RESUMO
Parkinson's disease (PD) is one of the most common neurodegenerative diseases and affects approximately 6.3 million people worldwide. To date, the treatment of PD remains a challenge, as available treatment options are known to be associated with serious side effects; hence, the search for new treatment strategies is critical. Extracts from the Amaryllidaceae plant family as well as their alkaloids have been reported to have neuroprotective potentials. This study, therefore, investigated the biological activities of Crossyne flava and its isolated alkaloids in an in vitro MPP+ (1-methyl-4-phenylpyridinium) PD model using SH-SY5Y cells. The effects of the total extract as well as the four compounds isolated from Crossyne flava (i.e., pancratinine B (1), bufanidrine (2), buphanisine (3), and epibuphanisine (4)) were evaluated for cell viability, neuroprotection, levels of reactive oxygen species (ROS), adenosine triphosphate activity (ATP), and caspase 3/7 activity in SH-SY5Y cells. The results obtained showed that pre-treatment with both the extract and the isolated compounds was effective in protecting the SH-SY5Y cells from MPP+-induced neurotoxicity and inhibited ROS generation, ATP depletion as well as apoptosis induction in the SH-SY5Y cells. The results of this study show that the Amaryllidaceae plant family may be a source of novel compounds for the treatment of neurodegenerative diseases, which validates the reported traditional uses.
Assuntos
Alcaloides de Amaryllidaceae/farmacologia , Amaryllidaceae/química , Intoxicação por MPTP/tratamento farmacológico , Fármacos Neuroprotetores/farmacologia , Estresse Oxidativo/efeitos dos fármacos , Transdução de Sinais/efeitos dos fármacos , Alcaloides de Amaryllidaceae/química , Alcaloides de Amaryllidaceae/isolamento & purificação , Linhagem Celular Tumoral , Humanos , Intoxicação por MPTP/metabolismo , Intoxicação por MPTP/patologia , Neuroproteção/efeitos dos fármacos , Fármacos Neuroprotetores/química , Fármacos Neuroprotetores/isolamento & purificaçãoRESUMO
Botrytis cinerea cause postharvest diseases on fruit and lead economic losses. Application of environment-friendly natural compounds is an alternative for synthetic fungicides to control postharvest disease. Lycorine is an indolizidine alkaloid which is widely used for human drug design, however, application of lycorine in controlling postharvest disease and the underlying mechanisms have not been reported. In this study, the effects of lycorine on mycelium growth, spore germination, disease development in apple fruit, cell viability, cell membrane integrity, cell wall deposition, and expression of mitogen-activated protein kinase (MAPK) and GTPase of B. cinerea were investigated. Our results showed that lycorine was effective in controlling postharvest gray mold caused by B. cinerea on apple fruit. In the in vitro tests, lycorine strongly inhibited spore germination and mycelium spreading in culture medium. Investigation via fluorescein diacetate and propidium iodide staining suggested that lycorine could damage the membrane integrity and impair cell viability of B. cinerea. Furthermore, the expression levels of several MAPK and GTPase coding genes were reduced upon the lycorine treatment. Taken together, lycorine is an effective and promising way to control postharvest disease caused by B. cinerea.
Assuntos
Alcaloides de Amaryllidaceae/farmacologia , Antifúngicos/farmacologia , Botrytis/fisiologia , Malus/crescimento & desenvolvimento , Fenantridinas/farmacologia , Alcaloides de Amaryllidaceae/isolamento & purificação , Antifúngicos/isolamento & purificação , Botrytis/química , Resistência à Doença , Proteínas Fúngicas/genética , GTP Fosfo-Hidrolases/genética , Regulação Enzimológica da Expressão Gênica/efeitos dos fármacos , Regulação Fúngica da Expressão Gênica/efeitos dos fármacos , Germinação , Malus/efeitos dos fármacos , Malus/microbiologia , Proteínas Quinases Ativadas por Mitógeno/genética , Fenantridinas/isolamento & purificação , Esporos Fúngicos/química , Esporos Fúngicos/fisiologiaRESUMO
A new alkaloid, amabiloid A (1) was isolated from Crinum amabile along with eleven known compounds. Their structures were determined by 1D and 2D NMR spectroscopic data. In addition, the acetyl- and butyrylcholinesterase inhibitory activities of the isolated compounds were evaluated.
