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1.
Int J Mol Sci ; 25(9)2024 Apr 24.
Artigo em Inglês | MEDLINE | ID: mdl-38731845

RESUMO

Moringa oleifera leaves are rich sources of bioactive compounds with potential health benefits, including antioxidants and anti-inflammatory agents. Pressurized liquid extraction (PLE) stands out as a promising technique for effectively extracting valuable compounds from natural sources. In this study, we aimed to optimize PLE parameters, such as temperature, extraction duration, and pressure, to maximize bioactive compound (polyphenols, flavonoids, and ascorbic acid) yield from M. oleifera leaves and evaluate their antioxidant and anti-inflammatory activities. According to the outcomes of this research, the maximum achieved total polyphenol content was 24.10 mg gallic acid equivalents (GAE)/g of dry weight (dw), and the total flavonoid content was increased up to 19.89 mg rutin equivalents (RtE)/g dw. Moreover, after HPLC-DAD analysis, neochlorogenic and chlorogenic acids, catechin and epicatechin, rutin, and narirutin were identified and quantified. As far as the optimum ascorbic acid content is concerned, it was found to be 4.77 mg/g dw. The antioxidant activity was evaluated by three different methods: ferric reducing antioxidant power (FRAP), the DPPH method, and the anti-hydrogen peroxide activity (AHPA) method, resulting in 124.29 µmol ascorbic acid equivalent (AAE)/g dw, 131.28 µmol AAE/g dw, and 229.38 µmol AAE/g dw values, respectively. Lastly, the albumin denaturation inhibition was found to be 37.54%. These findings underscore the potential of PLE as an efficient extraction method for preparing extracts from M. oleifera leaves with the maximum content of bioactive compounds.


Assuntos
Antioxidantes , Moringa oleifera , Extratos Vegetais , Folhas de Planta , Moringa oleifera/química , Folhas de Planta/química , Antioxidantes/farmacologia , Antioxidantes/química , Antioxidantes/isolamento & purificação , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Flavonoides/isolamento & purificação , Flavonoides/análise , Flavonoides/química , Flavonoides/farmacologia , Polifenóis/isolamento & purificação , Polifenóis/farmacologia , Polifenóis/análise , Polifenóis/química , Ácido Ascórbico/farmacologia , Anti-Inflamatórios/farmacologia , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Cromatografia Líquida de Alta Pressão/métodos , Pressão , Extração Líquido-Líquido/métodos , Compostos Fitoquímicos/química , Compostos Fitoquímicos/farmacologia , Compostos Fitoquímicos/isolamento & purificação
2.
J Sep Sci ; 47(9-10): e2300925, 2024 May.
Artigo em Inglês | MEDLINE | ID: mdl-38726740

RESUMO

Deep eutectic solvents (DESs), as a new type of eco-friendly solvent, have attracted increasing attention on the extraction and separation of flavonoid compounds from various samples, owing to their excellent properties such as biodegradability and ease of handling with very low toxicity. This article provides a status review of the applications of DESs in the extraction of flavonoids, including the introduction of flavonoid compounds, the properties and superiority of DESs, and extraction methods (ultrasonic-assisted extraction, heating reflux extraction, matrix solid-phase dispersion, and solid-phase extraction). Finally, prospects and challenges in the application of DESs on extraction and separation are extensively elucidated and critically reviewed.


Assuntos
Solventes Eutéticos Profundos , Flavonoides , Extração em Fase Sólida , Flavonoides/isolamento & purificação , Flavonoides/química , Solventes Eutéticos Profundos/química , Solventes/química
3.
Molecules ; 29(9)2024 Apr 25.
Artigo em Inglês | MEDLINE | ID: mdl-38731467

RESUMO

Flavonoids are important secondary metabolites found in Juglans mandshurica Maxim., which is a precious reservoir of bioactive substances in China. To explore the antitumor actions of flavonoids (JMFs) from the waste branches of J. mandshurica, the following optimized purification parameters of JMFs by macroporous resins were first obtained. The loading concentration, flow rate, and loading volume of raw flavonoid extracts were 1.4 mg/mL, 2.4 BV/h, and 5 BV, respectively, and for desorption, 60% ethanol (4 BV) was selected to elute JMFs-loaded AB-8 resin at a flow rate of 2.4 BV/h. This adsorption behavior can be explained by the pseudo-second-order kinetic model and Langmuir isotherm model. Subsequently, JMFs were identified using Fourier transform infrared combined with high-performance liquid chromatography and tandem mass spectrometry, and a total of 156 flavonoids were identified. Furthermore, the inhibitory potential of JMFs on the proliferation, migration, and invasion of HepG2 cells was demonstrated. The results also show that exposure to JMFs induced apoptotic cell death, which might be associated with extrinsic and intrinsic pathways. Additionally, flow cytometry detection found that JMFs exposure triggered S phase arrest and the generation of reactive oxygen species in HepG2 cells. These findings suggest that the JMFs purified in this study represent great potential for the treatment of liver cancer.


