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1.
Chem Biodivers ; 21(5): e202302112, 2024 May.
Artigo em Inglês | MEDLINE | ID: mdl-38531073

RESUMO

The essential oils of Senecio plants have been used to treat a wide range of ailments. The current study aimed to extract the essential oil of Senecio glaucus obtained from Egypt's Nile delta and determine its chemical profile using GC-MS and NMR analysis. Then, the antimicrobial activity of the oil has been investigated against different fungal and bacterial strains. In addition, its activity as radical scavenger has been evaluated using DPPH, ABTS, and metal chelating techniques. The results revealed the identification of 50 compounds representing 98.80 % of the oil total mass. Sesquiterpenes, including dehydrofukinone (27.15 %) and 4,5-di-epi-aristolochene (10.27 %), as well as monoterpenes, including p-cymene (4.77 %), represented the most predominant constituents. The dehydrofukinone has been isolated and structurally confirmed using 1D and 2D NMR techniques. The oil has showed remarkable antifungal activity against Candida glabrata and C. albicans where the minimum inhibitory concentration (MIC) and minimum fungicidal concentration (MFC) values were 3.13 µg/mL and 1.50 µg/mL and 12.50 µg/mL and 6.30 µg/mL, respectively that could be attributed to the sesquiterpene ketones present in the aerial tissues of the plant. Also, this oil inhibited the growth of the tested bacteria with MIC ranging from 12.50-100.00 µg/mL. In comparison to ascorbic acid and Trolox, the EO had remarkable scavenging activity of DPPH, ABTS and metal chelating with IC50 values of 313.17±13.4, 493.83±20.1, and 409.13±16.7 µg/mL. The docking studies of the identified compounds of the oil to different microbial targets, including Gyrase B and α-sterol demethylase, showed that the phytol possessed the best binding affinities toward the active sites of both enzymes with ΔG=-7.42 and -7.78 kcal/mol, respectively. In addition, the phytol revealed the highest binding affinity to tyrosine kinase Hck with ΔG=-7.44 kcal/mol.


Assuntos
Antioxidantes , Cromatografia Gasosa-Espectrometria de Massas , Espectroscopia de Ressonância Magnética , Testes de Sensibilidade Microbiana , Senécio , Antioxidantes/farmacologia , Antioxidantes/química , Antioxidantes/isolamento & purificação , Senécio/química , Bactérias/efeitos dos fármacos , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Óleos Voláteis/isolamento & purificação , Antibacterianos/farmacologia , Antibacterianos/química , Antibacterianos/isolamento & purificação , Anti-Infecciosos/farmacologia , Anti-Infecciosos/química , Anti-Infecciosos/isolamento & purificação , Fungos/efeitos dos fármacos , Antifúngicos/farmacologia , Antifúngicos/química , Antifúngicos/isolamento & purificação , Picratos/antagonistas & inibidores , Odorantes/análise , Compostos de Bifenilo/antagonistas & inibidores
2.
Anal Bioanal Chem ; 414(22): 6695-6705, 2022 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-35869992

RESUMO

Unambiguous identification of the components of a natural mixture remains a challenging and meticulous issue. Usually, different analytical techniques and laborious separation protocols are employed; nevertheless, in some cases, delicate and equivocal problems are hardly addressed by traditional methods. In this context, an original methodology for the analysis of natural samples consisting of recent mass spectrometry methods based on ion mobility (MS-IM) is proposed. As an example, a polar fraction obtained by the essential oil prepared from Senecio transiens, an endemic plant harvested on the Corsica Island, was selected for this study to show how IM-MS-based methods easily provide very useful insights suggesting the presence of two diastereomers. To unambiguously confirm this hypothesis and verify reliability of the IM-MS results, the purified compounds were further analysed by means of nuclear magnetic resonance (NMR) methodologies, allowing the structural elucidation and the identification of two new natural compounds, diastereomers of 4-acetoxy-5,9-dimethyl-3-(2-methylpropenyl)-2-oxabicyclo[4.4.0] dec-9-ene, reported here for the first time.


Assuntos
Óleos Voláteis , Senécio , Espectroscopia de Ressonância Magnética , Espectrometria de Massas/métodos , Óleos Voláteis/química , Reprodutibilidade dos Testes , Senécio/química
3.
Molecules ; 27(24)2022 Dec 13.
Artigo em Inglês | MEDLINE | ID: mdl-36558004