Assuntos
Alcaloides de Amaryllidaceae , Inibidores da Colinesterase/farmacologia , Crinum , Alcaloides de Amaryllidaceae/isolamento & purificação , Alcaloides de Amaryllidaceae/farmacologia , Butirilcolinesterase , Inibidores da Colinesterase/isolamento & purificação , Crinum/química , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Extratos VegetaisRESUMO
Amaryllidaceae are bulbous wild and cultivated plants well known for their beautiful flowers and pharmaceutical applications, essentially due to the alkaloids and flavonoids content. Hundreds of alkaloids have been isolated until now and several scientific publications reported their sources, chemical structures, and biological activities. During the last decade, some unstudied Amaryllidaceae plants were the object of in-depth investigations to isolate and chemically and biologically characterize new and already known alkaloids as well as some analogues. This review describes the isolation and chemical and biological characterization of the Amaryllidaceae alkaloids, and their analogues obtained in the last decade, focusing the discussion on the new ones.
Assuntos
Alcaloides de Amaryllidaceae/química , Alcaloides de Amaryllidaceae/farmacologia , Amaryllidaceae/química , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Alcaloides de Amaryllidaceae/isolamento & purificação , Medicina Tradicional , Fitoterapia , Extratos Vegetais/isolamento & purificação , Raízes de Plantas/química , Relação Estrutura-AtividadeRESUMO
BACKGROUND: Chagas disease, caused by the protozoan Trypanosoma cruzi, is a neglected disease that affects ~7 million people worldwide. Development of new drugs to treat the infection remains a priority since those currently available have frequent side effects and limited efficacy at the chronic stage. Natural products provide a pool of diversity structures to lead the chemical synthesis of novel molecules for this purpose. Herein we analyzed the anti-T. cruzi activity of nine alkaloids derived from plants of the family Amaryllidaceae. METHODS: The activity of each alkaloid was assessed by means of an anti-T. cruzi phenotypic assay. We further evaluated the compounds that inhibited parasite growth on two distinct cytotoxicity assays to discard those that were toxic to host cells and assure parasite selectivity. RESULTS: We identified a single compound (hippeastrine) that was selectively active against the parasite yielding selectivity indexes of 12.7 and 35.2 against Vero and HepG2 cells, respectively. Moreover, it showed specific activity against the amastigote stage (IC50 = 3.31 µM). CONCLUSIONS: Results reported here suggest that natural products are an interesting source of new compounds for the development of drugs against Chagas disease.
Assuntos
Alcaloides de Amaryllidaceae/farmacologia , Tripanossomicidas/farmacologia , Trypanosoma cruzi/efeitos dos fármacos , Alcaloides de Amaryllidaceae/isolamento & purificação , Animais , Chlorocebus aethiops , Avaliação Pré-Clínica de Medicamentos , Células Hep G2 , Humanos , Concentração Inibidora 50 , Compostos Fitoquímicos/farmacologia , Células VeroRESUMO
Plants of the Amaryllidaceae family are promising therapeutic tools for human diseases and have been used as alternative medicines. The specific secondary metabolites of this plant family, called Amaryllidaceae alkaloids (AA), have attracted considerable attention due to their interesting pharmacological activities. One of them, galantamine, is already used in the therapy of Alzheimer's disease as a long acting, selective, reversible inhibitor of acetylcholinesterase. One group of AA is the montanine-type, such as montanine, pancracine and others, which share a 5,11-methanomorphanthridine core. So far, only 14 montanine-type alkaloids have been isolated. Compared with other structural-types of AA, montanine-type alkaloids are predominantly present in plants in low concentrations, but some of them display promising biological properties, especially in vitro cytotoxic activity against different cancerous cell lines. The present review aims to summarize comprehensively the research that has been published on the Amaryllidaceae alkaloids of montanine-type.
