3 up to MS 7. The extract's acaricide activity against Rhipicephalus microplus was evaluated by in vitro (larval immersion test) and in silico tests. Results: HPTLC-DESI-MS n analysis was performed to identify a total of 13 aporphine and four benzylisoquinoline-type alkaloids reported for the first time in O. spixiana. In vitro evaluation of the extract and the alkaloid boldine showed significant activity against R. microplus larvae. It was established in silico that boldine had important intermolecular interactions with R. microplus acetylcholinesterase enzyme. Conclusion: The present study demonstrated that HPTLC-DESI-MS n is a useful analytical tool to identify isoquinoline alkaloids in plant extracts. The acaricide activity of the O. spixiana ethyl acetate extract can be correlated to the presence of alkaloids. K E Y W O R D S acaricide activity, alkaloids, HPTLC-DESI-MS n , Ocotea spixiana 1 | INTRODUCTION Ocotea is an expressive genus of the Lauraceae family, occurring mainly in tropical and subtropical areas. 1 Species of this genus are known for producing a variety of secondary metabolites, with neolignans, aporphine and benzylisoquinoline-type alkaloids as the most representative classes. 2,3 A wide range of biological activities from Ocotea species has been described in the literature, including

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“…The extracts obtained from Ocotea percoriacea containing alkaloids isocorydine N-oxide, isocorydine N-oxide derivative, palmatine, roemerine and roemerine N-Oxide were in vitro tested for acetylcholinesterase activity inhibition. The determination of anti-cholinesterase activity was performed by modified Ellman method with the application of 96-well microplate [ 41 ]. Only hexane and dichlorometane fractions of Ocotea percoriacea extracts at concentration 1 mg/mL showed high inhibition activity after 30 min from the beginning of the reaction (83.28% and 92.09%, respectively).…”

Section: Determination Of Anti-neurodegenerative Disease Activity Of ...mentioning

confidence: 99%

Determination of Anti-Alzheimer’s Disease Activity of Selected Plant Ingredients

Tuzimski

Petruczynik

2022

Molecules

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Neurodegenerative diseases, among which one of the more common is Alzheimer’s disease, are the one of the biggest global public health challenges facing our generation because of the increasing elderly population in most countries. With the growing burden of these diseases, it is essential to discover and develop new treatment options capable of preventing and treating them. Neurodegenerative diseases, among which one of the most common is Alzheimer’s disease, are a multifactorial disease and therefore demand multiple therapeutic approaches. One of the most important therapeutic strategies is controlling the level of acetylcholine—a neurotransmitter in cholinergic synapses—by blocking the degradation of acetylcholine using acetylcholinesterase inhibitors such as tacrine, galantamine, donepezil and rivastigmine. However, these drugs can cause some adverse side effects, such as hepatotoxicity and gastrointestinal disorder. Thus, the search for new, more effective drugs is very important. In the last few years, different active constituents from plants have been tested as potential drugs in neurodegenerative disease therapy. The availability, lower price and less toxic effects of herbal medicines compared with synthetic agents make them a simple and excellent choice in the treatment of neurodegenerative diseases. The empirical approach to discovering new drugs from the systematic screening of plant extracts or plant-derived compounds is still an important strategy when it comes to finding new biologically active substances. The aim of this review is to identify new, safe and effective compounds that are potential candidates for further in vivo and clinical tests from which more effective drugs for the treatment of Alzheimer’s disease could be selected. We reviewed the methods used to determine anti-Alzheimer’s disease activity. Here, we have discussed the relevance of plant-derived compounds with in vitro activity. Various plants and phytochemical compounds have shown different activity that could be beneficial in the treatment of Alzheimer’s disorders. Most often, medicinal plants and their active components have been investigated as acetylcholinesterase and/or butyrylcholinesterase activity inhibitors, modifiers of β-amyloid processing and antioxidant agents. This study also aims to highlight species with assessed efficacy, usable plant parts and the most active plant components in order to identify species and compounds of interest for further study. Future research directions are suggested and recommendations made to expand the use of medicinal plants, their formulations and plant-derived active compounds to prevent, mitigate and treat Alzheimer’s disease.

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Acetylcholinesterase inhibitory activities and bioguided fractionation of the Ocotea percoriacea extracts: HPLC-DAD-MS/MS characterization and molecular modeling of their alkaloids in the active fraction

Cited by 17 publications

References 58 publications

Application of HPLC-DAD for In Vitro Investigation of Acetylcholinesterase Inhibition Activity of Selected Isoquinoline Alkaloids from Sanguinaria canadensis Extracts

Application of HPLC-DAD for In Vitro Investigation of Acetylcholinesterase Inhibition Activity of Selected Isoquinoline Alkaloids from Sanguinaria canadensis Extracts

Rapid structural characterisation of benzylisoquinoline and aporphine alkaloids from Ocotea spixiana acaricide extract by HPTLC‐DESI‐MSⁿ

Determination of Anti-Alzheimer’s Disease Activity of Selected Plant Ingredients

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Acetylcholinesterase inhibitory activities and bioguided fractionation of the Ocotea percoriacea extracts: HPLC-DAD-MS/MS characterization and molecular modeling of their alkaloids in the active fraction

Cited by 17 publications

References 58 publications

Application of HPLC-DAD for In Vitro Investigation of Acetylcholinesterase Inhibition Activity of Selected Isoquinoline Alkaloids from Sanguinaria canadensis Extracts

Application of HPLC-DAD for In Vitro Investigation of Acetylcholinesterase Inhibition Activity of Selected Isoquinoline Alkaloids from Sanguinaria canadensis Extracts

Rapid structural characterisation of benzylisoquinoline and aporphine alkaloids from Ocotea spixiana acaricide extract by HPTLC‐DESI‐MSn

Determination of Anti-Alzheimer’s Disease Activity of Selected Plant Ingredients

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Rapid structural characterisation of benzylisoquinoline and aporphine alkaloids from Ocotea spixiana acaricide extract by HPTLC‐DESI‐MSⁿ