RESUMO
Five new terpenoids, including two vibsane-type diterpenoids (1, 2) and three iridoid allosides (3-5), together with eight known ones, were isolated from the leaves and twigs of Viburnum odoratissimum var.sessiliflorum. Their planar structures and relative configurations were determined by spectroscopic methods, especially 2D NMR techniques. The sugar moieties of the iridoids were confirmed as ß-D-allose by GC analysis after acid hydrolysis and acetylation. The absolute configurations of neovibsanin Q (1) and dehydrovibsanol B (2) were determined by quantum chemical calculation of their theoretical electronic circular dichroism (ECD) spectra and Rh2(OCOCF3)4-induced ECD analysis. The anti-inflammatory activities of compounds 1, 3, 4, and 5 were evaluated using an LPS-induced RAW264.7 cell model. Compounds 3suppressed the release of NO in a dose-dependent manner, with an IC50 value of 55.64 µmol·L-1. The cytotoxicities of compounds 1-5 on HCT-116 cells were assessed and the results showed that compounds 2 and 3 exhibited moderate inhibitory activities with IC50 values of 13.8 and 12.3 µmol·L-1, respectively.
Assuntos
Diterpenos , Viburnum , Terpenos/farmacologia , Viburnum/química , Estrutura Molecular , Diterpenos/química , Folhas de Planta/químicaRESUMO
Guelder rose (Viburnum opulus L.) is known for its health benefits. V. opulus contains phenolic compounds (flavonoids and phenolic acids), a group of plant metabolites with wide biological activities. They are good sources of natural antioxidants in human diets owing to their prevention of the oxidative damage responsible for many diseases. In recent years, observations have shown that an increase in temperature can change the quality of plant tissues. So far, little research has addressed the problem of the common impact of temperature and place of occurrence. Towards a better understanding of phenolics concentration that could indicate their potentials as therapeutic agents and towards predicting and controlling the quality of medicinal plants, the aim of this study was to compare phenolic acids and flavonoids content in the leaves of cultivation and wild collection V. opulus, and to examine the impacts of temperature and place of occurrence on their content and composition. Total phenolics were determined using the spectrophotometric method. Phenolic composition of V. opulus was determined using high-performance liquid chromatography (HPLC). The following hydroxybenzoic acids there were identified: gallic, p-hydroxybenzoic, syringic, salicylic, benzoic, as well as hydroxycinnamic acids: chlorogenic, caffeic, p-coumaric, ferulic, o-coumaric and t-cinnamic. The analysis of extracts from V. opulus leaves has indicated the presence of the following flavonoids: flavanols: (+)-catechin and (-)-epicatechin; flavonols: quercetin, rutin, kaempferol, myricetin; and flavones: luteolin, apigenin and chrysin. The dominant phenolic acids were p-coumaric and gallic acids. The major flavonoids found in V. opulus leaves were myricetin and kaempferol. Temperature and plant location affected the concentration of tested phenolic compounds. The present study shows the potential of naturally grown and wild V. opulus for the human.
Assuntos
Catequina , Vaccinium macrocarpon , Viburnum , Humanos , Quempferóis/metabolismo , Viburnum/química , Extratos Vegetais/química , Flavonoides/análise , Hidroxibenzoatos/análise , Fenóis , AntioxidantesRESUMO
Viburnum luzonicum is widely distributed in China. Its branch extracts showed potential α-amylase and α-glucosidase inhibitory activities. In order to discover new bioactive constituents, five undescribed phenolic glycosides, viburozosides A-E (1-5), were obtained by bioassay-guided isolation coupled with HPLC-QTOF-MS/MS analysis. Their structures were elucidated by spectroscopic analyses, including 1D NMR, 2D NMR, ECD, and ORD. All compounds were tested for their α-amylase and α-glucosidase inhibitory potency. Compound 1 showed significantly competitive inhibition against α-amylase (IC50 =17.5â µM) and α-glucosidase (IC50 =13.6â µM).
Assuntos
Glicosídeos , Viburnum , Glicosídeos/farmacologia , Glicosídeos/química , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Inibidores de Glicosídeo Hidrolases/farmacologia , Inibidores de Glicosídeo Hidrolases/química , Viburnum/química , alfa-Glucosidases , Espectrometria de Massas em Tandem , Fenóis/farmacologia , alfa-AmilasesRESUMO
Two undescribed split-ring iridoids (1-2) with six known triterpenes (3-8) and one steride (9) were isolated from the Viburnum chingii. Compound 2 possessed an unprecedented split-ring iridoid skeleton formed by electrocyclic reaction and split ring. The structures and absolute configurations of the new iridoids were established by NMR, HRESIMS, and ECD calculations. All the isolated compounds were tested for AChE inhibitory activity. Biologically, 1, 2, 3, 4, and 7 displayed significant AChE effects compared to the positive control donepezil, and have also been subjected to molecular docking studies.