Assuntos
Alcaloides de Amaryllidaceae/química , Amaryllidaceae/química , Antineoplásicos Fitogênicos/química , Antiprotozoários/química , Inibidores da Colinesterase/química , Nootrópicos/química , Amaryllidaceae/metabolismo , Alcaloides de Amaryllidaceae/isolamento & purificação , Alcaloides de Amaryllidaceae/farmacologia , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Antiprotozoários/isolamento & purificação , Antiprotozoários/farmacologia , Linhagem Celular Tumoral , Inibidores da Colinesterase/isolamento & purificação , Inibidores da Colinesterase/farmacologia , Galantamina/química , Galantamina/isolamento & purificação , Galantamina/farmacologia , Compostos Heterocíclicos de 4 ou mais Anéis/química , Compostos Heterocíclicos de 4 ou mais Anéis/isolamento & purificação , Compostos Heterocíclicos de 4 ou mais Anéis/farmacologia , Humanos , Concentração Inibidora 50 , Isoquinolinas/química , Isoquinolinas/isolamento & purificação , Isoquinolinas/farmacologia , Nootrópicos/isolamento & purificação , Nootrópicos/farmacologia , Fenantridinas/química , Fenantridinas/isolamento & purificação , Fenantridinas/farmacologia , Extratos Vegetais/química , Metabolismo SecundárioRESUMO
The Amaryllidaceae alkaloids are a distinctive chemotaxonomic feature of the subfamily Amaryllidoideae of the family Amaryllidaceae, which consists of 59 genera and >800 species distributed primarily in tropical and subtropical areas. Since the first isolation, ca. 140 ago, >600 structurally diverse Amaryllidaceae alkaloids have been reported from ca. 350 species (44% of all species in the subfamily). A few have been found in other plant families, but the majority are unique to the Amaryllidoideae. These alkaloids have attracted considerable research interest due to their wide range of biological and pharmacological activities, which have been extensively reviewed. In this chapter we provide a review of the 636 structures of isolated or tentatively identified alkaloids from plants of the Amaryllidoideae and their classification into 42 skeleton types, as well as a discussion on their distribution, and chemotaxonomical and chemoecological aspects.
Assuntos
Alcaloides de Amaryllidaceae/química , Amaryllidaceae/química , Alcaloides de Amaryllidaceae/isolamento & purificação , Alcaloides de Amaryllidaceae/metabolismo , Estrutura MolecularRESUMO
A new N-oxide, Pseudolycorine N-oxide (1) was characterised along with eleven known alkaloids homolycorine (2), O-methylmaritidine (3), 8-O-demethylhomolycorine (4), homolycorine N-oxide (5), lycorine (6), narciclasine (7), pseudolycorine (8), ungeremine (9), 8-O-demethylmaritidine (10), zefbetaine (11) and lycorine N-oxide (12), from Narcissus tazetta. Their structures were established on the basis of spectroscopic data analysis. The extract, fractions and isolated compounds were screened for in vitro cytotoxicity against two human cancer cell lines, human cervical cancer (SiHa) and human epidermoid carcinoma (KB) cells. The study demonstrated the cytotoxic potential of extract and its chloroform and n-butanol fractions. Further, the results revealed the bioactive potential of narciclasine, pseudolycorine and homolycorine alkaloids. However, new N-oxide (1) was not active against these cell lines.
Assuntos
Alcaloides/isolamento & purificação , Alcaloides de Amaryllidaceae/isolamento & purificação , Antineoplásicos Fitogênicos/isolamento & purificação , Narcissus/química , Óxidos/isolamento & purificação , Fenantridinas/isolamento & purificação , Extratos Vegetais/química , Alcaloides/química , Alcaloides de Amaryllidaceae/análise , Alcaloides de Amaryllidaceae/química , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , Humanos , Indolizinas/análise , Óxidos/química , Fenantridinas/análise , Fenantridinas/químicaRESUMO
A new narciclasine glycoside, narciclasine-4-O-ß-D-xylopyranoside (1) was characterised along with four known alkaloids pancratistatin (2), 1-O-(3-hydroxybutyryl) pancratistatin (3), vittatine (4), 9-O-demethylgalanthine (5) from Zephyranthes minuta. Their structures were established on the basis of spectroscopic data analysis. The in vitro cytotoxic study of extract, fractions and isolated compounds against two human cancer cell lines (KB and SiHa) indicated the potential activity of extract and n-butanol fraction due to presence of active alkaloids pancratistatin, 1-O-(3-hydroxybutyryl) pancratistatin, lycorine and haemanthamine.
