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1.
Molecules ; 27(9)2022 Apr 28.
Artigo em Inglês | MEDLINE | ID: mdl-35566166

RESUMO

The Chelidonium majus plant is rich in biologically active isoquinoline alkaloids. These alkaline polar compounds are isolated from raw materials with the use of acidified water or methanol; next, after alkalisation of the extract, they are extracted using chloroform or dichloromethane. This procedure requires the use of toxic solvents. The present study assessed the possibility of using volatile natural deep eutectic solvents (VNADESs) for the efficient and environmentally friendly extraction of Chelidonium alkaloids. The roots and herb of the plant were subjected three times to extraction with various menthol, thymol, and camphor mixtures and with water and methanol (acidified and nonacidified). It has been shown that alkaloids can be efficiently isolated using menthol-camphor and menthol-thymol mixtures. In comparison with the extraction with acidified methanol, the use of appropriate VNADESs formulations yielded higher amounts of protopine (by 16%), chelidonine (35%), berberine (76%), chelerythrine (12%), and coptisine (180%). Sanguinarine extraction efficiency was at the same level. Additionally, the values of the contact angles of the raw materials treated with the tested solvents were assessed, and higher wetting dynamics were observed in the case of VNADESs when compared with water. These results suggest that VNADESs can be used for the efficient and environmentally friendly extraction of Chelidonium alkaloids.


Assuntos
Alcaloides , Chelidonium , Cânfora , Solventes Eutéticos Profundos , Isoquinolinas , Mentol , Metanol , Extratos Vegetais , Solventes , Timol , Água
2.
Molecules ; 27(9)2022 May 05.
Artigo em Inglês | MEDLINE | ID: mdl-35566305

RESUMO

Deep eutectic solvents (DES), compared to classic ones, have interesting properties, such as the ability to solubilize compounds differing in polarity or increased dissolution of selected chemical compounds. They also offer specific interactions between the mobile and stationary phases. Those features make them promising solvents in chromatographic techniques, including the use in the separation of complicated samples. The first quantitative analysis with eutectic thin-layer chromatography (TLC) is presented in the paper. As a case study, five alkaloids from Chelidonium maius were selected as target compounds. A wide range of terpene-based DESs was investigated to develop the chromatographic system, both pure and after dilution. Moreover, a novel approach was employed to adjust polarity, involving mixing DESs differing in chromatographic properties. This procedure has proved to be effective. The best results were obtained with a 2:1 (wt/wt) mixture of DESs: camphor + phenol and menthol + limonene, with a 20% addition of methanol. The chromatographic system was validated and checked on the real sample, which made it the first applicable and operational quantitative eutectic TLC system.


Assuntos
Alcaloides , Chelidonium , Alcaloides/química , Chelidonium/química , Cromatografia em Camada Delgada/métodos , Extratos Vegetais/química , Solventes/química
3.
Pak J Biol Sci ; 25(3): 234-244, 2022 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-35234014

RESUMO

<b>Background and Objective:</b> Aflatoxins affect many species including humans and animals, therefore the present study was designed to investigate the protective effect of <i>Chelidonium majus</i> Ethanolic Extract (CMEE) on neurotoxicity induced by Aflatoxin B<sub>1</sub> (AFB1) in rats. <b>Materials and Methods:</b> Four groups of male Albino rats were treated orally for 28 days as follows: (1) Control group was daily given DMSO-PBS buffer (1.0 mL per rat), (2) CMEE (300 mg kg<sup>1</sup>/day) dissolved in DMSO-PBS buffer, (3) AFB1 (80 µg kg<sup>1</sup>/day) dissolved in DMSO-PBS buffer and (4) Received daily AFB1 (300 mg kg<sup>1</sup>) in combination with CMEE (300 mg kg<sup>1</sup>). <b>Results:</b> CMEE exhibits antioxidant activity <i>in vitro</i> and neuroameliorative efficiency <i>in vivo</i> as its administration in combination with AFB1 succeeded significantly in down regulating the elevated levels of inflammatory and apoptotic markers and restoring the values of neurochemical markers (AChE-ase, dopamine and serotonin) that were deteriorated by AFB1 intake. <b>Conclusion:</b> In conclusion, the neuroprotective effect of CMEE may be mediated through its antioxidant and free radical scavenging activity that proved from the data<i> </i>of ferric-reducing power ability and DPPH radical scavenging activity.