Assuntos
Triterpenos , Viburnum , Viburnum/química , Iridoides , Simulação de Acoplamento Molecular , Estrutura MolecularRESUMO
BACKGROUND: Hepatocellular carcinoma (HCC) is one of the most common cancers worldwide, with an elevated danger of metastasis and a short survival rate. Vibsane-type diterpenoids with novel structures possess marked antitumor activities against multiple cancer cells. However, the exact mechanism is poorly unclear. PURPOSE: To assess the antitumor mechanism of vibsane-type diterpenoids derived from Viburnum odoratissimum (V. odoratissimum) against HCC cells in vitro and in vivo. METHODS: The main constituents in the ethyl acetate extract of V. odoratissimum (EAVO) were identified by LC-MS/MS. The antiproliferative activity of EAVO in vitro was evaluated by MTT assays. Annexin V-FITC/PI, AO/EB, and Hoechst 33,258 staining were employed to detect apoptosis. JC-1 fluorescence dye was used to detect the mitochondrial membrane potential (MMP). The levels of intracellular ROS and mitochondrial superoxides were assessed by H2DCF-DA and MitoSox staining, respectively. The levels of oxidative stress were determined by ROS Green™ H2O2 probe, hydroxyphenyl fluorescein (HPF), and the C11 BODIPY 581/591 fluorescent probe. Transcriptomics was performed to investigate the antitumor mechanism of EAVO in HCC. The molecular mechanism by which EAVO suppressed HCC cells was verified by Western blot, RT-PCR, and HTRF® KinEASE™-STK S3 kits. The efficacy and safety of EAVO in vivo were evaluated using Hep3B xenograft models. RESULTS: Vibsane-type diterpenoids were the main constituents of EAVO by LC-MS/MS. EAVO suppressed proliferation, aggravated oxidative stress, and promoted apoptosis in HCC cells. Moreover, EAVO dramatically inhibited tumor growth in Hep3B xenograft models. Transcriptomics results indicated that EAVO inhibited HCC cell proliferation by regulating the PI3K/AKT pathway. Vibsanin B, vibsanol I, and vibsanin S isolated from EAVO was used to further verify the antitumor activity of vibsane-type diterpenoids subsequently. Interestingly, the kinase results showed that vibsanin B and vibsanol I exhibited vital AKT kinase inhibitory activities. CONCLUSIONS: Collectively, this study provided a comprehensive mechanism overview of vibsane-type diterpenoids against HCC cells in vitro and in vivo. It also laid a foundation for further antitumor investigation of vibsane-type diterpenoids in V. odoratissimum.
Assuntos
Carcinoma Hepatocelular , Diterpenos , Neoplasias Hepáticas , Viburnum , Humanos , Viburnum/química , Carcinoma Hepatocelular/tratamento farmacológico , Fosfatidilinositol 3-Quinases , Proteínas Proto-Oncogênicas c-akt , Cromatografia Líquida , Peróxido de Hidrogênio , Espécies Reativas de Oxigênio , Estrutura Molecular , Neoplasias Hepáticas/tratamento farmacológico , Espectrometria de Massas em Tandem , Diterpenos/química , Apoptose , Linhagem Celular Tumoral , Proliferação de CélulasRESUMO
This work addresses the mathematical model building to detect the diameter of the inhibition zone of gilaburu (Viburnum opulus L.) extract against eight different Fusarium strains isolated from diseased potato tubers. Gilaburu extracts were obtained with acetone, ethanol or methanol. The isolated Fusarium strains were: F. solani, F. oxysporum, F. sambucinum, F. graminearum, F. coeruleum, F. sulphureum, F. auneaceum and F. culmorum. In general, it was observed that ethanolic extracts showed highest antifungal activity. The antifungal activity of extracts was evaluated with machine learning (ML) methods. Several ML methods (classification and regression trees (CART), support vector machines (SVM), k-Nearest Neighbors (k-NN), artificial neural network (ANN), ensemble algorithms (EA), AdaBoost (AB) algorithm, gradient boosting (GBM) algorithm, random forests (RF) bagging algorithm and extra trees (ET)) were applied and compared for modeling fungal growth. From this research, it is clear that ML methods have the lowest error level. As a result, ML methods are reliable, fast, and cheap tools for predicting the antifungal activity of gilaburu extracts. These encouraging results will attract more research efforts to implement ML into the field of food microbiology instead of traditional methods.