RESUMO

The genus Senecio is one of the largest in Asteraceae. There are thousands of species across the globe, either confirmed or awaiting taxonomic delimitation. While the species are best known for the toxic pyrrolizidine alkaloids that contaminate honeys (as bees select pollen from the species) and teas via lateral transfer and accumulation from adjacent roots of Senecio in the rhizosphere, they are also associated with more serious cases leading to fatality of grazing ruminants or people by contamination or accidental harvesting for medicine. Surprisingly, there are significantly more sesquiterpenoid than pyrrolizidine alkaloid-containing species. The main chemical classes, aside from alkaloids, are flavonoids, cacalols, eremophilanes, and bisabolols, often in the form of furan derivatives or free acids. The chemistry of the species across the globe generally overlaps with the 469 confirmed species of Africa. A small number of species express multiple classes of compounds, meaning the presence of sesquiterpenes does not exclude alkaloids. It is possible that there are many species that express the pyrrolizidine alkaloids, in addition to the cacalols, eremophilanes, and bisabolols. The aim of the current communication is, thus, to identify the research gaps related to the chemistry of African species of Senecio and reveal the possible chemical groups in unexplored taxa by way of example, thereby creating a summary of references that could be used to guide chemical assignment in future studies.


Assuntos
Alcaloides , Alcaloides de Pirrolizidina , Senécio , Sesquiterpenos , Animais , Abelhas , Alcaloides de Pirrolizidina/química , Senécio/química , Terpenos , Lacunas de Evidências , África , Sesquiterpenos Policíclicos
4.
Arch Anim Nutr ; 76(2): 93-111, 2022 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-35766237

RESUMO

Pyrrolizidine alkaloid (PA) producing plants like Senecio jacobaea or Senecio vernalis are undesirable in fields for forage production, since PA are toxic to animals and humans. Previous studies have shown that ensiling can decrease the PA content in forages; however, no direct comparison of diverse PA from different Senecio spp. under various ensiling conditions has been made. Therefore, it was hypothesised that individual PA might react differently to ensiling, and silage inoculation with Lactobacillus will affect PA degradation because of a quick drop in pH, contrastingly to poor silage qualities resulting from contamination with soil. Laboratory scale grass silages were prepared in a multifactorial design with two levels of dry matter contents, four ensiling treatments and two storage durations (10 and 90 d). For each combination, four replicates were prepared individually. Ensiling treatments were (1) 10 ml water per kg fresh matter as control (CON), (2) 10 ml heterofermentative Lactobacillus buchneri strain LN4637 at 3 · 105 cfu/kg fresh matter plus 25 g molasses/kg fresh matter (LBHE), (3) 10 ml homofermentative lactobacilli at 3 · 105 cfu/kg fresh matter plus 25 g molasses/kg fresh matter (LBHO) and (4) 10 g soil/kg fresh matter (SOIL). Treatments affected formation of fermentation acids. Acetic acid was highest with treatment LBHE, and butyric acid was highest with treatment SOIL. All ensiling treatments effectively reduced total PA content by degrading the PA N-oxide (PANO) fraction. In parallel, though, the fraction of the tertiary base forms increased by around one-tenth of the original PANO content. Contents of jaconine and senkirkine were higher after ensiling than before, with regards to the sum of PA and PANO for jaconine, indicating higher stability or new formation through degradation of other PA. Overall, ensiling offers opportunities to decrease the PA-PANO content in feed and therefore lowers the risk of intoxication by Senecio in livestock.


Assuntos
Alcaloides de Pirrolizidina , Senécio , Ração Animal/análise , Animais , Dieta/veterinária , Fermentação , Humanos , Alcaloides de Pirrolizidina/metabolismo , Senécio/química , Silagem/análise , Solo , Zea mays/química
5.
Arch Microbiol ; 203(4): 1477-1488, 2021 May.
Artigo em Inglês | MEDLINE | ID: mdl-33394080

RESUMO

The gut microbiota inhabits the animal intestinal tract, and dysbiosis of the gut microbiota may result in disease. Senecio scandens has pharmaceutical antibacterial activities and is regarded as a broad-spectrum antibiotic in traditional Chinese medicine. Extracts of S. scandens are reported to show strong antimicrobial activity, and quercetin significantly decreases some species in the caecal microflora. However, the bactericidal effects of the extracts on the gut microbiota remain obscure. Here, we supplied ethanol extract of S. scandens, which might possibly be used as an alternative for chemical antibiotics, to mice to investigate the state of the intestinal microbiota. Our studies included a control group, low-, moderate-, and high-dose ethanol extract groups, and cefixime capsule group. The ethanol extract groups did not present reduced diversity or differences in the gut microbiota balance. There were significant differences between the ethanol extract and cefixime capsule groups in terms of the gut microbiota. The control and ethanol extract groups contained similar bacteria, which suggested that the ethanol extract has no inhibitory effect on the gut microbiota in vivo. Bifidobacteriales and Lactobacillus acidophilus were significantly increased in the high-dose group. Both secretory immunoglobulin A and mucin 2 concentrations increased as the dose of ethanol extract increased. The functional prediction differences between the control and ethanol extract groups decreased with increasing extract doses, which indicated that the low-dose and high-dose extract treatments might regulate different pathways and functions of the gut microbiota. The results also highlighted the prevention of bacterial drug resistance in the ethanol extract groups.