Assuntos
Apoptose , Proliferação de Células , Flavonoides , Juglans , Juglans/química , Humanos , Flavonoides/farmacologia , Flavonoides/química , Flavonoides/isolamento & purificação , Proliferação de Células/efeitos dos fármacos , Células Hep G2 , Apoptose/efeitos dos fármacos , Antineoplásicos Fitogênicos/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Movimento Celular/efeitos dos fármacos , Cromatografia Líquida de Alta Pressão , Antineoplásicos/farmacologia , Antineoplásicos/química
4.
Int J Mol Sci ; 25(8)2024 Apr 15.
Artigo em Inglês | MEDLINE | ID: mdl-38673942

RESUMO

Soluble epoxide hydrolase (sEH) is an enzyme targeted for the treatment of inflammation and cardiovascular diseases. Activated inflammatory cells produce nitric oxide (NO), which induces oxidative stress and exacerbates inflammation. We identify an inhibitor able to suppress sEH and thus NO production. Five flavonoids 1-5 isolated from Inula britannica flowers were evaluated for their abilities to inhibit sEH with IC50 values of 12.1 ± 0.1 to 62.8 ± 1.8 µM and for their effects on enzyme kinetics. A simulation study using computational chemistry was conducted as well. Furthermore, five inhibitors (1-5) were confirmed to suppress NO levels at 10 µM. The results showed that flavonoids 1-5 exhibited inhibitory activity in all tests, with compound 3 exhibiting the most significant efficacy. Thus, in the development of anti-inflammatory inhibitors, compound 3 is a promising natural candidate.


Assuntos
Epóxido Hidrolases , Flavonoides , Inula , Óxido Nítrico , Epóxido Hidrolases/antagonistas & inibidores , Epóxido Hidrolases/metabolismo , Animais , Óxido Nítrico/metabolismo , Camundongos , Células RAW 264.7 , Flavonoides/farmacologia , Flavonoides/química , Flavonoides/isolamento & purificação , Inula/química , Inibidores Enzimáticos/farmacologia , Inibidores Enzimáticos/química , Simulação de Acoplamento Molecular , Cinética , Anti-Inflamatórios/farmacologia , Anti-Inflamatórios/química , Flores/química
5.
Food Funct ; 15(8): 4122-4139, 2024 Apr 22.
Artigo em Inglês | MEDLINE | ID: mdl-38573168

RESUMO

The health-promoting effects of berries have attracted attention due to the possible application of their extracts as functional ingredients in food products. Natural deep eutectic solvents (NADESs) are a new generation of environmentally friendly solvents for the extraction of natural products, and they are green alternatives to organic solvents, and they can improve the solubility, stability, and bioavailability of isolated biocompounds. In this study, an efficient eco-friendly method was used for the extraction of phenolic compounds from different berries: chokeberries, blueberries, and black goji berries with a range of eutectic solvents consisting of hydrogen bond acceptors (HBAs) such as choline chloride, L-proline, L-glycine, and L-lysine and hydrogen bond donors (HBDs) such as malic, citric, tartaric, lactic and succinic acids, glucose and glycerol. The obtained results indicated the ability of NADESs towards selective extraction of phenolics; the eutectic system choline chloride : malic acid showed selective extraction of anthocyanins, while choline chloride : glycerol and choline chloride : urea showed selectivity towards flavonoids and phenolic acids. The methodology for screening of the NADES extraction performance, which included chromatographic profiling via high-performance thin layer chromatography combined with chemometrics and spectrophotometric essays, allowed effective assessment of optimal eutectic solvents for isolation of different groups of phenolics. Great antioxidant and antimicrobial activities of extracts, along with the green nature of eutectic solvents, enable NADES berry extracts to be used as "green-labelled" functional foods or ingredients.


Assuntos
Solventes Eutéticos Profundos , Frutas , Alimento Funcional , Fenóis , Extratos Vegetais , Frutas/química , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Fenóis/química , Fenóis/farmacologia , Fenóis/isolamento & purificação , Solventes Eutéticos Profundos/química , Antioxidantes/farmacologia , Antioxidantes/química , Mirtilos Azuis (Planta)/química , Flavonoides/farmacologia , Flavonoides/química , Flavonoides/isolamento & purificação , Coriandrum/química
6.
Biomolecules ; 14(4)2024 Apr 07.
Artigo em Inglês | MEDLINE | ID: mdl-38672467

RESUMO

Inflammation is a pivotal factor in the development and advancement of conditions like NAFLD and asthma. Diet can affect several phases of inflammation and significantly influence multiple inflammatory disorders. Siraitia grosvenorii, a traditional Chinese edible and medicinal plant, is considered beneficial to health. Flavonoids can suppress inflammatory cytokines, which play a crucial role in regulating inflammation. In the present experiments, kaempferol 3-O-α-L-rhamnoside-7-O-ß-D-xylosyl(1→2)-O-α-L-rhamnoside (SGPF) is a flavonoid glycoside that was first isolated from S. grosvenorii. A series of experimental investigations were carried out to investigate whether the flavonoid component has anti-inflammatory and hepatoprotective effects in this plant. The researchers showed that SGPF has a stronger modulation of protein expression in LPS-induced macrophages (MH-S) and OA-induced HepG2 cells. The drug was dose-dependent on cells, and in the TLR4/NF-κB/MyD88 pathway and Nrf2/HO-1 pathway, SGPF regulated all protein expression. SGPF has a clear anti-inflammatory and hepatoprotective function in inflammatory conditions.