Assuntos
Antifúngicos/farmacologia , Fusarium/crescimento & desenvolvimento , Aprendizado de Máquina , Extratos Vegetais/farmacologia , Solanum tuberosum/microbiologia , Viburnum/química , Algoritmos , Antioxidantes/farmacologia , Testes de Sensibilidade a Antimicrobianos por Disco-Difusão/métodos , Microbiologia de Alimentos , Fusarium/efeitos dos fármacos , Fusarium/isolamento & purificaçãoRESUMO
BACKGROUND: To compare the extract of Gilaburu (Viburnum opulus Linnaeus) and Tamsulosin as a medical expulsive therapy (MET) in patients with distal ureteral calculi of 10 mm or less. METHODS: Data of 86 patients were prospectively collected. The patients were divided into two groups. In the first group, Viburnum opulus 1000 mg peroral 3 × 2 and diclofenac 50 mg peroral on-demand (n = 43), in the second group Tamsulosin 0.4 mg peroral 1 × 1 and diclofenac 50 mg peroral on-demand (n = 43) was given for MET in patients with distal ureteral calculi. Stone expulsion rates, time until expulsion, additional analgesic requirement, need for emergency admission, need for additional treatment were evaluated. In addition, subgroup analyses of ≤5 and 5-10 mm were also performed. RESULTS: There was no difference between the groups in terms of stone expulsion rates and time until the expulsion in all stones. Additional analgesic requirement and need for emergency admission were found to be lower in the Viburnum opulus group (37.2% vs 65.1%, P = .017 and 11.6% vs 34.8%, P = .02, respectively). In subgroup analyses, while stone expulsion rates were similar in subgroups, it was found shorter in the time until expulsion, lower additional analgesic requirement and need for emergency admission in V. opulus group than Tamsulosin group in 5-10 mm stone size subgroup (7.1 ± 4.2 vs 11.8 ± 5.2, P = .005, 32.2% vs 77.7%, P = .001 and 12.9% vs 40.7%, respectively). CONCLUSION: V. opulus can be used effectively and safely for the treatment of MET in distal ureteral calculi.
Assuntos
Extratos Vegetais , Cálculos Ureterais , Viburnum , Humanos , Extratos Vegetais/uso terapêutico , Sulfonamidas , Tansulosina/uso terapêutico , Resultado do Tratamento , Cálculos Ureterais/tratamento farmacológico , Viburnum/químicaRESUMO
In the present study, an in vitro digestion method has been used to assay the influence of the physiological conditions in the mouth, stomach, and intestine on the stability and activity in different cell models of the main phenolic compounds from Viburnum opulus fresh juice (FJ), phenolic-rich juice (PJ), and the bioavailable fractions (DFJ and DPJ). The data obtained indicate that the V. opulus samples achieved after in vitro digestion had an influence on cellular glucose and lipid metabolism. The bioavailable fraction of both digested juices stimulated glucose uptake and decreased lipid accumulation by L6 myoblasts and HepG2 hepatocytes. Both DFJ and DPJ reduced the secretion of inflammatory cytokines by 3T3-L1 adipocytes: interleukin-6 (IL-6) and tumor necrosis factor-α (TNF-α). Simultaneously, DFJ and DPJ enhanced oxidative stress in MIN6 cells and decreased glucose-stimulated insulin secretion (GSIS). UPLC-MS analysis revealed qualitative and quantitative changes in hydroxycinnamic acids. In particular, the content of chlorogenic acid decreased drastically; its content in the bioavailable fraction was almost 7 times and 30 times lower than in the FJ and PJ, respectively. Our results suggested that although the phenolic compounds of V. opulus juices undergo transformation during digestion, they are still potent antioxidant agents with biological activity.
Assuntos
Antioxidantes/farmacologia , Digestão , Sucos de Frutas e Vegetais/análise , Mioblastos/efeitos dos fármacos , Estresse Oxidativo/efeitos dos fármacos , Extratos Vegetais/farmacologia , Viburnum/química , Células Hep G2 , Humanos , Mioblastos/citologia , Mioblastos/metabolismoRESUMO
Staphylococcus aureus is still one of the leading causes of both hospital- and community-acquired infections. Due to the very high percentage of drug-resistant strains, the participation of drug-tolerant biofilms in pathological changes, and thus the limited number of effective antibiotics, there is an urgent need to search for alternative methods of prevention or treatment for S. aureus infections. In the present study, biochemically characterized (HPLC/UPLC-QTOF-MS) acetonic, ethanolic, and water extracts from fruits and bark of Viburnum opulus L. were tested in vitro as diet additives that potentially prevent staphylococcal infections. The impacts of V. opulus extracts on sortase A (SrtA) activity (Fluorimetric Assay), staphylococcal protein A (SpA) expression (FITC-labelled specific antibodies), the lipid composition of bacterial cell membranes (LC-MS/MS, GC/MS), and biofilm formation (LIVE/DEAD BacLight) were assessed. The cytotoxicity of V. opulus extracts to the human fibroblast line HFF-1 was also tested (MTT reduction). V. opulus extracts strongly inhibited SrtA activity and SpA expression, caused modifications of S. aureus cell membrane, limited biofilm formation by staphylococci, and were non-cytotoxic. Therefore, they have pro-health potential. Nevertheless, their usefulness as diet supplements that are beneficial for the prevention of staphylococcal infections should be confirmed in animal models in the future.