Assuntos
Aflatoxina B1 , Chelidonium , Aflatoxina B1/toxicidade , Animais , Antioxidantes/farmacologia , Etanol , Extratos Vegetais/farmacologia , Ratos
4.
J Microbiol Biotechnol ; 32(4): 493-503, 2022 Apr 28.
Artigo em Inglês | MEDLINE | ID: mdl-35283423

RESUMO

Forkhead transcription factor 3a (Foxo3a) is believed to be a tumor suppressor as its inactivation leads to cell transformation and tumor development. However, further investigation is required regarding the involvement of the activating transcription factor 3 (ATF3)-mediated Tat-interactive protein 60 (Tip60)/Foxo3a pathway in cancer cell apoptosis. This study demonstrated that Chelidonium majus upregulated the expression of ATF3 and Tip60 and promoted Foxo3a nuclear translocation, ultimately increasing the level of Bcl-2-associated X protein (Bax) protein. ATF3 overexpression stimulated Tip60 expression, while ATF3 inhibition by siRNA repressed Tip60 expression. Furthermore, siRNA-mediated Tip60 inhibition significantly promoted Foxo3a phosphorylation, leading to blockade of Foxo3a translocation into the nucleus. Thus, we were able to deduce that ATF3 mediates the regulation of Foxo3a by Tip60. Moreover, siRNA-mediated Foxo3a inhibition suppressed the expression of Bax and subsequent apoptosis. Taken together, our data demonstrate that Chelidonium majus induces SKOV-3 cell death by increasing ATF3 levels and its downstream proteins Tip60 and Foxo3a. This suggests a potential therapeutic role of Chelidonium majus against ovarian cancer.


Assuntos
Chelidonium , Proteína Forkhead Box O3/metabolismo , Neoplasias Ovarianas , Fator 3 Ativador da Transcrição/genética , Fator 3 Ativador da Transcrição/metabolismo , Apoptose/genética , Linhagem Celular Tumoral , Chelidonium/genética , Chelidonium/metabolismo , Feminino , Fatores de Transcrição Forkhead/genética , Fatores de Transcrição Forkhead/metabolismo , Produtos do Gene tat , Humanos , RNA Interferente Pequeno/genética , Proteína X Associada a bcl-2
5.
Int J Biol Macromol ; 194: 974-981, 2022 Jan 01.
Artigo em Inglês | MEDLINE | ID: mdl-34856216

RESUMO

Essential oils (EOs) of greater celandine (GC) roots and leaves were extracted, and gas chromatography-mass spectrometry (GC-MS) was used for analyzing them. Then they were loaded into chitosan nanoparticles (CNPs) using emulsion-ionic gelation method. CNPs loaded with greater celandine root essential oil (GCREO) and leave essential oil (GCLEO) were synthesized (size 76.5-115.3 nm) using an emulsion-ionic gelation method. Fourier Transform Infrared (FT-IR), spectroscopy, scanning electron microscope (SEM), and dynamic light scattering (DLS) were used for characterization of the formed NPs. Good encapsulation efficiency was confirmed for GCREO (62.5%) and GCLEO (69.1%) in CNPs. According to the MTT results, the synthesized NPs showed a dose-dependent effect on MCF-7 cell line. The inhibitory concentration (IC50) values for GCREO, GCLEO, CSNRs-GCREO and CNPs-GCLEO samples were 126.4, 90.2, 77.6, and 41.5 µg/mL, respectively. The highest rate of apoptosis was obtained in the CNPs-GCLEO group (63.73%). The results revealed that the cytotoxicity of CSNRs-GCREO and CNPs-GCLEO against MCF-7 cell line was significantly higher than that of their free form, implying that encapsulation of GCREO and GCLEO in CNPs is an efficient technique for improving their anti-cancer activity against MCF-7 cell line.