Assuntos
Anti-Inflamatórios , Flavonoides , Glicosídeos , NF-kappa B , Receptor 4 Toll-Like , Humanos , Anti-Inflamatórios/farmacologia , Anti-Inflamatórios/química , Glicosídeos/farmacologia , Glicosídeos/química , Flavonoides/farmacologia , Flavonoides/química , Flavonoides/isolamento & purificação , Células Hep G2 , Animais , Receptor 4 Toll-Like/metabolismo , NF-kappa B/metabolismo , Cucurbitaceae/química , Camundongos , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Fator 88 de Diferenciação Mieloide/metabolismo , Transdução de Sinais/efeitos dos fármacos , Fator 2 Relacionado a NF-E2/metabolismo , Substâncias Protetoras/farmacologia , Substâncias Protetoras/química , Lipopolissacarídeos/farmacologia , Heme Oxigenase-1/metabolismo
7.
Biomolecules ; 14(4)2024 Apr 11.
Artigo em Inglês | MEDLINE | ID: mdl-38672484

RESUMO

A detailed phytochemical investigation has been carried out on the aerial parts of G. foetida leading to the isolation of 29 pure compounds, mainly belonging to the amorfrutin and polyphenol classes. Among them, the new amorfrutin N (5) and exiguaflavone L (21) were isolated and their structures elucidated by means of HR-ESIMS and NMR. All the isolated compounds were investigated for modulation of mitochondrial activity and stimulation of glucose uptake via GLUT transporters, two metabolic processes involved in intracellular glucose homeostasis, which, therefore, correlate with the incidence of metabolic syndrome. These experiments revealed that amorfrutins were active on both targets, with amorfrutin M (17) and decarboxyamorfrutin A (2) emerging as mitochondrial stimulators, and amorfrutin 2 (12) as a glucose uptake promoter. However, members of the rich chalcone/flavonoid fraction also proved to contribute to this activity.


Assuntos
Glucose , Síndrome Metabólica , Componentes Aéreos da Planta , Síndrome Metabólica/metabolismo , Síndrome Metabólica/tratamento farmacológico , Componentes Aéreos da Planta/química , Humanos , Glucose/metabolismo , Glycyrrhiza/química , Mitocôndrias/metabolismo , Mitocôndrias/efeitos dos fármacos , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Flavonoides/química , Flavonoides/farmacologia , Flavonoides/isolamento & purificação , Proteínas Facilitadoras de Transporte de Glucose/metabolismo , Proteínas Facilitadoras de Transporte de Glucose/genética
8.
Molecules ; 29(8)2024 Apr 17.
Artigo em Inglês | MEDLINE | ID: mdl-38675648

RESUMO

Currently, the planting of 'Qi-Nan' is continuously increasing, yet a substantial amount of 'Qi-Nan' leaves have not been properly exploited. To improve the 'Qi-Nan' tree 's utilization value, 'Qi-Nan' leaves were used as a raw material. An ultrasound-assisted method was performed to obtain the flavonoids from the 'Qi-Nan' leaves, followed by optimization of the extraction factors using a one-way and response surface methodology to enhance the extraction of flavonoids. Subsequently, the composition of the flavonoids, as well as their bioactive abilities, were analyzed by ultra-high-performance liquid chromatography-mass spectrometry (UHPLC-MS) and in vitro activity testing methods. The findings demonstrated that a 1:50 material-to-liquid ratio, 60% ethanol concentration, and ultrasound-assisted extraction time of 30 min were the ideal procedures for extracting flavonoids (flavonoid content: 6.68%). Meanwhile, the 'Qi-Nan' leaves possessed the antioxidant and medicinal potential to prevent diabetes and Alzheimer 's disease, as evidenced by the semi-inhibitory concentrations (IC50 values) of flavonoid extracts for scavenging DPPH• free radicals, scavenging ABTS•+ free radicals, inhibiting acetylcholinesterase, and inhibiting α-glucosidase, which were 12.64 µg/mL, 66.58 µg/mL, 102.31 µg/mL, and 38.76 µg/mL, respectively, which indicated that the 'Qi-Nan' leaves possessed the properties of antioxidant and medicinal potential for the prevention of Alzheimer 's disease and diabetes.