Assuntos
Antibacterianos/farmacologia , Biofilmes/efeitos dos fármacos , Fibroblastos , Staphylococcus aureus Resistente à Meticilina/fisiologia , Extratos Vegetais/farmacologia , Viburnum/química , Aminoaciltransferases/biossíntese , Antibacterianos/química , Proteínas de Bactérias/biossíntese , Linhagem Celular , Cisteína Endopeptidases/biossíntese , Fibroblastos/metabolismo , Fibroblastos/microbiologia , Fibroblastos/patologia , Frutas/química , Regulação Bacteriana da Expressão Gênica/efeitos dos fármacos , Humanos , Casca de Planta/química , Extratos Vegetais/químicaRESUMO
The potential biological activities of Viburnum stellato-tomentosum (VS), a plant mainly found in Costa Rica, have yet to be reported. Supplementation of VS extract for 17 weeks significantly decreased body weight gain, fat weight, fasting glucose, insulin, homeostasis model assessment of insulin resistance (HOMA-IR), and triglyceride levels in high-fat diet (HFD)-fed C57BL/6J mice. The molecular mechanisms underlying the anti-obesity and glucose-lowering effects of VS extract were investigated. VS extract suppressed adipocyte hypertrophy by regulating lipogenesis-related CCAAT/enhancer-binding protein α (C/EBPα) and insulin sensitivity-related peroxisome proliferator-activated receptor γ (Pparg) expression in adipose tissue (AT) and hepatic steatosis by inhibiting C/EBPα and lipid transport-related fatty acid binding protein 4 (FABP4) expression. VS extract enhanced muscular fatty acid ß-oxidation-related AMP-activated protein kinase (AMPK) and PPARα expression with increasing Pparg levels. Furthermore, VS extract contained a much higher content of amentoflavone (AMF) (29.4 mg/g extract) compared to that in other Viburnum species. AMF administration decreased Cebpa and Fabp4 levels in the AT and liver, as well as improved insulin signaling-related insulin receptor substrate 1 (Irs1) and glucose transporter 1 (Glut1) levels in the muscle of HFD-fed mice. This study elucidated the in vivo molecular mechanisms of AMF for the first time. Therefore, VS extract effectively diminished obesity and hyperglycemia by suppressing C/EBPα-mediated lipogenesis in the AT and liver, enhancing PPARα-mediated fatty acid ß-oxidation in muscle, and PPARγ-mediated insulin sensitivity in AT and muscle.
Assuntos
Fármacos Antiobesidade/uso terapêutico , Dieta Hiperlipídica , Hiperglicemia/tratamento farmacológico , Metabolismo dos Lipídeos , Obesidade/tratamento farmacológico , Obesidade/metabolismo , Extratos Vegetais/uso terapêutico , Viburnum/química , Adipócitos/efeitos dos fármacos , Adipócitos/metabolismo , Adipócitos/patologia , Adipogenia/efeitos dos fármacos , Tecido Adiposo Branco/patologia , Animais , Fármacos Antiobesidade/farmacologia , Biflavonoides/farmacologia , Peso Corporal/efeitos dos fármacos , Cromatografia Líquida de Alta Pressão , Fígado Gorduroso/sangue , Fígado Gorduroso/complicações , Fígado Gorduroso/tratamento farmacológico , Comportamento Alimentar , Glucose/metabolismo , Teste de Tolerância a Glucose , Homeostase/efeitos dos fármacos , Hiperglicemia/sangue , Hiperglicemia/complicações , Hiperglicemia/metabolismo , Hipertrofia , Insulina/metabolismo , Resistência à Insulina , Metabolismo dos Lipídeos/efeitos dos fármacos , Camundongos Endogâmicos C57BL , Músculo Esquelético/efeitos dos fármacos , Músculo Esquelético/patologia , Obesidade/sangue , Obesidade/complicações , Tamanho do Órgão/efeitos dos fármacos , Oxirredução , Extratos Vegetais/farmacologia , Transdução de Sinais/efeitos dos fármacosRESUMO
AIM: To investigate the effects of prenatal exposure to AgNPs obtained by green synthesis with Viburnum opulus L. extract on the testis in male offspring rats. MATERIAL AND METHODS: Two different doses of AgNPs (0.8 and 1.5 mg/kg b.w.) and vehicle (PBS) were administered to Wistar female rats on days 3-14 of gestation. At 6 weeks after birth, the ultrastructural changes in correlation with the amount of silver as well as the parameters of oxidative stress, inflammation and cell death mechanisms in the testis of male offspring were evaluated. RESULTS: AgNPs administered during pregnancy crossed the placental and testicular barriers and induced oxidative stress, DNA damage and autophagy as mechanism of cell toxicity. The markers of inflammation and apoptosis decreased after AgNPs exposure while the NFkB activation increased. TEM examination revealed important ultrastructural changes of Sertoli cells, numerous vacuoles and cytoplasmic changes suggestive of the cell's evolution towards necrosis. CONCLUSION: Phytoreduced silver nanoparticles with polyphenols from Viburnum opulus L. fruit extract, administered during the embryological development of the male gonad, have testicular toxic effects in offspring even at 6 weeks after birth.