Assuntos
Bactérias , Microbioma Gastrointestinal , Extratos Vegetais , Senécio , Animais , Bactérias/efeitos dos fármacos , Biodiversidade , Etanol/química , Microbioma Gastrointestinal/efeitos dos fármacos , Regulação da Expressão Gênica/efeitos dos fármacos , Imunoglobulina A/genética , Camundongos , Mucina-2/genética , Extratos Vegetais/farmacologia , Probióticos , Senécio/química
6.
Fish Shellfish Immunol ; 98: 681-690, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-31698071

RESUMO

The study mainly aimed at the effects of dietary Senecio scandens buch-ham extract (SSBE) on the growth performance, body composition, plasma biochemical index, intestinal and liver histology and the expression of antioxidant, apoptosis and inflammatory related genes in hybrid grouper (Epinephelus lanceolatus♂ × Epinephelus fuscoguttatus♀). Basal diets supplemented with SSBE (10:1) 0%, 0.05%, 0.1%, 0.2% and 0.4% were fed hybrid grouper for 8 weeks. The results showed that WGR and SGR were significantly increased in the week 2 and week 4 in Diet 0.05% group (P < 0.05). The total protein, globulin and albumin significantly increased whereas alanine aminotransferase, triglyceride and alkaline phosphate in the plasma were significantly decreased in Diet 0.1% group (P < 0.05). The villi length, width, muscle thickness and the cross-sectional area of intestine were improved in Diet 0.05% and Diet 0.1% group. The expression levels of PPAR-α and CPT-1 in the liver of hybrid grouper were significantly increased following the supplementation of SSBE (P < 0.05). The expression levels of antioxidant related genes (CAT, GPX, GR and Keap1) and anti-inflammatory factor (IL-10) in liver, head kidney and spleen of hybrid grouper decreased significantly (P < 0.05). In addition, diets supplemented with 0.05%-0.1% SSBE had a good liver-protecting effect, but it would have a detrimental effect on hepatocytes when the content exceeds 0.2%. The above results indicated that the suitable additive amount of SSBE in hybrid grouper feed was 0.05%-0.1%.


Assuntos
Bass/imunologia , Expressão Gênica , Extratos Vegetais/metabolismo , Senécio/química , Ração Animal/análise , Animais , Bass/sangue , Bass/genética , Bass/crescimento & desenvolvimento , Dieta/veterinária , Suplementos Nutricionais/análise , Relação Dose-Resposta a Droga , Proteínas de Peixes/genética , Proteínas de Peixes/metabolismo , Extratos Vegetais/administração & dosagem , Distribuição Aleatória
7.
Chem Biodivers ; 17(6): e1900507, 2020 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-32277597

RESUMO

The effect of a natural sesquiterpene ketone, 9,10-dehydrofukinone (DHF), on pathogenic Staphylococcus aureus and Pseudomonas aeruginosa strains isolated from chronic infectious processes, was the focus of the present study. Lipophilic DHF produced important antibacterial synergistic effects in association with ciprofloxacin (CPX) against two biofilm-forming strains of S. aureus HT1 (FIC=0.21) and P. aeruginosa HT5 (FIC=0.05). Hence, this mixture constitutes an excellent strategy to combat these biofilm-producing bacteria that overexpress drug efflux pumps as a resistance mechanism. Additionally, a substantial rise in beneficial Lactobacillus biofilm biomass was determined as a very significant finding of this association. Particularly, a non-pathogenic biofilm increment of 119 % was quantified when the mixture was added to a probiotic L. acidophilus ATCC SD-5212 culture. A surface activity enhanced in 71 % with respect to untreated L. acidophilus culture was also generated by the DHF and CPX association, and therefore, a glycoprotein synthesis induction mediated by the mixture is discussed. The results obtained could help in the development of new selective antibiotics. From an ecological standpoint, the present study strongly suggests that DHF is a polyfunctional organic molecule produced with a high yield in Senecio punae that exerts a positive impact on a non-pathogenic plant bacterium L. plantarum CE105.


Assuntos
Senécio/química , Sesquiterpenos/química , Compostos Orgânicos Voláteis/química , Antibacterianos/química , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Biofilmes/efeitos dos fármacos , Ciprofloxacina/farmacologia , Lactobacillus/efeitos dos fármacos , Lactobacillus/fisiologia , Testes de Sensibilidade Microbiana , Pseudomonas aeruginosa/efeitos dos fármacos , Pseudomonas aeruginosa/isolamento & purificação , Pseudomonas aeruginosa/fisiologia , Senécio/metabolismo , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , Staphylococcus aureus/efeitos dos fármacos , Staphylococcus aureus/isolamento & purificação , Staphylococcus aureus/fisiologia
8.
Zhongguo Zhong Yao Za Zhi ; 45(1): 92-97, 2020 Jan.
Artigo em Zh | MEDLINE | ID: mdl-32237416