Assuntos
Antioxidantes , Flavonoides , Extratos Vegetais , Folhas de Planta , Flavonoides/análise , Flavonoides/química , Flavonoides/isolamento & purificação , Folhas de Planta/química , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Antioxidantes/química , Antioxidantes/farmacologia , Cromatografia Líquida de Alta Pressão , Thymelaeaceae/química
9.
J Ethnopharmacol ; 330: 118195, 2024 Aug 10.
Artigo em Inglês | MEDLINE | ID: mdl-38641080

RESUMO

ETHNOPHARMACOLOGICAL RELEVANCE: Licorice is a frequently used herbal medicine worldwide, and is used to treat cough, hepatitis, cancer and influenza in clinical practice of traditional Chinese medicine. Modern pharmacological studies indicate that prenylated flavonoids play an important role in the anti-tumor activity of licorice, especially the tumors in stomach, lung, colon and liver. Wighteone is one of the main prenylated flavonoids in licorice, and its possible effect and target against colorectal cancer have not been investigated. AIM OF THE STUDY: This study aimed to investigate the anti-colorectal cancer effect and underlying mechanism of wighteone. MATERIALS AND METHODS: SW480 human colorectal cancer cells were used to evaluate the in vitro anti-colorectal cancer activity and Akt regulation effect of wighteone by flow cytometry, phosphoproteomic and Western blot analysis. Surface plasmon resonance (SPR) assay, molecular docking and dynamics simulation, and kinase activity assay were used to investigate the direct interaction between wighteone and Akt. A nude mouse xenograft model with SW480 cells was used to verify the in vivo anti-colorectal cancer activity of wighteone. RESULTS: Wighteone inhibited phosphorylation of Akt and its downstream kinases in SW480 cells, which led to a reduction in cell viability. Wighteone had direct interaction with both PH and kinase domains of Akt, which locked Akt in a "closed" conformation with allosteric inhibition, and Gln79, Tyr272, Arg273 and Lys297 played the most critical role due to their hydrogen bond and hydrophobic interactions with wighteone. Based on Akt overexpression or activation in SW480 cells, further mechanistic studies suggested that wighteone-induced Akt inhibition led to cycle arrest, apoptosis and autophagic death of SW480 cells. Moreover, wighteone exerted in vivo anti-colorectal cancer effect and Akt inhibition activity in the nude mouse xenograft model. CONCLUSION: Wighteone could inhibit growth of SW480 cells through allosteric inhibition of Akt, which led to cell cycle arrest, apoptosis and autophagic death. The results contributed to understanding of the anti-tumor mechanism of licorice, and also provided a rationale to design novel Akt allosteric inhibitors for the treatment of colorectal cancer.


Assuntos
Antineoplásicos Fitogênicos , Neoplasias Colorretais , Flavonoides , Glycyrrhiza , Camundongos Nus , Proteínas Proto-Oncogênicas c-akt , Humanos , Proteínas Proto-Oncogênicas c-akt/metabolismo , Animais , Glycyrrhiza/química , Neoplasias Colorretais/tratamento farmacológico , Neoplasias Colorretais/patologia , Linhagem Celular Tumoral , Flavonoides/farmacologia , Flavonoides/isolamento & purificação , Flavonoides/uso terapêutico , Flavonoides/química , Antineoplásicos Fitogênicos/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/uso terapêutico , Antineoplásicos Fitogênicos/isolamento & purificação , Simulação de Acoplamento Molecular , Proliferação de Células/efeitos dos fármacos , Ensaios Antitumorais Modelo de Xenoenxerto , Regulação Alostérica/efeitos dos fármacos , Camundongos , Camundongos Endogâmicos BALB C , Apoptose/efeitos dos fármacos , Masculino
10.
Phytochemistry ; 222: 114107, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38663823

RESUMO

The isolation of previously undescribed 12 compounds from the MeOH extract of Jacobaea vulgaris whole plants is disclosed, comprising 11 dihydrostilbenes (1-11) and one flavanone (12), and eight known compounds (six flavonoids, one dihydrostilbene, and one caffeoylquinic acid). Structural elucidation employed spectroscopic methods, including 1D and 2D NMR spectroscopy, HRESIMS, and ECD calculations. Evaluation of the compounds' effects on PCSK9 and LDLR mRNA expression revealed that compounds 1 and 3 downregulated PCSK9 mRNA while increasing LDLR mRNA expression, suggesting potential cholesterol-lowering properties.


Assuntos
Flavonoides , Estilbenos , Flavonoides/química , Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Estilbenos/química , Estilbenos/isolamento & purificação , Estilbenos/farmacologia , Estrutura Molecular , Pró-Proteína Convertase 9/metabolismo , Pró-Proteína Convertase 9/genética , Humanos , Receptores de LDL/metabolismo , RNA Mensageiro/metabolismo , RNA Mensageiro/genética
11.
Chem Biodivers ; 21(5): e202400300, 2024 May.
Artigo em Inglês | MEDLINE | ID: mdl-38430215

RESUMO

Sea buckthorn, a traditional medicinal plant, has been used for several years in China for the prevention and treatment of various diseases, a practice closely associated with its significant antioxidant activity. The aim of this study was to investigate the protective effects of sea buckthorn flavonoids on vascular endothelial cells in an oxidative stress environment. We isolated and extracted active compounds from sea buckthorn and investigated their impact on endothelial nitric oxide synthase (eNOS) activity through the PI3K/AKT-eNOS signaling pathway through a combination of network pharmacology and cellular experiments, elucidating the regulatory effects of these compounds on endothelial cell functions. Three flavonoids, named Fr.4-2-1, Fr.4-2-2 and Fr.4-2-3, were obtained from sea buckthorn. The results of network pharmacology indicated that they might exert their effects by regulating the PI3K-AKT signaling pathway. In vitro results showed that all three flavonoids were effective in alleviating the degree of oxidative stress in cells, among which Fr.4-2-1 exerted its antioxidant effects by modulating the PI3K/AKT-eNOS pathway. Flavonoids in sea buckthorn can effectively inhibit oxidative stress-induced cellular damage, preserving the integrity and functionality of endothelial cells, which is crucial for maintaining vascular health and function.


