Neuroprotective activity of isoquinoline alkaloids from of Chilean Amaryllidaceae plants against oxidative stress-induced cytotoxicity on human neuroblastoma SH-SY5Y cells and mouse hippocampal slice culture

Trujillo-Chacón, Lina M.; Alarcón‐Enos, Julio; Cespedes‐Acuña, Carlos L.; Bustamante, Luis; Baeza, Marcelo; López, Manuela G.; Fernández‐Mendívil, Cristina; Cabezas, Fabio; Pastene, Edgar

doi:10.1016/j.fct.2019.110665

Cited by 16 publications

(32 citation statements)

References 38 publications

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“…The cited studies are one of the few that have addressed the neuroprotective activity of individual AAs. Most of the studies dealing with the neuroprotective activity of AAs have used complex alkaloidal extracts accompanied by GC/MS analysis [ 82 , 83 , 84 ]. However, studies performed on mixtures are not able to identify which compound is responsible for the studied activity.…”

Section: Amaryllidaceae 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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Section: Amaryllidaceae 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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“…Furthermore, narwedine (33) is characterized by α,β-unsaturation and the consequent flattening of ring-C, which, together with the acceptor functions of the oxo group, could explain its better activity over galanthamine [29]. The evidence available suggests that C-3 substitution as with chlidanthine (39) offers no benefit as this compound was inactive (or poorly active) against as many as 18 cancer cells [33,34]. Both of these studies involved a screen in parallel with galanthamine (1), which, as expected, was also inactive [33,34].…”

Section: Structure-activity Relationshipsmentioning

confidence: 99%

Cytotoxic Agents in the Minor Alkaloid Groups of the Amaryllidaceae

Nair

Staden

2021

Planta Med

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Over 600 alkaloids have to date been identified in the plant family Amaryllidaceae. These have been arranged into as many as 15 different groups based on their characteristic structural features. The vast majority of studies on the biological properties of Amaryllidaceae alkaloids have probed their anticancer potential. While most efforts have focused on the major alkaloid groups, the volume and diversity afforded by the minor alkaloid groups have promoted their usefulness as targets for cancer cell line screening purposes. This survey is an in-depth review of such activities described for around 90 representatives from 10 minor alkaloid groups of the Amaryllidaceae. These have been evaluated against over 60 cell lines categorized into 18 different types of cancer. The montanine and cripowellin groups were identified as the most potent, with some in the latter demonstrating low nanomolar level antiproliferative activities. Despite their challenging molecular architectures, the minor alkaloid groups have allowed for facile adjustments to be made to their structures, thereby altering the size, geometry, and electronics of the targets available for structure-activity relationship studies. Nevertheless, it was seen with a regular frequency that the parent alkaloids were better cytotoxic agents than the corresponding semisynthetic derivatives. There has also been significant interest in how the minor alkaloid groups manifest their effects in cancer cells. Among the various targets and pathways in which they were seen to mediate, their ability to induce apoptosis in cancer cells is most appealing.

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“…The literature reports countless works which, through the use of LC-ESI-MS-MS or GC-MS-MS, give an account of the existence of these alkaloids in the different genera of this family, reaching the presence of 30 to 40 alkaloids in a plant. In a previous work with Rhodophiala pratensis through GC-MS our group reported 34 alkaloids, achieving the identification of 24 of them [5]. In the present work, the preliminary analysis by GC-MS of crude alkaloid extract of R. speciosum revealed the presence of alkaloids with lycorine, 5,6-dehydrolycorine, galanthamine, haemanthamine, and montanine skeleton, and a set of not identified alkaloids, although their fragmentation pattern suggests that they are lycorine derivatives ( Figure 1, Table 1).…”

Section: Gc-ms Analysis Of Rhodolirium Speciosummentioning

confidence: 99%

“…Previous studies in different species of the Rhodolirium genus report between 20 and 30 alkaloids, among which are galanthamine, lycorine, heamanthamine, and undulatine, together with a high number of unidentified alkaloids [4,5]. There is great evidence of the pharmacological potential of these metabolites, such as anticancer [6], cytotoxicity [7], antibacterial [8], and neuroprotection activity [5]. The potential for inhibition of acetylcholinesterase (AChE) that Amaryllidaceae alkaloids have is well known; enzyme inhibition suppresses hydrolysis of acetylcholine, a neurotransmitter that mediates the synaptic activity of the nervous system.…”

Section: Introductionmentioning

confidence: 99%

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Isolation of Three Lycorine Type Alkaloids from Rhodolirium speciosum (Herb.) Ravenna Using pH-Zone-Refinement Centrifugal Partition Chromatography and Their Acetylcholinesterase Inhibitory Activities

et al. 2020

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Preparative separation of three lycorine type alkaloids from Rhodolirum speciosum (Amaryllidaceae) was successfully carried out using pH-zone-refinement centrifugal partition chromatography (CPC) using the solvent system methyl-tert-butyl ether/acetonitrile/water (4:1:5, v/v/v) in descending mode. Using this system, Alkaloid 1 (165.7 mg, 88.2%, purity), 2 (60.1 mg, 97.7% purity) and 3 (12.3 mg, 84.4% purity) were obtained in one step. For structure elucidation, the pure alkaloids were subjected to spectroscopy analysis using nuclear magnetic resonance experiments (1H-NMR, 13C-NMR) and gas chromatography coupled with mass spectrometry (GC-MS). Alkaloids 1, 2, and 3 were identified as 1-O-acetyl-5,6-dehydrolycorine, 1-O-acetyl-lycorine, and 1,2-O-diacetyl-5,6-dehydrolycorine, respectively. The acetylcholinesterase inhibitory activity of these alkaloids was IC50 151.1 μg/mL, IC50 203.5 μg/mL, IC50 470.0 μg/mL, and IC50 17.1 μg/mL, respectively.

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Neuroprotective activity of isoquinoline alkaloids from of Chilean Amaryllidaceae plants against oxidative stress-induced cytotoxicity on human neuroblastoma SH-SY5Y cells and mouse hippocampal slice culture

Cited by 16 publications

References 38 publications

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

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

Cytotoxic Agents in the Minor Alkaloid Groups of the Amaryllidaceae

Isolation of Three Lycorine Type Alkaloids from Rhodolirium speciosum (Herb.) Ravenna Using pH-Zone-Refinement Centrifugal Partition Chromatography and Their Acetylcholinesterase Inhibitory Activities

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