Assuntos
Morte Celular/efeitos dos fármacos , Nanopartículas Metálicas/toxicidade , Extratos Vegetais/química , Efeitos Tardios da Exposição Pré-Natal , Prata/toxicidade , Viburnum/química , Animais , Citocinas/genética , Citocinas/metabolismo , Feminino , Regulação da Expressão Gênica/efeitos dos fármacos , Inflamação , Masculino , Nanopartículas Metálicas/química , Estresse Oxidativo/efeitos dos fármacos , Gravidez , Ratos , Prata/química , Testículo/citologiaRESUMO
Lipophilic extracts of Viburnum opulus (VOP) and Hippophae rhamnoides (SBP) berry pomace recovered by supercritical CO2 (SFE-CO2) were analysed by UPLC-Q-TOF-MS and GC × GC-TOF for their triacylglycerol, tocopherol, phytosterol and fatty acid composition, while oxidative stability was evaluated by Oxipres and Rancimat methods. SFE-CO2 recovered 16.99% and 26.24% of lipids from SBP and VOP, respectively. Linoleic, linolenic, oleic, palmitic and palmitoleic acids were major in SBP oil, while VOP oil was composed of almost equal amounts of linoleic and oleic acids. Therefore, remarkably higher diversity of triacylglycerols was identified in SBP. The content of ß-sitosterol and α-tocopherol was 359.5-514.5 and 65.38-118.6 mg/100 g, respectively. Hydrocarbons were other quantitatively important lipophilic components, including health beneficial squalene. All extracts improved oxidative stability of mayonnaise. The extracts of berry processing by-products by green extraction method contain valuable bioactive constituents and could be of high interest for applications in functional foods and nutraceuticals.
Assuntos
Dióxido de Carbono/química , Suplementos Nutricionais/análise , Frutas/química , Hippophae/química , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Viburnum/química , Alimentos , Interações Hidrofóbicas e HidrofílicasRESUMO
BACKGROUND: There is an urgent need to devise improved alternatives for the efficient delivery of drugs to develop improved therapeutic interventions against cancers. Nanotechnology-based drug delivery vehicles are in-use with obvious issues of toxicity and bio-distribution. Therefore, green synthetic routes are being deployed to replace the conventional nanoparticle formulations for effective drug delivery aiming at developing interventional strategies against cancer. OBJECTIVE: A simple, viable, and fast approach was used for the green synthesis of silver nanoparticles (AgNPs) using aqueous leaf-extract of Viburnum nervosum (VN) and to explore the anti-cancer potential of the crude extract of VN. METHODS: Silver NPs were synthesized by reacting silver nitrate (AgNO3) with leaf extract of VN. Various analytical techniques were used to characterize the AgNPs. Finally, the anti-cancer potential of VN was observed when delivered through AgNPs. RESULTS: The surface plasmon spectra for AgNPs exhibited absorbance peak at 445 nm, and Fourier-Transform Infrared Spectroscopy investigation revealed the presence of biomolecules acting as an effective reducing and capping agent for converting silver nitrate to AgNPs. Further, our results suggest the spherical size of synthesized AgNPs ranging from 12-17 nm. Moreover, in vitro studies conducted for VN extract with breast (MCF-7) and epidermal carcinoma (A431) cells showed biocompatibility. CONCLUSION: Doxorubicin loaded AgNPs documented an increased bioavailability of the drug compared to the free drug, suggesting the use of AgNPs as "novel drug delivery vectors".