RESUMO

Pyrrolizidine alkaloids(PAs) are a kind of natural toxins, which can cause severe hepatotoxicity, pulmonary toxicity, genotoxicity, neurotoxicity, embryotoxicity and even death. Therefore, international organizations and countries such as World Health Organization have paid great attention to herbal medicines and preparations containing PAs. PAs are widely distributed in Chinese herb medicines and contained in hundreds of traditional Chinese medicine preparations. The content of adonifoline, the main PAs in Senecionis Scandentis Herba, shall be less than 0.004% in herbal medicines as described in Chinese pharmacopeia. However, there is no guidance in preparations which contain Senecionis Scandentis Herba. In this study, 14 preparations were analyzed by an UPLC-MS method. Among them, 8 preparations were found to contain adonifoline much higher than the content limits of such countries as Germany, Netherlands and New Zealand. And the highest contents of adonifoline were found in Qianbai Biyan Tablets and Qianbai Biyan Capsules, which are officially recorded in Chinese Pharmacopeia. The contents of adonifoline varied in different batches of the same preparations. The highest content was 156.10 µg·g~(-1) Qianbai Biyan Tablets, whose daily intake of adonifoline was up to 1 030.26 µg according to the recommended dosage of the preparation. Our results showed the potential risk of these preparations, and the content limit of adonifoline shall be inspected Chinese medicine preparations containing Senecionis Scandentis Herba.


Assuntos
Medicamentos de Ervas Chinesas/análise , Lactonas/análise , Alcaloides de Pirrolizidina/análise , Senécio/química , Cromatografia Líquida , Medicamentos de Ervas Chinesas/normas , Medicina Tradicional Chinesa , Espectrometria de Massas em Tandem
9.
BMC Vet Res ; 15(1): 99, 2019 Mar 25.
Artigo em Inglês | MEDLINE | ID: mdl-30909906

RESUMO

BACKGROUND: Haemonchosis affects sheep husbandry and its treatment is often compromised due to the development of anthelminthic resistance. Plant-derived bioactive compounds have been studied as alternative to control Haemonchus contortus. The objective of this study was to evaluate the effect of Senecio brasiliensis extracts on H. contortus egg hatching and infective larvae migration. RESULTS: The aqueous extract from dried and fresh plant and alkaloid-enriched fraction of the previously dried leaves of S. brasiliensis inhibited H. contortus egg hatching. The main plant compound in alkaloid fraction was integerrimine, a pyrrolizidine alkaloid (PA). However, the aqueous extract from dried plant displayed higher efficacy when compared to their alkaloid enriched or non-polar fractions, meaning that, although PAs contributed to the ovicidal effect, other compounds in the plant can also contribute to their effect. Furthermore, the aqueous extract from dried plant also had higher efficacy than aqueous extract from fresh plant in larvae migration inhibition. Finally, extract from dried plant presented low in vitro cytotoxic effect. CONCLUSION: Taken together our results suggest a good anthelmintic effect of S. brasiliensis, especially when aqueous extract is prepared from dried plant. Further in vivo studies should be performed focused on forms of administration of this extract in rearing sheep.


Assuntos
Anti-Helmínticos/farmacologia , Haemonchus/efeitos dos fármacos , Extratos Vegetais/farmacologia , Folhas de Planta , Senécio , Animais , Técnicas In Vitro , Larva/efeitos dos fármacos , Óvulo/efeitos dos fármacos , Folhas de Planta/química , Alcaloides de Pirrolizidina/farmacologia , Senécio/química
10.
BMC Complement Altern Med ; 19(1): 52, 2019 Feb 28.
Artigo em Inglês | MEDLINE | ID: mdl-30819180

RESUMO

BACKGROUND: Senecio serratuloides DC is used in folk medicine for treating hypertension, skin disorders, internal and external sores, rashes, burns and wounds. This study aimed at investigating the antihypertensive effects of the hydroethanol extract of S. serratuloides (HESS) in N-Nitro-L-arginine methyl ester (L-NAME) induced hypertension in rats. METHODS: Acute toxicity of HESS was first determined to provide guidance on doses to be used in this study. Lorke's method was used to determine safety of the extract in mice. Female Wistar rats were treated orally once daily with L-NAME (40 mg/kg) for 4 weeks and then concomitantly with L-NAME (20 mg/kg) and plant extract (150 and 300 mg/kg), captopril (20 mg/kg) or saline as per assigned group for 2 weeks followed by a 2-week period of assigned treatments only. Blood pressure was monitored weekly. Lipid profile, nitric oxide, renin and angiotensin II concentrations were determined in serum while mineralocorticoid receptor concentration was quantified in the kidney homogenate. Nitric oxide (NO) concentration was determined in serum and cardiac histology performed. RESULTS: HESS was found to be non-toxic, having a LD50 greater than 5000 mg/kg. Blood pressure increased progressively in all animals from the second week of L-NAME treatment. HESS treatment significantly and dose-dependently lowered systolic blood pressure (p < 0.001), diastolic blood pressure (p < 0.01), low density lipoprotein cholesterol (p < 0.01) and triglycerides (p < 0.01). It significantly prevented L-NAME induced decrease in serum angiotensin II (p < 0.01), high density lipoprotein cholesterol (p < 0.001) and serum nitric oxide concentrations (p < 0.001). HESS also significantly (p < 0.01) prevented collagen deposition in cardiac tissue. CONCLUSION: The hydro-ethanol extract of Senecio serratuloides showed antihypertensive, antihyperlipidemic and cardioprotective effects in rats thus confirming its usefulness in traditional antihypertensive therapy and potential for antihypertensive drug development.