Assuntos
Alcaloides de Amaryllidaceae/isolamento & purificação , Amaryllidaceae/química , Glicosídeos/isolamento & purificação , Fenantridinas/isolamento & purificação , Alcaloides/química , Alcaloides/farmacologia , Alcaloides de Amaryllidaceae/química , Alcaloides de Amaryllidaceae/farmacologia , Glicosídeos Cardíacos , Linhagem Celular Tumoral , Citotoxinas/isolamento & purificação , Citotoxinas/farmacologia , Glicosídeos/química , Humanos , Isoquinolinas/farmacologia , Fenantridinas/química , Fenantridinas/farmacologia , Extratos Vegetais/químicaRESUMO
A simple and valid method for rapid screening of cathepsin B inhibitors from traditional Chinese medicines (TCMs) was established by the combination of immobilized enzyme microreactor (IMER) and capillary electrophoresis. Cathepsin B was immobilized on the inner surface of the capillary by glutaraldehyde method. The separation of substrate and product could be finished by baseline within 3â¯min. The activity of the immobilized cathepsin B remained approximately 90% after 50 runs. The quantification and statistical analysis of the product peak area was used to evaluate the catalytic activity of cathepsin B. The value of Michaelis-Menten constant of cathepsin B was 0.85â¯mM. The half-maximal inhibitory concentration (IC50) of L-trans-Epoxysuccinyl-leucylamido(4-guanidino)butane (E-64) was measured as 36.08â¯nM, which indicated that the cathepsin B reactor was successfully developed and was feasible for inhibitorscreening. The raised method was then applied to discover the inhibitory potential of 17 standard compounds from traditional Chinese medicines. Five natural products, including kaempferol, rutaecarpine, evodiamine, theophylline, lycobetaine showed potential inhibition for cathepsin B. Additionally, molecular docking study was investigated for supporting the interaction between enzyme and inhibitors.
Assuntos
Catepsina B/antagonistas & inibidores , Descoberta de Drogas/métodos , Medicamentos de Ervas Chinesas/análise , Alcaloides de Amaryllidaceae/química , Alcaloides de Amaryllidaceae/isolamento & purificação , Alcaloides de Amaryllidaceae/farmacologia , Catepsina B/química , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Eletroforese Capilar/métodos , Enzimas Imobilizadas/química , Estudos de Viabilidade , Alcaloides Indólicos/química , Alcaloides Indólicos/isolamento & purificação , Alcaloides Indólicos/farmacologia , Indolizinas/química , Indolizinas/isolamento & purificação , Indolizinas/farmacologia , Quempferóis/química , Quempferóis/isolamento & purificação , Quempferóis/farmacologia , Simulação de Acoplamento Molecular , Quinazolinas/química , Quinazolinas/isolamento & purificação , Quinazolinas/farmacologia , Teofilina/química , Teofilina/isolamento & purificação , Teofilina/farmacologiaRESUMO
Twenty-one known Amaryllidaceae alkaloids of various structural types and one undescribed alkaloid, named narcimatuline, have been isolated from fresh bulbs of Narcissus pseudonarcissus L. cv. Dutch Master. The chemical structures were elucidated by combination of MS, HRMS, 1D and 2D NMR spectroscopic techniques, and by comparison with literature data. Narcimatuline amalgamates two basic scaffolds of Amaryllidaceae alkaloids in its core, namely galanthamine and galanthindole. All isolated compounds were evaluated for their in vitro acetylcholinesterase (AChE), butyrylcholinesterase (BuChE), prolyl oligopeptidase (POP), and glycogen synthase kinase-3ß (GSK-3ß) inhibitory activities. The most interesting biological profile was demonstrated by newly isolated alkaloid narcimatuline.