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Química Verde , Nanopartículas Metálicas/química , Extratos Vegetais/farmacologia , Prata/farmacologia , Viburnum/química , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Estrutura Molecular , Tamanho da Partícula , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Folhas de Planta/química , Prata/química , Relação Estrutura-Atividade , Propriedades de SuperfícieRESUMO
ETHNOPHARMACOLOGICAL RELEVANCE: Viburnum taitoense Hayata has been used as folk medicine by the minority people in Southwestern China for a long history, especially in Guangxi Zhuang Autonomous Region. The minority in Guangxi including Zhuang, Miao and Yao people use the ethanol extract of V. taitoense Hayata to treat the fracture, kill the pain of rheumatism because of its definite therapeutic effects. AIM OF THE STUDY: So far, the scientific investigation of V. taitoense Hayata is done very little. Here, we first prepared the ethyl acetate extract of V. taitoense (EEVt), secondly measured the contents of phenols, flavonoids, and terpenoids in EEVt, and thirdly, the anti-inflammatory and analgesic activities of EEVt were investigated by invitro model of RAW 264.7 cells and invivo models of inflammation and pain in rats and mice. MATERIALS AND METHODS: The contents of phenols, flavonoids, and terpenoids in EEVt were determined by UV spectrophotometry, respectively. The anti-inflammatory effect of EEVt (5, 25, 50, 100, and 200 µg/mL) in vitro was tested by determining its inhibitory effect on the nitric oxide production of RAW264.7 cells activated by lipopolysaccharide (LPS). The anti-inflammatory and analgesic effects of EEVt in vivo were investigated in the following experimental rats and mice models: carrageenan-induced paw edema, corton-oil-induced ear edema, acetic acid writhing test, and formalin pain test. RESULTS: The contents of total phenolic, total flavonoids, and total triterpenoids in V. taitoense were measured to be 3.46 ± 0.04%, 2.38 ± 0.04%, and 14.96 ± 0.17%, respectively. In vitro test showed that EEVt at different tested dosages (5, 25, 50, 100, and 200 µg/mL) had no significant toxicity to RAW264.7 macrophages. At dosages of 37.5 and 75 µg/mL of EEVt significant inhibitory (p < 0.001) on the productions of nitric oxide (NO). High dosage (200 µg/mL) of EEVt displayed highly significant inhibitory (p < 0.001) on the productions of proinflammatory cytokines IL-6, IL-1ß, and TNF-α from the LPS-induced RAW264.7 macrophages. EEVt showed obvious anti-inflammatory activity at different time points after carrageenan injection (p < 0.05) in vivo test, and its anti-inflammatory activity reached the strongest 4 h. Similarly, through the ear swelling test, EEVt (200 mg/kg) showed significant (p < 0.05) anti-inflammatory activity. Besides, formalin and acetic acid writhing experiments also showed that EEVt has significant (p < 0.05) analgesic activity. CONCLUSION: EEVt was confirmed to be definite anti-inflammatory and analgesic effects, and the phytochemicals of EEVt was disclosed to be rich in triterpenoids, which was worthy to be further investigated.
Assuntos
Analgésicos/farmacologia , Anti-Inflamatórios/farmacologia , Inflamação/tratamento farmacológico , Dor/tratamento farmacológico , Extratos Vegetais/farmacologia , Viburnum/química , Acetatos/química , Analgésicos/uso terapêutico , Animais , Anti-Inflamatórios/uso terapêutico , Comportamento Animal/efeitos dos fármacos , Carragenina/toxicidade , China , Citocinas/antagonistas & inibidores , Modelos Animais de Doenças , Edema/induzido quimicamente , Edema/tratamento farmacológico , Flavonoides/análise , Flavonoides/química , Formaldeído/toxicidade , Inflamação/induzido quimicamente , Lipopolissacarídeos/toxicidade , Medicina Tradicional/métodos , Camundongos , Óxido Nítrico/antagonistas & inibidores , Dor/induzido quimicamente , Fenóis/análise , Fenóis/química , Extratos Vegetais/química , Extratos Vegetais/uso terapêutico , Células RAW 264.7 , Ratos Sprague-Dawley , Terpenos/análise , Terpenos/químicaRESUMO
Seven new diterpenoids (1-7), including five 7-membered ring vibsane-type diterpenoids, vibsanolide A-E (1-5) and a pair of epimers of 14,15,16,17-tetranorvibsane-type diterpenoids possessing bicyclo[4.2.1]nonane moiety, vibsanolide F-G (6-7), together with twelve known analogues (8-19) were isolated from the crude extracts of the leaves of Viburnum odoratissimum using Small Molecule Accurate Recognition Technology (SMART). These structures including absolute configurations were elucidated by means of comprehensive analyses of spectroscopic data, as well as comparison of the experimental and calculated electronic circular dichroism (ECD) spectra. These compounds were evaluated for their cytotoxic activities against A549 and HepG2 cells by MTT assay. The results showed that compound 2 exhibited potent cytotoxic activity against A549 cells with IC50 value of 1.11 µM. Further staining experiments indicated that 2 could promote apoptosis induction, enhance reactive oxygen species (ROS) level and attenuate mitochondrial membrane potential (MMP) in A549 cells. Taken together, these findings provided new insights into understanding the cytotoxic activity of vibsane-type diterpenoids and it is meaningful to further investigate the application potential of V. odoratissimum.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Diterpenos/farmacologia , Extratos Vegetais/farmacologia , Viburnum/química , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Apoptose/efeitos dos fármacos , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Diterpenos/química , Diterpenos/isolamento & purificação , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Espécies Reativas de Oxigênio/metabolismo , Relação Estrutura-AtividadeRESUMO
