Three (―)-cytisine derivatives and 1-hydroxyquinopimaric acid as acetylcholinesterase inhibitors

García-García, José D.; Segura-Ceniceros, Elda Patricia; Zaynullin, Radik A.; Кунакова, Р. В.; Vafina, G. F.; Tsypysheva, I. P.; Vargas-Segura, Alejandra; Ilyiná, Anna

doi:10.1016/j.toxrep.2019.08.011

Cited by 5 publications

(3 citation statements)

References 30 publications

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“…Cytisine derivatives have been explored as potential drugs against Alzheimer's and Parkinson's diseases as well as attention deficit hyperactivity disorder 2012 [4]. García-García et al studied in vitro acetylcholinesterase inhibition by cytisine derivatives [5]. Some studies have suggested that targeting the nicotinic acetylcholine receptors holds promise as a new therapeutic approach for the treatment of depression [6].…”

Section: Introductionmentioning

confidence: 99%

Determination of Cytisine and N-Methylcytisine from Selected Plant Extracts by High-Performance Liquid Chromatography and Comparison of Their Cytotoxic Activity

Petruczynik

Wróblewski

Misiurek

et al. 2020

Toxins

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Quinolizidine alkaloids exhibit various forms of biological activity. A lot of them were found in the Leguminosae family, including Laburnum and Genista. The aim of the study was the optimization of a chromatographic system for the analysis of cytisine and N-methylcytisine in various plant extracts as well as an investigation of the cytotoxic activities of selected alkaloids and plant extracts obtained from Laburnum anagyroides, Laburnum anagyroides L. quercifolium, Laburnum alpinum, Laburnum watereri, Genista germanica, and Genista tinctoria against various cancer cell lines. The determination of investigated compounds was performed by High Performance Liquid Chromatography with Diode Array Detection (HPLC-DAD), while High Performance Liquid Chromatography coupled with Quadrupole Time-of-Flight–Mass Spectrometry (HPLC-QTOF-MS) was applied for the qualitative analysis of plant extracts. The retention, separation selectivity, peaks shape, and systems efficiency obtained for cytisine and N-methylcytisine in different chromatographic systems were compared. The application of columns with alkylbonded and phenyl stationary phases led to a very weak retention of cytisine and N-methylcytisine, even when the mobile phases containing only 5% of organic modifiers were used. The strongest retention was observed when hydrophilic interaction chromatography (HILIC) or especially when ion exchange chromatography (IEC) were applied. The most optimal system in terms of alkaloid retention, peak shape, and system efficiency containing an strong cation exchange (SCX) stationary phase and a mobile phase consisted of 25% acetonitrile and formic buffer at pH 4.0 was applied for investigating alkaloids analysis in plant extracts. Cytotoxic properties of the investigated plant extracts as well as cytisine and N-methylcytisine were examined using human tongue squamous carcinoma cells (SCC-25), human pharyngeal squamous carcinoma cells (FaDu), human triple-negative breast adenocarcinoma cell line (MDA-MB-231), and human breast adenocarcinoma cell line (MCF-7). The highest cytotoxic activity against FaDu, MCF-7, and MDA-MB cancer cell lines was observed after applying the Genista germanica leaves extract. In contrast, the highest cytotoxic activity against SCC-25 cell line was obtained after treating with the seed extract of Laburnum watereri. The investigated plant extracts exhibit significant cytotoxicity against the tested human cancer cell lines and seem to be promising for further research on its anticancer activity.

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Section: Introductionmentioning

confidence: 99%

Determination of Cytisine and N-Methylcytisine from Selected Plant Extracts by High-Performance Liquid Chromatography and Comparison of Their Cytotoxic Activity

Petruczynik

Wróblewski

Misiurek

et al. 2020

Toxins

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“…Researchers can measure the activity of AChE in A. salina as an indicator of the potentially toxic effects of various substances. For example, if a substance inhibits the activity of AChE in A. salina , it may be a neurotoxin and could be harmful to other organisms, including humans [ 10 , 11 , 12 , 13 ]. This study is of paramount importance as it addresses gaps related to P. nigrum L., specifically the Guajarina cultivar.…”

Section: Introductionmentioning

confidence: 99%

Chemical Composition of Piper nigrum L. Cultivar Guajarina Essential Oils and Their Biological Activity