Assuntos
Flavonoides , Hippophae , Óxido Nítrico Sintase Tipo III , Estresse Oxidativo , Fosfatidilinositol 3-Quinases , Proteínas Proto-Oncogênicas c-akt , Transdução de Sinais , Hippophae/química , Óxido Nítrico Sintase Tipo III/metabolismo , Flavonoides/farmacologia , Flavonoides/isolamento & purificação , Flavonoides/química , Proteínas Proto-Oncogênicas c-akt/metabolismo , Estresse Oxidativo/efeitos dos fármacos , Fosfatidilinositol 3-Quinases/metabolismo , Transdução de Sinais/efeitos dos fármacos , Humanos , Antioxidantes/farmacologia , Antioxidantes/química , Antioxidantes/isolamento & purificação , Células Endoteliais/efeitos dos fármacos , Células Endoteliais/metabolismo , Células Endoteliais da Veia Umbilical Humana/efeitos dos fármacos , Células Endoteliais da Veia Umbilical Humana/metabolismo , Sobrevivência Celular/efeitos dos fármacos , Substâncias Protetoras/farmacologia , Substâncias Protetoras/química , Substâncias Protetoras/isolamento & purificação
12.
Chem Biodivers ; 21(4): e202301962, 2024 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-38415915

RESUMO

Stingless bees belong to the Meliponini tribe and are widely distributed in the tropics and subtropics, where they perform important ecological services. Among the best distributed groups of stingless bees is the genus Scaptotrigona, which includes 22 species distributed throughout the neotropical region, including the area from Mexico to Argentina. Bees of this genus are responsible for the production of products such as honey, propolis, geopropolis and fermented pollen ("saburá"). This review aimed to provide an overview of the chemical composition and biological activities associated with derived products from stingless bees of the genus Scaptotrigona. The bibliographic review was carried out through searches in the Scopus, Web of Science, ScienceDirect and PubMed databases, including publications from 2003 to January 2023. The study of the chemodiversity of products derived from Scaptotrigona demonstrated the mainly presence of flavonoids, phenolic acids, terpenoids and alkaloids. It was also demonstrated that products derived from bees of the genus Scaptotrigona exhibit a wide range of biological effects, such as antibacterial, antioxidant, anti-inflammatory and antifungal activities, among other bioactivities. This review provides an overview of phytochemical and pharmacological investigations of the genus Scaptotrigona. However, it is essential to clarify the toxicity and food safety of these products.


Assuntos
Mel , Himenópteros , Própole , Animais , Antibacterianos/farmacologia , Abelhas , México , Própole/farmacologia , Flavonoides/química , Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Hidroxibenzoatos/química , Hidroxibenzoatos/isolamento & purificação , Hidroxibenzoatos/farmacologia , Terpenos/química , Terpenos/isolamento & purificação , Terpenos/farmacologia , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia
13.
J Asian Nat Prod Res ; 26(6): 690-698, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38192122

RESUMO

Two neolignan glycosides including a new one (1), along with seven iridoid glycosides (3 - 9) and nine flavonoid glycosides (10 - 18), were isolated from the leaves of Vaccinium bracteatum. Their structures were established mainly on the basis of 1D/2D NMR and ESIMS analyses, as well as comparison to known compounds in the literature. The structure of 1 with absolute stereochemistry was also confirmed by chemical degradation and ECD calculation. Selective compounds showed antiradical activity against ABTS and/or DPPH. Moreover, several isolates also suppressed the production of ROS in RAW264.7 cells and exerted neuroprotective effect toward PC12 cells.


Assuntos
Flavonoides , Glicosídeos , Lignanas , Folhas de Planta , Folhas de Planta/química , Flavonoides/química , Flavonoides/farmacologia , Flavonoides/isolamento & purificação , Animais , Camundongos , Células PC12 , Glicosídeos/química , Glicosídeos/farmacologia , Glicosídeos/isolamento & purificação , Estrutura Molecular , Lignanas/química , Lignanas/farmacologia , Lignanas/isolamento & purificação , Ratos , Células RAW 264.7 , Vaccinium/química , Fármacos Neuroprotetores/farmacologia , Fármacos Neuroprotetores/química , Fármacos Neuroprotetores/isolamento & purificação , Iridoides/química , Iridoides/farmacologia , Iridoides/isolamento & purificação , Glicosídeos Iridoides/química , Glicosídeos Iridoides/farmacologia , Glicosídeos Iridoides/isolamento & purificação , Espécies Reativas de Oxigênio , Picratos/farmacologia
14.
Phytochemistry ; 213: 113742, 2023 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-37269935