Eight previously undescribed lignan glycosides, viburmacrosides A-H (1-8), and seven known analogues (9-15) were isolated from Viburnum macrocephalum f. keteleeri fruits through bioactivity-guided fractionation. Their structures and absolute configurations were elucidated by extensive spectroscopic analyses and chemical evidence. Using the well-recognized carbohydrate-hydrolyzing enzymes α-amylase and α-glucosidase, as well as the promising protein tyrosine phosphatase 1B (PTP1B), as inhibitory targets, all isolated compounds were tested for their antidiabetic potential in vitro. Compound 4 displayed potent inhibitory activities with IC50 values of 9.9 ± 0.6 and 8.9 ± 0.5 µM against α-glucosidase and PTP1B, respectively. The enzymatic kinetics results suggested that compound 4 competitively inhibited α-glucosidase while it suppressed α-amylase and PTP1B in the mixed-type manner. These findings supported that V. macrocephalum f. keteleeri fruits may be a new functional food resource with antidiabetic potential.
Assuntos
Inibidores Enzimáticos/química , Lignanas/química , Extratos Vegetais/química , Proteína Tirosina Fosfatase não Receptora Tipo 1/antagonistas & inibidores , Viburnum/química , alfa-Amilases/antagonistas & inibidores , Frutas/química , Inibidores de Glicosídeo Hidrolases/química , Humanos , Hipoglicemiantes/química , Cinética , Estrutura Molecular , Proteína Tirosina Fosfatase não Receptora Tipo 1/química , alfa-Amilases/química , alfa-Glucosidases/químicaRESUMO
Bone mass loss occurs with a decrease in osteoblast proliferation and differentiation, or the enhancement of bone resorption, which further leads to the impairment of bone mineral density and increase in bone fracture. Recent studies suggest that some phenolic compounds found in food play positive role in bone metabolism. High content of phenolic compounds with potential beneficial effects on bone metabolism have been identified in the Viburnum opulus fruit. The aim of the study was to determine the influence of V. opulus fresh juice (FJ) and juice purified by solid phase extraction (PJ) on osteogenesis processes with osteosarcoma Saos-2 cell lines. V. opulus purified juice revealed stronger potential as an inducer of Saos-2 osteogenic differentiation. Saos-2 cells matrix mineralization was evaluated with alkaline phosphatase (ALP) activity measurement and alizarin red S staining. Gene expression analysis showed the elevation of the mRNA levels of Runt-related transcription factor 2 (RUNX2), ALP, collagen type 1 and osteonectin, whereas the nuclear factor-κB ligand and osteoprotegerin ratio (RANKL/OPG) decreased. Furthermore, V. opulus was able to diminish the secretion of pro-inflammatory cytokines Il6 and TNFα, however had no effect on vascular endothelial growth factor (VEGF). It decreased intracellular oxidative stress and induced DNA repair, but had no effect on the growth inhibition of lactic acid beneficial microorganisms.
Assuntos
Conservadores da Densidade Óssea/farmacologia , Neoplasias Ósseas/patologia , Sucos de Frutas e Vegetais/análise , Osteogênese/efeitos dos fármacos , Osteossarcoma/patologia , Fenóis/farmacologia , Extratos Vegetais/farmacologia , Viburnum/química , Bactérias/efeitos dos fármacos , Diferenciação Celular/efeitos dos fármacos , Linhagem Celular Tumoral , Reparo do DNA/efeitos dos fármacos , Avaliação Pré-Clínica de Medicamentos , Microbioma Gastrointestinal/efeitos dos fármacos , Regulação Neoplásica da Expressão Gênica/efeitos dos fármacos , Humanos , Interleucina-6/metabolismo , Mitocôndrias/efeitos dos fármacos , Mitocôndrias/enzimologia , Proteínas de Neoplasias/biossíntese , Proteínas de Neoplasias/genética , Osteogênese/genética , Estresse Oxidativo/efeitos dos fármacos , Espécies Reativas de Oxigênio/metabolismo , Fator de Necrose Tumoral alfa/metabolismo , Fator A de Crescimento do Endotélio Vascular/metabolismoRESUMO
In this study the in vitro investigation of the inhibitory effect of ethanol extract of Viburnum opulus L. bark sample on Streptococcus mutans planctonic cells and biofilm has been intended. A Scanning electron microscopy analysis has been performed in order to investigate the inhibitory effect of the extract on Streptococcus mutans biofilms. Furthermore, the Exopolysaccharide and dextran production of this bacteria have been identified in the presence of the extract. It has been found out that the bark extract with the concentration of 2,5 mg/mL is able to inhibit more than 50% of the cells in the different times development phases. According to this, the exopolymeric matrix on the biofilm surface disperses and the Exopolysaccharide and dextran production get lowered in the presence of bark extract compared to the control group. It is considered that this extract can be used as an alternative approach for the new chemotherapeutic strategies against tooth decay.