Assuntos
Anti-Hipertensivos/farmacologia , Pressão Sanguínea/efeitos dos fármacos , Extratos Vegetais/farmacologia , Senécio/química , Animais , Anti-Hipertensivos/uso terapêutico , Anti-Hipertensivos/toxicidade , Etanol , Feminino , Coração/efeitos dos fármacos , Hipertensão/induzido quimicamente , Hipertensão/tratamento farmacológico , Lipídeos/sangue , Camundongos , NG-Nitroarginina Metil Éster/efeitos adversos , Extratos Vegetais/uso terapêutico , Extratos Vegetais/toxicidade , Ratos , Ratos Wistar
11.
Molecules ; 24(15)2019 Aug 01.
Artigo em Inglês | MEDLINE | ID: mdl-31374997

RESUMO

In recent years, heavy metals (HMs) levels in soil and vegetation have increased considerably due to traffic pollution. These pollutants can be taken up from the soil through the root system. The ability of plants to accumulate HMs into their tissues can therefore be used to monitor soil pollution. The aim of this study was to test the ruderal species Senecio vulgaris L., Polygonum aviculare L., and Poa annua L., as possible candidates for biomonitoring Cu, Zn, Cd, Cr, Ni and Pb in multiple environments. The soils analyzed in this work came from three different environments (urban, woodland, and ultramafic), and therefore deeply differed for their metal content, texture, pH, and organic matter (OM) content. All urban soils were characterized by high OM content and presence of anthropogenic metals like Pb, Zn, Cd, and Cu. Woodland soils were sandy and characterized by low metal content and low OM content, and ultramafic soils had high Ni and Cr content. This soil variability affected the bioindication properties of the three studied species, leading to the exclusion of most metals (Zn, Cu, Cr, Cd, and Pb) and one species (P. aviculare) due to the lack of linear relations between metal in soil and metal in plants. Senecio vulgaris and Poa annua, conversely, appeared to be good indicators of Ni in all the soils tested. A high linear correlation between total Ni in soil and Ni concentration in P. annua shoots (R2 = 0.78) was found and similar results were achieved for S. vulgaris (R2 = 0.88).


Assuntos
Monitoramento Ambiental , Metais Pesados/química , Plantas Daninhas/química , Poluentes do Solo/química , China , Metais Pesados/toxicidade , Plantas Daninhas/efeitos dos fármacos , Poa/química , Polygonum/química , Senécio/química , Solo/química , Poluentes do Solo/toxicidade
12.
J Sci Food Agric ; 99(14): 6649-6654, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-31368529

RESUMO

BACKGROUND: This study evaluated the degradation of pyrrolizidine alkaloids (PAs) from eastern groundsel (Senecio vernalis) in grass silage prepared with different inoculants. Silages were produced from ryegrass with 230 g kg-1 dry matter (DM) content and mixed with eastern groundsel (9:1; w/w fresh matter basis) containing 5.5 g kg-1 DM PA. Treatments were: CON (untreated control), LP (3.0 × 105 cfu g-1 Lactobacillus plantarum DSMZ 8862/8866) or LBLC (7.3 × 104 cfu g-1 Lactobacillus buchneri LN40177 / Lactobacillus casei LC32909), and each of the treatments in combination with 30 g kg-1 molasses. Silages were prepared in glass jars and opened after 3, 10, and 90 days. Fermentation characteristics were determined and the PAs analyzed. RESULTS: Although the levels of fermentation acids differed between treatments, results indicated good quality of all silages during 90 days. Significant time (P < 0.001) and treatment (P < 0.001) effects were observed for PAs. Concentrations of senecionine and seneciphylline decreased with molasses, declined over time, and were negatively correlated with lactic, propionic, and butyric acid, or with lactic and butyric acid in case of seneciphylline. In all silages, seneciphylline and senecionine N-oxides were undetectable after 3 days, whereas senkirkine, the most abundant PA, remained stable. CONCLUSIONS: Silage prepared from grass contaminated with eastern groundsel still contained high PA levels, and was hence a potential health hazard. Molasses supplementation reduced concentrations of senecionine and seneciphylline, while the bacterial inoculants had no effect. Other potentially toxic PA metabolites were not analyzed in the present study and further research is needed. © 2019 The Authors. Journal of The Science of Food and Agriculture published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.