Assuntos
Antineoplásicos/síntese química , Antineoplásicos/farmacologia , Chelidonium/química , Quitosana/química , Nanopartículas/química , Óleos Voláteis/química , Antineoplásicos/química , Sobrevivência Celular/efeitos dos fármacos , Fenômenos Químicos , Técnicas de Química Sintética , Composição de Medicamentos , Cromatografia Gasosa-Espectrometria de Massas , Humanos , Células MCF-7 , Espectroscopia de Infravermelho com Transformada de Fourier
6.
Int J Mol Sci ; 22(22)2021 Nov 17.
Artigo em Inglês | MEDLINE | ID: mdl-34830309

RESUMO

Latex, a sticky emulsion produced by specialized cells called laticifers, is a crucial part of a plant's defense system against herbivory and pathogens. It consists of a broad spectrum of active compounds, which are beneficial not only for plants, but for human health as well, enough to mention the use of morphine or codeine from poppy latex. Here, we reviewed latex's general role in plant physiology and the significance of particular compounds (alkaloids and proteins) to its defense system with the example of Chelidonium majus L. from the poppy family. We further attempt to present latex chemicals used so far in medicine and then focus on functional studies of proteins and other compounds with potential pharmacological activities using modern techniques such as CRISPR/Cas9 gene editing. Despite the centuries-old tradition of using latex-bearing plants in therapies, there are still a lot of promising molecules waiting to be explored.


Assuntos
Anti-Infecciosos/química , Antineoplásicos/química , Chelidonium/metabolismo , Fatores Imunológicos/química , Látex/química , Alcaloides Opiáceos/química , Papaver/metabolismo , Compostos Fitoquímicos/química , Proteínas de Plantas/química , Sistemas CRISPR-Cas , Linhagem Celular Tumoral , Chelidonium/genética , Descoberta de Drogas/métodos , Edição de Genes/métodos , Herbivoria/efeitos dos fármacos , Humanos , Papaver/genética , Plantas Geneticamente Modificadas
7.
Int J Mol Sci ; 22(21)2021 Oct 31.
Artigo em Inglês | MEDLINE | ID: mdl-34769268

RESUMO

Chelidonium majus L. is a latex-bearing plant used in traditional folk medicine to treat human papillomavirus (HPV)-caused warts, papillae, and condylomas. Its latex and extracts are rich in many low-molecular compounds and proteins, but there is little or no information on their potential interaction. We describe the isolation and identification of a novel major latex protein (CmMLP1) composed of 147 amino acids and present a model of its structure containing a conserved hydrophobic cavity with high affinity to berberine, 8-hydroxycheleritrine, and dihydroberberine. CmMLP1 and the accompanying three alkaloids were present in the eluted chromatographic fractions of latex. They decreased in vitro viability of human cervical cancer cells (HPV-negative and HPV-positive). We combined, for the first time, research on macromolecular and low-molecular-weight compounds of latex-bearing plants in contrast to other studies that investigated proteins and alkaloids separately. The observed interaction between latex protein and alkaloids may influence our knowledge on plant defense. The proposed toolbox may help in further understanding of plant disease resistance and in pharmacological research.


Assuntos
Alcaloides , Antineoplásicos Fitogênicos , Chelidonium/química , Látex/química , Extratos Vegetais/química , Proteínas de Plantas , Neoplasias do Colo do Útero/tratamento farmacológico , Alcaloides/química , Alcaloides/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Feminino , Células HeLa , Humanos , Proteínas de Plantas/química , Proteínas de Plantas/farmacologia , Neoplasias do Colo do Útero/metabolismo , Neoplasias do Colo do Útero/patologia
8.
Food Chem Toxicol ; 156: 112483, 2021 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-34375721