En este estudio se investigó el efecto inhibitorio in vitro del extracto de etanólico de una muestra de corteza de Viburnum opulus L. en biopelículas de células planctónicas de Streptococcus mutans. Se realizó un análisis de microscopía electrónica de barrido para investigar el efecto inhibitorio del extracto sobre las biopelículas de Streptococcus mutans. Además, se identificó la producción de exopolisacárido y dextrano de esta bacteria en presencia del extracto. Se descubrió que el extracto de corteza con una concentración de 2,5 mg/ml inhibió más del 50% de las células en las diferentes fases de desarrollo. Consecuentemente, la matriz exopolimérica en la superficie de la biopelícula se dispersa y la producción de exopolisacárido y dextrano se reduce en presencia de extracto de corteza en comparación con el grupo de control. Se sugiere que este extracto puede ser usado como un enfoque alternativo para las nuevas estrategias quimioterapéuticas contra la carie dental.
Assuntos
Streptococcus mutans/efeitos dos fármacos , Extratos Vegetais/farmacologia , Viburnum opulus/farmacologia , Viburnum/química , Polissacarídeos Bacterianos/análise , Streptococcus mutans/metabolismo , Técnicas In Vitro , Microscopia Eletrônica de Varredura , Dextranos/análise , Biofilmes/efeitos dos fármacos , Etanol , Incrustação BiológicaRESUMO
Viburnumfocesides A - D, four undescribed 1-O-isovaleroylated iridoid 11-O-allosides modified with (Z / E)-p-coumaric acid, were isolated from the aqueous EtOH extract of the twigs of Viburnum foetidum var. ceanothoides, together with seven known natural products. Their structures were identified on the basis of the spectroscopic data interpretation and chemical derivation studies. Cell-based estrogen biosynthesis assays indicated that viburnumfoceside D (4), (2S,3R)-2,3-dihydro-3-hydroxymethyl-7-methoxy-2-(4-hydroxy-3-methoxyphenyl)-5-benzofuranpropanol-3a-O-α-L-rhamnopyranoside (8), and (-)-eriodictyol (11) inhibit estrogen biosynthesis with IC50 values of 5.8, 1.5, and 1.1⯵M, respectively, in human ovarian granulosa-like KGN cells via decreasing the expression level of aromatase.
Assuntos
Inibidores da Aromatase/farmacologia , Células da Granulosa/efeitos dos fármacos , Iridoides/farmacologia , Viburnum/química , Inibidores da Aromatase/isolamento & purificação , Linhagem Celular , China , Estrogênios/biossíntese , Feminino , Humanos , Iridoides/isolamento & purificação , Estrutura Molecular , Ovário/citologia , Ovário/efeitos dos fármacos , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/químicaRESUMO
The present study investigated the effects of Cornus mas, Sorbus aucuparia and Viburnum opulus fruit extracts on arginase activity and arterial vasodilation. V. opulus fruit extract exerted the highest vasorelaxant activity in phenylephrine precontracted rat aortic rings (EC50â¯=â¯6.31⯱â¯1.61⯵g/mL) and a significant inhibition of arginase (IC50â¯=â¯71.02⯱â¯3.06⯵g/mL). By contrast, S. aucuparia and C. mas fruit extracts showed no important anti-arginase activity and a significantly weaker activity in the rat aortic rings relaxation assay (EC50â¯=â¯100.9⯱â¯11.63 and 78.52⯱â¯8.59⯵g/mL, respectively). For all extracts, the main mechanism of vasodilation was proven to be endothelium-dependent. HPLC-ESI-Q-TOF-MS/MS studies revealed a very complex metabolite profiling in all three extracts with chlorogenic acid accounting for 30.89, 0.72 and 2.03â¯mg/g in V. opulus, C. mas and S. aucuparia fruit extracts, respectively. All extracts were declared non-toxic in the brine shrimp acute toxicity test. Our study highlights potential benefits of V. opulus fruit extract in diseases associated with endothelial dysfunction and impaired vasodilation.