Assuntos
Ração Animal/análise , Manipulação de Alimentos/métodos , Lolium/química , Alcaloides de Pirrolizidina/química , Senécio/química , Silagem/análise , Ração Animal/microbiologia , Fermentação , Lactobacillus/metabolismo , Lactobacillus plantarum/metabolismo , Lolium/microbiologia , Melaço/análise , Alcaloides de Pirrolizidina/metabolismo , Alcaloides de Pirrolizidina/toxicidade , Senécio/toxicidade , Silagem/microbiologia
13.
J Nat Prod ; 81(11): 2329-2337, 2018 11 26.
Artigo em Inglês | MEDLINE | ID: mdl-30359016

RESUMO

Nine new eremophilanolides, with seven known sesquiterpenoids, and 4-hydroxyacetophenone were isolated from the aerial parts of Senecio volckmannii var. volckmannii. The structures of these compounds were fully characterized using a combination of spectroscopic techniques including multinuclear and multidimensional NMR and mass spectrometry. The recently published Computer Assisted 3D Structure Elucidation (CASE-3D) protocol was applied in the configurational and conformational analysis of many of these eremophilanolides on the basis of Residual Dipolar Couplings (RDCs) and/or DFT predicted 1H/13C chemical shifts.


Assuntos
Espectroscopia de Ressonância Magnética Nuclear de Carbono-13/métodos , Compostos Fitoquímicos/química , Espectroscopia de Prótons por Ressonância Magnética/métodos , Senécio/química , Estrutura Molecular
14.
Drug Dev Ind Pharm ; 44(8): 1357-1370, 2018 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-29542335

RESUMO

The optimization of process parameters of spray-dried powder containing fanhuncaoin, a newly discovered anti-inflammatorily active phenolic acid isolated from Chinese herb, was conducted using response surface methodology (RSM). The experimental results were fitted into partial cubic polynomial model to describe and predict the response quality in terms of the final angle of repose, aerodynamic diameter, respirable fraction (RF), and yield. The recommended optimum spray-drying parameters for the development of fanhuncaoin powder with optimum quality were 110 °C inlet temperature, 0.50 m3/min aspiration speed, and 7.95 ml/min feed flow rate. The obtained optimum process parameters were employed for the production of spray-dried fanhuncaoin powder and to check the validity of the partial cubic model. Small and insignificant deviations were found between the predicted values and the experimental ones, showing the efficiency of the model in predicting the quality attributes of fanhuncaoin powder. The optimized powder was further examined for its pharmacokinetic properties in rats. A UPLC/MS assay was used to determine plasma fanhuncaoin concentration. Statistical analysis demonstrated that there was no significant difference in the t1/2 and dose-normalized Cmax and AUC as well as other pharmacokinetic parameters between the groups dosed differently following intratracheal administration (p > .05), indicating that fanhuncaoin followed linear kinetics. The pharmacokinetic parameters of fanhuncaoin after intratracheal administration differed significantly from the ones observed after intravenous administration (p < .05). The lower values of Cmax and AUC(0-∞) obtained following intratracheal administration may lead to effective drug concentrations at the target site with minimal systemic bioavailability and side effects.


Assuntos
Anti-Inflamatórios/farmacocinética , Composição de Medicamentos/métodos , Medicamentos de Ervas Chinesas/farmacocinética , Pulmão/efeitos dos fármacos , 1,2-Dipalmitoilfosfatidilcolina , Administração por Inalação , Administração Intravenosa , Animais , Anti-Inflamatórios/administração & dosagem , Anti-Inflamatórios/química , Área Sob a Curva , Disponibilidade Biológica , Dessecação , Medicamentos de Ervas Chinesas/administração & dosagem , Medicamentos de Ervas Chinesas/química , Feminino , Hidroxibenzoatos/administração & dosagem , Hidroxibenzoatos/química , Masculino , Modelos Animais , Modelos Químicos , Tamanho da Partícula , Pós , Ratos , Ratos Wistar , Senécio/química , Temperatura
15.
Molecules ; 23(10)2018 Sep 29.
Artigo em Inglês | MEDLINE | ID: mdl-30274255

RESUMO

Antioxidant phytochemicals play a key role in oxidative stress control and in the prevention of related disorders, such as premature aging, degenerative diseases, diabetes, and cancer. The aim of this study was to investigate the potential antioxidant activity and the phytochemical profile of Senecio clivicolus Wedd., a perennial shrub, belonging to the Asteraceae family. Despite the wide interest of this family, this specie has not been investigated yet. S. clivicolus aerial parts were extracted with 96% ethanol. Then, the ethanol extract was fractionated by liquid/liquid extraction using an increasing solvents polarity. Total polyphenol and terpenoid contents were measured. Moreover, the antioxidant activity was evaluated by six different complementary in vitro assays. The Relative Antioxidant Capacity Index (RACI) was used to compare data obtained by different tests. The sample showing the highest RACI was subjected to characterization and quantitation of its phenolic composition using LC-MS/MS analysis. The ethyl acetate fraction, investigated by LC-MS/MS analysis, showed 30 compounds, most of them are chlorogenic acid and flavonoid derivatives. To the best of our knowledge, this is the first report about the evaluation of antioxidant activity and phytochemical profile of S. clivicolus, underlying the importance of this species as a source of health-promoting phytochemicals.


