Isoquinoline alkaloids from the roots of Zanthoxylum rigidum as multi-target inhibitors of cholinesterase, monoamine oxidase A and Aβ1-42 aggregation

Plazas, Erika; Hagenow, Stefanie; Murillo, M.; Stark, Holger; Cuca, Luis E.

doi:10.1016/j.bioorg.2020.103722

Cited by 40 publications

(23 citation statements)

References 49 publications

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“…AChE was taken as a valuable spot for controlling NDDs causing cholinergic signaling deficit [ 71 ]. The alkaloids were extracted from the root of Zanthoxylum rigidum ; nitidine and avicine showed inhibitory action against AChE with IC 50 of 0.65 ± 0.09 μ M and 0.15 ± 0.01 μ M, respectively [ 72 ]. Another study showed four pyrrolizidine alkaloids, namely, 7-O-angeloylechinatine-N-oxide, 3′-O-acetylheliospine-N-oxide, heliosupine N-oxide, and heliosupine, isolated from Solenanthus lanatus, which possess the AChE inhibitory activity with IC 50 values ranging from 0.0001–0.60 mM [ 73 ].…”

Section: Therapeutic Activities Of Plant-derived Alkaloidsmentioning

confidence: 99%

Potential Therapeutic Applications of Plant-Derived Alkaloids against Inflammatory and Neurodegenerative Diseases

Aryal

Raut

Bhattarai

et al. 2022

Evidence-Based Complementary and Alternative Medicine

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Alkaloids are a type of natural compound possessing different pharmacological activities. Natural products, including alkaloids, which originate from plants, have emerged as potential protective agents against neurodegenerative disorders (NDDs) and chronic inflammations. A wide array of prescription drugs are used against these conditions, however, not free of limitations of potency, side effects, and intolerability. In the context of personalized medicine, further research on alkaloids to unravel novel therapeutic approaches in reducing complications is critical. In this review, a systematic survey was executed to collect the literature on alkaloids and their health complications, from which we found that majority of alkaloids exhibit anti-inflammatory action via nuclear factor-κB and cyclooxygenase-2 (COX-2), and neuroprotective interaction through acetylcholinesterase (AChE), COX, and β-site amyloid precursor protein activity. In silico ADMET and ProTox-II-related descriptors were calculated to predict the pharmacological properties of 280 alkaloids isolated from traditional medicinal plants towards drug development. Out of which, eight alkaloids such as tetrahydropalmatine, berberine, tetrandrine, aloperine, sinomenine, oxymatrine, harmine, and galantamine are found to be optimal within the categorical range when compared to nicotine. These alkaloids could be exploited as starting materials for novel drug synthesis or, to a lesser extent, manage inflammation and neurodegenerative-related complications.

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Section: Therapeutic Activities Of Plant-derived Alkaloidsmentioning

confidence: 99%

Potential Therapeutic Applications of Plant-Derived Alkaloids against Inflammatory and Neurodegenerative Diseases

Aryal

Raut

Bhattarai

et al. 2022

Evidence-Based Complementary and Alternative Medicine

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“…Multi-step chromatography was used for the isolation of alkaloids from the root extract of Zanthoxylum rigidum (Rutaceae) [ 111 ]. Eight purified IAs were isolated, which were tested for Ee AChE, h AChE and Eq BuChE inhibitory activity, as well as for monoamine oxidase (MAO-A and B) and Aβ aggregation.…”

Section: Further Isoquinoline Alkaloidsmentioning

confidence: 99%

Recent Progress on Biological Activity of Amaryllidaceae and Further Isoquinoline Alkaloids in Connection with Alzheimer’s Disease

et al. 2021

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Alzheimer’s disease (AD) is a progressive age-related neurodegenerative disease recognized as the most common form of dementia among elderly people. Due to the fact that the exact pathogenesis of AD still remains to be fully elucidated, the treatment is only symptomatic and available drugs are not able to modify AD progression. Considering the increase in life expectancy worldwide, AD rates are predicted to increase enormously, and thus the search for new AD drugs is urgently needed. Due to their complex nitrogen-containing structures, alkaloids are considered to be promising candidates for use in the treatment of AD. Since the introduction of galanthamine as an antidementia drug in 2001, Amaryllidaceae alkaloids (AAs) and further isoquinoline alkaloids (IAs) have been one of the most studied groups of alkaloids. In the last few years, several compounds of new structure types have been isolated and evaluated for their biological activity connected with AD. The present review aims to comprehensively summarize recent progress on AAs and IAs since 2010 up to June 2021 as potential drugs for the treatment of AD.