RESUMO

Metabolic variations, antioxidant potential and cytotoxic effects were investigated in the different plant parts like the leaf, stem, flower, pod, and root of C. majus L. using spectroscopic and chromatographic methods. Total phenolics and flavonoids were studied in the different parts of C. majus L., leaf showed higher flavonoid content (137.43 mg/g), while the pod showed the highest phenolic (23.67 mg/g) content, when compared with the stem, flower and root. In the ABTS antioxidant assay, the flower extract showed 57.94% effect, while the leaf, pod and root extract exhibited 39.10%, 36.08% and 28.88% activity, respectively. The pod and leaf extracts demonstrated the potential effect, exhibiting 45.46 and 41.61% activity, respectively, for the DPPH assay. Similar to the phosphomolybdenum assay, the flower revealed higher antioxidant activity (46.82%) than the other plant parts. The in vitro SRB assay facilitated evaluation of the cytotoxic effect against the HeLa and CaSki human cervical cancerous cells. The extract displayed dose-dependent inhibitory effect on both the cell lines. The highest cytotoxic effect was observed in the pod and flower extracts post 48 h of exposure at 1000 µg/mL. The results of C. majus L. offered new insights in the preliminary steps regarding the development of a high value product for phytomedicine applications though promising metabolic variations with antioxidant and anticancer potentials.


Assuntos
Antineoplásicos/farmacologia , Antioxidantes/farmacologia , Chelidonium/metabolismo , Flavonoides/análise , Células HeLa , Humanos , Polifenóis/análise
9.
Molecules ; 26(5)2021 Mar 05.
Artigo em Inglês | MEDLINE | ID: mdl-33807597

RESUMO

Efforts to develop the necessary biotechnologies in Greater Celandine (Chelidonium majus L.), a leading plant resource for the development of plant-derived medicines, have been hampered by the lack of knowledge about transcriptome and metabolome regulations of its medicinal components. Therefore, this study aimed to examine the effect of abiotic elicitors, methyl jasmonate (MJ) and salicylic acid (SA), at different time courses (12, 24, 48, and 72 h), on expression and metabolome of key benzophenanthridine alkaloids (BPAs) in an optimized in vitro culture. Gene expression analysis indicated the upregulation of CFS (cheilanthifoline synthase) to 2.62, 4.85, and 7.28 times higher than the control at 12, 24, and 48 h respectively, under MJ elicitation. Besides, MJ upregulated the expression of TNMT (tetrahydroprotoberberine N-methyltransferase) to 2.79, 4.75, and 7.21 times at 12, 24, and 48 h respectively, compared to the control. Investigation of BPAs revealed a significant enhancement in the chelidonine content (9.86 µg/mg) after 72 h of MJ elicitation. Additionally, sanguinarine content increased to its highest level (3.42 µg/mg) after 24 h of MJ elicitation; however, no significant enhancement was detected in its content in shorter elicitation time courses. Generally, higher gene expression and BPAs' level was observed through longer elicitation courses (48 and 72 h). Our findings take part in improving the understanding of transcription and metabolic regulation of BPAs in cultured Greater Celandine cells.


Assuntos
Acetatos/farmacologia , Benzofenantridinas/metabolismo , Técnicas de Cultura de Células/métodos , Chelidonium/metabolismo , Ciclopentanos/farmacologia , Oxilipinas/farmacologia , Ácido Salicílico/farmacologia , Chelidonium/citologia , Chelidonium/efeitos dos fármacos , Chelidonium/genética , Enzimas/genética , Enzimas/metabolismo , Regulação da Expressão Gênica de Plantas/efeitos dos fármacos , Células Vegetais/efeitos dos fármacos , Células Vegetais/metabolismo , Proteínas de Plantas/genética , Proteínas de Plantas/metabolismo , Plantas Medicinais/citologia , Plantas Medicinais/efeitos dos fármacos , Plantas Medicinais/metabolismo
10.
Phytother Res ; 35(7): 3792-3798, 2021 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-33778996

RESUMO

In December 2019, an outbreak of coronavirus disease 2019 (COVID-19) occurred in Wuhan, China, with a rapid increase in cases worldwide. Until now, among several drugs tested, none demonstrated sufficient efficacy for its etiological treatment. Greater celandine (Chelidonium majus L.) is a well-known medicinal plant, traditionally indicated for digestive disorders and topically to remove warts. This study, performed at private offices in São Paulo and Aracaju (Brazil), describes 20 consecutive COVID-19 outpatients treated with greater celandine and their clinical evolution. The patients, aged 14-71 years (median of 41 years), were treated with Chelidonium majus 10% mother tincture, 20-30 drops three times a day for 3-12 days (median of 5 days). Clinical features were assessed during the treatment and at least until 1 week after its end. These cases were considered mild, as most COVID-19 cases. The symptoms were mainly fever, fatigue, cough, sore throat, coryza, anosmia, ageusia, and headache. Ten patients had comorbidities, such as hypertension, diabetes, and overweight. Complete or almost complete clinical improvement occurred within 1-9 days of treatment (median of 3 days). There were no adverse events. This casuistry, although small, may inspire other researchers to continue investigating Chelidonium majus as a healing treatment for COVID-19.