RESUMO

Phytoalexins are antimicrobial plant metabolites elicited by microbial attack or abiotic stress. We investigated phytoalexin profiles after foliar abiotic elicitation in the crucifer Barbarea vulgaris and interactions with the glucosinolate-myrosinase system. The treatment for abiotic elicitation was a foliar spray with CuCl2 solution, a usual eliciting agent, and three independent experiments were carried out. Two genotypes of B. vulgaris (G-type and P-type) accumulated the same three major phytoalexins in rosette leaves after treatment: phenyl-containing nasturlexin D and indole-containing cyclonasturlexin and cyclobrassinin. Phytoalexin levels were investigated daily by UHPLC-QToF MS and tended to differ among plant types and individual phytoalexins. In roots, phytoalexins were low or not detected. In treated leaves, typical total phytoalexin levels were in the range 1-10 nmol/g fresh wt. during three days after treatment while typical total glucosinolate (GSL) levels were three orders of magnitude higher. Levels of some minor GSLs responded to the treatment: phenethylGSL (PE) and 4-substituted indole GSLs. Levels of PE, a suggested nasturlexin D precursor, were lower in treated plants than controls. Another suggested precursor GSL, 3-hydroxyPE, was not detected, suggesting PE hydrolysis to be a key biosynthetic step. Levels of 4-substituted indole GSLs differed markedly between treated and control plants in most experiments, but not in a consistent way. The dominant GSLs, glucobarbarins, are not believed to be phytoalexin precursors. We observed statistically significant linear correlations between total major phytoalexins and the glucobarbarin products barbarin and resedine, suggesting that GSL turnover for phytoalexin biosynthesis was unspecific. In contrast, we did not find correlations between total major phytoalexins and raphanusamic acid or total glucobarbarins and barbarin. In conclusion, two groups of phytoalexins were detected in B. vulgaris, apparently derived from the GSLs PE and indol-3-ylmethylGSL. Phytoalexin biosynthesis was accompanied by depletion of the precursor PE and by turnover of major non-precursor GSLs to resedine. This work paves the way for identifying and characterizing genes and enzymes in the biosyntheses of phytoalexins and resedine.


Assuntos
Barbarea , Fitoalexinas , Barbarea/química , Barbarea/classificação , Barbarea/genética , Barbarea/metabolismo , Flavonoides/química , Flavonoides/isolamento & purificação , Flavonoides/metabolismo , Genótipo , Glucosinolatos/química , Glucosinolatos/isolamento & purificação , Glucosinolatos/metabolismo , Indóis/metabolismo , Fitoalexinas/biossíntese , Fitoalexinas/química , Fitoalexinas/isolamento & purificação , Fitoalexinas/metabolismo
15.
Molecules ; 27(5)2022 Mar 01.
Artigo em Inglês | MEDLINE | ID: mdl-35268738

RESUMO

A new flavonoid, Jusanin, (1) has been isolated from the aerial parts of Artemisia commutata. The chemical structure of Jusanin has been elucidated using 1D, 2D NMR, and HR-Ms spectroscopic methods to be 5,2',4'-trihydroxy-6,7,5'-trimethoxyflavone. Being new in nature, the inhibition potential of 1 has been estimated against SARS-CoV-2 using different in silico techniques. Firstly, molecular similarity and fingerprint studies have been conducted for Jusanin against co-crystallized ligands of eight different SARS-CoV-2 essential proteins. The studies indicated the similarity between 1 and X77, the co-crystallized ligand SARS-CoV-2 main protease (PDB ID: 6W63). To confirm the obtained results, a DFT study was carried out and indicated the similarity of (total energy, HOMO, LUMO, gap energy, and dipole moment) between 1 and X77. Accordingly, molecular docking studies of 1 against the target enzyme have been achieved and showed that 1 bonded correctly in the protein's active site with a binding energy of -19.54 Kcal/mol. Additionally, in silico ADMET in addition to the toxicity evaluation of Jusanin against seven models have been preceded and indicated the general safety and the likeness of Jusanin to be a drug. Finally, molecular dynamics simulation studies were applied to investigate the dynamic behavior of the Mpro-Jusanin complex and confirmed the correct binding at 100 ns. In addition to 1, three other metabolites have been isolated and identified to be сapillartemisin A (2), methyl-3-[S-hydroxyprenyl]-cumarate (3), and ß-sitosterol (4).