Assuntos
Doença de Alzheimer/tratamento farmacológico , Alcaloides de Amaryllidaceae/farmacologia , Inibidores da Colinesterase/farmacologia , Narcissus/química , Fármacos Neuroprotetores/farmacologia , Acetilcolinesterase/metabolismo , Doença de Alzheimer/metabolismo , Alcaloides de Amaryllidaceae/química , Alcaloides de Amaryllidaceae/isolamento & purificação , Butirilcolinesterase/metabolismo , Inibidores da Colinesterase/química , Inibidores da Colinesterase/isolamento & purificação , Relação Dose-Resposta a Droga , Glicogênio Sintase Quinase 3 beta/antagonistas & inibidores , Glicogênio Sintase Quinase 3 beta/metabolismo , Humanos , Estrutura Molecular , Fármacos Neuroprotetores/química , Fármacos Neuroprotetores/isolamento & purificação , Prolil Oligopeptidases , Serina Endopeptidases/metabolismo , Relação Estrutura-AtividadeRESUMO
The spread of malaria is thought to have followed human expansion out of Africa some 60â-â80 thousand years ago. With its prevalence in pantropical countries of the world and epicenter localized in Africa, malaria is now considered an unnecessary burden to overworked and under-resourced healthcare structures. Plants have long afforded a fertile hunting ground for the search and identification of structurally diverse antimalarial agents, such as quinine and artemisinin. This survey examines the antiparasitic properties of the family Amaryllidaceae via the antiplasmodial activities demonstrated for its lycorane alkaloid principles. Of these, 24 were natural compounds identified in 20 species from 11 genera of the Amaryllidaceae family, whilst the remaining 28 were synthetically derived entities based on the lycorane skeleton. These were screened against ten different strains of the malarial parasite Plasmodium falciparum, wherein the parent compound lycorine was shown to be the most potent with an IC50 of 0.029 µg/mL in the FCR-3 strain seen to be the best. Structure-activity relationship studies revealed that good activities were detectable across both the natural compounds as well as the synthetically accessed derivatives. Such studies also highlighted that there are several inherent structural features that define the lycorane alkaloid antiplasmodial pharmacophore, such as the nature of its ring systems and properties of its substituents. Mechanistically, a limited number of studies confirmed that lycorane alkaloids manifest their action by targeting enzymes associated with the plasmodial FAS-II biosynthetic pathways. Overall, these alkaloids have provided useful, convenient, and accessible scaffolds for antimalarial-based drug discovery.
Assuntos
Alcaloides de Amaryllidaceae/farmacologia , Amaryllidaceae/química , Antimaláricos/farmacologia , Alcaloides de Amaryllidaceae/química , Alcaloides de Amaryllidaceae/isolamento & purificação , Animais , Antimaláricos/química , Antimaláricos/isolamento & purificação , Humanos , Plasmodium falciparum/efeitos dos fármacos , Relação Estrutura-AtividadeRESUMO
Lycoris radiata (L'Her.) Herb. (L. radiata) was traditionally used as a folk medicine in China for treatment of Alzheimer's disease. However, the specific component responsible for its considerable toxicity remained unclear thus restricting its clinical trials. Narciclasine (NCS) was isolated from L. radiata and treatment of NCS for 72â¯h exhibited significant antiproliferative effects against L02, Hep G2, HT-29 and RAW264.7â¯cells. However, what needs to be emphasized is that at safe working concentrations of 0.001-0.016⯵M, administration of NCS for 24â¯h inhibited the mRNA expression of inducible nitric oxide synthase (iNOS), interleukin-6 (IL-6), tumor necrosis factor-alpha (TNF-É), interleukin-1beta (IL-1ß) and cyclooxygenase-2 (COX-2) in lipopolysaccharide (LPS)-induced macrophages thereby suppressing production of nitric oxide (NO), IL-6, TNF-É and IL-1ß. NCS supplementation also inhibited nuclear factor-kappa B (NF-κB) activation by suppressing NF-κB P65 phosphorylation and nuclear translocation, IκBÉ degradation and phosphorylation, and IκKÉ/ß phosphorylation. The phosphorylation of c-Jun N-terminal kinase (JNK) and P38, and expression of COX-2 was also attenuated by NCS. These results suggested that NCS might exert anti-inflammatory effects through inhibiting NF-κB and mitogen-activated protein kinase (MAPK) pathways even at very low doses.