Assuntos
COVID-19 , Chelidonium , Diabetes Mellitus Tipo 2 , Preparações de Plantas/uso terapêutico , Adolescente , Adulto , Idoso , Brasil , COVID-19/tratamento farmacológico , Chelidonium/química , Feminino , Humanos , Masculino , Pessoa de Meia-Idade , Plantas Medicinais/química , Adulto Jovem
11.
Pest Manag Sci ; 77(1): 510-517, 2021 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-32815231

RESUMO

BACKGROUND: Plant viral diseases are difficult to control and have caused serious damage to the agricultural industry. Recently, botanical biopesticides characterized by environment friendly, safe to non-target organism and not as susceptible to produce drug resistance, have exhibited great potential to be developed as antiviral agents. To screen the natural products with antiviral effect, three alkaloids possessed anti-tobacco mosaic virus (TMV) activity were isolated from Chelidonium majus and the modes of action were investigated. RESULT: The anti-TMV effect of crude extracts at 10 mg mL-1 was 51.73%. Bioassay-guided fractionation and isolation of the compounds with anti-TMV activity were performed on the methanol extract of C. majus yielding three bioactive alkaloids namely: chelerythrine (1), chelidonine (2), and sanguinarine (3). The results of bioassay showed that chelerythrine exhibited great inactivation, proliferation inhibition and protection effects against TMV at 0.5 mg mL-1 with the efficiency of 72.67%, 77.52% and 59.34%, respectively. Chelidonine at 0.1 mg mL-1 can provide 54.90% and 64.45% inhibitions on TMV through inducing resistance in two kinds of tobacco. Sanguinarine showed a weaker protection for resisting TMV in comparison to chelerythrine and chelidonine. CONCLUSION: Chelerythrine and chelidonine displayed significant inhibitions on TMV with different modes of action. These results provided important evidence that the extracts in C. majus might be a potential source of new drugs in controlling virus disease agriculturally.


Assuntos
Alcaloides , Antivirais , Chelidonium , Vírus do Mosaico do Tabaco , Alcaloides/farmacologia , Antivirais/farmacologia , Extratos Vegetais/farmacologia
12.
Angew Chem Int Ed Engl ; 59(40): 17556-17564, 2020 09 28.
Artigo em Inglês | MEDLINE | ID: mdl-32476195

RESUMO

We describe enantioselective syntheses of strychnos and chelidonium alkaloids. In the first case, indole acetic acid esters were established as excellent partner nucleophiles for enantioselective cooperative isothiourea/Pd catalyzed α-alkylation. This provides products containing indole-bearing stereocenters in high yield and with excellent levels of enantioinduction in a manner that is notably independent of the N-substituent. This led to concise syntheses of (-)-akuammicine and (-)-strychnine. In the second case, the poor performance of ortho-substituted cinnamyl electrophiles in the enantioselective cooperative isothiourea/Ir catalyzed α-alkylation was overcome by appropriate substituent choice, leading to enantioselective syntheses of (+)-chelidonine, (+)-norchelidonine, and (+)-chelamine.


Assuntos
Alcaloides/química , Chelidonium/química , Strychnos/química , Alcaloides/síntese química , Alquilação , Benzofenantridinas/síntese química , Benzofenantridinas/química , Alcaloides de Berberina/síntese química , Alcaloides de Berberina/química , Catálise , Chelidonium/metabolismo , Humanos , Indóis/síntese química , Indóis/química , Irídio/química , Paládio/química , Sirtuína 1/antagonistas & inibidores , Sirtuína 1/metabolismo , Estereoisomerismo , Estricnina/síntese química , Estricnina/química , Strychnos/metabolismo , Tioureia/química
13.
J Chromatogr A ; 1621: 461044, 2020 Jun 21.
Artigo em Inglês | MEDLINE | ID: mdl-32273090