Feitosa,

Ferreira,

Franco

et al. 2024

Molecules

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The essential oils and aroma derived from the leaves (L), stems (St), and spikes (s) of Piper nigrum L. cv. Guajarina were extracted; the essential oils were extracted using hydrodistillation (HD), and steam distillation (SD), and the aroma was obtained by simultaneous distillation and extraction (SDE). Chemical constituents were identified and quantified using GC/MS and GC-FID. Preliminary biological activity was assessed by determining the toxicity against Artemia salina Leach larvae, calculating mortality rates, and determining lethal concentration values (LC50). The predominant compounds in essential oil samples included α-pinene (0–5.6%), β-pinene (0–22.7%), limonene (0–19.3%), 35 linalool (0–5.3%), δ-elemene (0–10.1%), β-caryophyllene (0.5–21.9%), γ-elemene (7.5–33.9%), and curzerene (6.9–31.7%). Multivariate analysis, employing principal component analysis (PCA) and hierarchical cluster analysis (HCA), revealed three groups among the identified classes and two groups among individual compounds. The highest antioxidant activity was found for essential oils derived from the leaves (167.9 41 mg TE mL−1). Larvicidal potential against A. salina was observed in essential oils obtained from the leaves (LC50 6.40 μg mL−1) and spikes (LC50 6.44 μg mL−1). The in silico studies demonstrated that the main compounds can interact with acetylcholinesterase, thus showing the potential molecular interaction responsible for the toxicity of the essential oil in A. salina.

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“…Pesquisas relatam que produtos naturais e seus derivados são conhecidos por A reação de hidrólise da acetilcolina, catalisada pela enzima AChE (Figura 02) ocorre de forma natural no ser humano, cuja reação consiste em converter a acetilcolina nos produtos ácido acético e colina, por meio da hidrólise pela AChE(XU et al, 2019;IBRAHIM et al, 2009). A alta degradação de neurotransmissores, como a acetilcolina, em portadores da DA tem como consequência problemas de memória, comportamento e locomoção no indivíduo doente(GARCÍA-GARCÍA et al, 2019).…”

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Produtos naturais com implicações na farmacologia

Oliveira¹,

Silva²

2023

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Os autores desta obra: 1. Atestam não possuir qualquer interesse comercial que constitua um conflito de interesses em relação ao artigo científico publicado; 2.Declaram que participaram ativamente da construção dos respectivos manuscritos, preferencialmente na: a) Concepção do estudo, e/ou aquisição de dados, e/ou análise e interpretação de dados; b) Elaboração do artigo ou revisão com vistas a tornar o material intelectualmente relevante; c) Aprovação final do manuscrito para submissão.; 3. Certificam que os artigos científicos publicados estão completamente isentos de dados e/ou resultados fraudulentos; 4. Confirmam a citação e a referência correta de todos os dados e de interpretações de dados de outras pesquisas; 5.Reconhecem terem informado todas as fontes de financiamento recebidas para a consecução da pesquisa; 6. Autorizam a edição da obra, que incluem os registros de ficha catalográfica, ISBN, DOI e demais indexadores, projeto visual e criação de capa, diagramação de miolo, assim como lançamento e divulgação da mesma conforme critérios da Atena Editora. DECLARAÇÃO DA EDITORA A Atena Editora declara, para os devidos fins de direito, que: 1. A presente publicação constitui apenas transferência temporária dos direitos autorais, direito sobre a publicação, inclusive não constitui responsabilidade solidária na criação dos manuscritos publicados, nos termos previstos na Lei sobre direitos autorais (Lei 9610/98), no art. 184 do Código Penal e no art. 927 do Código Civil; 2. Autoriza e incentiva os autores a assinarem contratos com repositórios institucionais, com fins exclusivos de divulgação da obra, desde que com o devido reconhecimento de autoria e edição e sem qualquer finalidade comercial; 3. Todos os e-book são open access, desta forma não os comercializa em seu site, sites parceiros, plataformas de ecommerce, ou qualquer outro meio virtual ou físico, portanto, está isenta de repasses de direitos autorais aos autores; 4. Todos os membros do conselho editorial são doutores e vinculados a instituições de ensino superior públicas, conforme recomendação da CAPES para obtenção do Qualis livro; 5. Não cede, comercializa ou autoriza a utilização dos nomes e e-mails dos autores, bem como nenhum outro dado dos mesmos, para qualquer finalidade que não o escopo da divulgação desta obra.

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Three (―)-cytisine derivatives and 1-hydroxyquinopimaric acid as acetylcholinesterase inhibitors

Abstract: Graphical abstract

Cited by 5 publications

References 30 publications

Determination of Cytisine and N-Methylcytisine from Selected Plant Extracts by High-Performance Liquid Chromatography and Comparison of Their Cytotoxic Activity

Determination of Cytisine and N-Methylcytisine from Selected Plant Extracts by High-Performance Liquid Chromatography and Comparison of Their Cytotoxic Activity

Chemical Composition of Piper nigrum L. Cultivar Guajarina Essential Oils and Their Biological Activity

Produtos naturais com implicações na farmacologia

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