Assuntos
Alcaloides de Amaryllidaceae/farmacologia , Anti-Inflamatórios/farmacologia , Lycoris/química , Macrófagos/efeitos dos fármacos , Fenantridinas/farmacologia , Alcaloides de Amaryllidaceae/isolamento & purificação , Alcaloides de Amaryllidaceae/toxicidade , Animais , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/toxicidade , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Antineoplásicos/toxicidade , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Ciclo-Oxigenase 2/metabolismo , Citocinas/genética , Citocinas/metabolismo , Expressão Gênica/efeitos dos fármacos , Humanos , Inflamação/induzido quimicamente , Lipopolissacarídeos , Sistema de Sinalização das MAP Quinases/efeitos dos fármacos , Camundongos , NF-kappa B/metabolismo , Fenantridinas/isolamento & purificação , Fenantridinas/toxicidade , Componentes Aéreos da Planta/química , Células RAW 264.7 , RNA Mensageiro/genética , RNA Mensageiro/metabolismoRESUMO
Malaria is prevalent in tropical and subtropical regions of the globe. With over 200 million cases reported annually, particularly in sub-Saharan Africa, it is an unnecessary burden to already overworked and ailing healthcare structures. Traditional medicine (TM) remains vibrant in most of these regions wherein plants often serve as the first line of defense against malaria. Given this fact as well as the successes elsewhere of therapies such as Artemisia annua emanating from evidence-based TM, interest in plants as a source of new antimalarial drugs has been rejuvenated. The bulbous plant family Amaryllidaceae is recognized for its structurally-diverse alkaloid constituents which exhibit interesting biological properties. This review focuses on the in vitro activities demonstrated by its crinane alkaloids against various strains of the malaria-causing parasite Plasmodium falciparum. The survey embraces the twelve genera of the Amaryllidaceae whose nineteen representative species have been examined for antiplasmodial crinane alkaloid principles. A total of seventy-two compounds were screened against nine strains of P. falciparum, with the α-crinanes reflecting better overall activities than their corresponding ß-crinane subgroup congeners. In terms of potency, an ED50 of 0.14⯵g/mL (for augustine in the D-6 strain) and IC50 of 0.35⯵g/mL (for haemanthidine in the K1 strain) were the lowest activity indices observed. Structure-activity relationship studies afforded useful insight on the antiplasmodial pharmacophore and the features supporting its efficacy. Overall, crinane alkaloids have provided a useful platform for the study of antiplasmodial effects, not only in terms of potency but also in terms of structural diversity.
Assuntos
Alcaloides de Amaryllidaceae/farmacologia , Amaryllidaceae/química , Antimaláricos/farmacologia , Amaryllidaceae/classificação , Alcaloides de Amaryllidaceae/isolamento & purificação , Antimaláricos/isolamento & purificação , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Plasmodium falciparum/efeitos dos fármacosRESUMO
The separation of minor compounds, especially those with similar polarities from a complex sample, remains challenging. In the proposed study, an effective method based on medium-pressure liquid chromatography and recycling high-speed counter-current chromatography was developed for the enrichment and separation of three minor components from Dracocephalum tanguticum. The crude extract was directly introduced to medium-pressure liquid chromatography for the enrichment of the three minor components. Based on high-performance liquid chromatography analysis, the total content of these three compounds increased from 0.48% in the crude extract to 85.3% in the medium-pressure liquid chromatography fraction. In addition, high-speed counter-current chromatography was employed to separate the enriched compounds using the solvent system hexane/ethyl acetate/methanol/water (1.18:8.82:1.18:8.82, v/v/v/v). As a result, compound 3 and a mixture of compounds 1 and 2 were obtained. In order to improve the resolution of compounds 1 and 2 while saving separation time, a recycling and heart-cut mode was used. Finally, compounds 1 and 2 were obtained after five cycles. These compounds were identified as 3-phenylethyl ß-d-glucopyranoside (1), tazettoside E (2), and cirsiliol-4'-glucoside (3). Compounds 1 and 2 were primarily separated from D. tanguticum. Moreover, the developed method provided a reference for the separation of minor components from the complex sample.