RESUMO

The presented paper is the first to show thin layer chromatography (TLC) analysis based on eutectic mobile phases (Deep Eutectic Solvents - DES). During the experiment 25 eutectic mixtures were investigated for their chromatographic properties. Most of them belong to the natural deep eutectic solvents (NADES) group. Also, new eutectic liquids based on phenolics and terpenes, not previously employed in analytical practice, were tested. The eutectic liquids were investigated as pure or diluted with solvents used in chromatographic routine: methanol, water, acetone, chloroform or diethyl ether. The analyses were carried out using classic and high performance silica gel plates. The working solution was a mixture of five alkaloids found in genus Chelidonium, namely sanguinarine, coptisine, chelerythrine, chelidonine, and berberine, with UV light detection of 366 nm. This report proves that eutectic TLC is possible and that the eutectic interactions play a crucial role in the separation process. In most of the tested modifications at least partial separation was achieved. The most successful mobile phase, which enabled separation of all the tested alkaloids, was the equimolar mixture of menthol and phenol with a 35% addition of methanol. The system was also effective in separating alkaloids in the real Chelidonium maius extract sample.


Assuntos
Cromatografia em Camada Delgada/métodos , Alcaloides/análise , Chelidonium/química , Fenóis/química , Extratos Vegetais/química , Solventes/química , Terpenos/química
14.
Pestic Biochem Physiol ; 164: 140-148, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-32284120

RESUMO

Chelerythrine (CHE) possesses broad pharmacological activities. In this study, the extract of Chelidonium majus L. were characterized by high performance liquid chromatography (HPLC), infrared radiation (IR) spectroscopy and nuclear magnetic resonance (NMR). It was proved that the extract was CHE. The antifungal activity of CHE against five fungal pathogens of rice was researched in vitro, revealing that CHE inhibited Ustilaginoidea virens (U. virens) and Cochliobolus miyabeanus (C. miyabeanus) with 50% effective concentrations (EC50) of 6.53 × 10-3 mg/mL and 5.62 × 10-3 mg/mL, respectively. When the concentration of CHE was 7.5 × 10-3 mg/mL, the inhibition rate of U. virens reached 56.1%. Moreover, CHE (4 × 10-3 mg/mL) exhibited the greatest efficacy in inhibiting spore of U. virens growth with an inhibition rate as high as 86.7%. CHE displayed the best inhibitory activity against U. virens at the concentration of 7.5 × 10-3 mg/mL, compared with the other two isoquinoline alkaloids and commercial fungicide validamycin. After treating U. virens mycelia with CHE, twisted and atrophied mycelia were observed by optical microscopy. SEM results demonstrated narrow and locally fractured mycelium. TEM observations showed that the cell wall had become thin and broken, and most organelles were difficult to recognize. Furthermore, membrane of mycelia was destroyed and reactive oxygen species (ROS) of spores was accumulated, which induced apoptosis of pathogenic fungi. From these results, our understanding of the mechanisms of antifungal activity of CHE against U. virens was enriched and this research is relevant for developing novel pesticides.


Assuntos
Chelidonium , Oryza , Antifúngicos , Benzofenantridinas
15.
Artigo em Inglês | MEDLINE | ID: mdl-32120948

RESUMO

The milky juice of the greater celandine herb has been used in folk medicine and in homeopathy for treatment of viral warts for years. However, classical medicine fails to use properties of celandine herbs in treatment of diseases induced by papilloma viruses. Nevertheless, dermatological outpatient clinics are regularly visited by patients reporting efficacy of milky sap isolated from celandine herb in treatment of their own viral warts. Authors of this report decided to analyze the respective world literature in order to critically evaluate the potential for treatment of viral dermal warts using the milky sap of celandine. Moreover, the case of a 4-year old boy was presented, the parents of whom applied the milky sap of celandine on viral warts on hands. Thus, Ch. majus may be a potential therapeutic modality for skin warts, especially in a young patients, where conventional therapy may be difficult to apply.