Assuntos
Artemisia , Proteases 3C de Coronavírus , Flavonoides , SARS-CoV-2 , Animais , Humanos , Masculino , Ratos , Artemisia/química , Artemisia/metabolismo , Sítios de Ligação , Domínio Catalítico , Proteases 3C de Coronavírus/antagonistas & inibidores , Proteases 3C de Coronavírus/metabolismo , COVID-19/patologia , COVID-19/virologia , Teoria da Densidade Funcional , Flavonoides/química , Flavonoides/isolamento & purificação , Flavonoides/metabolismo , Flavonoides/farmacologia , Dose Letal Mediana , Conformação Molecular , Simulação de Acoplamento Molecular , Simulação de Dinâmica Molecular , SARS-CoV-2/enzimologia , SARS-CoV-2/isolamento & purificação , Pele/efeitos dos fármacos , Pele/patologia
16.
Food Funct ; 13(6): 3308-3317, 2022 Mar 21.
Artigo em Inglês | MEDLINE | ID: mdl-35254360

RESUMO

In Asia, the flower of Hosta plantaginea (Lam.) Aschers (hosta flower) is both an edible food and medicine. The hosta flower is often used as a material for cooking porridge and scented tea and in combination with other plants for alleviating pharyngitis. To clarify the anti-pharyngitis effect of the hosta flower and evaluate its potential active ingredients, an ethanol extract of the hosta flower was prepared and partially purified via chromatography on a column packed with D101 macroporous resin, which was eluted with different concentrations of ethanol. The anti-pharyngitis effect of the crude extract and the various partially purified fractions was examined in an ammonia-induced acute pharyngitis rat model. The 30% ethanol-eluted fraction significantly alleviated the severity of pharyngitis in the rat, as evaluated by changes in the levels of cytokines (IL-1ß, IL-6, and TNF-α) and histological changes in the pharynx tissues. Subsequent HPLC-QTOF/MS (high-performance liquid chromatography coupled with quadrupole-time of flight tandem mass spectrometry) analysis of this fraction revealed kaempferol and its glycosides as the main components. Three of the main components were isolated and identified by 1D NMR. Their pharmacokinetics were studied for the first time by UHPLC-QQQ/MS (ultrahigh-performance liquid chromatography coupled with mass spectrometry). The findings suggested that the 30% ethanol-eluted fraction of the hosta flower extract may be a potential functional food for treating pharyngitis.


Assuntos
Flavonoides/uso terapêutico , Glicosídeos/uso terapêutico , Hosta/química , Faringite/tratamento farmacológico , Extratos Vegetais/uso terapêutico , Animais , Flavonoides/química , Flavonoides/isolamento & purificação , Flavonoides/farmacocinética , Flores/química , Glicosídeos/química , Glicosídeos/isolamento & purificação , Glicosídeos/farmacocinética , Masculino , Faringite/patologia , Fitoterapia , Extratos Vegetais/química , Ratos , Ratos Sprague-Dawley
17.
Molecules ; 27(4)2022 Feb 15.
Artigo em Inglês | MEDLINE | ID: mdl-35209110

RESUMO

Dalbergia cochinchinensis has been widely used in traditional medicine because of its flavonoids; however, the impact of the flavonoids to modulate the inflammatory response to oral cells remains to be described. For this aim, we isolated 4,7,2'-trihydroxy-4'-methoxyisoflavanol (472T4MIF) and 6,4'-dihydroxy-7-methoxyflavane (64D7MF) from the heartwood of D. cochinchinensis and confirmed the chemical structure by nuclear magnetic resonance. We show here that both flavonoids are inhibitors of an inflammatory response of murine RAW 264.7 inflammatory macrophages stimulated by LPS. This is indicated by interleukin (IL)1, IL6, and chemokine CCL2 production besides the phosphorylation of p65. Consistently, in primary murine macrophages, both flavonoids decreased the inflammatory response by lowering LPS-induced IL1 and IL6 expression. To introduce oral cells, we have used human gingival fibroblasts and provoked the inflammatory response by exposing them to IL1ß and TNFα. Under these conditions, 472T4MIF, but not 64D7MF, reduced the expression of chemokines CXCL1 and CXCL2. Taken together, we identified two flavonoids that can reduce the expression of cytokines and chemokines in macrophages and fibroblastic cells.


Assuntos
Quimiocinas/genética , Citocinas/genética , Dalbergia/química , Flavonoides/farmacologia , Regulação da Expressão Gênica de Plantas/efeitos dos fármacos , Extratos Vegetais/farmacologia , Madeira/química , Animais , Quimiocinas/metabolismo , Citocinas/metabolismo , Fibroblastos/efeitos dos fármacos , Fibroblastos/metabolismo , Flavonoides/química , Flavonoides/isolamento & purificação , Camundongos , Estrutura Molecular , Fosforilação , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Células RAW 264.7
18.
Molecules ; 27(3)2022 Jan 21.
Artigo em Inglês | MEDLINE | ID: mdl-35163950