Assuntos
Alcaloides de Amaryllidaceae/isolamento & purificação , Distribuição Contracorrente , Glucose/isolamento & purificação , Lamiaceae/química , Componentes Aéreos da Planta/química , Pressão , Alcaloides de Amaryllidaceae/química , Cromatografia Líquida de Alta Pressão , Glucose/análogos & derivados , Glucose/químicaRESUMO
An undisputed trend in sample preparation at present is to meet the requirements of green chemistry especially in the field of natural products. Green technology continuously pursues new solvents to replace common organic solvents that possess inherent toxicity. Over the past two decades, non-ionic surfactants have gained enormous attention from the scientific community. The micelle-mediated extraction and cloud-point preconcentration (CPE) methods offer a convenient alternative to the conventional extraction systems. Recently, natural deep eutectic solvents (NDESs) have emerged as green and sustainable solvents for efficient extraction of bioactive compounds or drugs. They are generally composed of neutral, acidic or basic compounds that form liquids of high viscosity when mixed in certain molar ratio. The presented work aimed to comprehensively compare and evaluate the potential and effectiveness of NDES as well as non-ionic surfactants (Genapol X-080, Triton X-100 and Triton X-114) for extraction of Amaryllidaceae alkaloids from Crinum powellii bulbs as representative example of plant material, in comparison to the conventional solvents (methanol, ethanol and water).A new validated high-performance thin-layer chromatographic (HPTLC) method has been developed for the simultaneous quantitation of three alkaloids markers, lycorine, crinine and crinamine, in the bulbs of C. powellii. Extraction efficiency of the targeted alkaloids from the bulb matrix with organic and ecofriendly (green) solvents were studied. Results revealed that NDES and surfactants were significantly more efficient in alkaloid extraction than previous methods requiring the consumption of organic solvents and water. Genapol X-80 demonstrated 138%, 149% and 145%, while choline chloride: fructose (5:2): H2O (35%) NDES mixture demonstrated 243%, 225% and 238% of the total alkaloidal extraction capacity of ethanol, methanol and water, respectively at 50 °C for extraction time 1 h using ultrasonication for all experiments. Furthermore, Box-Behnken response surface design combined with the overall desirability value were successfully employed to optimize and study the individual and interactive effect of process variables such as extraction temperature, time and surfactant %, for Genapol X-80, and sonication extraction temperature, time and water concentration, for choline chloride: fructose: H2O NDES mixture, on the alkaloidal yield from C. powellii. It was evident that parameters interacting together can act in synergism if adjusted properly according to the optimized conditions to obtain maximum alkaloids extractability. It is for the first time that the efficiency of micelle-mediated extraction has been compared to that of natural deep eutectic solvents for the extraction of alkaloids and the results thoroughly discussed.
Assuntos
Alcaloides de Amaryllidaceae/isolamento & purificação , Cromatografia em Camada Fina , Química Verde/métodos , Solventes/química , Alcaloides/química , Alcaloides de Amaryllidaceae/análise , Produtos Biológicos/química , Produtos Biológicos/isolamento & purificação , Crinum/química , Fenantridinas/análise , Fenantridinas/isolamento & purificação , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Tensoativos/química , Água/químicaRESUMO
Three aporphine-type alkaloids (1-3), three lycorine-type alkaloids (4-6), two crinane type alkaloids (7, 8) and one phenanthridine-type alkaloid (9) were isolated from the chloroform soluble fraction of 70% ethanol extract of the bulbs of Lycoris radiata through various column chromatographies over silica gel, ODS, Sephadex LH-20 and MCI. Their structures were elucidated as (+)-N-methoxylcarbonyl-1,2-methylenedioxyl-isocorydione (1), isocorydione (2), 8-demethyl-dehydrocrebanine (3), (+)-3-hydroxy-anhydrolycorine N-oxide (4), vasconine (5), pancratinine D (6), yemenine A (7), 11-O-acetylhaemanthamine (8), and 5,6-dihydro-5-methyl-2-hydroxyphenanthridine (9) based on their chemical and physicochemical properlies and spectroscopic data. Compound 1 was a new compound and alkaloids 2-9 were isolated and identified from this plant for the first time.
Assuntos
Alcaloides de Amaryllidaceae/isolamento & purificação , Lycoris/química , Alcaloides de Amaryllidaceae/química , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Extratos Vegetais/química , Raízes de Plantas/químicaRESUMO
A bioassay-guided fractionation and chemical investigation of Amaryllis belladonna Steud. bulbs resulted in the isolation and identification of the new crinane alkaloid 1,4-dihydroxy-3-methoxy powellan (1), along with the 3 known crinane alkaloids 2-4 and the two lycorane alkaloids 5-6. The structures were elucidated by interpretation of combined HR-ESIMS, CD and 2D NMR spectroscopic data. Among these isolated compounds the lycorane-type alkaloid acetylcaranine (5) exhibited strong antiplasmodial activity, while compounds 3 and 4 were moderately active, and compounds 1 and 6 were inactive.