Assuntos
Chelidonium/química , Preparações de Plantas/uso terapêutico , Verrugas/terapia , Antivirais/uso terapêutico , Pré-Escolar , Mãos , Humanos , Masculino
16.
Molecules ; 25(4)2020 Feb 14.
Artigo em Inglês | MEDLINE | ID: mdl-32075082

RESUMO

Due to certain differences in terms of molecular structure, isoquinoline alkaloids from Chelidonium majus engage in various biological activities. Apart from their well-documented antimicrobial potential, some phenanthridine and protoberberine derivatives as well as C. majus extract present with anti-inflammatory and cytotoxic effects. In this study, the LC-MS/MS method was used to determine alkaloids, phenolic acids, carboxylic acids, and hydroxybenzoic acids. We investigated five individually tested alkaloids (coptisine, berberine, chelidonine, chelerythrine, and sanguinarine) as well as C. majus root extract for their effect on the secretion of IL-1ß, IL-8, and TNF-α in human polymorphonuclear leukocytes (neutrophils). Berberine, chelidonine, and chelerythrine significantly decreased the secretion of TNF-α in a concentration-dependent manner. Sanguinarine was found to be the most potent inhibitor of IL-1ß secretion. However, the overproduction of IL-8 and TNF-α and a high cytotoxicity for these compounds were observed. Coptisine was highly cytotoxic and slightly decreased the secretion of the studied cytokines. The extract (1.25-12.5 µg/mL) increased cytokine secretion in a concentration-dependent manner, but an increase in cytotoxicity was also noted. The alkaloids were active at very low concentrations (0.625-2.5 µM), but their potential cytotoxic effects, except for chelidonine and chelerythrine, should not be ignored.


Assuntos
Chelidonium/química , Citocinas/metabolismo , Neutrófilos/metabolismo , Extratos Vegetais/farmacologia , Alcaloides/química , Alcaloides/farmacologia , Citocinas/antagonistas & inibidores , Citocinas/biossíntese , Humanos , Lipopolissacarídeos/toxicidade , Neutrófilos/efeitos dos fármacos , Extratos Vegetais/química
17.
Molecules ; 25(4)2020 Feb 13.
Artigo em Inglês | MEDLINE | ID: mdl-32070017

RESUMO

Medicinal plants are often used as reducing agents to prepare metal nanoparticles through green-synthesis due to natural compounds and their potential as chemotherapeutic drugs. Thus, three types of eco-friendly Ag-MnO2 nanoparticles (Ag-MnO2NPs) were synthesized using C. majus (CmNPs), V. minor (VmNPs), and a 1:1 mixture of the two extracts (MNPs). These NPs were characterized using S/TEM, EDX, XRD, and FTIR methods, and their biological activity was assessed in vitro on normal keratinocytes (HaCaT) and skin melanoma cells (A375). All synthesized NPs had manganese oxide in the middle, and silver oxide and plant extract on the exterior. The NPs had different forms (polygonal, oval, and spherical), uniformly distributed, with crystalline structures and different sizes (9.3 nm for MNPs; 10 nm for VmNPs, and 32.4 nm for CmNPs). The best results were obtained with VmNPs, which reduced the viability of A375 cells up 38.8% and had a moderate cytotoxic effect on HaCaT (46.4%) at concentrations above 500 µg/mL. At the same concentrations, CmNPs had a rather proliferative effect, whereas MNPs negatively affected both cell lines. For the first time, this paper proved the synergistic action of the combined C. majus and V. minor extracts to form small and uniformly distributed Ag-MnO2NPs with high potential for selective treatments.


Assuntos
Chelidonium/metabolismo , Compostos de Manganês/química , Nanopartículas Metálicas/química , Óxidos/química , Extratos Vegetais/metabolismo , Prata/química , Vinca/metabolismo , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Humanos , Compostos de Manganês/farmacologia , Óxidos/farmacologia
18.
Molecules ; 24(19)2019 Oct 07.
Artigo em Inglês | MEDLINE | ID: mdl-31591371

RESUMO

Isoquinoline alkaloids are the main group of secondary metabolites present in Chelidonium majus extracts, and they are still the object of interest of many researchers. Therefore, the development of methods for the investigation and separation of the alkaloids is still an important task. In this work, the application potential of a silica-based monolithic column for the separation of alkaloids was assessed. The influence of the organic modifier, temperature, salt concentration, and pH of the eluent on basic chromatographic parameters such as retention, resolution between neighboring peaks, chromatographic plate numbers, and peak asymmetry were investigated. Based on the obtained results, a gradient elution program was developed and used to separate and quantitatively determine the main alkaloids in a Chelidonium majus root extract.