RESUMO

Polygala species are frequently used worldwide in the treatment of various diseases, such as inflammatory and autoimmune disorders as well as metabolic and neurodegenerative diseases, due to the large number of secondary metabolites they contain. The present study was performed on Polygala inexpectata, which is a narrow endemic species for the flora of Turkey, and resulted in the isolation of nine known compounds, 6,3'-disinapoyl-sucrose (1), 6-O-sinapoyl,3'-O-trimethoxy-cinnamoyl-sucrose (tenuifoliside C) (2), 3'-O-(O-methyl-feruloyl)-sucrose (3), 3'-O-(sinapoyl)-sucrose (4), 3'-O-trimethoxy-cinnamoyl-sucrose (glomeratose) (5), 3'-O-feruloyl-sucrose (sibiricose A5) (6), sinapyl alcohol 4-O-glucoside (syringin or eleutheroside B) (7), liriodendrin (8), and 7,4'-di-O-methylquercetin-3-O-ß-rutinoside (ombuin 3-O-rutinoside or ombuoside) (9). The structures of the compounds were determined by the spectroscopic methods including 1D-NMR (1H NMR, 13C NMR, DEPT-135), 2D-NMR (COSY, NOESY, HSQC, HMBC), and HRMS. The isolated compounds were shown in an in silico setting to be accommodated well within the inhibitor-binding pockets of myeloperoxidase and inducible nitric oxide synthase and anchored mainly through hydrogen-bonding interactions and π-effects. It is therefore plausible to suggest that the previously established anti-inflammatory properties of some Polygala-derived phytochemicals may be due, in part, to the modulation of pro-inflammatory enzyme activities.


Assuntos
Compostos Fitoquímicos/análise , Extratos Vegetais/farmacologia , Polygala/metabolismo , Anti-Inflamatórios/análise , Cromatografia Líquida de Alta Pressão/métodos , Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Glucosídeos/isolamento & purificação , Glucosídeos/farmacologia , Simulação de Acoplamento Molecular , Estrutura Molecular , Fenilpropionatos/isolamento & purificação , Fenilpropionatos/farmacologia , Compostos Fitoquímicos/isolamento & purificação , Raízes de Plantas/química , Polygala/genética , Sacarose/isolamento & purificação , Sacarose/metabolismo , Turquia
19.
Molecules ; 27(3)2022 Jan 27.
Artigo em Inglês | MEDLINE | ID: mdl-35164115

RESUMO

Myrica rubra pomace accounts for 20% of the fruit's weight that is not utilized when it is juiced. The pomace contains bioactive phenolic substances such as anthocyanins and flavonoids. To improve the utilization value of Myrica rubra pomace, an optimized extraction method for the residual polyphenols was developed using response surface methodology (RSM). The resulting extract was analyzed by high performance liquid chromatography (HPLC), and the in vitro hypoglycemic activity and antioxidant activity of the polyphenolic compounds obtained were also investigated. The optimum extraction conditions (yielding 24.37 mg·g-1 total polyphenols content) were: extraction temperature 60 °C, ultrasonic power 270 W, ethanol concentration 53%, extraction time 57 min, and solid to liquid ratio 1:34. Four polyphenolic compounds were identified in the pomace extract by HPLC: myricitrin, cyanidin-O-glucoside, hyperoside, and quercitrin. DPPH and hydroxyl radical scavenging tests showed that the Myrica rubra polyphenols extract had strong antioxidant abilities. It is evident that the residual polyphenols present in Myrica rubra pomace have strong hypoglycemic activity and the juiced fruits can be further exploited for medicinal purposes.


Assuntos
Flavonoides , Sequestradores de Radicais Livres , Hipoglicemiantes , Myrica/química , Cromatografia Líquida de Alta Pressão , Flavonoides/química , Flavonoides/isolamento & purificação , Sequestradores de Radicais Livres/química , Sequestradores de Radicais Livres/isolamento & purificação , Hipoglicemiantes/química , Hipoglicemiantes/isolamento & purificação
20.
Molecules ; 27(3)2022 Jan 29.
Artigo em Inglês | MEDLINE | ID: mdl-35164188

RESUMO

In recent years, green extraction of bioactive compounds from herbal medicines has generated widespread interest. Deep eutectic solvents (DES) have widely replaced traditional organic solvents in the extraction process. In this study, the efficiencies of eight DESs in extracting flavonoids from Acanthopanax senticosus (AS) were compared. Response surface methodology (RSM) was employed to optimize the independent variable including ultrasonic power, water content, solid-liquid ratio, extraction temperature, and extraction time. DES composed of glycerol and levulinic acid (1:1) was chosen as the most suitable extraction medium. Optimal conditions were ultrasonic power of 500 W, water content of 28%, solid-liquid ratio of 1:18 g·mL-1, extraction temperature of 55 °C, and extraction time of 73 min. The extraction yield of total flavonoids reached 23.928 ± 0.071 mg·g-1, which was 40.7% higher compared with ultrasonic-assisted ethanol extraction. Macroporous resin (D-101, HPD-600, S-8 and AB-8) was used to recover flavonoids from extracts. The AB-8 resin showed higher adsorption/desorption performance, with a recovery rate of total flavonoids of up to 71.56 ± 0.256%. In addition, DES solvent could efficiently be reused twice. In summary, ultrasonic-assisted DES combined with the macroporous resin enrichment method is exceptionally effective in recovering flavonoids from AS, and provides a promising environmentally friendly and recyclable strategy for flavonoid extraction from natural plant sources.


Assuntos
Eleutherococcus/química , Flavonoides/isolamento & purificação , Química Verde , Solventes/química , Etanol/química , Microscopia Eletrônica de Varredura , Espectroscopia de Infravermelho com Transformada de Fourier/métodos
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