Assuntos
Alcaloides/química , Alcaloides de Amaryllidaceae/química , Antimaláricos/química , Asparagales/química , Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Alcaloides de Amaryllidaceae/isolamento & purificação , Alcaloides de Amaryllidaceae/farmacologia , Antimaláricos/isolamento & purificação , Antimaláricos/farmacologia , Asparagales/metabolismo , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Dicroísmo Circular , Humanos , Espectroscopia de Ressonância Magnética , Conformação Molecular , Extratos Vegetais/química , Raízes de Plantas/química , Raízes de Plantas/metabolismo , Plasmodium falciparum/efeitos dos fármacos , Espectrometria de Massas por Ionização por ElectrosprayRESUMO
Scadoxus puniceus (Amaryllidaceae), a medicinal plant of high value in South Africa, is used as a component of a traditional herbal tonic prescribed to treat several ailments. Ultra-high performance liquid chromatography-tandem mass spectrometry quantified the phenolic compounds in different organs of S. puniceus. Gravity column chromatography was used to separate fractions and active compounds. The structure of these compounds was determined using 1D and 2D nuclear magnetic resonance and mass spectroscopic techniques. A microplate technique was used to determine the acetylcholinesterase inhibitory activity of the pure compounds. Metabolite profiling revealed a greater profusion of hydroxycinnamic acids (69.5%), as opposed to hydroxybenzoic acids (30.5%). Chlorogenic acid was the most abundant (49.6% of hydroxycinnamic acids) compound. In addition to chlorogenic acid, the study is the first to report the presence of sinapic, gallic, and m-hydroxybenzoic acids in the Amaryllidaceae. Chromatographic separation of S. puniceus led to the isolation of haemanthamine (1), haemanthidine (2), and a rare chlorinated amide, metolachlor (3), the natural occurrence of which is described for the first time. Haemanthamine, haemanthidine, and metolachlor displayed strong acetylcholinesterase inhibitory activity (IC50 ; 23.1, 23.7, and 11.5 µM, respectively). These results substantiate the frequent use of S. puniceus as a medicinal plant and hold much promise for further pharmaceutical development.
Assuntos
Amaryllidaceae/química , Inibidores da Colinesterase/química , Inibidores da Colinesterase/farmacologia , Ácidos Cumáricos/química , Ácidos Cumáricos/farmacologia , Plantas Medicinais/química , Acetamidas/química , Acetamidas/isolamento & purificação , Acetamidas/metabolismo , Acetamidas/farmacologia , Amaryllidaceae/metabolismo , Alcaloides de Amaryllidaceae/química , Alcaloides de Amaryllidaceae/isolamento & purificação , Alcaloides de Amaryllidaceae/metabolismo , Alcaloides de Amaryllidaceae/farmacologia , Inibidores da Colinesterase/isolamento & purificação , Cromatografia Líquida de Alta Pressão , Ácidos Cumáricos/isolamento & purificação , Ácidos Cumáricos/metabolismo , Fenantridinas/química , Fenantridinas/isolamento & purificação , Fenantridinas/metabolismo , Fenantridinas/farmacologia , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/metabolismo , Extratos Vegetais/farmacologia , África do Sul , Espectrometria de Massas em TandemRESUMO
Lycorine is an alkaloid isolated from bulbs of Pancratium foetidum Pom Amaryllidaceae of the genus Lycoris. It has very strong pharmacodynamics properties and biological effects, among others, antimalarial, antiviral, antitumor, and anti-inflammatory. Lycorine has been identified and characterized by thin layer chromatography, IR and NMR (1H and 13C NMR, COZY, HMBC, HSQC and NOESY). The antibacterial activity of lycorine has been evaluated. Lycorine has a moderate antibacterial activity on the majority of strains studied, nevertheless it is more effective than Streptomycin and Ampicillin against bacteria: P. aeruginosa, En. cloacae. To confirm these results, it is necessary to use qualitative techniques and methods, etc We performed a virtual docking ligand-lycorine protein screening study to predict and characterize their mode of interaction with the LpxC receptor. Docking results have shown that lycorine can interact with target amino residues studied by hydrogen and metal-ion bonds. In addition, the ADME-Tox profile study has shown that lycorine is all in agreement, either with Lipinski's critics or with the toxicity standards.