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“…An important strategy for treating neurodegenerative diseases is to maintain the levels of acetylcholine in the synaptic cleft by blocking the activity of cholinesterases [ 3 ]. Cholinesterases play an important role in the regulation of neurotransmission by catalyzing the degradation of neurotransmitter acetylcholine [ 4 ]. Currently, the cholinergic hypothesis associates the memory impairment and cognitive disturbances in Alzheimer’s disease with the large loss of cholinergic hippocampal neurons as a response to acetylcholine deficit which causes a cholinergic hypofunction and deficits of different cortical cholinergic markers.…”

Section: Introductionmentioning

confidence: 99%

“…For the determination of alkaloid contents in plant materials, various analytical techniques are applied. Most often, alkaloids are determined by chromatographic methods such as liquid chromatography coupled with tandem mass spectrometry (LC-MS/MS) [ 3 , 7 , 9 , 23 ], ultra-high-performance liquid chromatography with diode array detection (UPLC-DAD) [ 4 ], gas chromatography with mass spectrometry (GC-MS) [ 8 , 13 , 15 , 24 ].…”

Section: Introductionmentioning

confidence: 99%

Isoquinoline Alkaloid Contents in Macleaya cordata Extracts and Their Acetylcholinesterase and Butyrylcholinesterase Inhibition

et al. 2022

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An important strategy for treating neurodegenerative disorders is to maintain the levels of acetylcholine in the synaptic cleft by blocking the cholinesterases. Searching for new effective compounds with inhibited acetylcholinesterase and butyrylcholinesterase activity is one of the most significant challenges of the modern scientific research. The aim of this study was the optimization of the condition for cholinesterase activity determination by high-performance liquid chromatography coupled with diode array detector (HPLC-DAD) in terms of concentrations of enzymatic reaction mixture components, temperature of incubation, and incubation time. In vitro investigation of acetylcholinesterase and butyrylcholinesterase activity inhibition by some isoquinoline alkaloids and extracts obtained from the aerial part and roots of Macleaya cordata collected in May, July, and September. Acetylcholinesterase and butyrylcholinesterase activity inhibition of the extracts obtained from the plant had not been tested previously. The application of the HPLC method allowed eliminating absorption of interfering components, for example, alkaloids such as sanguinarine and berberine. The HPLC method was successfully applied for the evaluation of the acetylcholinesterase inhibitory activity in samples such as plant extracts, especially those containing colored components adsorbing at the same wavelength as the adsorption wavelength of 5-thio-2-nitro-benzoic acid, which is the product of the reaction between thiocholine (product of the hydrolysis of acetyl/butyrylthiocholine reaction) with Ellman’s reagent. Moreover, liquid chromatography coupled with a triple quadrupole mass spectrometer (LC–QqQ–ESI–MS/MS) analysis allowed evaluating the identification of relevant bioactive compounds in the obtained plant extracts. The investigated alkaloids, especially sanguinarine and chelerythrine, and all the Macleaya cordata extracts, especially the extract obtained from the aerial part collected in May, exhibited very high cholinesterase activity inhibition. HPLC-DAD was also applied for the kinetics study of the most active alkaloids sanguinarine and chelerythrine. Our investigations demonstrated that these plant extracts can be recommended for further in vivo experiments to confirm their cholinesterase inhibition activity.

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Isoquinoline alkaloids from the roots of Zanthoxylum rigidum as multi-target inhibitors of cholinesterase, monoamine oxidase A and Aβ1-42 aggregation

Cited by 40 publications

References 49 publications

Potential Therapeutic Applications of Plant-Derived Alkaloids against Inflammatory and Neurodegenerative Diseases

Potential Therapeutic Applications of Plant-Derived Alkaloids against Inflammatory and Neurodegenerative Diseases

Recent Progress on Biological Activity of Amaryllidaceae and Further Isoquinoline Alkaloids in Connection with Alzheimer’s Disease

Isoquinoline Alkaloid Contents in Macleaya cordata Extracts and Their Acetylcholinesterase and Butyrylcholinesterase Inhibition

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