Assuntos
Antioxidantes/química , Compostos Fitoquímicos/química , Extratos Vegetais/química , Senécio/química , Antioxidantes/isolamento & purificação , Ácido Clorogênico/análogos & derivados , Ácido Clorogênico/química , Cromatografia Líquida de Alta Pressão/métodos , Flavonoides/química , Óxido Nítrico/química , Oxirredução , Compostos Fitoquímicos/isolamento & purificação , Extratos Vegetais/isolamento & purificação , Polifenóis/química , Solventes , Espectrometria de Massas em Tandem/métodos , Terpenos/química
16.
Chem Biodivers ; 14(1)2017 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-27546067

RESUMO

Nine eremophilane sesquiterpenes 1 - 9, two flavonoids 11 and 12, and two known pirrolizidine alkaloids 13 and 14, were isolated from Senecio adenotrichius DC. Their structures were elucidated on the basis of spectroscopic data and by comparison with previously reported spectroscopic data of similar compounds. Compounds 5, 7, and 9 have not been previously reported as natural products. The antifeedant activity of these compounds was tested against Spodoptera litoralis and Myzus persicae. Eremophilanes 1, 3, and 8 were strong antifeedants to M. persicae, and 1 and 8 to Spodoptera littoralis. Their ixodicidal activity was tested against the tick Hyalomma lusitanicum, with eremophilanes 1, 3, and 8, being strong ixodicidal agents.


Assuntos
Inseticidas/química , Senécio/química , Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Animais , Afídeos/efeitos dos fármacos , Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Inseticidas/isolamento & purificação , Inseticidas/farmacologia , Extratos Vegetais/química , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , Spodoptera/efeitos dos fármacos , Relação Estrutura-Atividade
17.
Chem Biodivers ; 14(9)2017 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-28657132

RESUMO

Phytochemical investigation on the aerial parts of Senecio hadiensis Forssk. led to the isolation of two new sesquiterpenoids, presilphiperfolan-2α,5α,8α-triol (1) and presilphiperfolan-2α,5α,8α,10α-tetraol (2) featuring the rare presilphiperfolane-type frameworks. The structures of 1 and 2 were elucidated on the basis of extensive spectroscopic (1D- and 2D-NMR, HR-ESI-MS) methods and by comparison with the literature data. The isolates 1 and 2 were evaluated in-vitro for antiinflammatory, cytotoxic, and peroxisome proliferator activated receptor alpha and gamma (PPARα and PPARγ) agonistic activities.


Assuntos
Anti-Inflamatórios/química , Antineoplásicos Fitogênicos/química , PPAR alfa/agonistas , PPAR gama/agonistas , Senécio/química , Sesquiterpenos/química , Animais , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , Chlorocebus aethiops , Células Hep G2 , Humanos , Espectroscopia de Ressonância Magnética , Camundongos , Células RAW 264.7 , Arábia Saudita , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , Espectrometria de Massas por Ionização por Electrospray , Células Vero
18.
J Sci Food Agric ; 97(7): 2238-2244, 2017 May.
Artigo em Inglês | MEDLINE | ID: mdl-27620169

RESUMO

BACKGROUND: Rocket is a popular salad vegetable used all over the world and it has many health benefits. However, like with all plant material, there exists a danger of contamination with toxic substances. In the case of rocket, contamination with groundsel has occurred. Groundsel is a common weed in rocket crops, and it contains very toxic pyrrolizidine alkaloids. In our study infrared spectroscopy was used to distinguish groundsel samples from rocket leaves. Infrared spectroscopy is a very simple analytical technique; however, some specific conditions are more easily implemented in industrial environment than others. Some of these conditions and parameters of infrared spectroscopy were explored in detail. RESULTS: We tested for the influence of different parameters of attenuated total reflectance and transmission infrared method. Our results show that a 100 % correct classification can be obtained under conditions most suitable for industry: using fresh samples and parameters that enable fast spectral measurement. CONCLUSION: Infrared spectroscopy is a fast and easy-to-use method that has been shown to be able to differentiate between rocket and groundsel leaves. Therefore, it could be further studied for implementation in the safety control of rocket salads. © 2016 Society of Chemical Industry.