Assuntos
Alcaloides/isolamento & purificação , Chelidonium/química , Cromatografia Líquida de Alta Pressão/métodos , Isoquinolinas/isolamento & purificação , Alcaloides/análise , Isoquinolinas/análise , Extratos Vegetais/química , Dióxido de Silício
19.
Fitoterapia ; 139: 104359, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-31629049

RESUMO

Two new lignanamides, majusamides A and B (1 and 2), and two new alkaloids, chelidoniumine (3) and tetrahydrocoptisine N-oxide (4), together with six known hydroxycinnamic acid amides (HCCA) were isolated from the 75% ethanol extract of Chelidonium majus through the silica gel, Sephadex LH-20, MCI, ODS column chromatography, and semi-HPLC. Their structures were determined on the basis of spectroscopic data and physico-chemical methods. The absolute configurations of 1-3 were determined by electronic circular dichroism (ECD) calculations. The anti-inflammatory activities of all the isolates on the NO production in lipopolysaccharide (LPS)-induced macrophages were evaluated. Compounds 7 and 9 exhibited moderate inhibitory activity with IC50 values of 25.3 ±â€¯0.5 and 23.5 ±â€¯1.7 µM, respectively.


Assuntos
Alcaloides/farmacologia , Amidas/farmacologia , Anti-Inflamatórios/farmacologia , Chelidonium/química , Lignanas/farmacologia , Óxido Nítrico/metabolismo , Alcaloides/isolamento & purificação , Amidas/isolamento & purificação , Animais , Anti-Inflamatórios/isolamento & purificação , Linhagem Celular , China , Lignanas/isolamento & purificação , Camundongos , Microglia/efeitos dos fármacos , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Componentes Aéreos da Planta/química
20.
Molecules ; 24(19)2019 Sep 20.
Artigo em Inglês | MEDLINE | ID: mdl-31547046

RESUMO

Background: Plants are an important origin of natural substances that the raw material for various pharmaceutical and therapeutic applications due to the presence of phytochemicals, such as alkaloids. Alkaloids, which are found in different plant species, possess numerous biological activities. Some alkaloids have strong cytotoxic effects on various cancer cells. The search for new drugs to treat various cancers is one of the most important challenges of modern scientific research. Objective: This study aimed to investigate of cytotoxic activity of extracts that were obtained from Chelidonium Majus; Berberis sp.; Thalictrum foetidum containing various alkaloids on selected cancer cell lines. The aim was also the quantification of selected alkaloids in the investigated extracts by HPLC. Methods: The analysis of alkaloids contents were performed while using HPLC in reversed phase (RP) mode using Polar RP column and mobile phase containing acetonitrile, water, and ionic liquid. The cytotoxic effect of the tested plant extracts and respective alkaloids' standards were examined while using human pharyngeal squamous carcinoma cells (FaDu), human tongue squamous carcinoma cells (SCC-25), human breast adenocarcinoma cell line (MCF-7), and human triple-negative breast adenocarcinoma cell line (MDA-MB-231). Conclusion: All of the investigated plant extracts possess cytotoxic activity against cancer cell lines: FaDu, SCC-25, MCF-7, and MDA-MB-231. The highest cytotoxic activity against FaDu and MDA-MB-231 cells was observed for Chelidonium majus root extract, while the highest cytotoxic activity against SCC-25 and MCF-7 cells was estimated for the Thalictrum foetidum root extract. There obtained significant differences in the cytotoxic activity of extracts that were obtained from the roots and herbs of Chelidonium majus and Thalictrum foetidum. Based on these results, investigated plant extracts can be recommended for further investigations of anticancer activity.


Assuntos
Alcaloides/química , Alcaloides/farmacologia , Berberis/química , Chelidonium/química , Cromatografia Líquida de Alta Pressão/métodos , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Thalictrum/química , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Humanos , Isoquinolinas/química , Isoquinolinas/farmacologia , Células MCF-7
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