Assuntos
Brassicaceae/química , Contaminação de Alimentos/análise , Senécio/química , Espectroscopia de Infravermelho com Transformada de Fourier/métodos , Verduras/química , Folhas de Planta/química
19.
Regul Toxicol Pharmacol ; 79: 25-34, 2016 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-27177820

RESUMO

Senecio candicans DC. (Asteraceae) is used as a remedy for gastric ulcer and stomach pain in the Nilgiris, district, Tamil Nadu. The present investigation was carried out to evaluate the sub-chronic toxicity of an aqueous extract of Senecio candicans (AESC) plant in Wistar albino rats. The study was conducted in consideration of the OECD 408 study design (Repeated Dose 90-Day Oral Toxicity Study in Rodents) and the extract was administered via gavage at doses of 250, 500 or 750 mg/kg body weight per day for 90-days. Hematological, biochemical parameters were determined on days 0, 30, 60 and 90 of administration. Animals were euthanized after 90 d treatment and its liver and kidney sections were taken for histological study. The results of sub-chronic study showed significant increase (P < 0.05) in serum uric acid, creatinine, aspartate transaminase (AST) and alanine transaminase (ALP) levels. Histological examination of liver showed mild mononuclear infiltration in the portal trait, enlarged nucleus around the central vein and mild loss of hepatocyte architecture in rats treated with 750 mg/kg of AESC. Histological examination of kidney showed focal interstitial fibrosis, crowding of glomeruli and mild hydropic change with hypercellular glomeruli in rats treated with 750 mg/kg of AESC. However, no remarkable histoarchitectural change in hepatocytes and glomeruli were observed in rats treated with lower concentrations (250 and 500 mg/kg b.w.) of AESC compared to control group animals. The no-observed adverse effect level (NOAEL) of AESC in the present study was 500 mg/kg b.w. Signs of toxic effects are evident from the current study. Although AESC contains low concentrations of PA, findings from this study suggest that regular consumers of herbal remedies derived from this plant may develop kidney and liver toxicity. Further studies on the isolation and characterization of PAs are necessary to determine the safe dose level of the extract for therapeutic use in traditional medicine.


Assuntos
Antiulcerosos/toxicidade , Doença Hepática Induzida por Substâncias e Drogas/etiologia , Nefropatias/induzido quimicamente , Rim/efeitos dos fármacos , Fígado/efeitos dos fármacos , Extratos Vegetais/toxicidade , Alcaloides de Pirrolizidina/toxicidade , Senécio/toxicidade , Testes de Toxicidade Subcrônica , Administração Oral , Animais , Antiulcerosos/administração & dosagem , Antiulcerosos/isolamento & purificação , Biomarcadores/sangue , Doença Hepática Induzida por Substâncias e Drogas/sangue , Doença Hepática Induzida por Substâncias e Drogas/patologia , Relação Dose-Resposta a Droga , Feminino , Fibrose , Rim/metabolismo , Rim/patologia , Nefropatias/sangue , Nefropatias/patologia , Fígado/metabolismo , Fígado/patologia , Masculino , Nível de Efeito Adverso não Observado , Fitoterapia , Extratos Vegetais/administração & dosagem , Extratos Vegetais/isolamento & purificação , Plantas Medicinais , Alcaloides de Pirrolizidina/administração & dosagem , Alcaloides de Pirrolizidina/isolamento & purificação , Ratos Wistar , Medição de Risco , Senécio/química , Fatores de Tempo
20.
Ecology ; 96(1): 164-75, 2015 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-26236901

RESUMO

Neighboring plants can influence arthropods on a focal plant, and this can result in associational resistance or associational susceptibility. These effects can be mediated by above- and belowground interactions between the neighbor and focal plant, but determining the relative contribution of the above- and belowground effects remains an open challenge. We performed a common garden experiment with a design that enabled us to disentangle the above- and belowground effects of five different plant species on the growth and chemistry of the focal plant ragwort (Jacobaea vulgaris), and the arthropod community associated with this plant. Aboveground effects of different neighboring plant species were more important for the growth and quality of J. vulgaris and for the arthropod abundance on this plant than belowground effects of neighbors. This remained true when only indirect neighbor effects (via affecting the biomass or quality of the focal plant) were considered. The aboveground neighbor effects on arthropod abundance on the focal plant were strongly negative. However, the magnitude of the effect depended on the identity of the neighboring species, and herbivore abundance on the focal plant was higher when surrounded by conspecific than when surrounded by heterospecific plants. We also observed interactions between above- and belowground neighbor effects, indicating that these effects may be nonadditive. We conclude that above- and belowground associational effects are not equally strong, and that neighbor effects on plant-arthropod interactions occur predominantly aboveground.


Assuntos
Artrópodes , Ecossistema , Senécio/crescimento & desenvolvimento , Animais , Herbivoria , Análise de Componente Principal , Senécio/química
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